We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals with Pools in Wintergreen

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Payment Protection
    Use a credit card to book with our Peace of Mind Protection.Learn more
    Find a rental
    Price range
    ($254 Average)
    $0per night $2,000+
    Bedrooms
    Any
    Amenities
    Select
    Payment
    Select
    Go to map view
    More filters
    loading...
    Travellers to Wintergreen are booking August dates now. Secure your holiday rental today, and have the perfect trip.
    Sort by
    From
    $233
    / Night
    Payment Protection
    View Details
    1 / 6
    4.5 of 5 stars (2) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (2) Make Enquiry
    From
    $733
    / Night
    Payment Protection
    View Details
    1 / 48
    5 of 5 stars (3) Excellent
    5 Bedrooms / 6 Bathrooms / Sleeps 13
    travellers have booked this property
    Overview Reviews (3) Make Enquiry
    From
    $366
    / Night
    View Details
    1 / 36
    5 of 5 stars (5) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 7
    Overview Reviews (5) Make Enquiry
    From
    $158
    / Night
    Payment Protection
    View Details
    1 / 26
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Sauna
    • Pool Table
    • Hot Tub
    • Mountain Views
    • Shared Indoor Pool
    • Wi-Fi
    • Air Conditioning
    • Shared Tennis Court
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    We are full members of Wintergreen. This means as a guest of our condo you will receive a guest pass (up to 4 guests) to resort amenities that are closed to the public including the Aquatics/Fitness Center; Tennis Courts; Mountain Golf Course etc. (fees apply for these amenities). Mountaintop... View all property information
    Make Enquiry
    Location Information
    Wintergreen, Virginia 22958
    5 of 5 stars Reviewed 2 June 2014
    My husband and I travel all over this beautiful country of ours and around the world. We try to stay in condos whenever possible. Thank you Copelands and Flipkey for making this...
    See all reviews
    From
    $127
    / Night
    Payment Protection
    View Details
    1 / 12
    5 of 5 stars (7) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (7) Make Enquiry
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Sauna
    • Shared Tennis Court
    • Mountain Views
    • Satellite TV
    • Shared Indoor Pool
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Top Floor with views, Fireplace, 2 bedroom (queen, double and single), 2 sofa beds, 2 baths, 3 Flat Screen TVs, cable, DVD player, XBOX, Movies, Keurig coffee maker BRAND NEW Full Size Washer & Dryer, WiFi, VOIP, near top of advanced slope, top floor end unit, non-smoking Near pool and spa, short... View all property information
    Make Enquiry
    Location Information
    Wintergreen, Virginia 22967
    5 of 5 stars Reviewed 3 June 2015
    The condo was very comfortable and clean. The view every morning and evening was fantastic. Very peaceful with little noise. Exceptional value for the experience. Walking...
    5 of 5 stars Reviewed 10 May 2015
    Had a great stay, the view is simply amazing. Virtually no drawbacks. Everything went well, EZ check in. The owner returned my call when I had a question. Just got my deposit...
    See all reviews
    From
    $333
    / Night
    Payment Protection
    View Details
    1 / 13
    5 of 5 stars (5) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Reviews (5) Make Enquiry
    Amenities & Details
    • Hot Tub
    • Internet Access
    • Sauna
    • Satellite TV
    • Shared Indoor Pool
    • Mountain Views
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Jul 5-8 available at special discount Inquire for discounted rates. Book now for summer vacations! July dates are almost all gone/booked. There is still availability for August. We have the Wintergreen Resort membership! 3500+sq ft Gorgeous/Custom Built House *** Two Master Bedroom/Bath Suites... View all property information
    Make Enquiry
    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...
    See all reviews
    From
    $190
    / Night
    Payment Protection
    View Details
    1 / 23
    5 of 5 stars (1) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Water Views
    • Mountain Views
    • DVD Player
    • Waterfront
    • Shared Outdoor Pool...
    • Stereo System
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Make Enquiry
    Location Information
    Wintergreen, Virginia 22952
    From
    $173
    / Night
    Payment Protection
    View Details
    1 / 33
    5 of 5 stars (10) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 7
    travellers have booked this property
    Overview Reviews (10) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Mountain Views
    • Shared Tennis Court
    • Sauna
    • Wi-Fi
    • Swingset
    • Shared Indoor Pool
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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
    Make Enquiry
    Location Information
    Wintergreen, Virginia 22958
    5 of 5 stars Reviewed 4 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!
    See all reviews
    From
    $218
    / Night
    Payment Protection
    View Details
    1 / 10
    4.5 of 5 stars (3) Very good
    3 Bedrooms / 1 Bathroom / Sleeps 8
    travellers have booked this property
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Mountain Views
    • Internet Access
    • DVD Player
    • Shared Outdoor Pool...
