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Holiday Homes in New Preston

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    All 31 Rentals in New Preston
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    Rhubarb Hill, a Charming 1850's Farmhouse1 / 21
    (1)Excellent
    New Preston
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    New Preston
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    The following rentals are within 15 kilometres of New Preston.
    20'x40' inground private pool just for you&house with 4bedrooms1 / 36
    (4)Excellent
    New Milford
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Country Estate newly renovated that sleeps 16!1 / 31
    (1)Excellent
    Bethlehem
    5 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    • Parking
    • Grill
    • Housekeeping Included
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 March 2019
    Walking into this home was like walking into my parents home. The home is the epitome of a "turn key" home.; it had everything we needed to be comfortable. I highly...
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    About this property
    Judd Farm House is situated on 33 acres, the house is in farm country. It is surrounded by rolling hills of Litchfield. There are country roads for walking and biking with very little traffic. It is a perfect retreat for a group. There are generous size bedrooms that are tastefully decorated....
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    06795, Bethlehem, Connecticut
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 16
    Litchfield
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Housekeeping Included
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the Litchfield Hills from this newly renovated one bedroom apartment with private entrance. Amenities include full kitchen, living room, bedroom with queen bed, and full en suite bathroom. WiFi and cable TV included. All located less than 2 miles from historic Litchfield Center. Our property...
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    06759, Litchfield, Connecticut
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Wits End Farm B&B1 / 14
    (1)Excellent
    Bethlehem
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 2017
    Our family stayed at Wits End Farm B&B for a weekend in early June for our son's graduation from a local boarding school. We can't say enough about our time there. Our host...
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    About this property
    This sophisticated and modernized 18th Century rambling farmhouse is set amount towering tress, huge lawns, flower beds, parterre vegetable and herb gardens, 2 ponds, stone walls, pasture and woods. There are five bedrooms, including one huge family suite with a Q bed, twin bed and a crib. All...
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    06751, Bethlehem, Connecticut
    Private Room - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Wits End Farm1 / 16
    (1)Excellent
    Bethlehem
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • Patio
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 2017
    Our family stayed at Wits End Farm B&B for a weekend in early June for our son's graduation from a local boarding school. We can't say enough about our time there. Our host...
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    About this property
    This sophisticated and modernized 18th Century rambling farmhouse is set amount towering tress, huge lawns, flower beds, parterre vegetable and herb gardens, 2 ponds, stone walls, pasture and woods. There are five bedrooms, including one huge family suite with a Q bed, twin bed and a crib. All...
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    06751, Bethlehem, Connecticut
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
    Cornwall Bridge
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Mountain Views
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    • Internet Access
    • Private Indoor Pool
    • Air Conditioning
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Prana Residence-Spa creates an environment for relaxation and the rejuvenation of vital life (prana). If you appreciate tranquility in the pursuit of personal happiness and are inspired by unique surroundings, personal spa facilities and select services, Prana Residence-Spa is waiting for you....
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    06754, Cornwall Bridge, Connecticut
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    Modern Litchfield Home on 1/2-Acre near Town Center1 / 25
    (1)Excellent
    Litchfield
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Washer
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 November 2017
    Litchfield is a charming small town that is a popular weekend destination for New Yorkers. It has a few good restaurants and boutique shopping, plus the interesting historical...
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    About this property
    Relish in the luxuries and comforts of this 3-bedroom, 2-bath vacation rental house in Litchfield! 'Stone-Peca' is a quintessential New England property sitting on a half acre of land, offering a 4-season sun porch as well as a spacious backyard with a deck and patio. Stylish, high-end decor adorns...
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    06750, Litchfield, Connecticut
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Evie's Turning Point Farm1 / 11
    (1)Excellent
    Warren
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 February 2019
    The room was large, clean, unique, and so relaxing! They provided amazing amenities and there was so much privacy! The house is on a large property and the space to rent part of...
