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Wintergreen Vacation Rentals

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Vacation Rentals in Wintergreen

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

Roseland
9.0 out of 10, Wonderful, (298)
"Great view!!"
United States
Suzanne W.
$210 nightly
The price is $236
Dec 1 - Dec 2
Total with taxes and fees
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Top of Mountain 2 BR Condo, Short Walk to scenic overlooks of the Mtns. in Fall

Wintergreen Resort
9.8 out of 10, Exceptional, (53)
"Great place to stay in Wintergreen!"
United States
Caroline w.
Top of Mountain 2 BR Condo, Short Walk to scenic overlooks of the Mtns. in Fall

Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

Wintergreen Resort
9.8 out of 10, Exceptional, (7)
Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

Wow! What A View!

Wintergreen Resort
10.0 out of 10, Exceptional, (54)
"Very clean, very comfortable, easy to access - we honestly didn't want to leave."
United States
Josh W.
Wow! What A View!

New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly

Roseland
9.6 out of 10, Exceptional, (142)
"Great stay in Wintergreen!"
United States
Pete K.
$222 nightly
The price is $249
Dec 1 - Dec 2
Total with taxes and fees
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly

New Build! Log Cabin with Hot Tub in Wintergreen

Chestnut Springs
10.0 out of 10, Exceptional, (3)
"Well appointed kitchen, beautiful cabin!"
United States
Curtis
New Build! Log Cabin with Hot Tub in Wintergreen

2min to Ski Hot Tub EV Charger Mountain View DogOK

Wintergreen Resort
10.0 out of 10, Exceptional, (17)
"It was great "
United States
Sergio o.
2min to Ski Hot Tub EV Charger Mountain View DogOK

Amazing Mountain views - Ski In Ski Out - Wifi - fireplace - Pets OK

Wintergreen
9.8 out of 10, Exceptional, (181)
"Absolutely gorgeous area and it was nice to escape the summer heat for a few days! My husband and I love the stay so much and we are considering renting for a month or two next summer! Thank you so much Sarah!"
United States
Yan
Amazing Mountain views - Ski In Ski Out - Wifi - fireplace - Pets OK

Large and Luxurious Exec 5BR Chalet

Pedlars Edge
10.0 out of 10, Exceptional, (250)
"Perfect location for family ski trip"
United States
Angie S.
Large and Luxurious Exec 5BR Chalet

Cozy Cabin with private HOT TUB!

Nellysford
10.0 out of 10, Exceptional, (28)
"This location was a nice place to relax and enjoy family time."
United States
Melissa H.
Cozy Cabin with private HOT TUB!

Best views on Mountain! Breathtaking 5 Star condo!. Available New Years Eve!!

Wintergreen
10.0 out of 10, Exceptional, (251)
"The condo was absolutely lovely! We had great time in Wintergreen and will definitely go back. "
United States
Dawn C.
Best views on Mountain! Breathtaking 5 Star condo!. Available New Years Eve!!

The newest and largest edition to the Wintergreen Retreat portfolio!

Wintergreen Resort
9.8 out of 10, Exceptional, (47)
"Very comfortable and plenty of room for our 7 adults and 5 children - no surprises - happy with accommodations—"
United States
Marion B.
The newest and largest edition to the Wintergreen Retreat portfolio!

Wintergreen. Sunset Vista Villa - Sea of Mountains

Wintergreen Resort
10.0 out of 10, Exceptional, (90)
"Another great stay at Sunset Vista! Clean, comfortable, convenient, well stocked, great views, amazing host - what more could we ask for? We will be back!"
United States
Judy C.
$234 nightly
The price is $263
Nov 23 - Nov 24
Total with taxes and fees
Wintergreen. Sunset Vista Villa - Sea of Mountains

Walking Distance to Ski Slopes! Cozy Condo that sleeps 4!

Wintergreen Resort
9.4 out of 10, Exceptional, (21)
"It was the perfect spot for I’m working and a very clean place"
United States
Eric E.
Walking Distance to Ski Slopes! Cozy Condo that sleeps 4!

Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!

Wintergreen Resort
9.8 out of 10, Exceptional, (137)
"Loved convenience to restaurants and Market. Condo had everything we needed. "
United States
Lisa O.
Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!

Dobie condo, renovated top to bottom! LOTS OF DETAILED INFO LISTED ☺️

Wintergreen Resort
10.0 out of 10, Exceptional, (179)
"Quiet, clean and everything was organized."
United States
Paul R.
Dobie condo, renovated top to bottom! LOTS OF DETAILED INFO LISTED ☺️

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

Wintergreen Resort
9.6 out of 10, Exceptional, (54)
"Had a great stay..hosts quick to respond to questions. Patio was a nice plus!"
United States
eric s.
Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes

Ski-In/Ski-Out Comfy Condo

Wintergreen
10.0 out of 10, Exceptional, (29)
"Condo was clean and well equipped. Location was right next to the main lodge which was convenient. "
United States
Todd
Ski-In/Ski-Out Comfy Condo

Hiker’s paradise! Come relax this summer!!!

Roseland
10.0 out of 10, Exceptional, (36)
"Best place we have stayed around wintergreen hands down."
United States
Allen M.
Hiker’s paradise! Come relax this summer!!!

Mountain Views, Hot Tub, Impeccable Design

Wintergreen Resort
9.2 out of 10, Wonderful, (5)
"An amazing view of the valley, the home was gorgeous, well stocked with essential items and more. The beds were very comfortable, the whole house had a comfy, welcoming atmosphere. The adventures we went on were within 30 minutes of the house.We had a wonderful time there!"
United States
Sid V.
Mountain Views, Hot Tub, Impeccable Design
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

Everything you need to know about Wintergreen vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Wintergreen vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Wintergreen vacation 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 low season months. For more hustle and bustle, you may prefer to visit Wintergreen in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $236 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Wintergreen rentals

At Expedia, we put the best Wintergreen vacation 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 vacation.

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 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?

Luxury Wintergreen 5BR • Hot Tub • Sleeps 16+ • Dog Friendly: Visitors give good reviews to this Wintergreen vacation home rental, which offers a fireplace, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 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 Large and Luxurious Exec 5BR Chalet and Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!.

How many vacation rentals are there in Wintergreen?

Choose from 225 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. While here, Bold Rock Hard Cider Nellysford Cidery and Stoney Creek Golf Course are other places worth a visit.

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.