Wintergreen Cottages

A dense forest with a variety of coniferous trees and a small clearing with grass and a few scattered trees.

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Our top choices for Wintergreen cottages

Cottage, Private Bathroom (Bluebird Cottage) | Exterior

1. Bluebird Cottage

Roseland

includes taxes & fees

13 Sept - 14 Sept

2. Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat

Afton

Caitlin S.

includes taxes & fees

15 Sept - 16 Sept

3. Bluebird Cottage: Near 151 + Appalachian Trail

Roseland

Art B.

includes taxes & fees

13 Sept - 14 Sept

4. Modern Nellysford Getaway on 40 Private Acres!

Nellysford

includes taxes & fees

9 Sept - 10 Sept

5. Afton Cottage w/ Hot Tub, Firepit, Mountain Views

Afton

Liz D.

includes taxes & fees

3 Sept - 4 Sept

6. Creekfront Cabin • Fire Pit • Fenced Yard • Near Crabtree Falls

Tyro

Nicole B.

includes taxes & fees

4 Sept - 5 Sept

7. Artisan's Cottage: Woodsy+Private, Central to 151

Afton

includes taxes & fees

2 Sept - 3 Sept

8. Little Haven Cottage: Walk to Meade Tasting

Afton

"House was clean except for the two dirty hand towels lying on the bed when we arrived. Washer and dryer were behind a locked door so I had to message the host to get a code to open it. She first insisted it wouldn’t be inside a locked door, so I had to wait for her to find out about it and she replied quickly enough with the access code. I’m guessing nobody ever needed to use the washer before us? Strange. Rooms could have used dressers or something to put clothes in. Vanities in master...

Anonymous traveller

includes taxes & fees

2 Sept - 3 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!"

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."

New Build! Log Cabin with Hot Tub in Wintergreen

10/10 Excellent

"Our family had a wonderful time during our stay at Chestnut Springs. The home is beautiful and nestled in the hills. There was plenty of room for six adults and five kids ages eight to sixteen. The hot tub was a big hit as was the comfortable furnishings and the wood burning fireplace. The kitchen is well stocked with cookware and dinnerware.Our host was very pleasant and quick to respond via email to my questions.We all enjoyed nearby Lake Monocan located at the Stoney Creek area of Wintergreen. We also enjoyed the two breweries/restaurants in nearby Nellyville.A great time was had by all!"

Cozy Cabin with private HOT TUB!

10/10 Excellent

"The property was very clean and beautiful. It had some modern touches,yet felt rustic mountain. Plenty of room and comfortable. Beautiful views. Unfortunately it rained our three days,so we were unable to use the hot tub. But the rain on the surrounding trees sounded beautiful and the windows looking out gave a peaceful warm feeling. Gave us valuable family time. Hosts were great at communication."

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