Wintergreen Holiday Rentals

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Check prices for these dates

In two weeks
13 Feb - 15 Feb
In two months
27 Mar - 29 Mar
In three months
24 Apr - 26 Apr
In four months
22 May - 24 May

Our top choices for Wintergreen holiday rentals

Exterior

Laurelwood Hollow: Walk to Ski & Swim

Laurelwood Hollow: Walk to Ski & Swim
Wintergreen Resort
10.0 out of 10, Exceptional, (4 reviews)
"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.
The price is HK$741
HK$2,178 total
includes taxes & fees
2 Feb - 3 Feb
Laurelwood Hollow: Walk to Ski & Swim
Exterior

Wintergreen. Sunset Vista Villa - Close to the ski slopes

Wintergreen. Sunset Vista Villa - Close to the ski slopes
Wintergreen Resort
10.0 out of 10, Exceptional, (97 reviews)
"Fantastic stay again! Condo is perfect for a get away! "
United States
Jenna M.
The price is HK$1,299
HK$2,563 total
includes taxes & fees
2 Feb - 3 Feb
Wintergreen. Sunset Vista Villa - Close to the ski slopes
Terrace/patio

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

Pine Cottage: Hot Tub, 2 mins to Bold Rock!
Nellysford
10.0 out of 10, Exceptional, (24 reviews)
"The house was so nice and clean and the host was great also and we had a great stay and would highly recommend it. "
United States
Jody W.
The price is HK$1,475
HK$3,627 total
includes taxes & fees
2 Feb - 3 Feb
Pine Cottage: Hot Tub, 2 mins to Bold Rock!
Fireplace

The Modern Mountain Condo

The Modern Mountain Condo
Wintergreen Resort
10.0 out of 10, Exceptional, (41 reviews)
"Quiet, one-night stay while in the area for an event. "
United States
Julie M.
The price is HK$736
HK$1,842 total
includes taxes & fees
2 Feb - 3 Feb
The Modern Mountain Condo
Fridge, microwave, oven, stovetop

Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf

Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
Wintergreen Resort
9.8 out of 10, Exceptional, (7 reviews)
"We enjoyed our stay here. Brought the whole family."
United States
Caroline D.
The price is HK$936
HK$2,392 total
includes taxes & fees
3 Feb - 4 Feb
Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
Terrace/patio

New Build! Log Cabin with Hot Tub in Wintergreen

New Build! Log Cabin with Hot Tub in Wintergreen
Chestnut Springs
10.0 out of 10, Exceptional, (7 reviews)
"Well appointed kitchen, beautiful cabin!"
United States
Curtis
New Build! Log Cabin with Hot Tub in Wintergreen
Interior

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Roseland
9.8 out of 10, Exceptional, (26 reviews)
"Great communication from the startReturn texts the same day on any questionsGreat location for our tripVery cleanViews around property are greatNice restaurant A plus for what we neededDog friendly Thanks againHope to be back"
United States
Phil P.
The price is HK$936
HK$1,945 total
includes taxes & fees
3 Feb - 4 Feb
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

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

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Roseland
9.0 out of 10, Wonderful, (309 reviews)
"Outstanding views from the deck!! Loved it!"
United States
Kerry M.
The price is HK$807
HK$1,879 total
includes taxes & fees
2 Feb - 3 Feb
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Property grounds

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

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Roseland
9.6 out of 10, Exceptional, (145 reviews)
"Very clean and pet-friendly "
United States
Heston
The price is HK$952
HK$1,989 total
includes taxes & fees
24 Feb - 25 Feb
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Exterior detail

Cozy Wintergreen Retreat- Clean, Updated & Convenient, King Bed, Non-Smoking

Cozy Wintergreen Retreat- Clean, Updated & Convenient, King Bed, Non-Smoking
Wintergreen Resort
10.0 out of 10, Exceptional, (41 reviews)
"The property was clean and well furnished and we and our little dog had a great time."
United States
Sandra S.
The price is HK$906
HK$2,086 total
includes taxes & fees
1 Feb - 2 Feb
Cozy Wintergreen Retreat- Clean, Updated & Convenient, King Bed, Non-Smoking
Exterior detail

Little Mountain Haven. True ski-in, ski-out. First floor!

