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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

B&B in Wintergreen

Frederick House
Patrick-27 | Iron/ironing board, free WiFi, bed sheets

Frederick House

3.5 star property
9.4 out of 10, Exceptional, (401)
"We stayed in Patrick 26. Wonderful stay! Clean, comfortable, historic, walkable to many great restaurants, winery, breweries. Staff are friendly and breakfast delicious. "
The price is AED 563
AED 631 total
includes taxes & fees
25 Jul - 26 Jul
Frederick House
The Crossroads Inn
Winery

The Crossroads Inn

5.0 star property
10.0 out of 10, Exceptional, (30)
"Wonderful stay! "
The Crossroads Inn
Sugar Tree Inn
Room, Private Bathroom (Tye River) | Premium bedding, pillowtop beds, individually decorated

Sugar Tree Inn

3.5 star property
9.4 out of 10, Exceptional, (101)
"Friendly owners, amazing breakfast and pristine room! EV charger is a very nice added bonus too."
The price is AED 770
AED 888 total
includes taxes & fees
21 Jul - 22 Jul
Sugar Tree Inn
Osceola Mill
Exterior

Osceola Mill

2.0 star property
10.0 out of 10, Exceptional, (4)
"Welcoming host in an interesting converted building. There’s not much in the immediate area we travelled out to Staunton to eat which was also a nice town."
The price is AED 625
AED 720 total
includes taxes & fees
20 Jul - 21 Jul
Osceola Mill
The Farmhouse at Veritas
Exterior

The Farmhouse at Veritas

4.0 star property
9.8 out of 10, Exceptional, (32)
"Nice location a staff. Dining in the vineyard was excellent."
The price is AED 1,194
AED 1,341 total
includes taxes & fees
23 Jul - 24 Jul
The Farmhouse at Veritas
Woodville Bed and Breakfast
Seasonal outdoor pool

Woodville Bed and Breakfast

4.0 star property
10.0 out of 10, Exceptional, (51)
"Second time staying here and we will be back. Marvelous hospitality and divine breakfast. "
The price is AED 915
AED 1,045 total
includes taxes & fees
27 Jul - 28 Jul
Woodville Bed and Breakfast
Osceola Mill is a B&B inn located in the Shenandoah Valley 20 minutes from Lexington and Staunton.
Terrace/patio

Osceola Mill is a B&B inn located in the Shenandoah Valley 20 minutes from Lexington and Staunton.

10.0 out of 10, Exceptional, (1)
"The pictures do not do this room justice! absolutely beautiful and so very comfortable. our 12 year old used the pull out and said it was the most comfortable one ever! Linda is a fantastic host and so very friendly and welcoming. I wish we could have stayed multiple nights. Of all the places we stayed during our vacation this was, by far, our favorite!! I can't say enough - stay here and you'll be happy you did!"
The price is AED 848
AED 1,114 total
includes taxes & fees
20 Jul - 21 Jul
Osceola Mill is a B&B inn located in the Shenandoah Valley 20 minutes from Lexington and Staunton.
Osceola Mill is a B&B inn located in the Shenandoah Valley 20 minutes from Lexington and Staunton.
Terrace/patio

Osceola Mill is a B&B inn located in the Shenandoah Valley 20 minutes from Lexington and Staunton.

10.0 out of 10, Exceptional, (5)
"We had a very pleasant stay. Host graciously made muffins and pastries and had fresh fruit out for us. Room had refrigerator with bottled water, and flavored seltzer water, as well as an Keurig and a Nespresso. Both had a variety of pis choices. Room and bathroom was very spacious. Everything was neat and clean and smelled wonderful. W"
The price is AED 679
AED 880 total
includes taxes & fees
6 Aug - 7 Aug
Osceola Mill is a B&B inn located in the Shenandoah Valley 20 minutes from Lexington and Staunton.
Orchard House B&B
Exterior

Orchard House B&B

3.5 star property
9.2 out of 10, Wonderful, (263)
"The Orchard House is an amazing B&B! From the folks taking care of us to the delicious meals to the views, everything was a 10 out of 10! I highly recommend!"
Orchard House B&B
Osceola Mill is a B&B inn located in the Shenandoah Valley 20 minutes from Lexington and Staunton.
Terrace/patio

Osceola Mill is a B&B inn located in the Shenandoah Valley 20 minutes from Lexington and Staunton.

10.0 out of 10, Exceptional, (1)
"Booked this property for 3 nights as we were attending a VMI graduation and a wedding. This was perfect. Linda made our stay awesome. We did a red-eye in and were able to check in early for a quick nap. The breakfast every morning was sooooo good. She even arranged a tea tasting, which unfortunately we were not able to attend because of our conflicting schedule. The room was large and comfortable. They use StarLink WiFi so no problems with connectivity. Linda's attitude made the visit in...
The price is AED 679
AED 893 total
includes taxes & fees
20 Jul - 21 Jul
Osceola Mill is a B&B inn located in the Shenandoah Valley 20 minutes from Lexington and Staunton.
Osceola Mill is a B&B inn located in the Shenandoah Valley 20 minutes from Lexington and Staunton.
Terrace/patio

Osceola Mill is a B&B inn located in the Shenandoah Valley 20 minutes from Lexington and Staunton.

