Find a Bed and Breakfast in Wintergreen from CA $202

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Check prices for these dates

Next weekend
Feb 13 - Feb 15
In two weeks
Feb 20 - Feb 22
In one month
Mar 6 - Mar 8
In two months
Apr 3 - Apr 5

Our top choices for Wintergreen bed & breakfast

Terrace/patio

Frederick House

Frederick House
3.5 star property
Staunton
9.4 out of 10, Exceptional, (428 reviews)
"The room was spotless and the breakfast was great. "
United States
Paula
The price is CA $180
CA $202 total
includes taxes & fees
Feb 22 - Feb 23
Frederick House
Winery

The Crossroads Inn

The Crossroads Inn
5.0 star property
North Garden
10.0 out of 10, Exceptional, (44 reviews)
"The staff were excellent. Very friendly, great hospitality. We will definitely book again."
United States
Sharon
The Crossroads Inn
Exterior

Osceola Mill

Osceola Mill
2.0 star property
Raphine
10.0 out of 10, Exceptional, (9 reviews)
"Fun place to stay. Thanks!"
United States
Peter
The price is CA $203
CA $235 total
includes taxes & fees
Feb 16 - Feb 17
Osceola Mill
Porch

The Farmhouse at Veritas

The Farmhouse at Veritas
4.0 star property
Afton
9.8 out of 10, Exceptional, (33 reviews)
"Nice location a staff. Dining in the vineyard was excellent."
United States
John
The price is CA $301
CA $338 total
includes taxes & fees
Feb 9 - Feb 10
The Farmhouse at Veritas
Property entrance

Steeles Tavern Manor

Steeles Tavern Manor
4.0 star property
Raphine
9.6 out of 10, Exceptional, (141 reviews)
"Sandra made sure we know the code for the door if we got oj late but was there to meet us when we got in. She’s so accommodating and the inn is lovely!"
United States
Will
The price is CA $353
CA $407 total
includes taxes & fees
Feb 17 - Feb 18
Steeles Tavern Manor
Exterior

Stay in a 1795 Log Cabin on a working farm, George Washington Swoope, Jr Suite

Stay in a 1795 Log Cabin on a working farm, George Washington Swoope, Jr Suite
Swoope
10.0 out of 10, Exceptional, (10 reviews)
"Welcoming, beautiful, and peaceful!Such a wonderful place to stay everything was spotless, and the rustic décor made it feel cozy and inviting. The home-cooked breakfast was absolutely delicious, and the owner and staff were so kind and friendly. I only wish we could have stayed longer!"
United States
Jennifer Z.
The price is CA $239
CA $301 total
includes taxes & fees
Feb 9 - Feb 10
Stay in a 1795 Log Cabin on a working farm, George Washington Swoope, Jr Suite
Free daily local cuisine breakfast

Harmony Haill Bed and Breakfast

Harmony Haill Bed and Breakfast
2.0 star property
Arrington
8.0 out of 10, Very good, (2 reviews)
"Harmony Hill was a great place to spend a quiet night after exploring the area. It was very clean, and the hosts Mary and Bill were kind and attentive. Breakfast was abundant and well prepared, and my husband's dietary needs were well attended to. We enjoyed!"
United States
Emily
The price is CA $263
CA $296 total
includes taxes & fees
Feb 9 - Feb 10
Harmony Haill Bed and Breakfast
Room, Private Bathroom (Sugar Tree Country) | Deep soaking bathtub

Sugar Tree Inn

Sugar Tree Inn
3.5 star property
Vesuvius
9.6 out of 10, Exceptional, (107 reviews)
"Friendly owners, amazing breakfast and pristine room! EV charger is a very nice added bonus too."
United States
Andrei
The price is CA $274
CA $316 total
includes taxes & fees
Feb 15 - Feb 16
Sugar Tree Inn
Terrace/patio

Woodville Bed and Breakfast

Woodville Bed and Breakfast
4.0 star property
Esmont
10.0 out of 10, Exceptional, (55 reviews)
"Awesome place to stay and the people there are so friendly and welcoming! I’d definitely recommend visiting again "
United States
Patrick
The price is CA $306
CA $350 total
includes taxes & fees
Feb 17 - Feb 18
Woodville Bed and Breakfast
Exterior