Little Mountain Haven. True ski-in, ski-out. First floor!
Wintergreen Resort
10.0 out of 10, Exceptional, (3 reviews)
"AMAZING location, excellent communication, and the place was clean, cozy, full of thoughtful amenities! Overall, a great experience and will definitely be back!"
United States
JPBII
The price is HK$687
HK$1,787 total
includes taxes & fees
11 Feb - 12 Feb
Little Mountain Haven. True ski-in, ski-out. First floor!
Dining

"Glass & Pine" Home close to Bold Rock & Vineyards

"Glass & Pine" Home close to Bold Rock & Vineyards
Nellysford
10.0 out of 10, Exceptional, (2 reviews)
"We only stayed one night but wished we could have stayed longer! The place was super clean and the views were beautiful once the rain finally stopped! Close to our favorite brewery and cidery. There were issues with TV reception (buffering) which may just be the area. Not much time for TV watching anyway with all the beautiful things to explore. We enjoyed our stay. "
United States
Robert H.
The price is HK$1,352
HK$3,230 total
includes taxes & fees
2 Feb - 3 Feb
"Glass & Pine" Home close to Bold Rock & Vineyards
Fridge, microwave, oven, stovetop

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

Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Wintergreen Resort
10.0 out of 10, Exceptional, (30 reviews)
"The property is extremely clean, well decorated and stocked. We had a fantastic time and absolutely would stay here again. "
United States
Cassie H.
The price is HK$995
HK$2,633 total
includes taxes & fees
1 Feb - 2 Feb
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Smart TV, fireplace, books

Spacious + Serene Mtn Top Escape, 4 En Suites

Spacious + Serene Mtn Top Escape, 4 En Suites
Wintergreen Resort
10.0 out of 10, Exceptional, (50 reviews)
"Great stay, clean, comfortable and plenty of room for all. We would rent again. Thanks so much!"
United States
Victoria S.
The price is HK$1,236
HK$3,570 total
includes taxes & fees
2 Feb - 3 Feb
Spacious + Serene Mtn Top Escape, 4 En Suites
Property grounds

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
Wintergreen Resort
10.0 out of 10, Exceptional, (6 reviews)
"We loved the 'ski-in/ski-out' convenience. Cute condo with everything you need for your stay. The water and snacks were a nice gesture. "
United States
Esperanza
The price is HK$780
HK$1,840 total
includes taxes & fees
1 Mar - 2 Mar
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
Lounge

Blackwood Chalet

Blackwood Chalet
2.0 star property
Nellysford
10.0 out of 10, Exceptional, (3 reviews)
"Love the area"
United States
Toni
The price is HK$1,459
HK$3,199 total
includes taxes & fees
3 Feb - 4 Feb
Blackwood Chalet
Outdoor dining

Overlook 180 degree views w/Peloton!

Overlook 180 degree views w/Peloton!
Wintergreen Resort
9.4 out of 10, Exceptional, (3 reviews)
"Excellent stay. Thank you!"
United States
Kimberly B.
The price is HK$1,409
HK$3,126 total
includes taxes & fees
25 Feb - 26 Feb
Overlook 180 degree views w/Peloton!
Property grounds

Spacious 3BR 3BA Pet Friendly Resort Condo

Spacious 3BR 3BA Pet Friendly Resort Condo
Wintergreen Resort
10.0 out of 10, Exceptional, (3 reviews)
"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.
The price is HK$2,013
HK$4,057 total
includes taxes & fees
4 Feb - 5 Feb
Spacious 3BR 3BA Pet Friendly Resort Condo
Outdoor spa tub

Bear Tracks Cottage: New Hot Tub + Fire Pit

Bear Tracks Cottage: New Hot Tub + Fire Pit
Nellysford
10.0 out of 10, Exceptional, (31 reviews)
"Perfect location for a golf trip to Stoney Creek Golf Club!"
United States
Randy R.
The price is HK$1,428
HK$3,399 total
includes taxes & fees
2 Feb - 3 Feb
Bear Tracks Cottage: New Hot Tub + Fire Pit
Smart TV, fireplace, books

Beautiful 4-season Mountain Home- New Listing

Beautiful 4-season Mountain Home- New Listing
Wintergreen Resort
10.0 out of 10, Exceptional, (40 reviews)
"The property is clean, bed rooms are spacious. 3.5 bath, kitchen has latest appliances, bedding & accessories are star hotel standard. We loved our stay. "
United States
Mridul G.
The price is HK$1,553
HK$4,223 total
includes taxes & fees
2 Feb - 3 Feb
Beautiful 4-season Mountain Home- New Listing
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

The Modern Mountain Condo

The Modern Mountain Condo

10/10 Excellent
"Excellent location, walked right over to the top of the slopes and about 30 yards from the market. Everything was clean, in good working order and perfect for our party of three"
George P. 1-night trip
Posted 5 days ago
The Modern Mountain Condo

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
  • Use the map to find apartments and other holiday homes in the Wintergreen neighbourhood you prefer
  • 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 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?

4 BR cabin mins to trails & breweries pets welcome: This highly rated holiday home rental in Wintergreen offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind. Some other top choices in Wintergreen are Upscale and Family-Friendly in Wintergreen and Mountain Views in Wintergreen.

How many holiday rentals are there in Wintergreen?

Choose from 230 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. While here, Bold Rock Hard Cider Nellysford Cidery and Wintergreen Resort are other places worth a visit.

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.