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Check prices for these dates

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

Frederick House

3.5 star property
9.4 out of 10, Exceptional, (392)
"Lovely room, convenient location! "
The price is SAR 551
SAR 617 total
includes taxes & fees
29 May - 30 May
Frederick House

The Crossroads Inn

4.5 star property
10.0 out of 10, Exceptional, (24)
"Wonderful stay! "
The price is SAR 771
SAR 881 total
includes taxes & fees
1 Jun - 2 Jun
The Crossroads Inn

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 SAR 1,219
SAR 1,369 total
includes taxes & fees
4 Jun - 5 Jun
The Farmhouse at Veritas

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 SAR 662
SAR 763 total
includes taxes & fees
29 May - 30 May
Osceola Mill

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 SAR 702
SAR 810 total
includes taxes & fees
11 Jun - 12 Jun
Sugar Tree Inn

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 SAR 934
SAR 1,068 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.

The price is SAR 827
SAR 1,088 total
includes taxes & fees
29 May - 30 May
Osceola Mill is a B&B inn located in the Shenandoah Valley 20 minutes from Lexington and Staunton.

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

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

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 SAR 662
SAR 867 total
includes taxes & fees
29 May - 30 May
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.

The price is SAR 662
SAR 867 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

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.

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 SAR 571
SAR 745 total
includes taxes & fees
14 Jun - 15 Jun
Osceola Mill is a B&B inn located in the Shenandoah Valley 20 minutes from Lexington and Staunton.

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

Fenton Inn

3.5 star property
9.8 out of 10, Exceptional, (82)
Fenton Inn

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

The price is SAR 1,083
SAR 1,426 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.

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

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

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. Sugar Tree Inn: 11 rooms. 14.4 mi (23.2 km) from the heart of downtown. Enjoy the free full breakfast and deli. Osceola Mill: 5 rooms. Located 16.2 mi (26.1 km) from the core of Wintergreen. Enjoy the local cuisine breakfast and designer toiletries.
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.