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.

Vacation rentals in Wintergreen, VA

Payment Protection
Use a credit card to book with our Peace of Mind Protection.Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
Find more rentals you can book on TripAdvisor!   We're showing you properties you can book on TripAdvisor first.
All 24 Rentals in Wintergreen
loading...
Sort by
From
$157
Per Night
View Details
1 / 4
Payment Protection
3 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
Details Reviews (2) Make Enquiry
From
$193
Per Night
View Details
1 / 10
Payment Protection
3 Bedrooms, 1 Bathroom, Sleeps 8
Bookings
Details Reviews (3) Make Enquiry
From
$163
Per Night
View Details
1 / 6
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (2) Make Enquiry
From
$227
Per Night
View Details
1 / 11
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Reviews (7) Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
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
4 of 5 stars Reviewed 15 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 24 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
$202
Per Night
View Details
1 / 26
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Balcony
  • Dryer
  • Fireplace
  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Sauna
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
** UPDATE ** We are happy to announce we have become 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... View all property information
Make Enquiry
5 of 5 stars Reviewed 1 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
$151
Per Night
View Details
1 / 33
Payment Protection
3 Bedrooms, 3 Bathrooms, Sleeps 7
Bookings
Details Reviews (7) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Gym
  • Hot Tub
  • Internet Access
  • Mountain Views
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 (no longer lift tickets/rentals and only good through 11/30/14). View all property information
Make Enquiry
5 of 5 stars Reviewed 12 October 2014
Our stay at 3213 Northridge this summer was great. The unit is well furnished and equipped for folks looking for an easy vacation experience. Located in the Wintergreen resort...
See all reviews
From
$291
Per Night
View Details
1 / 14
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (1) Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • 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
Make Enquiry
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.
See all reviews
From
$116
Per Night
View Details
1 / 13
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Gym
  • Internet Access
  • Mountain Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
2 bedroom (queen, double and single), 2 sofa beds, 2 baths, 3 Flat Screen TVs, cable, DVD player, XBOX, Movies, Keurig, WiFi, VOIP, near top of advanced slope, top floor end unit, view, non-smoking View all property information
Make Enquiry
5 of 5 stars Reviewed 18 December 2014
I stayed at the Wintergreen Resort this pass weekend for my birthday weekend (Dec 12-14) and the views are priceless. I stayed at the Highridge Court in a beautiful unit looking...
5 of 5 stars Reviewed 8 June 2014
we have been visiting wintergreen for 20 years and now have the perfect condo for our family of 6 to continue building memories. it's perfect for ski-in, ski-out vacations for...
See all reviews
From
$166
Per Night
View Details
1 / 9
Payment Protection
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Fireplace
  • 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
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
From
$122
Per Night
View Details
1 / 12
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (7) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Cozy and Convenient! Our Condo is centrally located for easy walking access to the full-service SPA, Golf course and indoor-outdoor Tennis facilities. We have been owners of this Condo for the past 9 years and love the Wintergreen Resort. We manage the Condo ourselves, to ensure the Condo is... View all property information
Make Enquiry
4 of 5 stars Reviewed 21 June 2014
The condo was immaculate and well stocked, thankfully not a shortage of towels! This condo is at the very top of Wintergreen, while it does not have a view, just a walk accross...
5 of 5 stars Reviewed 10 March 2014
The owner was wonderful and a pleasure to work with. Condo was beautiful, very spacious and had all the necessities. Will definitely be staying again:)
See all reviews
Get the List
From
$349
Per Night
View Details
1 / 20
Payment Protection
4 Bedrooms, 3 Bathrooms, Sleeps 10
Booking
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
A luxurious 4 season family vacation or weekend getaway in WINTERGREEN RESORT! Our mountain home includes GUEST PASSES, which allow access (fees required) to the Wintergarden Indoor Pool and Spa, two golf courses, and children's Out of Bounds recreation activities. Your passes also give you... View all property information
Make Enquiry
From
$110
Per Night
View Details
1 / 11
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Enquiry
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
Make Enquiry
From
$349
Per Night
View Details
1 / 9
Payment Protection
5 Bedrooms, 3 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Gym
  • Internet Access
  • Mountain Views
  • Satellite TV
  • Shared Outdoor Pool...
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
Make Enquiry
From
$639
Per Night
View Details
1 / 48
Payment Protection
5 Bedrooms, 6 Bathrooms, Sleeps 13
Bookings
Details Make Enquiry
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
Make Enquiry
From
$465
Per Night
View Details
1 / 5
Payment Protection
4 Bedrooms, 3 Bathrooms, Sleeps 12
