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Holiday Rentals with Pools in Wintergreen

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    Travellers to Wintergreen are booking May dates now. Secure your holiday rental today, and have the perfect trip.
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    1 / 46
    5 of 5 bubbles (18) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    1 / 48
    5 of 5 bubbles (9) Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 13 | Quick View
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    1 / 26
    5 of 5 bubbles (6) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 23
    5 of 5 bubbles (9) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Children's Pool
    • Satellite TV
    • Private Garden
    • Washer
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    We built our log cabin in 2005 just after we fell in love with the Wintergreen community. Much like you we searched for a place to stay at Wintergreen and after such a great experieince we decided to come back and look for a lot to build on. For us Wintergreen was perfect for a young family living... View all property information
    Location Information
    Wintergreen, Virginia 22958
    5 of 5 bubbles Reviewed 14 February 2017
    Visited with my fiancé and 4 other friends for a ski weekend .... Love the place! No complaints what so ever! Easy access... owner communication was great... very comfortable. We...
    5 of 5 bubbles Reviewed 3 November 2016
    The cabin was a pleasantly rustic in design, but very clean and modern in construction. The location was convenient for exploring the surrounding mountains, and the rental process...
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    1 / 27
    5 of 5 bubbles (7) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Children's Pool
    • Mountain Views
    • Wi-Fi
    • Satellite TV
    • Washer
    • DVD Player
    • Central Heating
    • Housekeeping...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Wintergreen, Virginia 22958
    5 of 5 bubbles 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, not...
    5 of 5 bubbles Reviewed 11 October 2016
    We had 8 adults getting together for a long weekend of visiting many Wineries, Cidery's and Breweries just outside of Charlottesville. this is an ideal central location and Dawn...
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    1 / 24
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Satellite TV
    • Mountain Views
    • Hot Tub
    • Internet Access
    • Sauna
    • Shared Outdoor Pool...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Have a truly special stay at this extraordinary 2-bedroom, 2-bathroom condo with room to comfortably accommodate 6 guests. Once you witness the serene sunset vistas overlooking the valley and mountain, you will never want to leave! Upon arrival, you’ll find that the adjacent free off-street... View all property information
    Location Information
    Wintergreen, Virginia 22958
    5 of 5 bubbles Reviewed 14 September 2016
    This condo is the perfect size for a couple or small family. It is really comfortable with warm, overstuffed couches, large TVs, a gaming system and internet. The accents are...
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    1 / 12
    5 of 5 bubbles (19) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Internet Access
    • Air Conditioning
    • Sauna
    • Mountain Views
    • Satellite TV
    • DVD Player
    • Shared Indoor Pool
    • Skiing: Property Is...
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Wintergreen, Virginia 22967
    5 of 5 bubbles Reviewed 14 December 2016
    Had a great time at Wintergreen condo. Excellent accommodations, beds were comfortable, view was breath taking. Loved the Xbox, enjoyed the dancing game, and also watched a...
    5 of 5 bubbles Reviewed 16 October 2016
    This condo has great views of the mountains.Wintergreen Resort was 5 minutes from the Blue Ridge Parkway.Resturaunts in the resort were good food and convenient .
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    1 / 6
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
    • Satellite TV
    • Washer
    • Air Conditioning
    • Skiing: Property Is...
    • Patio
    • Ocean Views
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Ski Slope Access across the street - Mountain Cabin/Chalet - Pet Friendly - Nature awaits you A beautiful Guest Cabin/Chalet/ or call it a peaceful home with windows all around so you can look out and see mountains, hills, forest, trees, wildlife and all that nature has to offer. She is a... View all property information
    Location Information
    Wintergreen, Virginia 22967
    1 / 13
    5 of 5 bubbles (5) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Hot Tub
    • Internet Access
    • Sauna
    • Satellite TV
    • Shared Indoor Pool
    • Mountain Views
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Book now for Spring/Summer vacations. We have the Wintergreen Resort membership so you have access to resort facilities that are closed to the public! 3500+sq ft Gorgeous/Custom Built House *** Two Master Bedroom/Bath Suites with flat screen TV's *** FREE Wi-Fi *** FREE long-distance calling in... View all property information
    Location Information
    Wintergreen, Virginia 22957
    5 of 5 bubbles 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 away...
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    1 / 19
    4.5 of 5 bubbles (3) Very good
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • Mountain Views
    • Air Conditioning
    • DVD Player
    • Shared Outdoor Pool...
    • Washer
    • Grill
    • Parking
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Wintergreen, Virginia 22952
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    1 / 20
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
    • Mountain Views
    • Shared Outdoor Pool...
