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Holiday Rentals with Pools in Roseland

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    24 Matching Rentals in the Roseland AreaView all 50 rentals
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    The following rentals are within 25 kilometers of Roseland.
    Chestnut Place Mountain Lodge1 / 13
    (1)Excellent
    Wintergreen
    5 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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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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    Simple Pleasures -N Ridge - Holidays Upon Us1 / 46
    (20)Excellent
    Wintergreen
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Fit for a KING ( king size beds!)1 / 64
    (8)Excellent
    Wintergreen
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Children's Pool
    • Mountain Views
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Central Heating
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 November 2017
    This was our family's second trip to Fit for a King, and we are already planning our third next fall. This location is absolutely gorgeous in the fall, and with the close...
    Reviewed 25 October 2016
    My family (and extended family) stayed during the peak leafing weekend of the year. The house was incredible and suited our needs perfectly. The host was extremely helpful...
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    About this property
    Now HERE is a really great house! Fit for a KING or two. This house has 4 large bedrooms with 2 of them having KING size beds. Then there is a Queen & 2 twins and then the loft has a twin day bed that has a pop up trundle so this could be another KING (that makes 3) ..or they can separate into...
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    Wintergreen, Virginia 22958
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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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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    Wintergreen, Virginia 22967
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    Amenities & Details
    • Hot Tub
    • Internet Access
    • Sauna
    • Cable/satellite TV
    • Shared Indoor Pool
    • Mountain Views
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 July 2017
    My wife and I are from Michigan and were looking for a central location to get together with our son, daughter-in-law, daughter, and 2 year old grandson who all live in...
    Reviewed 25 June 2014
    I recently rented this home for a bachelorette weekend for a friend who is more the outdoors type then the Vegas type. It was close to our home in Northern Virginia ~3 hours...
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    About this property
    Book now for Spring/Summer. We have been booked every weekend (Sep -Oct). Some March weekends still available. We have brand new living room furniture - so new that the pictures are not yet posted online. We have the Wintergreen Resort membership so you have access to resort facilities that are...
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    Wintergreen, Virginia 22957
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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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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    Wintergreen, Virginia 22952
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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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    Amenities & Details
    • Washer
    • Housekeeping Included
    • Mountain Views
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Shared Indoor Pool
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 February 2017
    We had a large group of ski patrol women and this house was perfect! Dawn was great at communication and was always available via text. The location was great. The large...
    Reviewed 9 January 2017
    Booked the house for the New Year's weekend for family skiing, hiking and celebration. Mission accomplished! House was great with plenty of room. The house was well appointed...
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    About this property
    This is a really amazing home! It is so perfect for all kinds of groups because it has 3 SERIOUS master suites. You could say it is perfect for 'separate togetherness'. The main floor has the kitchen that overlooks a huge deck right on the 16th tee box of Devils Knob Golf course, a big dinning...
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    Wintergreen, Virginia 22958
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 13
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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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    Wintergreen, Virginia 22967
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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
    Wintergreen, Virginia 22967
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    Tyro, Virginia 22952
    Holiday Rental House - 3 Bedrooms, 2 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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    Amenities & Details
    • 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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    Location Information
    Wintergreen, Virginia 22952
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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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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    Amenities & Details
    • 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
    Wintergreen, Virginia 22967
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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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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    Wintergreen, Virginia 22967
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    Certificate of Excellence
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    Amenities & Details
    • 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
    Wintergreen, Virginia 22958
    Cabin Holiday Rental - 3 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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    Tyro, Virginia 22952
    Cabin Holiday Rental - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Wintergreen
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    • DVD Player
    • Washer
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    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
    Wintergreen, Virginia 22967
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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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
    Wintergreen, Virginia 23831
    Holiday Rental House - 5 Bedrooms, 3 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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    Location Information
    Wintergreen, Virginia 22958
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Wintergreen
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Sauna
    • Cable/satellite TV
    • Patio
    • Washer
    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    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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    Wintergreen, Virginia 22967
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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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
    Wintergreen, Virginia 22967
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Wintergreen
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Sauna
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    • 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
    Wintergreen, Virginia 22967
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Lovingston
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Outdoor Pool (Unheated)
    • Mountain Views
    • Parking
    • Air Conditioning
    • Private Garden
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We are located in the Village of Lovingston, VA. There are wineries, breweries, and distilleries. We have Wintergreen Ski Resort. The Lockn' Festival each August. Crabtree Falls and Humpback Rock for hiking. In Nelson Co., the Blue Ridge Parkway and Skyland Drive began. Nearby we have UVa's...
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    Location Information
    Lovingston, Virginia 22949
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Wintergreen
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Sauna
    • Air Conditioning
    • Skiing: Property Is In A Ski Resort
    • Mountain Views
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Washer
    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
    Wintergreen, Virginia 22967
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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