Bed&Breakfast in a 1795 Log Cabin on working farm, Margaret Baylor-Swoope suite

Bed&Breakfast in a 1795 Log Cabin on working farm, Margaret Baylor-Swoope suite
Swoope
10.0 out of 10, Exceptional, (36 reviews)
"The place is wonderful. It is so peaceful, surrounded by nature (field, trees, flowers and sheep). Our room was super clear, spacious and very comfortable. No TV in the room which is a blessing! Breakfast was plentiful and we were happy to chat with our host Bill who is very knowledgeable about the area's history and culture. Staunton has a lot to offer and is a nice destination. I would come back in a heartbeat! "
United States
Sabine
The price is CA $239
CA $301 total
includes taxes & fees
Feb 9 - Feb 10
Bed&Breakfast in a 1795 Log Cabin on working farm, Margaret Baylor-Swoope suite
Exterior

Bed & Breakfast in a 1795 Log Cabin on working farm, Eliza Trent Swoope Suite

Bed & Breakfast in a 1795 Log Cabin on working farm, Eliza Trent Swoope Suite
Swoope
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful place and setting. Very relaxed and friendly host team."
United States
Brian H.
The price is CA $274
CA $347 total
includes taxes & fees
Feb 9 - Feb 10
Bed & Breakfast in a 1795 Log Cabin on working farm, Eliza Trent Swoope Suite
Dining

Bed & Breakfast in a 1795 Log Cabin on working farm, George Washington, Sr Suite

Bed & Breakfast in a 1795 Log Cabin on working farm, George Washington, Sr Suite
Swoope
10.0 out of 10, Exceptional, (2 reviews)
"We pulled in at 5pm and were promptly greeted by Bill (Judie's husband). He checked us in and gave us a brief tour of the building and the farm. Our room was spacious and well appointed, and the bathroom with the slipper claw foot tub was very nice. It was modern but maintained much of the character we appreciate. Breakfast was excellent, and included an impromptu lesson from Bill on (re)construction of the premises. Unfortunately Judie was under the weather, so we didn't get a chance to meet...
United States
charles a.
The price is CA $403
CA $511 total
includes taxes & fees
Feb 9 - Feb 10
Bed & Breakfast in a 1795 Log Cabin on working farm, George Washington, Sr Suite
Exterior

Bed&Breakfast in a 1795 Log Cabin on working farm, Honorable Jacob Swoope Suite

Bed&Breakfast in a 1795 Log Cabin on working farm, Honorable Jacob Swoope Suite
Swoope
10.0 out of 10, Exceptional, (19 reviews)
"Phenomenal in every way! The beautiful and cozy log cabin with a beautiful big copper tub, the fireplace, the comfy bed…… Bill and the ladies were so kind and personable! And breakfasts were scrumptious! The inn made a wonderful base for doing all the fun things we planned for our 5 day stay. Sure hope to be back! "
United States
Lisa G.
The price is CA $513
CA $650 total
includes taxes & fees
Feb 9 - Feb 10
Bed&Breakfast in a 1795 Log Cabin on working farm, Honorable Jacob Swoope Suite
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

Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!

Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!

10/10 Excellent
"Fantastic views! Gorgeous setting. Comfortable beds and furniture. Spacious and well-appointed. We will be back soon. Maureen is also a delight and made us feel right at home. "
Jacquelyn L. 2-night trip
Posted 1 day ago
Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!

Find out more about Wintergreen

Wintergreen B&B information

Number of reviews
760
Accommodation
0 B&B
Lowest Price
CA $202
Highest Price
CA $650

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 interested in playing some golf on your trip, Stoney Creek Golf Course is a good spot to tee off.
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 designer toiletries. Osceola Mill: 5 rooms. Situated 16.2 mi (26.1 km) from the heart of Wintergreen. Enjoy the local cuisine breakfast and designer toiletries. The Farmhouse at Veritas: 8 rooms. 9.5 mi (15.4 km) from the heart of downtown. Enjoy the free full breakfast and massage services. Steeles Tavern Manor: 5 rooms. Located 16.8 mi (27 km) from the core of Wintergreen. Enjoy the free full breakfast and in-room pools.
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?
If you're looking for some activities to entertain you on your trip, consider visiting Stoney Creek Golf Course and Wintergreen Resort. You might put Bold Rock Hard Cider Nellysford Cidery and Raven's Roost Overlook on your list 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.

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