We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Homes in Canaan

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    R 6 587 Average
    |||
    |||
    R 0R 19 000+
    Suitability
    More filters
    Don't let other travellers get your favourite Canaan area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 41 Rentals in Canaan
    Sort by:
    Default
    Canaan
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    The following rentals are within 15 kilometres of Canaan.
    Great Vacation House in the Berkshires by Richmond Pond1 / 10
    (4)Excellent
    Richmond, MA
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Ghent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Gartner House, a charming home in Lenox1 / 21
    (33)Excellent
    Lenox, MA
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Porch
    • Washer
    • Parking
    • Internet Access
    • Central Heating
    • Grill
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 September 2019
    Perfect location for walking to all the shops and restaurants in Lenox. The home was comfortable. I'll book again when I'm next in Lenox!
    Reviewed 28 August 2019
    We went to the Gartner House for a ladies weekend and it was a perfect weekend. Just a little walk to restaurants and shops in the lovely town of Lennox, short drive to...
    See all reviews
    About this property
    Located on a quiet side street in the charming Berkshire town of Lenox, Gartner House is a great place to call home while exploring this scenic, historical, and culturally rich area of Western Massachusetts. Walk to breakfast, lunch or dinner at one of the town's many charming restaurants, explore...
    View all property information
    Location Information
    01240, Lenox, Berkshires
    Condo/Apartment - 4 Bedrooms, 1 Bathroom, Sleeps 7
    To Ski or Not to Ski?  Great conditions Great fireplace.Your Choice.1 / 18
    (7)Excellent
    West Stockbridge, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Wi-Fi
    • Balcony
    • Patio
    • Grill
    • Washer
    • Porch
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 September 2018
    The house was so comfortable; the location was perfect -- close to so many beautiful places and Berkshires attractions, especially Tanglewood!; Cassandra was so helpful when I...
    Reviewed 27 August 2016
    We had a wonderful stay in this large, lovely house that contained everything we needed for comfort and convenience. We were impressed with the degree to which details were...
    See all reviews
    About this property
    Enjoy this perfectly located home to pursue what brings you to the Berkshires. Ski and warm up next to the fire in the winter. Go to Kripalu but enjoy all the comforts of this home just 8 minutes away. Enjoy fabulous foods, and make new friends. Located in West Stockbridge minutes from everything ....
    View all property information
    Location Information
    01266, West Stockbridge, Berkshires
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Berkshire Farmhouse Vacation1 / 20
    (42)Excellent
    West Stockbridge, MA
    5 Bedrooms, 2 Bathrooms, Sleeps 15 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Grill
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 December 2019
    We stayed in the Berkshire Farmhouse during our winter school break as a large group of 9 with adults and children (including teenagers). Very comfortable, clean, cozy and warm...
    Reviewed 23 September 2019
    We are 4 women in our 70's and 80"s who have been going away together for one week a year for the past 33 years. This year we decided to go to the Berkshires. The...
    See all reviews
    About this property
    Quaint, , 2 story 1850's farmhouse in the Berkshires with original ceiling beams and 16' floor boards in much of the house. Fully furnished with 5 bedrooms, 2 full baths and a gorgeous screened-in porch overlooking 4 acres of gardens, stream and wooded mountains. Country kitchen with dish washer,...
    View all property information
    Location Information
    01266, West Stockbridge, Berkshires
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 15
    Comfortable Farmhouse in the Berkshires1 / 10
    (4)Excellent
    West Stockbridge, MA
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Grill
    • Air Conditioning
    • Patio
    • Wi-Fi
    • DVD Player
    • Mountain Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 August 2017
    Nice house, great spot for our family reunion. Convenient to many of the Berkshires attractions. Nice kitchen for cooking and eating in for a group.
    Reviewed 5 June 2017
    House was comfortable and well furnished. The Berkshires are beautiful with lots of activities, galleries, shopping and restaurants. Our hosts were helpful and responsive to...
    See all reviews
    About this property
    Rent a comfortable 1840 farmhouse with 26 acres in the Berkshire mountains. Walk to the village of West Stockbridge or a short drive to all the Berkshire attractions. Close to the ski resorts of Butternut, Bousquet, Catamount and Jiminy Peak. The house sleeps 10 to 12 people and is fully equipped....