    • Waterfront
    • Washer
    • Patio
    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Wintergreen, Virginia 22952
    1 / 5
    5 of 5 bubbles (4) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Mountain Views
    • Internet Access
    • Washer
    • Satellite TV
    • Parking
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Revel in this condominium atop the Blue Ridge at award-winning Wintergreen Resort, 45 minutes southwest of Charlottesville, two hours and 45 minutes from Washington. The unit is available for weekly/weekend rentals at super discount rates from the owner. You'll have most amenities of the resort at... View all property information
    Location Information
    Wintergreen, Virginia 22958
    5 of 5 bubbles Reviewed 27 December 2016
    Our family stayed 4 nights over Christmas and we had a wonderful, comfortable stay. We liked having three beds and three baths. The kitchen functioned well and we cooked dinner...
    5 of 5 bubbles Reviewed 8 December 2014
    very nice accomidations. We had plenty to do around us and enjoyed our time there. Condo was nicely furnished.
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    1 / 37
    5 of 5 bubbles (6) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    Amenities & Details
    • Mountain Views
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Skiing: Property Is...
    • Hot Tub
    • Shared Indoor Pool
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Wintergreen, Virginia 22958
    4 of 5 bubbles 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 on...
    5 of 5 bubbles Reviewed 24 June 2014
    Our family of 6 plus a small child had a fun, relaxing week at this condo. The owner was very helpful and responsive during the planning period. We found the condo to be...
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    1 / 19
    4 of 5 bubbles (1) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Wi-Fi
    • DVD Player
    • Patio
    • Shared Outdoor Pool...
    • Air Conditioning
    • Mountain Views
    • Skiing: Property Is...
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    We invite you to stay in our newly renovated golf-front 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 access to the shuttle just outside the door. The Wintergarden Spa and the Nature Foundation are just... View all property information
    Location Information
    Wintergreen, Virginia 22967
    4 of 5 bubbles 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 again...
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    1 / 5
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
    • Shared Outdoor Pool...
    • DVD Player
    • Patio
    • Air Conditioning
    • Mountain Views
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The Wintergreen Retreat is a vacation rental home within the Wintergreen Resort in Virginia, set among the beautiful Blue Ridge Mountains. This brand new charming mountain getaway is nestled on Wintergreen Mountain, just a few hundred yards from gorgeous scenic overlooks – and the perfect retreat... View all property information
    Location Information
    Wintergreen, Virginia 22958
    1 / 9
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    other travellers have booked this property
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    Amenities & Details
    • Mountain Views
    • Wi-Fi
    • Washer
    • DVD Player
    • Satellite TV
    • Central Heating
    • Secure Parking
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Wintergreen, Virginia 23831
    1 / 14
    4.5 of 5 bubbles (28) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    Amenities & Details
    • Shared Outdoor Pool...
    • Washer
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Waterfront
    • Mountain Views
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    **BRAND-NEW KITCHEN & UPDATED BATHROOMS** Welcome to 'Point of View'! Enjoy the beautiful year-round views from our cozy mountain home located directly on the Tyro ski slope. This is a true four-season get-away. In the winter, step out the door, put on your skis and head down the mountain. If... View all property information
    Location Information
    Wintergreen, Virginia 22958
    5 of 5 bubbles Reviewed 5 February 2017
    Great house located right on Tyro ski slope with ski-in ski-out access and fantastic view. Walk steps to the slope and you're off. Tyro is not a beginner slope but it is not...
    5 of 5 bubbles Reviewed 15 November 2016
    Great place to stay! Beautiful home with spectacular mountain views! Everything you need for an enjoyable getaway! Close to many wineries and breweries, too! Can't wait to come...
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    1 / 15
    5 Bedrooms, 5 Bathrooms, Sleeps 16 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Mountain Views
    • Washer
    • Satellite TV
    • Skiing: Property Is...
    • DVD Player
    • Grill
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Unique Benefits include passes and close proximity to the summer-time pool, the Shamokin Nature Preserve, the Nature Foundation, the Post Office, the Spa, and a dog park. This home is on the Mountaintop part of Wintergreen, near Sherando Lake (a National Park), the Blue Ridge Parkway and The... View all property information
    Location Information
    Wintergreen, Virginia 22967
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Sauna
    • Shared Outdoor Pool...
    • Hot Tub
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The ultimate Blue Ridge Mountain getaway in Wintergreen, Virginia awaits you at this 3-bedroom, 2-bathroom house with awe-inspiring views of the mountains. Located at the summit of Eagle’s Swoop, this spectacular home has ski-in/ski-out access to one of Wintergreen Resort’s main ski slopes. Whether... View all property information
    Location Information
    Wintergreen, Virginia 22967