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Wintergreen Vacation Rentals

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Check prices for these dates

In two weeks
Oct 17 - Oct 19
In one month
Oct 31 - Nov 2
In two months
Nov 28 - Nov 30
In three months
Dec 26 - Dec 28

Vacation Rentals in Wintergreen

Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

10.0 out of 10, Exceptional, (327)
"The property is nestled very nicely on the mountain and convenient to the main lodge, restaurants and other attractions. We really enjoyed our stay. The condo was plenty big for the two of us and our dog. It is well-appointed Kudos to the owner, Heather, for thinking of everything to make our stay great. "
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!
Property grounds

Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!

10.0 out of 10, Exceptional, (62)
"Loved our stay - the house, location, and amenities were perfect for us!"
The price is ￥59,168
￥105,483 total
includes taxes & fees
Oct 27 - Oct 28
Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!
The Modern Mountain Condo
Property grounds

The Modern Mountain Condo

10.0 out of 10, Exceptional, (28)
"Ideal location for skiing at Wintergreen. "
The price is ￥14,878
￥36,067 total
includes taxes & fees
Oct 2 - Oct 3
The Modern Mountain Condo
NEW! Warren’s Woods! Spacious 5-bedroom house in fantastic Wintergreen Resort
Property grounds

NEW! Warren’s Woods! Spacious 5-bedroom house in fantastic Wintergreen Resort

NEW! Warren’s Woods! Spacious 5-bedroom house in fantastic Wintergreen Resort
Cozy 6-bedroom cabin in Wintergreen Resort
Interior

Cozy 6-bedroom cabin in Wintergreen Resort

9.8 out of 10, Exceptional, (9)
"Place was great we had a blast ! Only about a 5 min walk to the slopes!"
Cozy 6-bedroom cabin in Wintergreen Resort
Luxury Chalet, Best Views in Virginia
Outdoor spa tub

Luxury Chalet, Best Views in Virginia

9.8 out of 10, Exceptional, (30)
"Great house, great owner, incredible views. As good as it gets in the entire mid-Atlantic"
Luxury Chalet, Best Views in Virginia
Retreat @ 3 Ridges / 2min->Slopes / Walk to Dining
Interior

Retreat @ 3 Ridges / 2min->Slopes / Walk to Dining

2.0 star property
10.0 out of 10, Exceptional, (21)
"Loved our short stay at the property. Everything was as described. Would stay again."
The price is ￥11,888
￥41,385 total
includes taxes & fees
Oct 5 - Oct 6
Retreat @ 3 Ridges / 2min->Slopes / Walk to Dining
Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK
Dining

Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK

9.4 out of 10, Exceptional, (88)
"Wonderful stay"
Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK
The Distinguished Squirrel Chalet walking distance
Terrace/patio

The Distinguished Squirrel Chalet walking distance

9.8 out of 10, Exceptional, (6)
"The house was beautiful and well stocked. The owner thought of everything and all the light switches were labeled which helped a lot. All of the appliances were top notch and the Keurig coffee maker had everything that was needed. Beds were very comfortable and each room had its own thermostat. Overall, excellent stay!"
The price is ￥28,844
￥65,786 total
includes taxes & fees
Oct 2 - Oct 3
The Distinguished Squirrel Chalet walking distance
Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!
Fridge, microwave, oven, stovetop

Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!

9.8 out of 10, Exceptional, (175)
"Nice property and views. "
Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!
Large and Luxurious Exec 5BR Chalet
Property grounds

Large and Luxurious Exec 5BR Chalet

10.0 out of 10, Exceptional, (249)
"Perfect location for family ski trip"
Large and Luxurious Exec 5BR Chalet
Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!!
Outdoor spa tub

Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!!

10.0 out of 10, Exceptional, (49)
"House was great. We had friends with us for a wonderful birthday celebration. "
Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!!
Pine Cottage: Hot Tub, 2 mins to Bold Rock!
Terrace/patio

Pine Cottage: Hot Tub, 2 mins to Bold Rock!