10.0 out of 10, Exceptional, (1)
The price is AED 679
AED 893 total
includes taxes & fees
20 Jul - 21 Jul
Osceola Mill is a B&B inn located in the Shenandoah Valley 20 minutes from Lexington and Staunton.
Red Hill Bed and Breakfast
BBQ/picnic area

Red Hill Bed and Breakfast

3.0 star property
7.4 out of 10, Good, (24)
"They we closed ... out of business "
Red Hill Bed and Breakfast
Steeles Tavern Manor
Fishing

Steeles Tavern Manor

4.0 star property
9.6 out of 10, Exceptional, (137)
"Lovely country home, very well kept, and with gracious hosts and great breakfasts!"
The price is AED 862
AED 994 total
includes taxes & fees
26 Jul - 27 Jul
Steeles Tavern Manor
Family-friendly 10-bedroom B&B near Wintergreen golf & ski. Great for groups!
Private kitchen

Family-friendly 10-bedroom B&B near Wintergreen golf & ski. Great for groups!

Family-friendly 10-bedroom B&B near Wintergreen golf & ski. Great for groups!
Fenton Inn
Outdoor spa tub

Fenton Inn

3.5 star property
9.8 out of 10, Exceptional, (82)
Fenton Inn
Lexington-Raphine Bed And Bagel
Exterior

Lexington-Raphine Bed And Bagel

2.0 star property
10.0 out of 10, Exceptional, (2)
"I stayed at this place because it was one of the few places still available in the area. I completely lucked out and had the most amazing experience. Not only was everything cozy and clean but we had almost hte entire upstairs to ourself. We had a spacious bathroom with a tub to definitely write home about, a kitchenette area, a common room, and the bedroom. I definitely got my money's worth and more!"
Lexington-Raphine Bed And Bagel
Osceola Mill is a B&B inn located in the Shenandoah Valley 20 minutes from Lexington and Staunton.
Interior

Osceola Mill is a B&B inn located in the Shenandoah Valley 20 minutes from Lexington and Staunton.

The price is AED 1,111
AED 1,459 total
includes taxes & fees
20 Jul - 21 Jul
Osceola Mill is a B&B inn located in the Shenandoah Valley 20 minutes from Lexington and Staunton.
Artist's Historic Farmhouse + Mountain Cideries + Bed & Breakfast, Fire pit
Exterior

Artist's Historic Farmhouse + Mountain Cideries + Bed & Breakfast, Fire pit

Artist's Historic Farmhouse + Mountain Cideries + Bed & Breakfast, Fire pit
The Mark Addy Bed & Breakfast
Front of property - evening/night

The Mark Addy Bed & Breakfast

3.5 star property
7.2 out of 10, Good, (148)
"Great but had trouble finding house. Gps sent us to wrong house"
The Mark Addy Bed & Breakfast
Frederick House
Exterior

Frederick House

2.0 star property
9.8 out of 10, Exceptional, (6)
"Our room was roomy and comfy, I would love to return, the city is perfect. "
Frederick House
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

Searching for B&Bs in Wintergreen?
If you want to find an accommodation with a small number of rooms and a more personalized environment, a bed and breakfast may be the perfect thing for your vacation to Wintergreen. If you're looking to hit the slopes on your trip to Wintergreen, Wintergreen Resort is worth a visit.
How do you know if a B&B is the best choice for you?
With attentive service, opportunities to interact with the owner, and of course a full breakfast to start the day, B&Bs offer a one-of-a-kind setting.
What are the top B&Bs in Wintergreen?
Here are some B&Bs in the surrounding area: The Crossroads Inn: 6 rooms. 14 mi (22.5 km) from the heart of Wintergreen. Enjoy the free full breakfast and designer toiletries. Sugar Tree Inn: 11 rooms. Situated 14.4 mi (23.2 km) from the heart of Wintergreen. Enjoy the free full breakfast and deli. Osceola Mill: 5 rooms. 16.2 mi (26.1 km) from the heart of downtown. Enjoy the local cuisine breakfast and designer toiletries. The Farmhouse at Veritas: 8 rooms. Located 9.5 mi (15.4 km) from the core of Wintergreen. Enjoy the free full breakfast and massage services.
What's the best time of year to book my B&B in Wintergreen?
When you're dreaming of a escape to Wintergreen, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 73°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Wintergreen is 48 inches.
What is there to do in Wintergreen?
When you want to check out some attractions in town, you might consider a visit to Wintergreen Resort and George Washington National Forest. Bold Rock Hard Cider Nellysford Cidery and Stoney Creek Golf Course are also some sites to visit if you want to see more of the area.
How can I get to and around Wintergreen?
Mapping out your trip in and around Wintergreen is easy with these transportation options. Fly into Weyers Cave, VA (SHD-Shenandoah Valley Regional), which is located 26.2 mi (42.1 km) away from the city center. You can also search for flights into Charlottesville-Albemarle Airport (CHO), which is 30.3 mi (48.8 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights.