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Find a Bed and Breakfast in Wintergreen from CA $211

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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

Browse Select Wintergreen B&B

Frederick House
Patrick-27

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!"
The price is CA $211
CA $237 total
includes taxes & fees
Aug 21 - Aug 22
Frederick House
The Crossroads Inn
Pippin Cottage

The Crossroads Inn

5.0 star property
10.0 out of 10, Exceptional, (31)
"Wonderful stay! "
The price is CA $256
CA $293 total
includes taxes & fees
Aug 25 - Aug 26
The Crossroads Inn
Sugar Tree Inn
Room, Private Bathroom (Tye River)

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."
The price is CA $276
CA $318 total
includes taxes & fees
Aug 21 - Aug 22
Sugar Tree Inn
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 CA $451
CA $506 total
includes taxes & fees
Aug 21 - Aug 22
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 CA $311
CA $355 total
includes taxes & fees
Sep 3 - Sep 4
Woodville Bed and Breakfast
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)
"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 CA $320
CA $422 total
includes taxes & fees
Aug 21 - Aug 22
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."
The price is CA $257
CA $297 total
includes taxes & fees
Aug 26 - Aug 27
Osceola Mill
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!
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 CA $256
CA $339 total
includes taxes & fees
Aug 21 - Aug 22
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...
The price is CA $256
CA $339 total
includes taxes & fees
Aug 21 - Aug 22
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 CA $256
CA $339 total
includes taxes & fees
Aug 21 - Aug 22
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!"
The price is CA $375
CA $432 total
includes taxes & fees
Sep 4 - Sep 5
Steeles Tavern Manor
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
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
Fenton Inn
Outdoor spa tub

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.
Interior

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

The price is CA $419
CA $551 total
includes taxes & fees
Aug 26 - Aug 27
Osceola Mill is a B&B inn located in the Shenandoah Valley 20 minutes from Lexington and Staunton.
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
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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Top Wintergreen Hotel Reviews

The Blackburn Inn and Conference Center

The Blackburn Inn and Conference Center

10/10 Excellent
"The Blackburn Inn is a very unique inn and one I would highly recommend. "
christopher 1-night trip
Posted 23 hours ago
The Blackburn Inn and Conference Center