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Vacation rentals in Wintergreen, VA

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All 24 Rentals in Wintergreen
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From
$177
Per Night
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1 / 6
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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$165
Per Night
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1 / 33
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3 Bedrooms, 3 Bathrooms, Sleeps 7
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$133
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1 / 12
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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$171
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1 / 4
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3 Bedrooms, 3 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • 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
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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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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$317
Per Night
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1 / 14
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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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
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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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From
$247
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1 / 11
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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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
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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...
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From
$208
Per Night
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1 / 10
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3 Bedrooms, 1 Bathroom, Sleeps 8
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Amenities & Details
  • 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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From
$181
Per Night
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1 / 23
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2 Bedrooms, 1 Bathroom, Sleeps 4
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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
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From
$220
Per Night
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1 / 26
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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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
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
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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...
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From
$317
Per Night
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1 / 13
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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
Ski weekends sold out through March 13-15. Mid weeks sill available at discount. Our 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 premium parking ski pass for our guests to use right... View all property information
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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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From
$412
Per Night
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1 / 21
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4 Bedrooms, 4 Bathrooms, Sleeps 8
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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
This is a BRAND NEW HOME to any rental site... that is why there are no reviews. 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... View all property information
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From
$380
Per Night
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1 / 20
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4 Bedrooms, 3 Bathrooms, Sleeps 10
Bookings
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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
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From
$190
Per Night
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1 / 6
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1 Bedroom, 1 Bathroom, Sleeps 3
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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
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From
$380
Per Night
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1 / 9
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5 Bedrooms, 2 Bathrooms, Sleeps 10
Booking
Details 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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From
$507
Per Night
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1 / 5
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4 Bedrooms, 3 Bathrooms, Sleeps 12
Booking
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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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From
$696
Per Night
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1 / 48
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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
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From
$120
Per Night
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1 / 11
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
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
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From
$323
Per Night
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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
Special 2 Week Nights with very early check in OR very late check out: 450 for up to 6 adults! That is just 75 per person! Come play outside on the mountain in the heart of Wintergreen Resort. You'll be right beside the Spa and two minutes to the slopes! Chilly? Turn on the fireplace. Our place is... View all property information
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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...
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From
$158
Per Night
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1 / 14
3 Bedrooms, 2 Bathrooms, Sleeps 7
Details Reviews (10) 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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5 of 5 stars Reviewed 29 December 2014
The Point of View is a perfect mountain getaway with a beautiful view. If you are looking for a great location, this home will exceed your expectations. Our children loved having...
5 of 5 stars Reviewed 22 December 2014
I rented this property for two couples who were staying at Wintergreen with me and my family for the weekend. We found the house to be very comfortable and easily able to...
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From
$507
Per Night
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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
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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...
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From
$417
Per Night
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1 / 21
6 Bedrooms, 5 Bathrooms, Sleeps 14
Details Reviews (1) 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
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5 of 5 stars Reviewed 7 January 2015
We spent 10 days of our Christmas Holiday in this home at Wintergreen Resort. It was a great house with plenty of room... 8 adults & 4 kids all had plenty of space. The kitchen...
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From
$253
Per Night
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1 / 8
3 Bedrooms, 2 Bathrooms, Sleeps 6
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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
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From
$417
Per Night
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1 / 9
6 Bedrooms, 5 Bathrooms, Sleeps 16
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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
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From
$247
Per Night
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1 / 13
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (3) 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
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, WiFi, VOIP, near top of advanced slope, top floor end unit, view, non-smoking Near pool and spa, short walk behind building to access slopes... View all property information
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5 of 5 stars Reviewed 30 December 2014
Our family of five with grown children enjoyed our stay in this condo. The view was spectacular and we enjoyed the deck where we could take pictures of the view. The condo is very...
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...
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