Wintergreen Holiday Homes from €247: Search Top House Rentals

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Our top choices for Wintergreen holiday homes

A room with two armchairs, a small table with a lamp, and a view of a balcony with a railing.

1. Spacious + Serene Mtn Top Escape, 4 En Suites

Wintergreen Resort

Stephen M.

includes taxes & fees

1 Sept - 2 Sept

A cabin with a large window, surrounded by trees.

2. Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!

Wintergreen Resort

Stanley W.

includes taxes & fees

1 Sept - 2 Sept

A modern kitchen with wooden beams, a large island, and a dining area with a bench.

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

Nellysford

Robert H.

A spacious living room with a stone fireplace, a wooden ceiling, and large windows offering a view of trees.

4. 4 BR cabin mins to trails & breweries pets welcome

Chestnut Springs

RK D.

includes taxes & fees

21 Sept - 22 Sept

A wooden deck with outdoor seating and a fire pit.

5. Mountain Mindset

Laurel Ridge

includes taxes & fees

1 Sept - 2 Sept

A cabin with a deck, outdoor seating, and a fire pit.

6. Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch

Chestnut Springs

Cheryl P.

A spacious living room with a large sectional sofa, a glass coffee table, and a dining area with wooden chairs and a table.

7. The Distinguished Squirrel Chalet walking distance

Treeloft

Mark H.

8. Pet-Friendly Mountain Retreat with Fireplace & Walkable Village Access Near Wintergreen Resort, Virginia

Wintergreen Resort

A balcony with wicker furniture and a table, overlooking a scenic view of mountains and autumn foliage.

9. Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!

Nellysford

Rachel F.

A hot tub with a view of a forested landscape.

10. Stunning Views, Hot Tub, Impeccable Design

Wintergreen Resort

Lauren M.

A golf course with a mountain backdrop and autumn foliage.

11. The Snow House New Hot Tub Pet Friendly Creek PacMan

Wintergreen Resort

Justin L.

12. Mountain Retreat: HotTub, Game Room, Family & Pet-Friendly, 3 King Beds

Laurel Ridge

Mindy M.

includes taxes & fees

1 Sept - 2 Sept

A two-story cabin with a deck, large windows, and a hot tub.

13. Sauna & Hot Tub - 7th Hole Chalet - Sleeps 14

Wintergreen Resort

"We enjoyed our stay at the 7th hole chalet and would return. The house is spacious and was clean and included everything we needed. It did seem to have a lot of extra, unnecessary furniture in some of the rooms and pictures weren't exactly like listing. The landscaping was overgrown and messy out front. There are lots of controls for the heating and air throughout the house, but they are very hard to use and no instructions posted. The hot tub was nice and enjoyed by our crew, but the cover lift...

Paula L.

includes taxes & fees

7 Sept - 8 Sept

A two-story stone house with a deck, outdoor seating, and a fireplace.

14. Red White and Wintergreen

Pedlars Edge

includes taxes & fees

1 Sept - 2 Sept

A spacious living room with large windows, a wooden ceiling, and a chandelier.

15. Designer Home w/ Incredible Views, Sleeps 16

Wintergreen Resort

Neda A.

16. Mountain Retreat: Year-Round Getaway, Pup Friendly

Laurel Ridge

A bunk bed room with a red and white chevron rug, a white door, and a red dresser.

17. Red White & WTG: Hot Tub, 5 Bedrooms!

Pedlars Edge

Kate T.

18. Art & Soul

Nellysford

includes taxes & fees

1 Sept - 2 Sept

A wooden deck with a yellow door, a table with chairs, and a rocking chair.

19. Tucked Inn: Upper Unit

Nellysford

includes taxes & fees

1 Sept - 2 Sept

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Top Wintergreen Hotel Reviews

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

10/10 Excellent

"Just wrapped up a fantastic 3-night stay with my husband and our dog—this place is a total gem! Spacious, spotless, comfy, and truly pet-welcoming with everything you would need including thoughtful touches for the fur baby. We loved the king bed (so comfy!), and cozy fireplace for our surprisingly chilly August nights. You can tell the owner really cares for this place, and it shows in every detail—from the decor, entertainment options, furnishings and more, to the well-stocked kitchen. Also, the location within Wintergreen Resort is ideal. Heather, our host, was super responsive and a real pleasure to rent from. You'd be hard-pressed to find a better place or host."

Newly Built Designer Home in Wintergreen

10/10 Excellent

"This is one of the finest properties we've ever visited in all of our trips to Wintergreen. We have been coming since 1978. The location is great. It's snuggled into the lower elevations of the resort. That will pay dividends during your stay. Less vehicular and foot traffic. Combine that with easy access to the Appalachian Trail for some of the best hiking and views in the Blue Ridge. Ideal for kids and pets.The property itself? Beautiful, clean, tasteful, accommodating. The lighting and furnishings are designer quality. The well stocked kitchen is a joy to use with all of the necessary gadgets and utensils. Prefer pour over coffee? Your goose neck kettle is waiting. More of a French press kind of person? The Fellow Clara press is ready to go.The bedrooms and bathrooms are beautifully appointed. The wifi and entertainment setup are top drawer. You will not be disappointed. Highly recommended!"

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

10/10 Excellent

"Overall it was a quiet wintergreen summer experience. Close to the market and inn though we didn’t use either on the trip. Kitchen had the basics but don’t plan to prep anything complicated."

Updated! Sleeps 14 - Hot Tub, Games, Fireplace, Pet Friendly, Firepits & Grill

10/10 Excellent

"Great house in a great location. Wonderful getaway for our three generation family vacation (ages 13-85 plus a dog). We really loved the deck, fire pit and hot tub plus the nearby nature trail loop. Cooking for our crowd was easy, and there were multiple places for different groups to hang out. The weather was too wet to do as much outdoors as we wanted but there were lots of things to keep us busy in the house (puzzles, movies, baking, hot tub, games). Highly recommend this great house in Wintergreen Resort."

Wintergreen Luxury, Best Views in VA!

10/10 Excellent

"House was great for our family vacation. An actual million dollar view. Family had a wonderful week enjoying the surrounding area with hiking, fishing and local distilleries.House is very well appointed and our host Aubrey was excellent with communication before and during our trip. One tip- Definitely suggest bringing as much food supply as possible to save some driving time to store."

Find out more about Wintergreen

Wintergreen Holiday Homes information

Number of reviews	205
Accommodation	204 Holiday Homes
Lowest Price	€247
Highest Price	€834

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Check prices for these dates

Our top choices for Wintergreen holiday homes

1. Spacious + Serene Mtn Top Escape, 4 En Suites

2. Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!

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