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Holiday Rentals with Pools in Wintergreen

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    €176 Average
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    Travellers to Wintergreen are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    17 Matching Rentals in WintergreenView all 33 rentals
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    CRAZY AMAZING get-a-way! (Crazy, in a GOOD way)1 / 48
    (9)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 13 Quick View
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    Simple Pleasures -N Ridge - Holidays Upon Us1 / 46
    (18)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    The Bear Dance Cabin at Wintergreen1 / 20
    (9)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Wintergreen -  Slope Side  w/ Resort Pass1 / 12
    (20)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Sauna
    • Mountain Views
    • Satellite TV
    • DVD Player
    • Shared Indoor Pool
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 May 2017
    This location provided us with a perfect weekend getaway less then 2 hours from Richmond. The condo had beautiful views and furnished very comfortably. Great location for hiking...
    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...
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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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    Wintergreen, Virginia 22967
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Secluded 2BR Pet-Friendly Cabin on Mountain Stream-Screen Porch1 / 20
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • 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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    Fit for a KING ( king size beds!)1 / 27
    (7)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Children's Pool
    • Mountain Views
    • Wi-Fi
    • Satellite TV
    • Washer
    • DVD Player
    • Central Heating
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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...
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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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    Location Information
    Wintergreen, Virginia 22958
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Pet Friendly Virginia Blue Ridge Mountain Cabin Rental-Foxwood1 / 19
    (3)Very good
    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 Newly Renovated Private and Cozy!1 / 19
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Wi-Fi
    • 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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Hot Tub
    • DVD Player
    • Mountain Views
    • Wi-Fi
    • Shared Indoor Pool
    • Sauna
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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, during the winter season. CHECK OUT OUR OTHER 2BR/2BA PROPERTY DIRECTLY BELOW THIS UNIT: PROPERTY ID 8742760 Do you have a large group/family. Do you...
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    Location Information
    Wintergreen, Virginia 22967
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Book now for Spring/Summer -  Luxury House on Golf Course with Resort Membership1 / 13
    (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
    Kid friendly
    Smoking allowed
    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 Summer vacations. Inquire about June specials 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...
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    Location Information
    Wintergreen, Virginia 22957
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    The Mountain House1 / 9
    (1)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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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
    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 10
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    Cozy 2BR Wintergreen Condo w/Private Balcony1 / 24
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Satellite TV
    • Mountain Views
    • Hot Tub
    • Internet Access
    • Sauna
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    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...
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    Location Information
    Wintergreen, Virginia 22958
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    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
    • 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, during the winter season. 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...
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    Location Information
    Wintergreen, Virginia 22967
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Patio
    • Air Conditioning
    • Mountain Views
    • Satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Wintergreen, Virginia 22958
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Cozy Home with Beautiful Views, Ski in/Out!1 / 14
    (28)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Washer
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Waterfront
    • Mountain Views
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    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...
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    Location Information
    Wintergreen, Virginia 22958
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Mountaintop Resort-Center 3 Kings Twins PASSes1 / 37
    (6)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Mountain Views
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Hot Tub
    • Shared Indoor Pool
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    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 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Sauna
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The ultimate Blue Ridge Mountain getaway in Wintergreen, Virginia awaits you at this 3-bedroom, 2-bathroom house. 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 you’re seeking outdoor excitement, wine...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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