    View all property information
    Location Information
    01266, West Stockbridge, Berkshires
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Austerlitz
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Washer
    • Parking
    • Shared Garden
    • Internet Access
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 3 Bedroom 2.5 bathroom recently constructed home sits on 40 wooded, secluded acres in Austerlitz, Columbia County, just 4 miles from the Massachusetts border. It offers stunning views of the Catskills, peace and quite and plenty of nature to watch from the back porch. Chatham, NY is 15 minutes...
    View all property information
    Location Information
    12017, Austerlitz, New York
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    West Stockbridge, MA
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by the fireplace in the living room, fall foliage and scenic atmosphere in the area, and soak in the...
    View all property information
    Location Information
    01266, West Stockbridge, Berkshires
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Berkshire Country Estate - The Library Suite1 / 21
    (1)Excellent
    Old Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 September 2018
    We were looking for a one night stay while in the neighbourhood. We could not have asked for a better place. This amazing house will take you away from everyday business and...
    See all reviews
    About this property
    The beautiful Berkshire Country Estate is located on 60 acres in the foothills of the Berkshires, minutes from Lenox MA & Hudson NY, less than a 2 1/2 drive from New York City. Library Suite: Luxuriate in our spacious two room suite to accommodate 2-4 guests with fireplace, full bath w/ deep soak...
    View all property information
    Location Information
    12136, Old Chatham, New York
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Save time - get the best Canaan rentals sent straight to your email!
    Get the List
    Cozy & Modern Home -mins from Tanglewood & Kripalu1 / 8
    (3)Excellent
    West Stockbridge, MA
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 August 2019
    Great location - quiet, private, and felt like our own little home. Close to the lake with the beach. Only 4 minutes drive to Tanglewood.Next time I visit I will sure look to...
    Reviewed 18 December 2013
    We stayed at this home in Housatonic, which is part of Great Barrington, the Smithsonian pic for best small town in the USA. I hope you all don't however as one of the best...
    See all reviews
    About this property
    Cozy and modern two bedroom and one bath vacation home with lake nearby Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by the fireplace in the living...
    View all property information
    Location Information
    01266, West Stockbridge, Berkshires
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Old Chatham
    8 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Housekeeping Included
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Berkshire Country Estate is located on 60 acres in the foothills of the Berkshires, only 2 1/2 hours from New York City and Boston. Surrounded by the beauty of the Berkshires, the estate is very private, with a 1/8 mile driveway leading to the 10 acre front lawn. A large elegant, yet...
    View all property information
    Location Information
    12136, Old Chatham, New York
    Holiday Rental House - 8 Bedrooms, 5 Bathrooms, Sleeps 16
    Berkshire Blueberry Lodge LLC - Near Jiminy Peak1 / 22
    (7)Very good
    Stephentown
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Mountain Views
    • Wi-Fi
    • Grill
    • DVD Player
    • Outdoor Dining Area
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 September 2016
    My siblings and I (8 adults total) spent a wonderful weekend at the Blueberry Lodge. Most of our time was spent at the lodge except for an afternoon and evening attending the...
    Reviewed 8 March 2016
    My girlfriends and I have been going on yearly ski trips primarily in NH, VT, and ME for the past 29 years. This year we decided to try the Berkshires, for some place different...
    See all reviews
    About this property
    Countryside setting with a fantastic view of the Berkshires and centrally located. 10 minutes to Jiminy Peak ski area, 30 minutes to Tanglewood, 25 minutes to Stockbridge, 20 minutes to Mt. Greylock, 25 minutes to Williamstown theater. the lodge has a 400 square foot grand room for parties,...
    View all property information
    Location Information
    12168, Stephentown, New York
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Pittsfield, MA
    7 Bedrooms, 3 Bathrooms, Sleeps 18 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Grill
    • Terrace
    • Washer
    • Balcony
    • Patio
    • Hot Tub
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a beautiful 7 bedroom home with over 4000 sq. ft. of nicely furnished large rooms. Nestled in the heart of the Berkshire Mountains, between 2 lakes and located in a quiet family friendly neighborhood. Just minutes from the New York border. Our home is a fantastic deal for the wonderfully...
