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Wintergreen Holiday Rentals

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Check prices for these dates

Tonight
3 Aug - 4 Aug
Tomorrow
4 Aug - 5 Aug
Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug

Holiday Rentals in Wintergreen

Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!
Miscellaneous

Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!

10.0 out of 10, Exceptional, (238)
"Tremendous view and perfect accommodations. We used for a base to visit Staunton and Charlottesville. "
Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

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

10.0 out of 10, Exceptional, (321)
"I’ve stayed here a few times now with various members of my family and all of us love this place! The accommodations are great, the place is well stocked with careful attention to detail, and we always look forward to returning. Thanks again for a great stay!"
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Walk to Market/Private community outdoor pool!
Fridge, microwave, oven, stovetop

Walk to Market/Private community outdoor pool!

9.8 out of 10, Exceptional, (71)
"Nice condo, near all the Wintergreen activities."
Walk to Market/Private community outdoor pool!
Charming 2-bedroom condo in beautiful Wintergreen Resort
Microwave, oven, stovetop, dishwasher

Charming 2-bedroom condo in beautiful Wintergreen Resort

10.0 out of 10, Exceptional, (1)
"We stayed here for a couple of nights over July 4th and it was a nice short getaway. The condo is in a good location - 5 min walk to resort restaurants - and is very comfortable. The kitchen is well-equipped with plenty of cooking tools. The living room seating space was comfortable and allowed for just hanging out. We really enjoyed our stay! "
The price is HK$1,177
HK$2,997 total
includes taxes & fees
4 Aug - 5 Aug
Charming 2-bedroom condo in beautiful Wintergreen Resort
Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!
Property grounds

Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!

10.0 out of 10, Exceptional, (57)
"Great location, amenities and owner's willingness to address all our questions/issues."
Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!
Pine Cottage: Hot Tub, 2 mins to Bold Rock!
Terrace/patio

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

10.0 out of 10, Exceptional, (19)
"The house was super cute and accommodated our whole group. It was close to a good amount of breweries and wineries. "
The price is HK$1,484
HK$3,632 total
includes taxes & fees
4 Aug - 5 Aug
Pine Cottage: Hot Tub, 2 mins to Bold Rock!
Blue Ridge Mountain Retreat in Wintergreen
Golf

Blue Ridge Mountain Retreat in Wintergreen

9.2 out of 10, Wonderful, (65)
"Enjoyed our 2nd year here. Lots of room and fabulous kitchen. "
Blue Ridge Mountain Retreat in Wintergreen
Blackwood Chalet
Exterior

Blackwood Chalet

2.0 star property
10.0 out of 10, Exceptional, (2)
"Everything was amazing. "
Blackwood Chalet
Hike, Bike & Explore: Wintergreen Resort Condo
Interior

Hike, Bike & Explore: Wintergreen Resort Condo

2.0 star property
10.0 out of 10, Exceptional, (2)
"We were extremely pleasantly surprised to realize we were actually on the resort when we got there. Originally booked somewhere else and saw this last minute and it was so easy to book, it was very easy to check in. It was a very nice place in the resort and in the condo. We were right at the slopes so we could easily take breaks through the day and go back to the room. 10/10 would recommend and I will stay here again!"
Hike, Bike & Explore: Wintergreen Resort Condo
Valley Extended Suites
Private kitchen

Valley Extended Suites

3.0 star property
9.0 out of 10, Wonderful, (190)
"Quite and Accommodating.office staff was great "
The price is HK$787
HK$876 total
includes taxes & fees
12 Aug - 13 Aug
Valley Extended Suites
Luxury Log Cabin Getaway: Near Wintergreen Resort & Shenandoah Valley
Property grounds

Luxury Log Cabin Getaway: Near Wintergreen Resort & Shenandoah Valley

10.0 out of 10, Exceptional, (14)
"We loved staying at this property. Easily accommodated our family and was such a pretty setting. Host was excellent in answering questions and providing information. Would definitely stay here in the future."
Luxury Log Cabin Getaway: Near Wintergreen Resort & Shenandoah Valley
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

