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Holiday Rentals with Pools in Montebello

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    25 Matching Rentals in the Montebello AreaView all 57 rentals
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    The following rentals are within 25 kilometres of Montebello.
    Fit for a KING ( king size beds!)1 / 64
    (8)Excellent
    Wintergreen
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Feb 23-25 Weekend: Luxury Mountain House near Ski Slopes w/ Resort Membership1 / 13
    (7)Excellent
    Wintergreen
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    CRAZY AMAZING get-a-way! (Crazy, in a GOOD way)1 / 41
    (9)Excellent
    Wintergreen
    5 Bedrooms, 6 Bathrooms, Sleeps 13 Quick View
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    Chestnut Place Mountain Lodge1 / 26
    (1)Excellent
    Wintergreen
    5 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Housekeeping Included
    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    • Cable/satellite TV
    • Children's Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 January 2018
    We rented the house for a family and friends holiday get together and everyone had a great time. The house was well located, had excellent views, and was nice and quiet. The...
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    About this property
    This is a SUPER beautiful modern home with 5 bedrooms, 3 full bathrooms and 2 half baths. All hardwood floors except for the tile kitchen.There are 2 big family rooms perfect for big families or groups of friends. 3 big flat screen TVs and pingpong. Two large dining room tables. Beautiful kitchen....
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    22958, Wintergreen, Virginia
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 15
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    Up-On 18th! Walk to Golf Clubhouse, Spa, Pool, Membership Access to Facilities1 / 15
    (2)Excellent
    Wintergreen
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • DVD Player
    • Mountain Views
    • Wi-Fi
    • Shared Indoor Pool
    • Sauna
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 January 2018
    It was an unbelievable location. The kitchen was great, beds were comfortable, and the view was beautiful.
    Reviewed 30 August 2017
    Our weekend at your condo in Wintergreen was superb! The layout, decor and practicality of the condo fit us to a tee! Thank you for allowing us to rent it for one night! We...
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    About this property
    Gorgeous Views/Beautiful Weather/Perfect Sectional Couch to relax!Golf/Pool Pass Please be advised we request a two night stay on the weekends. CHECK OUT OUR OTHER 2BR/2BA PROPERTY DIRECTLY BELOW THIS UNIT: PROPERTY ID 8742760 Do you have a large group/family. Do you need 4 Bedrooms? Do you need...
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    22967, Wintergreen, Virginia
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Secluded 2BR Pet-Friendly Cabin on Mountain Stream-Screen Porch1 / 20
    (1)Excellent
    Wintergreen
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Mountain Views
    • Shared Outdoor Pool (Unheated)
    • Waterfront
    • Washer
    • Patio
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Right on a mountain stream, this two-bedroom cabin is very private. No other cabins or homes can be seen. Two double beds make this very accommodating for four. The full kitchen with stove, refrigerator, microwave, coffeemaker, toaster, dishes, pots & pans, and silverware has everything you need...
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    22952, Wintergreen, Virginia
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Greenville
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Parking
    • Shared Garden
    • Shared Outdoor Pool (Unheated)
    • Mountain Views
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely & Cozy log cabin at charming country retreat at a working farm and equestrian center. Cabins are fully furnished and fully stocked with linens,towels, pots, pans, dishes and more. The facility has a full equestrian center, a lake for fishing and canoeing, lots of trails for walking or...
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    Location Information
    24440, Greenville, Virginia
    Cabin Holiday Rental - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Simple Pleasures -N Ridge - Holidays Upon Us1 / 46
    (20)Excellent
    Wintergreen
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Mountain Views
    • Hot Tub
    • Skiing: Property Is In A Ski Resort
    • Cable/satellite TV
    • Sauna
    • Wi-Fi
    • Air Conditioning
    • Shared Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 December 2017
    Condo was well stocked and very comfortable for family of five. Loved the Christmas decorations and the fireplace. Could be cleaned a little better. Especially the oven that...
    Reviewed 27 February 2017
    What a lovely little place. We stayed with our family 2 sons and their wives and 2 of my grandchildren. Very accommodating. Although it was a bad weekend for tubing and...
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    About this property
    North Ridge Condos at Wintergreen Resort, VA - top of the mountain near Wintergarden and Devils Knob Golf/Tennis. WiFi available along with TV in each bedroom and den. Discount passes available for limited sporting activities. Walking distance to Wintergarden/ Devil's Knob Golf Course/Tennis Courts...
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    22958, Wintergreen, Virginia
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Wintergreen -  Slope Side  w/ Resort Pass1 / 11
    (27)Excellent
    Wintergreen
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Sauna
    • Mountain Views
    • Cable/satellite TV
    • DVD Player
    • Shared Indoor Pool
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 February 2018
    So glad I spent 4 nights at this comfortable condo. I spent the first night enjoying pizza and a great fire in the wood fireplace. The owner left fire starter and there was...