Booking
Details 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
Make Enquiry
From
$320
Per Night
View Details
1 / 36
3 Bedrooms, 3 Bathrooms, Sleeps 7
Details Reviews (5) Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • 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 on the peak called Devil's Knob right beside the Spa, and you'll be two minutes to the slopes! Chilly? Turn on the fireplace. Our place is quiet and private but close to everything. Twenty or so different activities... View all property information
Make Enquiry
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 31 January 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...
See all reviews
From
$291
Per Night
View Details
1 / 13
Payment Protection
3 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
Details Reviews (5) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Mountain Views
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Christmas/New Years Weeks sold out. Jan 9th weekend is only weekend left in January. Inquire about January mid-week discounted nights. House is located in popular are of resort - near the ski slopes and Spa/Fitness Center. We have exclusive rights to Wintergreen Resort Club and have a special... View all property information
Make Enquiry
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
$174
Per Night
View Details
1 / 14
3 Bedrooms, 2 Bathrooms, Sleeps 7
Details Reviews (8) 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
Make Enquiry
5 of 5 stars Reviewed 29 November 2014
Point of View is a nice home nestled in the mountains right beside one of the Wintergreen slopes. You can ski right up to your door and watch skiers from the wonderful view from...
5 of 5 stars Reviewed 1 November 2014
Nicely appointed cabin with great views. We hiked around Wintergreen but wanted to check out future ski spots and this is it. Cozy decor, beautiful mountain outside large...
See all reviews
From
$465
Per Night
View Details
1 / 24
5 Bedrooms, 3 Bathrooms, Sleeps 10
Details Reviews (16) Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Mountain Views
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
**** GUEST PASSES - WI-FI - FLAT SCREEN TV - HOT TUB - SCREENED IN PORCH - 2 MASTERS - RELAXATION - PEACE - & TRANQUILITY ALWAYS **** Bonnie Fagan has designed and built a fabulously luxurious 4-bedroom, 3-bath, log and stone vacation home in the Wintergreen VA Resort. The Fagan's offer this... View all property information
Make Enquiry
5 of 5 stars Reviewed 14 October 2014
Went there with 11 girls for a bachelorette weekend! It was fantastic with the fireplace, hot tub and all the common living space. There were so many nooks and rooms that no one...
5 of 5 stars Reviewed 14 October 2014
A large group of friends and cousins stayed here for a bachelorette weekend getaway. This place was great! very accommodating and cozy. Even though our weather wasn't the best, we...
See all reviews
From
$382
Per Night
View Details
1 / 9
6 Bedrooms, 5 Bathrooms, Sleeps 16
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Newly built in 2004, this is a beautiful 6 bedroom, 4.5 bath home in the heart of Wintergreen Resort. Approximately 2.5 miles from the Mountain Inn, this home is convenient yet sits on a quiet street with little traffic. The yard is fenced (dogs are welcome), there are two master bedrooms on the... View all property information
Make Enquiry
From
$382
Per Night
View Details
1 / 21
6 Bedrooms, 5 Bathrooms, Sleeps 14
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
The Wintergreen Chalet is a sprawling 6-bedroom 4.5 bath home located at the top of Devil's Knob Mountain within the Wintergreen Resort in the Blue Ridge Mountains of Virginia. The home sleeps 12-14 comfortably and is available for rent daily or weekly throughout the year. Our home is set on a... View all property information
Make Enquiry
From
$145
Per Night
View Details
1 / 6
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 3
Booking
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Designer decorated private apartment in Post and Beam 2006 built home in Wintergreen Resort The home is next to Tyro ski slope with access at the end of the driveway. The separate lock off apartment has its own private entrance from the beautiful deck overlooking the mountains. . This is an... View all property information
Make Enquiry
From
$233
Per Night
View Details
1 / 8
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
walking distance to ski slopes, mountain inn restaurants, market, hiking trails hot tub, pool table, pets considered home on half acre lot with birds deer and bear winter views of valley non winter all rooms are shaded and serenaded by leaf rustling 3 decks and grill flat screen... View all property information
Make Enquiry
From
$523
Per Night
View Details
1 / 21
Payment Protection
4 Bedrooms, 4 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Gym
  • Housekeeping...
  • Mountain Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
The Hemlock house is secluded and has AMAZING views of the Shenandoah Valley and the George Washington National Park. There are 4 bedrooms 3 & 1/2 bath and 2 living rooms. The top floor has the kitchen and dining room & sunken livingroom with a fireplace & large flat screen tv, also the master... View all property information
Make Enquiry
Go to map view
Book Online(17)
Use filters to find the best results!

Suitability

  • Wheelchair access (1)
  • Elder access (13)
  • Suitable for children (1)
  • Pet friendly (6)
  • Smoking allowed (0)

Amenities

  • Other outdoor space (20)
  • Washer/Dryer (20)
  • Fireplace (19)
  • Internet (19)
  • Air Conditioning (15)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
Nearby cities