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Wintergreen Holiday Rentals

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Holiday Rentals in Wintergreen

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

10.0 out of 10, Exceptional, (328)
"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!

10.0 out of 10, Exceptional, (62)
"Loved our stay - the house, location, and amenities were perfect for us!"
The price is AU$1,089
includes taxes & fees
27 Oct - 28 Oct
Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!

The Modern Mountain Condo

10.0 out of 10, Exceptional, (29)
"Ideal location for skiing at Wintergreen. "
The price is AU$367
includes taxes & fees
13 Oct - 14 Oct
The Modern Mountain Condo

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

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

9.8 out of 10, Exceptional, (30)
"Great house, great owner, incredible views. As good as it gets in the entire mid-Atlantic"
The price is AU$2,524
includes taxes & fees
5 Nov - 6 Nov
Luxury Chalet, Best Views in Virginia

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

9.4 out of 10, Exceptional, (88)
"This was a beautiful place in the mountains. Much cooler than down below, and the deck is a nice place to be. We enjoyed the house, and the property manager was wonderful."
Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK

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 AU$713
includes taxes & fees
4 Nov - 5 Nov
The Distinguished Squirrel Chalet walking distance

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

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!!!

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!

10.0 out of 10, Exceptional, (22)
"The house was super cute and accommodated our whole group. It was close to a good amount of breweries and wineries. "
The price is AU$713
includes taxes & fees
29 Oct - 30 Oct
Pine Cottage: Hot Tub, 2 mins to Bold Rock!

Valley Extended Suites

3.0 star property
9.0 out of 10, Wonderful, (205)
"Nice stay"
The price is AU$192
includes taxes & fees
20 Oct - 21 Oct
Valley Extended Suites

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!

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.

9.0 out of 10, Wonderful, (293)
"Will certainly look to book again in the future. Very nice condo with a spectacular view."
The price is AU$370
includes taxes & fees
19 Oct - 20 Oct
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

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

10.0 out of 10, Exceptional, (35)
"Great property and host"
The price is AU$352
includes taxes & fees
28 Oct - 29 Oct
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

9.6 out of 10, Exceptional, (50)
"The condo was very clean, cozy and well appointed. The view of the golf course was beautiful and the mountain was quiet that week, which we were in need of some peace and quiet. My wife and I are already talking about our next trip to Wintergreen and we will likely stay here again. "
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

9.8 out of 10, Exceptional, (54)
"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

Love Ridge Mountain Lodging

3.0 star property
10.0 out of 10, Exceptional, (12)
"Amazing stay I had, very peaceful and very quiet. "
The price is AU$453
includes taxes & fees
9 Oct - 10 Oct
Love Ridge Mountain Lodging
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

Find out more about Wintergreen

Find out more about Wintergreen

Everything you need to know about Wintergreen holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Wintergreen holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wintergreen holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Wintergreen holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wintergreen. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wintergreen holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wintergreen holiday rentals we have selected for you start as low as AU$192 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Wintergreen rentals

At Expedia, we put the best Wintergreen holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Wintergreen rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wintergreen holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Wintergreen. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Wintergreen?

Yes, there are holiday rentals close to the most popular sights in Wintergreen, or you can select a more secluded option if you're looking for a relaxing stay. Discover why Wintergreen is known for its ski slopes and mountain landscape. Make sure you have time to check out the wineries and coffee shops during your trip.

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

Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!: This highly rated holiday home rental in Wintergreen is located in the mountains, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub. Some other top choices in Wintergreen are NEW! Warren’s Woods! Spacious 5-bedroom house in fantastic Wintergreen Resort and Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK.

How many holiday rentals are there in Wintergreen?

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

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 wider area.

What’s a holiday rental in Wintergreen like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Wintergreen. Holiday rentals feature amenities such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a family getaway.