    View all property information
    Location Information
    01201, Pittsfield, Berkshires
    Holiday Rental House - 7 Bedrooms, 3 Bathrooms, Sleeps 18
    Heart of Lenox1 / 7
    (2)Excellent
    Lenox, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 August 2018
    1/2 house, with owners in other half, which was handy for questions and suggestions. Very clean, and queen bed was really comfortable. Other BR has twin bedsKitchen has...
    Reviewed 28 May 2017
    Title sums it up! Excellent choice for our recent visit to Lenox. The house is very clean and comfortable and the owners are very accommodating. Location is great, just steps...
    See all reviews
    About this property
    Just rated Best Small Town in the Northeast by USA Today, our home is located in the heart of Lenox MA! Come relax in our lovely home, situated in a quiet neighborhood just steps from downtown. Walk to Zagat rated restaurants, shop unique boutique shops, hike in Kennedy Park. Whether you love the...
    View all property information
    Location Information
    01240, Lenox, Berkshires
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Austerlitz
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Hot Tub
    • Central Heating
    • Balcony
    • Grill
    • Patio
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The beautiful renovated Georgian Colonial home sits amongst 40 acres of natural beauty. The house overlooks a serene pond and all its beauty with views of natural forrest beyond. The house itself has a oversized chef's eat in kitchen. The Kitchen has all the amenities to host wonderful meals and...
    View all property information
    Location Information
    12017, Austerlitz, New York
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
    Stephentown
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Outdoor Dining Area
    • Washer
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Two story cape that can sleep up to 12 people on 50 acres. Fully equipped kitchen, laundry area and dining & living room that faces the Berkshire Mountains. Relaxingy deck with barbecue. Walking trails and swimming pond make it a perfect getaway place. Wifi, a/c tv Near all Berkshire attractions,...
    View all property information
    Location Information
    12168, Stephentown, New York
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    Hudson Valley Cottage1 / 13
    (1)Excellent
    Ghent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Mountain Views
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Grill
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 August 2013
    This was the perfect location for a base camp from which to explore the Hudson River Valley area. We took in a Tanglewood concert (40-minute drive) and explored the backroads...
    See all reviews
    About this property
    Enjoy a newly renovated and furnished, one bedroom guest cottage, in an enchanting and quiet area. Located behind a stone castle on a 2 1/2 acre park-like property it's a beautiful place to vacation. You also have access to a large 6 person hot tub and all the deck areas. The bedroom and living...
    View all property information
    Location Information
    12075, Ghent, New York
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Old Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on 60 acres in the foothills of the Berkshires, minutes from Lenox MA & Hudson NY, less than a 2 1/2 drive from New York City. It is an elegant, yet comfortable family Georgian estate, privately sited with a long driveway and a 10 acre front lawn. Luxuriate in the Rose Suite, a nearly 1,100...
    View all property information
    Location Information
    12136, Old Chatham, New York
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Lenox, MA
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely renovated 2 bedroom downtown apartment with open floor plan in Lenox MA. Enjoy walks around the downtown area and visit the many attractions in Berkshire County. Endless restaurants to choose from, golf courses within 7 miles, Kennedy Park and Tanglewood close by. Minutes down the road...
    View all property information
    Location Information
    01240, Lenox, Berkshires
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    List your property for free!
    List your holiday rental where Tripadvisor travellers can find it.
    Add a Listing
    nesteldown pet friendly1 / 5
    (1)Excellent
    Old Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Grill
    • Waterfront
    • Patio
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 November 2015
    This was such a great place for us to stay , it had everything , even went fishing - biking , the house was just perfect , we even had friends over and we had plenty of room...
    See all reviews
    About this property
    'One of a kind' listing. Gated , 4BR Elegant Colonial Estate on Pristine River/stream in most desirable area in Columbia County. Set in sleepy upscale Historic Hamlet on Park-like grounds. Bordered by over 150 acres of fields with Sunset views. The best Swimming , fantastic Fishing, stone Campfire...
