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Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 19 B&B in Wintergreen with updated reviews, rates, and availability.

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

Frederick House

3.5 star property
9.4 out of 10, Exceptional, (393)
"Loved exploring the town. "
The price is AED 545
AED 611 total
includes taxes & fees
1 Jun - 2 Jun
Frederick House
The Crossroads Inn
Winery

The Crossroads Inn

4.5 star property
10.0 out of 10, Exceptional, (24)
"Wonderful stay! "
The price is AED 755
AED 862 total
includes taxes & fees
9 Jun - 10 Jun
The Crossroads Inn
The Farmhouse at Veritas
Exterior

The Farmhouse at Veritas

4.0 star property
9.8 out of 10, Exceptional, (30)
"Spectacular stay. You walk in and are immediately greeted and ushered to your room. A lot of staff for just a small place. Nice bottle of wine in your room. Free beer and soda in the fridge. Chocolate cookies always available. Amazing happy hour (all the wine you want plus charcuterie). Super nice place, lots of places to find a private place to read a book. Gorgeous view of the winery/grapes. 7 minute walk to the winery. Great place to meet and chat with other guests. Spectacular white...
The price is AED 1,194
AED 1,341 total
includes taxes & fees
4 Jun - 5 Jun
The Farmhouse at Veritas
Osceola Mill
Exterior

Osceola Mill

2.0 star property
10.0 out of 10, Exceptional, (3)
"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 656
AED 756 total
includes taxes & fees
1 Jun - 2 Jun
Osceola Mill
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, (99)
"This was a beautiful, quiet and serene setting as a stop over on our way to our son’s graduation in Lynchburg. Brenda and Kevin were very accommodating and kind. The place was so quaint and full of character! Loved our room and the bed was so comfy!"
The price is AED 688
AED 793 total
includes taxes & fees
14 Jun - 15 Jun
Sugar Tree Inn
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
2 Jun - 3 Jun
Woodville Bed and Breakfast
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 810
AED 1,065 total
includes taxes & fees
9 Jun - 10 Jun
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, (262)
"Friendly staff and the breakfasts were exceptional. "
Orchard House B&B
Red Hill Bed and Breakfast
Interior

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
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 648
AED 849 total
includes taxes & fees
1 Jun - 2 Jun
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.
Interior

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

10.0 out of 10, Exceptional, (4)
"Such a great hostess! Lovely accommodations, great breakfast! "
The price is AED 648
AED 849 total
includes taxes & fees
1 Jun - 2 Jun
Osceola Mill is a B&B inn located in the Shenandoah Valley 20 minutes from Lexington and Staunton.
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!"
Steeles Tavern Manor
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.

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 648
AED 849 total
includes taxes & fees
1 Jun - 2 Jun
Osceola Mill is a B&B inn located in the Shenandoah Valley 20 minutes from Lexington and Staunton.
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 1,061
AED 1,392 total
includes taxes & fees
9 Jun - 10 Jun
Osceola Mill is a B&B inn located in the Shenandoah Valley 20 minutes from Lexington and Staunton.
Fenton Inn
Outdoor spa tub

Fenton Inn

3.5 star property
9.8 out of 10, Exceptional, (82)
Fenton Inn
Artist's Historic Farmhouse + Mountain Cideries + Bed & Breakfast, Fire pit
Interior

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
Porch

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 downtown core. Enjoy the free full breakfast and winery. The Farmhouse at Veritas: 8 rooms. Situated 9.5 mi (15.4 km) from the heart of Wintergreen. Enjoy the free full breakfast and massage services. Osceola Mill: 5 rooms. 16.2 mi (26.1 km) from the heart of downtown. Enjoy the local cuisine breakfast and designer toiletries. Sugar Tree Inn: 11 rooms. Located 14.4 mi (23.2 km) from the core of Wintergreen. Enjoy the free full breakfast and deli.
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.