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

9.0 out of 10, Wonderful, (288)
"The condo has just the right amenities, nicely decorated, and yes, a million dollar view."
The price is HK$824
HK$1,913 total
includes taxes & fees
5 Aug - 6 Aug
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA
Exterior

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

10.0 out of 10, Exceptional, (27)
"Great place to stay while enjoying the mountains."
The price is HK$1,138
HK$1,781 total
includes taxes & fees
4 Aug - 5 Aug
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA
Ivy Rose Cottage nestled b/t Cville & Vineyards
Fridge, microwave, oven, stovetop

Ivy Rose Cottage nestled b/t Cville & Vineyards

10.0 out of 10, Exceptional, (57)
"The cottage was super adorable and perfect for our little weekend getaway!!! "
The price is HK$1,406
HK$2,657 total
includes taxes & fees
10 Aug - 11 Aug
Ivy Rose Cottage nestled b/t Cville & Vineyards
New Cabin Right on The Rockfish River! Peacefull River Sounds, Stunning views!
2 bedrooms, iron/ironing board, free WiFi, bed sheets

New Cabin Right on The Rockfish River! Peacefull River Sounds, Stunning views!

10.0 out of 10, Exceptional, (45)
"Well designed modern cabin on the Rockfish River south of CVille. Plenty of space to amble around with a small beach where you could launch kayaks (provided) or do some fishing.Had great time even though it was a little rainy."
New Cabin Right on The Rockfish River! Peacefull River Sounds, Stunning views!
Love Ridge Mountain Lodging
Terrace/patio

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 HK$1,410
HK$2,054 total
includes taxes & fees
4 Aug - 5 Aug
Love Ridge Mountain Lodging
Spy Run Hideaway is a 1/2 mile from the Blue Ridge Parkway & pet friendly!
Fridge, microwave, oven, stovetop

Spy Run Hideaway is a 1/2 mile from the Blue Ridge Parkway & pet friendly!

9.8 out of 10, Exceptional, (41)
"Beautiful property and very responsive host. Nice place to stay. "
The price is HK$1,272
HK$2,362 total
includes taxes & fees
5 Aug - 6 Aug
Spy Run Hideaway is a 1/2 mile from the Blue Ridge Parkway & pet friendly!
Whimsical Creekside Cabin
Property grounds

Whimsical Creekside Cabin

10.0 out of 10, Exceptional, (26)
"Had a very quiet relaxing stay "
The price is HK$777
HK$1,711 total
includes taxes & fees
25 Aug - 26 Aug
Whimsical Creekside Cabin
Family Friendly Log Cabin Nestled in Blue Ridge Foothills
Dining

Family Friendly Log Cabin Nestled in Blue Ridge Foothills

2.0 star property
9.8 out of 10, Exceptional, (9)
"Very well equipped and clean! The owner was super nice and responsive! Great stay!"
Family Friendly Log Cabin Nestled in Blue Ridge Foothills
Hot Tub EV Charger Pool Dog OK Grill Tennis Hiking
Fridge, microwave, oven, stovetop

Hot Tub EV Charger Pool Dog OK Grill Tennis Hiking

10.0 out of 10, Exceptional, (12)
"The house was lovely. The location was great. Plenty of space for everyone. We really enjoyed this home."
Hot Tub EV Charger Pool Dog OK Grill Tennis Hiking
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

avid hotel Staunton by IHG

avid hotel Staunton by IHG

10/10 Excellent
"Staff was very friendly and rooms were very comfortable."
MaryClaire 1-night trip
Posted 1 day ago
avid hotel Staunton by IHG

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. Our travellers also rate Blue Ridge Mountain Retreat in Wintergreen as a favourite home for rent in Wintergreen.

How many holiday rentals are there in Wintergreen?

Choose from 50 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.