    • Stereo System
    • Boat Available
    • Deck
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Make Enquiry
    Location Information
    Wintergreen, Virginia 22952
    From
    $519
    / Night
    Payment Protection
    View Details
    1 / 27
    5 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Pool Table
    • Mountain Views
    • Shared Indoor Pool
    • Satellite TV
    • Deck
    • DVD Player
    • Central Heating
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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
    Make Enquiry
    Location Information
    Wintergreen, Virginia 22958
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    From
    $266
    / Night
    Payment Protection
    View Details
    1 / 10
    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Satellite TV
    • Washer
    • Stereo System
    • DVD Player
    • Dishwasher
    • Dryer
    • Refrigerator
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • 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 that we decided to come back and look for a lot to build on. Our cabin is located near the very top of the mountain and... View all property information
    Make Enquiry
    Location Information
    Wintergreen, Virginia 22958
    5 of 5 stars Reviewed 23 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.
    See all reviews
    From
    $260
    / Night
    Payment Protection
    View Details
    1 / 11
    4.5 of 5 stars (7) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Reviews (7) Make Enquiry
    Amenities & Details
    • Satellite TV
    • Shared Tennis Court
    • Deck
    • Internet Access
    • Central Heating
    • Shared Outdoor Pool...
    • DVD Player
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Nestled in the heart of Wintergreen, a year round resort, this cozy chalet home is a brief walk to the Mountain Inn, ski slopes, restaurants, shops, and market. The house is conveniently located on a private, wooded lot and offers a view of the mountain ranges during the winter months. On warm... View all property information
    Make Enquiry
    Location Information
    Wintergreen, Virginia 22958
    4 of 5 stars Reviewed 16 October 2014
    We stayed there with our friends. The location is perfect, just a walking distance to all attractions. The house was comfy with good size rooms.
    5 of 5 stars Reviewed 25 August 2014
    We stayed two nights and enjoyed ourselves immensely! The home has plenty of sleeping space with two bathrooms, kitchen, den and mud/laundry room. Comfortable with all the...
    See all reviews
    From
    $180
    / Night
    Payment Protection
    View Details
    1 / 4
    5 of 5 stars (2) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Mountain Views
    • Internet Access
    • Deck
    • Satellite TV
    • Fireplace
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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
    Make Enquiry
    Location Information
    Wintergreen, Virginia 22958
    5 of 5 stars Reviewed 9 December 2014
    very nice accomidations. We had plenty to do around us and enjoyed our time there. Condo was nicely furnished.
    See all reviews
    From
    $166
    / Night
    View Details
    1 / 14
    5 of 5 stars (16) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    Overview Reviews (16) Make Enquiry
    Amenities & Details
    • Shared Outdoor Pool...
    • Stereo System
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Waterfront
    • Mountain Views
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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
    Make Enquiry
    Location Information
    Wintergreen, Virginia 22958
    5 of 5 stars Reviewed 9 June 2015
    We just spent a long weekend at Point of View. The cottage was perfect for the 4 of us. Chilly nights needed the cheery gas fireplace. We grilled out on the deck and slept well in...
    4 of 5 stars Reviewed 6 June 2015
    We stayed here in mid May as our daughter we had a daughter graduate UVA. I feel that it was a great alternative to staying in a crowded hotel in Charlottesville. The space was...
    See all reviews
    From
    $533
    / Night
    Payment Protection
    View Details
    1 / 5
    4 Bedrooms / 3 Bathrooms / Sleeps 12
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Internet Access
    • Shared Outdoor Pool...
    • DVD Player
    • Deck
    • Air Conditioning
    • Mountain Views
    • Satellite TV
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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
    Make Enquiry
    Location Information
    Wintergreen, Virginia 22958
    From
    $127
    / Night
    Payment Protection
    View Details
    1 / 11
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Fireplace
    • Deck
    • Satellite TV
    • DVD Player
    • Internet Access
    • Stereo System
    • Shared Outdoor Pool...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Make Enquiry
    Location Information
    Wintergreen, Virginia 22958
    From
    $212
    / Night
    Payment Protection
    View Details
    1 / 44
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • TV
    • Wi-Fi
    • Mountain Views
    • DVD Player
    • Fireplace
    • Shared Outdoor Pool...
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • 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
    Make Enquiry
    Location Information
    Wintergreen, Virginia 22958
    From
    $333
    / Night
    Payment Protection
    View Details
    1 / 9
    5 Bedrooms / 2 Bathrooms / Sleeps 10
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Shared Tennis Court
    • Wi-Fi
    • DVD Player
    • Satellite TV
    • Mountain Views
    • Central Heating
    • Stereo System
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Make Enquiry
    Location Information
    Wintergreen, Virginia 23831