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    About this property
    This home is a beautiful farm built in 1750! Perfect location for boarding schools, vineyards, tours, AT Hiking, and girls getaway! • 2 large bedrooms • Close to great hikes, quaint towns, and family activities • Gorgeous balcony overlooking the pond • Huge living space • Secluded and romantic...
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    06754, Warren, Connecticut
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Sherman
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Washer
    • Mountain Views
    • Grill
    • Housekeeping Included
    • Waterfront
    • Central Heating
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private secure community with million dollar homes. Perfect weekend retreat. 90 minutes from NYC. This two bedroom cottage has all the necessary amenities. Includes access to two private beaches on Candlewood Lake and Green Pond. Just renovated with new wood floors, new appliances, new...
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    06784, Sherman, Connecticut
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Kent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
    • Air Conditioning
    • Patio
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Room with private bath, queen bed, antique furniture, air conditioning, and radiator heat. Shared living room, dining room, porch, and kitchen. On Main Street in town. Plenty of parking. Please enjoy all the common areas in the home. We do not live in the home and there may be a total of up to...
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    06757, Kent, Connecticut
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Kent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Patio
    • Private Garden
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This former servant's quarters w/full bed has private bath with claw foot tub/shower. Original back staircase just outside the door which leads directly to the kitchen. Please enjoy all the common areas in the home. We do not live in the home and there may be a total of up to ten people staying...
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    06757, Kent, Connecticut
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Kent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully decorated room with private bath, queen bed, antique furniture and Cable TV. Shared living room, dining room, porch, and kitchen. On Main Street in town. Plenty of parking. Please enjoy all the common areas in the home. We do not live in the home and there may be a total of up to ten...
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    06757, Kent, Connecticut
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Litchfield
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Tentrr Meadow Ridge Farm campsite is a 110-acre working dairy farm. But don't be misled, the site is very secluded, located over a quarter a mile away from anything. You will get to the campsite by driving down the gravel road past corn fields and pastures. This is an exclusive Tentrr site....
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    06759, Litchfield, Connecticut
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Litchfield
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Tentrr - Meadow Ridge Farm Woods Campsite is a secluded woodsy spot on the oldest dairy farm in Litchfield. Get away from it all and reconnect with nature! This is an exclusive Tentrr site. Tentrr offers fully-equipped individual campsites on beautiful private land. Meadow Ridge Farm is a...
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    06759, Litchfield, Connecticut
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Kent
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Grill
    • Private Garden
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    First floor suite king bed, couch and desk. Sitting room with single bed, chairs, television and desk. Large bath with stall shower. Shared living room, dining room, porch and kitchen. Please enjoy all the common areas in the home. We do not live in the home and there may be a total of up to ten...
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    06757, Kent, Connecticut
    Private Room - 2 Bedrooms, 1 Bathroom, Sleeps 3
    Roxbury
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
    • Mountain Views
    • Air Conditioning
    • Grill
    • Secure Parking
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The best way to experience Roxbury Connecticut... A completely Private Apartment in Modern contemporary home located on Route 67 in Roxbury Connecticut. 2 Bedrooms, Full Kitchen, Full Bathroom, Living Room, Oversized Deck, Outdoor Grill, and 3+ Acres of Land with Outdoor Seating. Close to...
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    06783, Roxbury, Connecticut
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    New Milford
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our house has a soul. It is not like a fancy hotel but instead all elements of decor have some story to tell. The indoor is painted by an artist. We have grand piano which if you know how to play will make time together more fun. The pool is just amazing. Deep end has 8' and shallow 4.5'.We love it...
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    06776, New Milford, Connecticut
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Washington Depot
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    If you are searching for the perfect country setting within an easy drive to wonderful local restaurants, spas, shopping, antiquing, skiing, water activities, hiking, historic homes and museums, then Country Cottage is for you. Wonderful family activities such as apple picking, farm stands, country...
