Photo by Melissa Smestad

Wintergreen Holiday Rentals

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Wintergreen holiday rentals

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

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

Best views on Mountain! Breathtaking 5 Star condo!. Available New Years Eve!!
Wintergreen
10.0 out of 10, Exceptional, (253)
"Stayed 3 nights for a wedding at Wintergreen. Wonderful place with spectacular views "
United States
Michael S.
Best views on Mountain! Breathtaking 5 Star condo!. Available New Years Eve!!
Terrace/patio
New Build! Log Cabin with Hot Tub in Wintergreen

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, (4)
"Well appointed kitchen, beautiful cabin!"
United States
Curtis
The price is HK$4,087
HK$8,375 total
includes taxes & fees
7 Jan - 8 Jan 2026
New Build! Log Cabin with Hot Tub in Wintergreen
Outdoor dining
RARE 3B/2B Mountain Top Condo Walk to the Slopes and Resturants! Slope Views!

RARE 3B/2B Mountain Top Condo Walk to the Slopes and Resturants! Slope Views!

RARE 3B/2B Mountain Top Condo Walk to the Slopes and Resturants! Slope Views!
Wintergreen Resort
9.8 out of 10, Exceptional, (28)
"Enjoyed the property and surrounding area "
United States
Ronald
RARE 3B/2B Mountain Top Condo Walk to the Slopes and Resturants! Slope Views!
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

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, (302)
"Great view!!"
United States
Suzanne W.
The price is HK$694
HK$1,706 total
includes taxes & fees
15 Dec - 16 Dec
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Smart TV, fireplace, DVD player
Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC

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

Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC
Wintergreen Resort
9.8 out of 10, Exceptional, (59)
"Good location. Great view. "
United States
Elizabeth G.
Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC
Exterior
Wow! What A View!

Wow! What A View!

Wow! What A View!
Wintergreen Resort
10.0 out of 10, Exceptional, (55)
"Very clean, very comfortable, easy to access - we honestly didn't want to leave."
United States
Josh W.
Wow! What A View!
A heated pool
Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!

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

Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!
Wintergreen Resort
9.8 out of 10, Exceptional, (137)
"Perfect location right across from the village. Very comfortable and clean. "
United States
Erin F.
The price is HK$1,946
HK$3,444 total
includes taxes & fees
4 Jan - 5 Jan 2026
Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!
Golf
Amazing Mountain views - Ski In Ski Out - Wifi - fireplace - Pets OK

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

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
Property grounds
The Modern Mountain Condo

The Modern Mountain Condo

The Modern Mountain Condo
Wintergreen Resort
10.0 out of 10, Exceptional, (34)
"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.
The price is HK$734
HK$1,786 total
includes taxes & fees
15 Dec - 16 Dec
The Modern Mountain Condo
Interior
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining

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

Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
2.0 star property
Wintergreen Resort
10.0 out of 10, Exceptional, (24)
"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$1,051
HK$2,710 total
includes taxes & fees
14 Dec - 15 Dec
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Property grounds
You deserve it all! Awesome Views, Comfy Condo & Elevator!

You deserve it all! Awesome Views, Comfy Condo & Elevator!

You deserve it all! Awesome Views, Comfy Condo & Elevator!
Chestnut Springs
9.8 out of 10, Exceptional, (196)
"Nice view along with a spacious layout. Was very nice location. "
United States
Daniel
You deserve it all! Awesome Views, Comfy Condo & Elevator!
Interior
Lofty Pursuits: Spectacular View + EV Charger

Lofty Pursuits: Spectacular View + EV Charger

Lofty Pursuits: Spectacular View + EV Charger
Treeloft
10.0 out of 10, Exceptional, (4)
"Will definitely stay at this location again!!"
United States
Richard W.
The price is HK$1,316
HK$3,015 total
includes taxes & fees
7 Jan - 8 Jan 2026
Lofty Pursuits: Spectacular View + EV Charger
Property grounds
Recently updated - breathtaking view of the Blue Ridge Mountains

Recently updated - breathtaking view of the Blue Ridge Mountains

Recently updated - breathtaking view of the Blue Ridge Mountains
Wintergreen Resort
10.0 out of 10, Exceptional, (42)
"Excellent property and very gracious hosts!"
United States
Asha T.
Recently updated - breathtaking view of the Blue Ridge Mountains
Pool
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

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Roseland
9.6 out of 10, Exceptional, (142)
"Great stay in Wintergreen!"
United States
Pete K.
The price is HK$950
HK$2,046 total
includes taxes & fees
14 Dec - 15 Dec
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Outdoor dining
Mountain Views in Wintergreen

Mountain Views in Wintergreen

Mountain Views in Wintergreen
Laurel Ridge
10.0 out of 10, Exceptional, (9)
"We had a great trip! The house was beautiful with so much space! We loved using the hot tub at night. The host was helpful and responsive to all my questions. Would be happy to book this house again."
United States
Kara S.
Mountain Views in Wintergreen
Interior
Wintergreen. Sunset Vista Villa - Close to the ski slopes

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, (92)
"Beautiful property! Had everything we needed and was very clean! Highly recommend!"
United States
Amanda W.
The price is HK$911
HK$2,046 total
includes taxes & fees
14 Dec - 15 Dec
Wintergreen. Sunset Vista Villa - Close to the ski slopes
Smart TV, fireplace, video games, DVD player
Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop

Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop

Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop
Wintergreen Resort
10.0 out of 10, Exceptional, (302)
"Large well appointed home. Perfect for our family who likes to hang out and cook together and play games in the evening. Beautiful area! Recommended!"
United States
Kristen S.
Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop
Outdoor dining
Travelers' Rest--Your Wintergreen Retreat in the Center of it All!

Travelers' Rest--Your Wintergreen Retreat in the Center of it All!

Travelers' Rest--Your Wintergreen Retreat in the Center of it All!
Wintergreen Resort
9.6 out of 10, Exceptional, (29)
"Great place to stay, would book again!"
United States
Jessica P.
Travelers' Rest--Your Wintergreen Retreat in the Center of it All!
Exterior
"SERENITY 4 ALL SEASONS"

"SERENITY 4 ALL SEASONS"

"SERENITY 4 ALL SEASONS"
Wintergreen Resort
9.8 out of 10, Exceptional, (87)
"great location for ski trip"
United States
Sarah W.
"SERENITY 4 ALL SEASONS"
Interior
Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
Wintergreen Resort
10.0 out of 10, Exceptional, (25)
"The location is very convenient with amazing views of the slopes and terrain park. "
United States
Meredith G.
Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
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

Wintergreen. Sunset Vista Villa - Sea of Mountains

Wintergreen. Sunset Vista Villa - Sea of Mountains

10/10 Excellent
"We love staying at Sunset Vista, especially in December. The condo is clean and has everything we need to enjoy a weekend away. Rebecca and Matt are so helpful, quickly responding to all our questions and needs. Can't wait to go back. This year was extra beautiful with snow! "
Brian B. 3-night trip
Posted 4 days ago
Wintergreen. Sunset Vista Villa - Sea of Mountains

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?

Large and Luxurious Exec 5BR Chalet: This highly rated holiday home rental in Wintergreen is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. Some other top choices in Wintergreen are Hiker’s paradise! Come relax this summer!!! and Wintergreen Oasis - PRIVATE POOL & SAUNA.

How many holiday rentals are there in Wintergreen?

Choose from 229 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 Stoney Creek Golf Course 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.