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Holiday Rentals with Pools in Wintergreen

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    Travellers to Wintergreen are booking July dates now. Secure your holiday rental today, and have the perfect trip.
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    €179
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    1 / 11
    4.5 of 5 stars (7) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    €83
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    5 of 5 stars (6) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    €124
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    1 / 26
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    €131
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    1 / 23
    5 of 5 stars (1) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Dryer
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    • Grill
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    • Mountain Views
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • 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
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    Wintergreen, Virginia 22952
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    1 / 4
    5 of 5 stars (2) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    travellers have booked this property
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
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    • Mountain Views
    • Satellite TV
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    • Suitable for children
    • ?
    • x
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    • 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
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    Wintergreen, Virginia 22958
    5 of 5 stars 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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    €184
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    1 / 10
    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
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    • Elder access
    • x
    About this property
    Our log cabin was built in 2005 just after we fell in love with the Wintergreen community. Much like you we searched for a place to stay at Wintergreen. We had such a great time on our family vacation that we decided to come back and look for a lot to build on. Our cabin is located towards to... View all property information
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    Wintergreen, Virginia 22958
    5 of 5 stars Reviewed 22 February 2014
    The cabin was fantastic! It was nicely decorated and very functional. The living room/kitchen area is really spacious. The owner was courteous and helpful too.
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    €151
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    1 / 10
    4.5 of 5 stars (3) Very good
    3 Bedrooms / 1 Bathroom / Sleeps 8
    travellers have booked this property
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    • Air Conditioning
    • Dryer
    • Grill
    • Internet Access
    • Mountain Views
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    You'll be delighted with this 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 on the Blue... View all property information
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    Wintergreen, Virginia 22952
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    €115
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    1 / 33
    5 of 5 stars (10) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 7
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    • Air Conditioning
    • Dishwasher
    • Fireplace
    • Hot Tub
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Sauna
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    North Ridge Condos at Wintergreen Resort, VA - top of the mountain near Wintergarden and Black Bear Café. 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 and... View all property information
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    Location Information
    Wintergreen, Virginia 22958
    5 of 5 stars Reviewed 3 March 2015
    This was our first time to Wintergreen and we had the absolute best weekend. The condo was fully stocked with all the comforts of home! Thank you for allowing us this experience.
    5 of 5 stars Reviewed 10 February 2015
    The condo was great, just perfect for our family! The owners were very prompt answering questions. We had a wonderful trip. Would definitely stay here again. Thank you!
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    €505
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    1 / 48
    5 of 5 stars (3) Excellent
    5 Bedrooms / 6 Bathrooms / Sleeps 13
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Mountain Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    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... View all property information
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    Location Information
    Wintergreen, Virginia 22958
    5 of 5 stars Reviewed 13 May 2015
    You rent something on line and you sort of imagine it won't be as nice as the listing describes. Well, this house is so much better than I could have imagined. We rented it for a...
    5 of 5 stars Reviewed 1 March 2015
    A beautiful home --lovely furnishings and well stocked with all the necessities. Wonderful manager to work with--responsive and very helpful. Floor plan offers plenty of...
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    €161
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    1 / 6
    4.5 of 5 stars (2) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Housekeeping...
    • Internet Access
    • Mountain Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Chalet style. High ceilings and airy feel. Walking distance to all major attractions on mountain. Minutes away by car from breweries and restaurants. Clean and comfortable. A great value for a great get away. View all property information
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    Location Information
    Wintergreen, Virginia 22967
    4 of 5 stars Reviewed 2 December 2014
    You can't get a better location at Wintergreen to enjoy winter sports. The house is comfortable and well equipped. Thsi was a last minute thing and Alex (the owner) was super...
    5 of 5 stars Reviewed 25 November 2014
    Awesome rental and the owners are super nice, really enjoyed our stay. Great location, close to everything, including breweries and restaurants. Slopes were very close and had...
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    €230
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    1 / 13
    5 of 5 stars (5) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Book now for summer vacations! Last weekend in May (May 29-31) still available. Summer weeks are filing up fast. We have the Wintergreen Resort membership! 3500+sq ft Gorgeous/Custom Built House *** Two Master Bedroom/Bath Suites with flat screen TV's *** FREE Wi-Fi *** FREE long-distance... View all property information
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    Location Information
    Wintergreen, Virginia 22957
    5 of 5 stars 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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    €87
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    1 / 11
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Beautiful 2BR/2BA condo on golf course and near ski lodge. The condo has a pull-out sofa (which could sleep an additional person or two) in the living room, a patio overlooking the golf course, and a fireplace (with fire wood provided). Direct TV, wireless DSL, WIFI, and a phone with unlimited... View all property information
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    Location Information
    Wintergreen, Virginia 22958
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    €230
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    1 / 9
    5 Bedrooms / 2 Bathrooms / Sleeps 10
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • 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
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    Location Information
    Wintergreen, Virginia 23831
    From
    €367
    / Night
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    1 / 5
    4 Bedrooms / 3 Bathrooms / Sleeps 12
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • 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
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    Location Information
    Wintergreen, Virginia 22958
    From
    €146
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    1 / 44
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Internet Access
    • Mountain Views
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    We've made every effort to make your stay at our new 2BR/2BA condo truly special! The property features many upgrades including premium bedding, HD flat screen televisions in all rooms, granite countertops, new Bosch kitchen appliances, high speed internet and cable channels, play-station 3, fresh... View all property information
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    Location Information
    Wintergreen, Virginia 22958
    From
    €234
    / Night
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    1 / 36
    5 of 5 stars (5) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 7
    Overview Reviews (5) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Fireplace
    • Gym
    • Hot Tub
    • Internet Access
    • Mountain Views
    • Private Fishing...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Come play outside on the mountain in the heart of Wintergreen Resort. You'll be right beside the Spa and the golf course. Chilly? Turn on the fireplace. Private but close to everything. PASSES cover all our guests for Aquatics and Fitness Center right next door with its beautiful indoor and outdoor... View all property information
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    Location Information
    Wintergreen, Virginia 22958
    5 of 5 stars 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...
    5 of 5 stars Reviewed 1 February 2011
    We rented this condo for a fun filled weekend of skiing. The condo was only minutes to the slopes, great location!! The price included discounts on lift tickets. Yay!! It was...
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    €115
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    1 / 14
    5 of 5 stars (14) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    Overview Reviews (14) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • 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
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    Location Information
    Wintergreen, Virginia 22958
    5 of 5 stars Reviewed 11 May 2015
    We had an excellent stay at this house during a cold spring weekend. The house is easy to find and the street was quiet. The kitchen is modern and there was plenty of space for us...
    5 of 5 stars Reviewed 13 April 2015
    Just stayed at the cabin this past weekend and I can't say enough about your place. The view was amazing and the hiking trails were beautiful especially when we got to the...
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    €358
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    1 / 9
    5 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Pool Table
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Now HERE is a really great house! Fit for a KING or actually 3 of them. This house has 4 large bedrooms with 3 of them having KING size beds. Then there is a Queen & a twin day bed that has a pop up trundle so this could be another KING (that makes 4) ..or they can separate into separate twins.... View all property information
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    Location Information
    Wintergreen, Virginia 22958