    View all property information
    Location Information
    12136, Old Chatham, New York
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Richmond, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Porch
    • Internet Access
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly furnished 3 bedroom (with AC) & 2 1/2 bath single family home with stunning deck and in ground pool nestled in the quiet countryside opposite a horse farm. Situated minutes from West Stockbridge convenience stores and restaurants. Property is on 2 quiet tree lined acres with an enclosed...
    View all property information
    Location Information
    01254, Richmond, Berkshires
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Chatham
    4 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Patio
    • Terrace
    • Housekeeping Included
    • Balcony
    • Central Heating
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fully renovated 1800s farm house on 100 acres with heated in ground gunnite pool, hiking trails located on a beautiful creek. We also have a guest house with two more bedrooms and a full kitchen by the pool that is perfect for bringing your in-laws or babysitter. The house has a chef's kitchen...
    View all property information
    Location Information
    12037, Chatham, New York
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 6
    Lenox, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    No matter the season, you'll find the getaway you crave while staying at this 3-bed, 2.5-bath house in Lenox! This welcoming vacation rental features room for 6, numerous amenities, and an incredible location just minutes from the Tanglewood Music Center. In addition, enjoy easy access to the...
    View all property information
    Location Information
    01240, Lenox, Berkshires
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Stephentown
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Parking
    • Washer
    • Mountain Views
    • Private Garden
    • Grill
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect weekend retreat or short term furnished rental close to all Berkshire, MA amenities and Jiminy Peak Mountain Resort, museums, theatre, restaurants, shopping and more! 20 Minutes to Williamstown, 25 to Pittsfield, 30 to Albany. Home is efficient, easily maintained in an adorable 1870's...
    View all property information
    Location Information
    12168, Stephentown, New York
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    East Chatham
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Grill
    • Washer
    • Mountain Views
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    100MBPS WIFI NOW AVAILABLE! Enjoy the Berkshires in this recently renovated Chalet on 18 acres, centrally located between 4 ski resorts. 20 minutes from tanglewood. Basement- Washer and dryer 1st floor- Features a huge wrap around deck, open concept kitchen/living room w/ couch and fireplace,...
    View all property information
    Location Information
    12060, East Chatham, New York
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Lenox, MA
    4 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Smart New first time rental of 4 BR, 4.5 BA, Ranch style, sleeps 10-12+. New fully equipped kitchen w/breakfast bar, outdoor barbecue, fireplace, large deck with 8 person hot tub and super seating for beautiful sunsets, . Fabulous great room with 65' HD Smart TV and 4 additional TV's for you...
    View all property information
    Location Information
    01238, Lenox, Berkshires
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 11
    Lenox, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Quintessential Lenox Farmhouse with 1881 charm and a shiny new finish. Lovingly renovated and restored, this house is nestled on 4.5 private acres within minutes of the town of Lenox and Tanglewood. The house boasts a chef's Kitchen with all new stainless steel appliances, large farmhouse porcelain...
    View all property information
    Location Information
    01240, Lenox, Berkshires
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Malden Bridge
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Grill
    • Terrace
    • Central Heating
    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house is surrounded by 40 acres of sprawling meadows and wood.2 1/2 hours from NYC and Boston, and 3 to Montreal Arts scene, with Ellsworth Kelly and Marina Abramovic also, and a lot of younger NYC artists relocating nearby much in the way that the 50s artists sought out the space of the...
    View all property information
    Location Information
    12123, Malden Bridge, New York
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Lenox, MA
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    • Shared Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fabulous great room with pool table, 65' HD Smart TV for you sports fans. Great indoor / outdoor sound system and don't worry about the neighbors. Summer weeks include 2 rounds of golf at nearby Cranwell Country club or Spa treatments for two at the Cranwell Spa or trade them for show tickets,...
    View all property information
    Location Information
    01238, Lenox, Berkshires
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
    Lenox, MA
    5 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Grill
    • Balcony
    • Housekeeping Included
    • Terrace
    • Patio
    • DVD Player
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    5 BR, 5 Full Bath's (Jetted tub), Newly Expanded open floor plan, 3 fireplaces, firepit, grill, large outdoor patio, screened porch, sleeps 15+. Large backyard with volleyball, football, badminton, bocce, croquet, ping pong and hammock. About 600 feet to Tanglewood Music Center. Across the street...