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    06794, Washington Depot, Washington
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Washington Depot
    8 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunny Ridge Farm is a magnificent country estate on 14 acres in the Sunny Ridge Historic District. It is the largest home (17,000 SF) in Washington, the most exclusive town in rural Litchfield County. The estate has been meticulously restored and has almost every possible amenity - 8 over sized...
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    06794, Washington Depot, Washington
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 16
    Washington Depot
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Very Large 4300 SF Single-Family 5-Bedroom home with heated pool, large eat-in kitchen plus second kitchen, high ceilings, 2 fireplaces, best Roxbury quiet (no parties, events, multi-person shares) estate neighborhood surrounded by land preserves overlooking a pond and across from a hundred-acre...
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    06794, Washington Depot, Washington
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    Washington Depot
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    About this property
    Luxury exceptional design 4 Bedroom home in the best Roxbury location with firepaces and heated pool. Fully restored with a luxury kitchen, great room porch, den with a sleeper sofa, 4 bedrooms, 4 full bathrooms. Frette sheets, bathrobes, linens, down feather beds, comforters and pillows. Flat...
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    06794, Washington Depot, Washington
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
    Washington Depot
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    About this property
    Private Mint 5-Bedroom, 4-Bath Country Estate in one of Washington's Best neighborhoods surrounded by large estates. Heated pool, trampoline, game room, gas bbq, 2 gas fireplaces. A short drive to the Mayflower Inn & Spa and other Washington Restaurants, Galleries, Shops and Litchfield Shopping and...
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    06794, Washington Depot, Washington
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Washington Depot
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    About this property
    If you are searching for the perfect country escape, Shaker Modern is for you! Set on 11 groomed hill-top acres, this meticulously restored home overlooks and abuts the Steep Rock Land Preserve on the Washington/Roxbury border. This light and airy mint home has 6 bedrooms and 4.5 marble bathrooms,...
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    06794, Washington Depot, Washington
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    Washington Depot
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    About this property
    Perfect 6BR 3.5 Bath 4 Fire-Place home with heated pool and child's play gym on a scenic country dirt road that leads into a land preserve along the Shepaug River - perfect for walking, jogging, biking. The most desirable rural historic location within 2 hours of NYC - Roxbury and Washington CT....
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    06794, Washington Depot, Washington
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    Washington Depot
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Located in the heart of Washington in the best location, this renovated cottage is perched on 25-acres offering total privacy and spectacular 270-degree views. The home has a perfect entertaining terrace wit a gas barbecue and a heated infinity waterfall pool. The first story has 3 bedrooms, a...
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    06794, Washington Depot, Washington
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Roxbury
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Grill
    • Private Outdoor Pool (Heated)
    • Patio
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Meticulously restored country house on scenic dirt road in historic Roxbury near Washington town line. Barn, small pond, stream on a great flat dirt road perfect for walking, jogging, biking. 5 minutes to the Mayflower Inn & Spa and Washington Center and Steeprock Preserve. Close to Lake...
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    06783, Roxbury, Connecticut
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Kent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Parking
    • Grill
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large master suite with private bath including claw foot tub and stall shower. Queen bed with sitting room area, window air conditioner. Shared living room, dining room, porch and kitchen. On Main Street in town. Please enjoy all the common areas in the home. We do not live in the home and there...
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    06757, Kent, Connecticut
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Washington Depot
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the best historic walking/biking/running neighborhood in Washington! Pristine barn-style home, 5 bedrooms, 4 wood-burning fireplaces, pool, giant terrace with gas bbq set in an apple orchard with a heated pool. The gourmet kitchen is fully equipped with a Viking 6-burner gas range and...
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    06794, Washington Depot, Washington
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    Sherman
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • Cable/satellite TV
    • Mountain Views
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pack your bags, swimsuits, and family into the car and make your way to Sherman,a quaint scenic town set on Squantz Pond, just north of Candlewood Lake. All types of fantastic outdoor recreation will be at your fingertips, including trout fishing, and swimming! Enjoy an unbeatable waterfront...
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    06784, Sherman, Connecticut
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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