    Reviewed 24 November 2017
    Great place. Beautiful view, comfortable and well maintained. This condo has everything you need. We enjoyed our stay immensely.
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    About this property
    Welcome to Wintergreen! This condo is located near the top of the Highlands lift, within walking distance to the slopes and the nearby fitness and spa center. The included membership guest passes allow access to the fitness center, spa, golf, and tennis areas of the resort with a small fee. These...
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    22967, Wintergreen, Virginia
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    On A Mountain Stream, Pet Friendly 3BR - Oakwood1 / 36
    (4)Very good
    Tyro
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Balcony
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Mountain Views
    • DVD Player
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful, pet-friendly vacation home is full of country charm, with country-style paintings on doors and walls scattered throughout. There's plenty of room to spread out, with a large living/dining room, a sun room, a covered deck overlooking the creek, and three bedrooms. The living room...
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    Location Information
    22952, Tyro, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Down On 18th! Walk to Golf Clubhouse, Spa, Pool, Membership Access to Facilities1 / 16
    (1)Excellent
    Wintergreen
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Mountain Views
    • Shared Indoor Pool
    • Hot Tub
    • DVD Player
    • Wi-Fi
    • Sauna
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax, Golf, Beautiful Views, Passes for Golf, Tennis and Pool Please be advised we request a two night stay on the weekends. CHECK OUT OUR OTHER 2BR/2BA PROPERTY DIRECTLY ABOVE THIS UNIT: 8743003 Do you have a large group/family. Do you need 4 Bedrooms? Do you need some space during your...
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    Location Information
    22967, Wintergreen, Virginia
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Romantic, Pet-Friendly Cabin in Blue Ridge Mountains - Barnwood1 / 26
    (5)Excellent
    Tyro
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Mountain Views
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This romantic one-bedroom cabin in the Blue Ridge Mountains of Virginia is a delightful setting to bring that special person in your life. The peacefulness of the stream, just outside of the cabin, is a place to relax and let the worries of life fall away. The queen-size handmade pencil poster...
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    Location Information
    22952, Tyro, Virginia
    Cabin Holiday Rental - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2BR Walkout Condo Private and Cozy!1 / 19
    (3)Very good
    Wintergreen
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Air Conditioning
    • Mountain Views
    • Shared Outdoor Pool (Unheated)
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 March 2017
    The owner of this condo obviously cares a great deal about every detail and wanted to make sure our stay was an enjoyable one. The condo is immaculately clean, the beds are...
    Reviewed 9 March 2016
    We loved staying here. Most everything we needed was supplied--even coffee and basic toiletries! The bedrooms were very nice. Full washer and dryer. We plan to stay here...
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    About this property
    We invite you to stay in our lovely totally updated golf-front walk-out condo, right in the heart of the Devils Knob area of Wintergreen Resort. Relax in the private, cozy cottage feel of our condo while having easy access to resort amenities. The Wintergarden Spa and the Nature Foundation are...
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    Location Information
    22967, Wintergreen, Virginia
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    A Cajun Chalet1 / 28
    (1)Excellent
    Wintergreen
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Shared Indoor Pool
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 March 2018
    What a great (long) weekend we had at the Cajun Chalet ! Dawn has everything you’ll need to cook at home after a day exploring the mountain.The secluded master bedroom upstairs...
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    About this property
    Welcome to A Cajun Chalet! We are located in the Blue Ridge Mountains, inside Wintergreen Resort. Beautiful modern home with 4 bedrooms, and 3 bathrooms, with a hot tub and a stream, and central AC and the All Access passes! The passes allow you to do the 3 things at Wintergreen that are Private....
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    Location Information
    22967, Wintergreen, Virginia
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Pet Friendly Virginia Blue Ridge Mountain Cabin Rental-Foxwood1 / 19
    (4)Excellent
    Wintergreen
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Mountain Views
    • Air Conditioning
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Grill
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You'll be delighted with our Pet-Friendly, fully furnished mountain home, located just two miles from the Blue Ridge Parkway, and one mile from Sherando Lake. With all the comforts of home, you'll be able to enjoy the outdoors without roughing it! Spend the day hiking on mountains trails, driving...
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    22952, Wintergreen, Virginia
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    The Bear Dance Cabin at Wintergreen1 / 20
    (16)Excellent
    Wintergreen
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Children's Pool
    • Cable/satellite TV
    • Private Garden
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 February 2018
    We had a great stay recently at Bear Dance Cabin at Wintergreen. The cabin has a wonderful fire place which is great after a day of skiing. The location is very convenient to...
    Reviewed 30 December 2017
    Thank you for sharing your beautiful cozy cabin with us! We had a delightful Christmas getaway! The cabin has everything we needed for our fun quality family time. Convenient...
