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Check prices for these dates

Next weekend
Jul 4 - Jul 6
In two weeks
Jul 11 - Jul 13
In one month
Jul 25 - Jul 27
In two months
Aug 22 - Aug 24

Compare 23 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, (395)
"Loved exploring the town. "
$168 nightly
The price is $189
Jul 24 - Jul 25
Total includes taxes and fees
Frederick House
The Crossroads Inn
Winery

The Crossroads Inn

4.5 star property
10.0 out of 10, Exceptional, (27)
"Wonderful stay! "
$174 nightly
The price is $199
Jun 30 - Jul 1
Total includes taxes and fees
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, (100)
"Friendly owners, amazing breakfast and pristine room! EV charger is a very nice added bonus too."
$233 nightly
The price is $269
Jun 26 - Jun 27
Total includes taxes and fees
Sugar Tree Inn
The Farmhouse at Veritas
Exterior

The Farmhouse at Veritas

4.0 star property
9.8 out of 10, Exceptional, (31)
"Nice location a staff. Dining in the vineyard was excellent."
$325 nightly
The price is $365
Jun 30 - Jul 1
Total includes taxes and fees
The Farmhouse at Veritas
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)
"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!"
$252 nightly
The price is $290
Jun 29 - Jun 30
Total includes taxes and fees
Osceola Mill is a B&B inn located in the Shenandoah Valley 20 minutes from Lexington and Staunton.
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."
$219 nightly
The price is $252
Jun 28 - Jun 29
Total includes taxes and fees
Osceola Mill
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. "
$249 nightly
The price is $285
Jun 29 - Jun 30
Total includes taxes and fees
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.

10.0 out of 10, Exceptional, (5)
"Linda is creating a true gem in her property and experiences for guest stays. We were the only couple staying the night we were there and treated to a beautiful and delicious breakfast spread in the morning. She gave us space but was also very personable and delightful to talk with. I wish we had more time to spend there and would love to go back as the property and guest experiences continue to evolve!"
$201 nightly
The price is $232
Jun 29 - Jun 30
Total includes taxes and fees
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)
"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.
Interior

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

$201 nightly
The price is $232
Jun 29 - Jun 30
Total includes taxes and fees
Osceola Mill is a B&B inn located in the Shenandoah Valley 20 minutes from Lexington and Staunton.
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.

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...
$201 nightly
The price is $232
Jun 29 - Jun 30
Total includes taxes and fees
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
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.

$329 nightly
The price is $379
Jun 29 - Jun 30
Total includes taxes and fees
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
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
Harmony Haill Bed and Breakfast
Front of property

Harmony Haill Bed and Breakfast

2.0 star property
Harmony Haill Bed and Breakfast
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

What is the nightly rate for a Bed and Breakfast in Wintergreen?
Prices for B&Bs in Wintergreen often vary, but you can find a great deal from $189 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Wintergreen B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed & Breakfast in Wintergreen?
January is the most popular month to book a B&B in Wintergreen, coinciding with the peak travel season that spans from December to February. During this time, the resort is bustling with visitors eager to embrace winter sports and the breathtaking scenery of the Blue Ridge Mountains. With temperatures typically ranging from the mid-20s to low 40s Fahrenheit, it's an ideal setting for skiing, snowboarding, and cozying up by the fireplace after a day on the slopes.
The winter months offer an abundance of outdoor activities, making it a prime time for those who appreciate a lively atmosphere filled with fellow adventurers. You can also take advantage of nearby attractions like scenic hiking trails and charming local shops, all while enjoying the crisp mountain air.
If you're looking for a more budget-friendly time to visit, consider planning your trip in May. This month ushers in beautiful spring weather, with temperatures rising into the 50s and 60s Fahrenheit, making it great for hiking and enjoying the blooming landscape without the crowds. May offers a chance to experience the tranquility of Wintergreen and its surroundings, allowing you to immerse yourself in nature's beauty at your own pace.
What is the difference between a Wintergreen Bed & Breakfast and a hotel?
Every Wintergreen B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Wintergreen B&Bs.