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Wintergreen Holiday Rentals

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Holiday Rentals in Wintergreen

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

9.6 out of 10, Exceptional, (308)
"Exactly as advertised. Clean, everything worked, great location."
The price is NZ$628
includes taxes & fees
30 July - 31 July
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

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

10.0 out of 10, Exceptional, (237)
"Absolutely loved my second stay at the gorgeous property! The sunrise and sunset views can’t be beat. "
Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!

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 NZ$634
includes taxes & fees
15 July - 16 July
Charming 2-bedroom condo in beautiful Wintergreen Resort

Wintergreen Resort Studio w/ Deck & Ski-Out Access

9.8 out of 10, Exceptional, (33)
"Awesome spot! Very clean, super close to the slopes like 1 minute walk."
Wintergreen Resort Studio w/ Deck & Ski-Out Access

Unwind at Bear Pause, located right at Wintergreen Resort.

The price is NZ$908
includes taxes & fees
17 July - 18 July
Unwind at Bear Pause, located right at Wintergreen Resort.

Modern Luxe Treetop Retreat w/ Hot Tub, Gas Fire Pit, Steps to Ski! 100% 5 Star!

10.0 out of 10, Exceptional, (57)
"Great location, amenities and owner's willingness to address all our questions/issues."
Modern Luxe Treetop Retreat w/ Hot Tub, Gas Fire Pit, Steps to Ski! 100% 5 Star!

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

The Modern Mountain Condo

10.0 out of 10, Exceptional, (25)
"Wonderful! "
The price is NZ$400
includes taxes & fees
15 July - 16 July
The Modern Mountain Condo

Blackwood Chalet

2.0 star property
10.0 out of 10, Exceptional, (2)
"Everything was amazing. "
The price is NZ$611
includes taxes & fees
15 July - 16 July
Blackwood Chalet

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

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 NZ$768
includes taxes & fees
15 July - 16 July
Pine Cottage: Hot Tub, 2 mins to Bold Rock!

Valley Extended Suites

3.0 star property
9.0 out of 10, Wonderful, (189)
"I liked that it's has regular door keys. Loved it!"
The price is NZ$175
includes taxes & fees
16 July - 17 July
Valley Extended Suites

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

10.0 out of 10, Exceptional, (27)
"The cabins are great for couples. My wife and I had a great weekend here. If you are looking for a place to out away from things and quiet then I recommend it. "
The price is NZ$378
includes taxes & fees
15 July - 16 July
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

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

9.0 out of 10, Wonderful, (283)
"The condo has just the right amenities, nicely decorated, and yes, a million dollar view."
The price is NZ$406
includes taxes & fees
20 July - 21 July
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Luxury Log Cabin Getaway: Near Wintergreen Resort & Shenandoah Valley

10.0 out of 10, Exceptional, (13)
"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

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 NZ$436
includes taxes & fees
15 July - 16 July
Love Ridge Mountain Lodging

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

9.6 out of 10, Exceptional, (40)
"Property was incredibly clean and well-maintained. Enjoyed this condo!"
Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes

Afton Mountain Vineyards

2.5 star property
The price is NZ$631
includes taxes & fees
15 July - 16 July
Afton Mountain Vineyards

Top of Mountain 2 BR Condo, Short Walk to Highlands Ski Lift and Scenic Views

9.8 out of 10, Exceptional, (48)
"Great place, easy to find, and quick drive to the Wontergreen Resort!"
Top of Mountain 2 BR Condo, Short Walk to Highlands Ski Lift and Scenic Views

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

10.0 out of 10, Exceptional, (37)
"Beautiful property and very responsive host. Nice place to stay. "
The price is NZ$501
includes taxes & fees
21 July - 22 July
Spy Run Hideaway is a 1/2 mile from the Blue Ridge Parkway & pet friendly!
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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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?

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.: This highly rated holiday home rental in Wintergreen is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease 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. It offers a balcony, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. Our travellers also rate Modern Luxe Treetop Retreat w/ Hot Tub, Gas Fire Pit, Steps to Ski! 100% 5 Star! as a favourite home for rent in Wintergreen.

How many holiday rentals are there in Wintergreen?

Choose from 48 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.