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    About this property
    We decided to build our cabin after a family trip to WTG. We fell in love with the Wintergreen community and much like you we searched for a place to stay at Wintergreen. For us and our guests Wintergreen is a perfect getaway. Our cabin is located near the very top of the mountain and is on the...
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    Location Information
    22958, Wintergreen, Virginia
    Cabin Holiday Rental - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Middlebrook
    4 Bedrooms, 2 Bathrooms, Sleeps 15 Quick View
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    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Patio
    • Mountain Views
    • Washer
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Four Girls Farm Guest Cottage is part of a larger farm that makes up hundreds of verdant acres to explore and enjoy. There is a lovely pond to relax by or go fishing! The house is large and spacious but cozy with a fireplace to gather around and a sun room to enjoy. Fire pit and miscellaneous...
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    24459, Middlebrook, Virginia
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 15
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    Wintergreen
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Mountain Views
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    • Washer
    • Patio
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    * 15% discount for 1 week bookings * Explore all the best of Wintergreen, Virginia from this newly built 5-bedroom, 4.5-bath vacation rental home that sleeps 12. Boasting a spacious deck with views, an outdoor grill and close proximity to a wide range of indoor and outdoor activities, this...
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    Location Information
    22967, Wintergreen, Virginia
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Mountaintop Resort-Center 3 Kings Twins PASSes1 / 37
    (7)Very good
    Wintergreen
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Hot Tub
    • Shared Indoor Pool
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 February 2018
    Great condo located on Wintergreen mountain convenient to everything. Three bedroom all with comfortable king size beds and each has its own full bathroom. Lots of pillows...
    Reviewed 10 December 2015
    I stayed at this condo with my husband, daughter, and friends for a wedding. The location is great and near different attractions. The condo was clean and the owners had labels...
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    About this property
    Come play on the mountain! The best location In the heart of Wintergreen Resort. Private but close to everything. 2 minutes to the slopes! You'll be right beside the pool, spa and the mountaintop golf course. All Resort PASSES cover all our guests for Aquatics and Fitness Center right next door...
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    22958, Wintergreen, Virginia
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    wintergreen pet ski hot tub fireplace hike golf pool pets firepl1 / 38
    (6)Average
    Wintergreen
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Mountain Views
    • Central Heating
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Home on one acre in wintergreen ski resort 5 - 10min walk to ski slopes, mountain inn restaurants ice rink basketball court ourdoor grill gift and ski equip shops rental and ticket office, market store deli beer wine pizza sundries, hiking , overlooks, newyears and july fourth fireworks Pets...
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    Location Information
    22967, Wintergreen, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Mountain House1 / 9
    (1)Excellent
    Wintergreen
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Mountain Views
    • Wi-Fi
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Central Heating
    • Secure Parking
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 5 bedroom, 2 1/2 bath home located in the Blue Ridge Mountains at Wintergreen Resort, Va.We are a four season community, with golf, tennis, swimming, boating, hiking (Appalachian Trail), skiing, ice skating, tubing, horseback riding, wine tasting, and more, located on our near our...
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    Location Information
    23831, Wintergreen, Virginia
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Wintergreen
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Sauna
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The ultimate Blue Ridge Mountain getaway awaits you at this 3-bedroom, 2-bath vacation rental house which sleeps 8 in Wintergreen. Located at the summit of Eagle's Swoop, this home has ski-in/out access to Wintergreen Resort's main ski slope, along with a private hot tub surrounded by towering...
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    Location Information
    22967, Wintergreen, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Wintergreen
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Shared Indoor Pool
    • Wi-Fi
    • Mountain Views
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful, custom built and spacious three bedroom home located right on Devil’s Knob Golf Course at Wintergreen Resort, just a short distance to the ski slopes. This gorgeous post and beam designed home has three bedrooms: a king, queen, and a room with a full bed and a twin. There is a brand new...
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    Location Information
    22967, Wintergreen, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Wintergreen
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Washer
    • Mountain Views
    • Internet Access
    • Patio
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled at the top of Wintergreen Mountain Resort within the Virginia wilderness, this 4-bedroom, 3-bath vacation rental house that sleeps 9 is the perfect destination for your next ski trip or relaxing getaway. With hiking trails, wineries, breweries, state parks, and world-class ski slopes within...
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    Location Information
    22967, Wintergreen, Virginia
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Wintergreen
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Sauna
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Hot Tub
    • Cable/satellite TV
    • Mountain Views
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to the Wintergreen mountains in this custom 3-bedroom, 3.5 bathroom vacation rental home. Plush furnishings and modern amenities comfortably accommodate up to 10 guests throughout 3,500 square feet of well-appointed living space. This home is ideally situated on the Virginia mountainside in...
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    Location Information
    22967, Wintergreen, Virginia
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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