Photo by Melissa Smestad

Wintergreen Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

In two weeks
Dec 5 - Dec 7
In two months
Jan 16 - Jan 18
In three months
Feb 13 - Feb 15
In four months
Mar 13 - Mar 15

Vacation Rentals in Wintergreen

Interior
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining

Condo in Wintergreen Resort

2.0 star property
10.0 out of 10, Exceptional, (24)
"Excellent stay! Easy check in, Paul was super responsive and gave all the information we needed up front. Perfect for our overnight get away! Would absolutely stay again."
United States
Taylor H.
$260 nightly
The price is $292
Nov 23 - Nov 24
Total with taxes and fees
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Property grounds
The Modern Mountain Condo

Condo in Wintergreen Resort

10.0 out of 10, Exceptional, (31)
"Fantastic stay at the Modern Mountain Condo! The check-in process was a breeze, the location is exactly as pictured and was very clean. Spacious location for a couples getaway. Host was extremely responsive to any questions and provided us great instructions and details about the space. Will stay again in the future! "
United States
Kelsey N.
$214 nightly
The price is $240
Nov 23 - Nov 24
Total with taxes and fees
The Modern Mountain Condo
Cabin, Private Bathroom (Blackwood Chalet) | Exterior
Blackwood Chalet

Cabin in Nellysford

2.0 star property
10.0 out of 10, Exceptional, (3)
"Love the area"
United States
Toni
$369 nightly
The price is $390
Nov 23 - Nov 24
Total with taxes and fees
Blackwood Chalet
Terrace/patio
Wintergreen Condo -Steps to Ski and restaurants

Condo in Wintergreen Resort

9.8 out of 10, Exceptional, (29)
"Had everything we needed, snacks and coffee were great for a cold weekend."
United States
Michael L.
$236 nightly
The price is $265
Nov 23 - Nov 24
Total with taxes and fees
Wintergreen Condo -Steps to Ski and restaurants
Outdoor dining
Escape to the Blue Ridge Mountains at Wine-tergreen!

Condo in Wintergreen Resort

9.8 out of 10, Exceptional, (122)
"The condo was very nice. Located on top of the mountain resort having spectacular views for the outlook just a short walk away. We will be boocking again for our next trip. "
United States
John
$220 nightly
The price is $247
Nov 23 - Nov 24
Total with taxes and fees
Escape to the Blue Ridge Mountains at Wine-tergreen!
Smart TV, fireplace, books
Stylish-Updated-Central -Walk to Slopes-Dogs OK!

Condo in Wintergreen Resort

9.8 out of 10, Exceptional, (26)
"Great little place for family to rest after long days of hiking!"
United States
joseph G.
$209 nightly
The price is $235
Nov 24 - Nov 25
Total with taxes and fees
Stylish-Updated-Central -Walk to Slopes-Dogs OK!
Interior
Wintergreen. Sunset Vista Villa - Sea of Mountains

Condo in 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
Terrace/patio
Pine Cottage: Hot Tub, 2 mins to Bold Rock!

Cottage in Nellysford

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. "
United States
Claire B.
$411 nightly
The price is $462
Nov 23 - Nov 24
Total with taxes and fees
Pine Cottage: Hot Tub, 2 mins to Bold Rock!
Property grounds
Ready for Ski Season! Book NOW!

Apartment in Wintergreen Resort

9.8 out of 10, Exceptional, (25)
"Love everything about our stay there "
United States
Natalia S.
$316 nightly
The price is $320
Nov 23 - Nov 24
Total with taxes and fees
Ready for Ski Season! Book NOW!
Exterior
Laurelwood Hollow: Walk to Ski & Swim

Apartment in Wintergreen Resort

10.0 out of 10, Exceptional, (2)
"We really enjoyed our stay here! Great location, and the condo was very clean and well stocked. Communication with the host was excellent as well. We look forward to returning back some day!"
United States
Alexander H.
$265 nightly
The price is $279
Nov 30 - Dec 1
Total with taxes and fees
Laurelwood Hollow: Walk to Ski & Swim
Outdoor spa tub
Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!

