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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

B&B in Wintergreen

Property entrance
The Crossroads Inn

The Crossroads Inn

5.0 star property
North Garden
10.0 out of 10, Exceptional, (42)
"The staff were excellent. Very friendly, great hospitality. We will definitely book again."
United States
Sharon
The Crossroads Inn
Patrick-27 | Iron/ironing board, free WiFi, bed sheets
Frederick House

Frederick House

3.5 star property
Staunton
9.4 out of 10, Exceptional, (427)
"The room was spotless and the breakfast was great. "
United States
Paula
The price is AED 433
AED 485 total
includes taxes & fees
5 Jan - 6 January 2026
Frederick House
Exterior
The Farmhouse at Veritas

The Farmhouse at Veritas

4.0 star property
Afton
9.8 out of 10, Exceptional, (33)
"Nice location a staff. Dining in the vineyard was excellent."
United States
John
The price is AED 808
AED 907 total
includes taxes & fees
5 Jan - 6 January 2026
The Farmhouse at Veritas
Fishing
Steeles Tavern Manor

Steeles Tavern Manor

4.0 star property
Raphine
9.6 out of 10, Exceptional, (140)
"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 AED 862
AED 994 total
includes taxes & fees
10 Dec - 11 Dec
Steeles Tavern Manor
Terrace/patio
Osceola Mill

Osceola Mill

2.0 star property
Raphine
10.0 out of 10, Exceptional, (6)
"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."
United Kingdom
Adrian
The price is AED 599
AED 691 total
includes taxes & fees
21 Dec - 22 Dec
Osceola Mill
1 bedroom, WiFi, bed sheets
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)
"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 AED 643
AED 818 total
includes taxes & fees
10 Dec - 11 Dec
Bed&Breakfast in a 1795 Log Cabin on working farm, Margaret Baylor-Swoope suite
Room, Private Bathroom (Tye River) | Premium bedding, pillowtop beds, individually decorated
Sugar Tree Inn

Sugar Tree Inn

3.5 star property
Vesuvius
9.6 out of 10, Exceptional, (107)
"Friendly owners, amazing breakfast and pristine room! EV charger is a very nice added bonus too."
United States
Andrei
The price is AED 737
AED 850 total
includes taxes & fees
20 Dec - 21 Dec
Sugar Tree Inn
Front of property
Harmony Haill Bed and Breakfast

Harmony Haill Bed and Breakfast

2.0 star property
Arrington
6.0 out of 10, (1)
"Unique in appearance and decor. Did not like lack of heat downstairs. "
United States
marsha
The price is AED 713
AED 800 total
includes taxes & fees
10 Dec - 11 Dec
Harmony Haill Bed and Breakfast
Seasonal outdoor pool
Woodville Bed and Breakfast

Woodville Bed and Breakfast

4.0 star property
Esmont
10.0 out of 10, Exceptional, (55)
"Awesome place to stay and the people there are so friendly and welcoming! I’d definitely recommend visiting again "
United States
Patrick
Woodville Bed and Breakfast
Property grounds
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)
"We had a lovely weekend at Meadowcroft and hope to visit again. The room was well appointed, comfortable and clean, the scenery around the Inn was gorgeous, and the owner was kind and engaging. "
United States
Ellie R.
The price is AED 643
AED 818 total
includes taxes & fees
10 Dec - 11 Dec
Stay in a 1795 Log Cabin on a working farm, George Washington Swoope, Jr Suite
Property grounds
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)
"Wonderful hosts, treated me like family! Very clean, spacious room, filled with sunlight and amenities."
United States
Margaret
The price is AED 735
AED 936 total
includes taxes & fees
10 Dec - 11 Dec
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)
"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 AED 1,083
AED 1,378 total
includes taxes & fees
10 Dec - 11 Dec
Bed & Breakfast in a 1795 Log Cabin on working farm, George Washington, Sr Suite
Property grounds
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, (18)
"Perfect place to escape. Gorgeous functioning farm property with rolling hills, beautiful sunsets and a sky full of stars at night. Owner was more than accommodating and the room was cozy and comfortable. Enjoy the jams and pickles made on site as well!"
United States
Henry H.
The price is AED 1,377
AED 1,754 total
includes taxes & fees
10 Dec - 11 Dec
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
"The host was exceptionally friendly, informative and helpful. I had questions for the host before booking. She answered our questions quickly and was always gracious. When we asked if there was a mixer and specific baking dish, she said that she would order one for us. That was above and beyond our expectations. The condo is lovely, was clean and ready for guests. The furnishings are stylish, clean and comfortable. The beds were comfortable as well. The view!!! We took so many pictures of the beautiful view from the condo. That expansive view inspired us to go hiking. We found two great hiking trails close to the condo. When we got back from the hike, we used the unlimited firewood to have a wonderful fire in the fireplace. We played games and enjoyed watching something together on the tv over the fireplace. On Thanksgiving, we used the kitchen to make a wonderful meal and we dined at the dining table enjoying the view. There is a small market on the mountain if you need any last minute groceries. I encourage you to stay at this condo. Our family had a great time at this condo. Maureen is a wonderful host."
Mary G. 2-night trip
Posted 5 days ago
Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!

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: Osceola Mill: 5 rooms. 16.2 mi (26.1 km) from the downtown core. Enjoy the local cuisine breakfast and designer toiletries. The Crossroads Inn: 6 rooms. Situated 14 mi (22.5 km) from the heart of Wintergreen. Enjoy the free full breakfast and designer toiletries. Steeles Tavern Manor: 5 rooms. 16.8 mi (27 km) from the heart of downtown. Enjoy the free full breakfast and in-room pools. Harmony Haill Bed and Breakfast: 6 rooms. Located 14.1 mi (22.7 km) from the core of Wintergreen. Enjoy the local cuisine breakfast and hot tubs.
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.