10.0 out of 10, Exceptional, (21)
"The house was super cute and accommodated our whole group. It was close to a good amount of breweries and wineries. "
The price is ￥29,126
￥68,755 total
includes taxes & fees
Oct 6 - Oct 7
Pine Cottage: Hot Tub, 2 mins to Bold Rock!
Valley Extended Suites
Studio Suite | Private kitchen | Full-size fridge, microwave, oven, stovetop

Valley Extended Suites

3.0 star property
9.0 out of 10, Wonderful, (202)
"Nice stay"
The price is ￥16,863
￥18,769 total
includes taxes & fees
Oct 5 - Oct 6
Valley Extended Suites
Unwind in Seclusion: Log Cabin Retreat with Wood Burning Stove & Game Table
Property grounds

Unwind in Seclusion: Log Cabin Retreat with Wood Burning Stove & Game Table

10.0 out of 10, Exceptional, (15)
"Nice time exploring the area"
Unwind in Seclusion: Log Cabin Retreat with Wood Burning Stove & Game Table
Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!
Miscellaneous

Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!

10.0 out of 10, Exceptional, (244)
"Tremendous view and perfect accommodations. We used for a base to visit Staunton and Charlottesville. "
Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

9.0 out of 10, Wonderful, (293)
"Beautiful location and million dollar views are so true. The condo was clean and comfortable. Will stay again and recommend to everybody. "
The price is ￥15,603
￥36,046 total
includes taxes & fees
Oct 2 - Oct 3
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA
Exterior

Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

10.0 out of 10, Exceptional, (34)
"Great property and host"
The price is ￥21,448
￥33,555 total
includes taxes & fees
Oct 5 - Oct 6
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA
Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes
Fridge, microwave, oven, stovetop

Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes

9.6 out of 10, Exceptional, (49)
"We had the best weekend! Loved Lake Monocan and Devil’s Knob Spa. Also visited Three Notched and Devil’s Backbone. Condo worked very well. Beds were so comfortable and we lived kicking back on the patio. Will definitely rent again since it’s so close. Thanks for great communications!"
Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes
Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC
Smart TV, fireplace, DVD player

Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC

9.8 out of 10, Exceptional, (53)
"This was our second stay in Wintergreen. First time at this property. The condo was beautifully decorated, had all the necessities and the view was breathtaking. "
Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Wintergreen Hotel Reviews

Motel 6 Staunton, VA

Motel 6 Staunton, VA

10/10 Excellent
"Staff was very friendly. Pets were welcome without an additional fee."
David 2-night trip
Posted 1 day ago
Motel 6 Staunton, VA

Find out more about Wintergreen

Find out more about Wintergreen

Search for holiday rentals in Wintergreen on Expedia! You can easily find your home rentals, villas, holiday apartments in Wintergreen using one of the methods below:

  • View our selection of featured holiday rentals in Wintergreen
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  • Enter your travel dates to view the best deals on holiday rentals in Wintergreen while they last

Look no further and take a look at our great range of rental properties in Wintergreen!

Frequently asked questions

Can I find vacation rentals in Wintergreen?

Yes, there are vacation rentals close to the most popular points of interest in Wintergreen, or you can select a secluded option if you'd like a relaxing place to stay. Discover why Wintergreen is known for its ski slopes and mountain landscape. Make sure you have time to check out the wineries and coffeehouses during your trip.

What are some of the best vacation rentals that Wintergreen has to offer?

Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!: Visitors give good reviews to this Wintergreen vacation home rental, which is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub. Some other top choices in Wintergreen are NEW! Warren’s Woods! Spacious 5-bedroom house in fantastic Wintergreen Resort and The Distinguished Squirrel Chalet walking distance.

How many vacation rentals are there in Wintergreen?

Choose from 52 Expedia vacation rentals in Wintergreen for a memorable vacation.

What can I see and do in Wintergreen?

While exploring the area, visit family-friendly sights like War Fields, or get outside and enjoy nature at George Washington National Forest. Wintergreen Resort and Bold Rock Hard Cider Nellysford Cidery are a couple of places you'll find in the larger area.

What’s a vacation rental in Wintergreen like?

A vacation rental is a private property where you can stay for several days or longer in Wintergreen. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a family trip.