Vacation Home in Wintergreen Resort

10.0 out of 10, Exceptional, (24)
"A wonderful property to see mountain views and visit the surrounding area."
United States
Peggy B.
$294 nightly
The price is $330
Dec 3 - Dec 4
Total with taxes and fees
Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!
Outdoor spa tub
Bear Tracks Cottage: New Hot Tub + Fire Pit

Cabin in Nellysford

10.0 out of 10, Exceptional, (28)
"Great for taking advantage of all Nelson County's attractions. "
United States
Darrell D.
$409 nightly
The price is $435
Nov 23 - Nov 24
Total with taxes and fees
Bear Tracks Cottage: New Hot Tub + Fire Pit
Microwave, oven, stovetop, dishwasher
Overlook 180 degree views w/Peloton!

Condo in Wintergreen Resort

9.0 out of 10, Wonderful, (2)
"Property exactly as promised, owner did a great job communicating before the stay.View was perfection, kitchen had two of everything I needed."
United States
harvey p.
$276 nightly
The price is $315
Nov 23 - Nov 24
Total with taxes and fees
Overlook 180 degree views w/Peloton!
Outdoor dining
Cozy Modern getaway at Wintergreen Resort with skiing, hiking & Blue Ridge Views

Condo in Wintergreen Resort

10.0 out of 10, Exceptional, (1)
"Awesome just Awesome place. Definitely recommend this place. Very well taken care of and everything you needed all rolled into one place. Thank you so much again and we will definitely be coming back. "
United States
Lance B.
$299 nightly
The price is $304
Nov 24 - Nov 25
Total with taxes and fees
Cozy Modern getaway at Wintergreen Resort with skiing, hiking & Blue Ridge Views
Property grounds
Design-Lover’s Getaway • Game Room • Hot Tub

Cabin in Wintergreen Resort

9.8 out of 10, Exceptional, (6)
"Peaceful family trip. The cabin was beautiful, lots of space, and very clean. The cabin had everything we needed. The game room, board games and puzzles were a hit with our kids. Hot tub was huge, clean had its own separate gated area. "
United States
Victoria R.
$508 nightly
The price is $570
Nov 23 - Nov 24
Total with taxes and fees
Design-Lover’s Getaway • Game Room • Hot Tub
Terrace/patio
Cozy Cute Condo in Wintergreen Resort

Condo in Roseland

10.0 out of 10, Exceptional, (2)
"Great Location!"
United States
Thomas W.
$323 nightly
The price is $328
Nov 23 - Nov 24
Total with taxes and fees
Cozy Cute Condo in Wintergreen Resort
TV, fireplace
Panoramic Peak: Wintergreen Condo with Views

Condo in Wintergreen Resort

9.6 out of 10, Exceptional, (32)
"With its breathtaking views, this property is a hidden gem. It is also very well maintained. "
United States
Abhishek S.
$258 nightly
The price is $290
Nov 23 - Nov 24
Total with taxes and fees
Panoramic Peak: Wintergreen Condo with Views
Property grounds
4 BR cabin mins to trails & breweries pets welcome

Vacation Home in Chestnut Springs

9.6 out of 10, Exceptional, (28)
"Nice place and very clean "
United States
Melad K.
$522 nightly
The price is $586
Nov 23 - Nov 24
Total with taxes and fees
4 BR cabin mins to trails & breweries pets welcome
Pool
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly

Condo in 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
Fridge, microwave, oven, stovetop
4 BD Modern Cabin w/ Game Room + Golf Course View

Cabin in Wintergreen Resort

10.0 out of 10, Exceptional, (2)
"Cozy cabin. Perfect for a quick family getaway! "
United States
Kurt W.
$653 nightly
The price is $712
Nov 23 - Nov 24
Total with taxes and fees
4 BD Modern Cabin w/ Game Room + Golf Course View
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.
View all properties

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Wintergreen Hotel Reviews

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

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

10/10 Excellent
"Very cozy home. Clean and comfortable. Wonderful area for a Fall getaway. "
Darlene V. 3-night trip
Posted 8 days ago
Top of Mountain 2 BR Condo, Short Walk to scenic overlooks of the Mtns. in Fall

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.

Explore a world of travel with Expedia

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.