Wintergreen is a small town in Virginia that is filled with fun activities and scenic beauty! If you love golfing, skiing, mountain climbing, hiking and biking, then this is a great place to visit. After a long day of enjoying these activities, here are some of the best Vrbo accommodations for relaxing and enjoying yourself, while in Wintergreen.
We handpicked these listings carefully, considering (wherever possible) Superhost status. recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on August 03, 2023.
1. Charming cottage in Nellysford (from USD 142)
For year-round outdoor adventures in Nellysford, book this charming vacation cottage that can comfortably accommodate up to four guests. The property is close to Wintergreen Resort where you can spend your days skiing and is less than 2 miles (3.2 kilometers) from easily accessible hiking trails. Other nearby attractions include Silver Fox Lavender Farm, Bold Rock Cider, and Wild Wolf Brewery.
When staying on-site for outdoor relaxation, you can hang out on the back porch for birdwatching, fire up the gas grill for a delicious dinner, or simply relax by the fire pit. The spacious interior features a comfy living room with a smart TV, a dining table for four, and a kitchen stocked with spices and basic cookware. Free WiFi completes its wonderful set of amenities.
Top guest reviews
Amenities & Room:
the cottage was nicely decorated and very comfortableHost:
the owner recommended several local restaurants that we tried and thoroughly enjoyedRead more reviewsLocation:
perfect size and close to everything we wanted to check out while in the area
2. Remodeled rental with spectacular views (from USD 236)
The views from this completely remodeled condo unit are so divine you may never want to leave. The living room with a fireplace, cable TV, and pull-out twin-size bed offers a front-row seat to spectacular sunrises. The dining area that extends to an outdoor deck can accommodate up to eight guests and equally provides great mountain views. To enable your skillful cooking, the kitchen is fully equipped and comes with essential appliances.
While the unit is at the highest point on the ridge, it remains accessible to many recreation areas such as the Devil’s Knob golf course and tennis courts as well as Wintergarden Pool and Spa. The building has a shuttle stop in its parking lot, making it effortless to visit nearby spots, including Mountain Inn.
Top guest reviews
Amenities & Room:
the views are incredible and everything was very comfortablethe kitchen is very well-equipped for cooking and entertainingCleanliness:
the condo was clean well stocked and very comfortableit is spotless comfortable and beautifully furnishedthis condo was great the cleanliness and updated features were amazingHost:
maureen was a great hostmaureen is a gem to work with and was super responsive when i had any questionsRead more reviewsLocation:
this was a great place for a quick getaway trip
3. Homey condo unit in The Cliffs (from USD 165)
Located in the complex of The Cliffs at the peak of Wintergreen Resort, this homey condo captures spectacular mountain views and sunrises for you to enjoy. It is a comfortable home that provides the conveniences of complimentary WiFi, a fireplace with free seasoned wood, and three HDTVs. Its kitchen is well equipped and complete with utensils and cookware so you can sort out all your meal plans during your stay.
For outdoor leisure, this property provides guest passes to the seasonally heated pool of Chestnut Springs and Rodes Farm so you get to have a full resort experience. The place is a great base during winter, too, as the ski shuttle is close by and the neighboring slopes are perfect for ski adventures.
Top guest reviews
Amenities & Room:
comfortable beds walk in shower and fully stocked kitchenCleanliness:
very clean condo especially to be pet friendlythe condo was very clean with all the essentialsgreat property-clean spacious and peacefulthe place was immaculately clean upon check-in and everything in the condo is in working orderwe had a wonderful time the condo was well equipped clean and the sunrise was amazingRead more reviewsLocation:
the location was perfectvery quiet out of season location it was a great choice for my writing weekendthe view from the condo is breathtaking and it is located close to everything on the mountain
4. Conveniently located retreat (from USD 175)
You’ll definitely want to venture into outdoor activities when you stay at this warm and inviting abode. This condo unit’s building is right in front of the shuttle service, making it easy to explore the area no matter the season. With golfing, hiking, wine tasting, skiing, and skateboarding within easy reach, there’s something for everyone in the neighborhood. If you prefer to relax, Wintergarden Pool and Spa is the right place to visit as it offers an indoor and outdoor pool, spa treatments, and a fitness center.
The property has a wood-burning fireplace in the living room so you can cozy up while catching your favorite shows on the flat-screen cable TV. Free WiFi is available but only in the cafe right next door. A telephone, however, is provided for local calls to keep you in touch with life back home.
