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Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

B&B in Wintergreen

The Crossroads Inn
Pippin Cottage | 1 bedroom, Frette Italian sheets, premium bedding, down comforters

The Crossroads Inn

5.0 star property
10.0 out of 10, Exceptional, (31)
"Wonderful stay! "
$205 nightly
The price is $235
Aug 25 - Aug 26
Total with 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, (102)
"Friendly owners, amazing breakfast and pristine room! EV charger is a very nice added bonus too."
$221 nightly
The price is $255
Aug 24 - Aug 25
Total with taxes and fees
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. "
$249 nightly
The price is $285
Aug 25 - Aug 26
Total with taxes and fees
Woodville Bed and Breakfast
Frederick House
Patrick-27 | Iron/ironing board, free WiFi, bed sheets

Frederick House

3.5 star property
9.4 out of 10, Exceptional, (405)
"Very clean and quiet location but easy to walk to everything. Our hosts and all the staff were so welcoming. The beds were extremely comfortable and the breakfast was delicious and quickly served. A great experience and we would certainly come back!"
$143 nightly
The price is $161
Aug 24 - Aug 25
Total with taxes and fees
Frederick House
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."
$195 nightly
The price is $225
Sep 6 - Sep 7
Total with taxes and fees
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."
$325 nightly
The price is $365
Aug 25 - Aug 26
Total with taxes and fees
The Farmhouse at Veritas
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!"
$262 nightly
The price is $303
Sep 7 - Sep 8
Total with taxes and fees
Steeles Tavern Manor
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)
$212 nightly
The price is $244
Aug 27 - Aug 28
Total with taxes and fees
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"
$211 nightly
The price is $243
Aug 26 - Aug 27
Total with taxes and fees
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)
"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...
$211 nightly
The price is $243
Aug 26 - Aug 27
Total with taxes and fees
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 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!"
$263 nightly
The price is $303
Aug 26 - Aug 27
Total with taxes and fees
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.

$345 nightly
The price is $397
Aug 26 - Aug 27
Total with taxes and fees
Osceola Mill is a B&B inn located in the Shenandoah Valley 20 minutes from Lexington and Staunton.
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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Top Wintergreen Hotel Reviews

Hotel 24 South

Hotel 24 South

10/10 Excellent
"Great Place "
Cary 1-night trip
Posted 9 hours ago
Hotel 24 South

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 $161 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.