    View all property information
    Location Information
    01240, Lenox, Berkshires
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 15
    West Stockbridge, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Washer
    • Balcony
    • Air Conditioning
    • Housekeeping Included
    • Mountain Views
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We offer two bedrooms accessible via a private staircase in our recently renovated Victorian farm house located on two beautifully landscaped acres with seasonal gardens and adjoining woods and fields. Each bedroom sleeps 2; they can be booked individually or together at $105/bedroom/night. We...
    View all property information
    Location Information
    01266, West Stockbridge, Berkshires
    Private Room - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    West Lebanon
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Patio
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is an exclusive Tentrr site. Tentrr partners with farmers, ranchers, and other property owners to offer unique outdoor accommodations on beautiful private land. Each Tentrr Signature site includes a 10'x12' safari-style canvas tent on a raised platform, and you'll find a queen-size single or...
    View all property information
    Location Information
    12062, West Lebanon, New York
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
    Richmond, MA
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is an exclusive Tentrr site. Tentrr partners with farmers, ranchers, and other property owners to offer unique outdoor accommodations on beautiful private land. Each Tentrr Signature site includes a 10'x12' safari-style canvas tent on a raised platform, and you'll find a queen-size single or...
    View all property information
    Location Information
    01254, Richmond, Berkshires
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Ghent
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Central Heating
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is an exclusive Tentrr site. Tentrr partners with farmers, ranchers, and other property owners to offer unique outdoor accommodations on beautiful private land. Each Tentrr Signature site includes a 10'x12' safari-style canvas tent on a raised platform, and you'll find a queen-size single or...
    View all property information
    Location Information
    12075, Ghent, New York
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
    Spencertown
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Parking
    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spend some time in this charming cottage with spectacular views overlooking the Hudson Valley in upstate New York. We have over 80 private acres of beautiful woods, meadows, and ancient stone walls. Secluded, yet only a short drive to the Berkshires, where music, theater, history, and natural...
    View all property information
    Location Information
    12165, Spencertown, New York
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Richmond, MA
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is an exclusive Tentrr site. Tentrr partners with farmers, ranchers, and other property owners to offer unique outdoor accommodations on beautiful private land. Each Tentrr Signature site includes a 10'x12' safari-style canvas tent on a raised platform, and you'll find a queen-size single or...
    View all property information
    Location Information
    12029, Richmond, Berkshires
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
    Stephentown
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Balcony
    • Terrace
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cozy cottage is perfect for a small group of friends or a family getaway in the beautiful Berkshires. We're on 120 acres of private woods but only 7 miles from Jiminy Peak. The main space features a cathedral ceiling in the open living/dining area, with a glass-front woodstove for chilly...
    View all property information
    Location Information
    12168, Stephentown, New York
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Lenox, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    • Patio
    • Washer
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy leisurely lakeside days just a walk away as you stay at this 3-bed, 1.5-bath vacation rental house that sleeps 6 in Stockbridge! With mossy grounds below and age-old oaks towering above, this cozy cottage is a dreamy retreat, perfect for those looking for a bit of the great outdoors without...
    View all property information
    Location Information
    01262, Lenox, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Spencertown
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Parking
    • Patio
    • Cable/satellite TV
    • Internet Access
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Frank Lloyd Wright-inspired retreat is the perfect country escape for city dwellers. Set on 30 private acres with trails for hiking and a lake, this professionally decorated home blends rustic charm with modernity. There are two bedrooms, one with a fireplace, two bathrooms, plus a sleeping...
    View all property information
    Location Information
    12165, Spencertown, New York
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Lenox, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    • Washer
    • Mountain Views
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Situated in the heart of the Berkshires, this 3-bed, 2-bath vacation rental offers a modern living space, a large yard and an ideal location near many attractions. Adventure seekers will enjoy easy access to the Appalachian Trail and Catamount Ski Resort, music fans can catch the Boston Symphony...
    View all property information
    Location Information
    01240, Lenox, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    List your property
    Owner log in