5. Lovely slopeside flat in Diamond Hill (from USD 289)
Perched on a slope at Wintergreen Resort, this lovely rental in the Diamond Hill community will have you celebrating the outdoors. The property is within walking distance to the main lodge and allows you to admire fabulous views of the mountains and wildlife. You can visit The Nature Foundation and venture into the hiking trails and waterfalls or Lake Monacan for a fun time on the sandy beach and enjoy water activities.
The property will pamper you with its great features after a successful day in the open air. Its great room has a stunning 180-degree view of the mountains. The living space highlights a fireplace with free firewood to help you cozy up. There’s complimentary high-speed WiFi and flat-screen HDTV with cable services for your browsing and viewing pleasures.
Top guest reviews
Amenities & Room:
you could see the mountains from the living room and balcony it was preciousRead more reviewsLocation:
great location and would recommend to anyone
6. Apartment in mountain retreat (from 175 USD)
If you’re looking for a little bit of country life with some modern sophistication, then this is the best apartment for you. This three bedroom apartment has a private master suite with a king size bed, a private deck with a two person hot tub and a large master bathroom with heated floors and a huge walk in shower. There is also a queen size bed in the loft, with a closet and armoire. Last (but certainly not least), the apartment has a wonderful gourmet kitchen, with a large dining area.
Apartment in mountain retreat
Price: from 175 USD
Number of Guests: 6
7. A condo in three ridges (from 110 USD)
This is a newly renovated, chic condo that has two bedrooms located in three ridges. The condo offers a walk-in shower with a teak ceiling, as well as two bedrooms - one of which is a master bedroom with a queen size bed. The other bedroom offers a queen size Murphy Bed. There is also a fireplace and a fully equipped kitchen.
A condo In three ridges
Price: from 110 USD
Number of Guests: 6
8. A 5-star condo (from USD 185)
This is a beautiful 5-star condo, located at the High Ridge Place. It is a three-bedroom, three-bathroom condo that is beautifully decorated and offers a stunning view from the deck. It also has a kitchen, equipped with all the essentials and a nice living room, stocked with entertainment options. If you are looking for a luxury place to stay, then this is it.
Top guest reviews
Amenities & Room:
spacious comfortable condo with great viewso especially appreciated that lee provides some of the basics like toilet paper trash bags and paper towelsgreat views and one of the best stocked kitchens we've hadCleanliness:
awesome condo very clean and comfortableboth the condo and the owner are exceptional communication was seamless and the condo is well furnished and cleanperfect spot with beautiful view very clean and well supplied to make our stay at easeHost:
the owners are very responsive and accommodatingthe owner even called us the night of check-in to make sure all was oklee was very responsive and genuinely cared about our comfortlee was very responsive to any needs we hadRead more reviewsLocation:
the location was perfect for exploring the blue ridge and shenandoah areait’s a great location with a beautiful viewit's close to devil's knob which is greatwe had a great long weekend at lee's place everything was as advertised
9. A Wintergreen resort (from USD 350)
This beautiful vacation rental has four bedrooms and three private bathrooms for you, your family or your friends. The rental comes complete with a furnished kitchen that is stocked with all the essentials, as well as a nice dining area for meals with your favourite people.
Top guest reviews
Amenities & Room:
lots of great amenities; pool table fire pitplenty of room for everyone comfortable and clean thoroughly enjoyed the sound of music in an alpine settingCleanliness:
the house is always immaculately clean and well-stockedit was beautiful clean and fully stockedeverything was so clean and the kitchen had everything we needed to make mealsHost:
the owner was very responsivethe owner was very responsive and accommodatingfantastic property that exceeded expectations as owners anticipated vacay needs and provided superbly equipped homeRead more reviewsLocation:
experienced close encounters with welcomed wildlife activity
10. A Luxurious apartment (from 290 USD)
This is a nice, five bedroom luxury apartment with queen size beds and bunk beds that are perfect for children. You can also kick back with some quality entertainment of your choice in the spacious living room. The kitchen is fully equipped with all the essentials you’ll need for your stay, making this apartment feel as comfortable and familiar as home!
A luxurious apartment
Price: from 290 USD
Number of Guests: 12
A perfect vacation
The town of Wintergreen is the perfect spot for anyone to spend a nice vacation. With its natural beauty and comfortable accommodation options, Wintergreen is worth checking out with friends, family or that special someone. Book your rooms today!
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