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Book Wintergreen Bed & Breakfast

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Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11
In one month
Jan 23 - Jan 25
In two months
Feb 20 - Feb 22

Our top choices for Wintergreen bed & breakfast

Winery
The Crossroads Inn

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
$185 nightly
The price is $211
Dec 24 - Dec 25
Total with taxes and fees
The Crossroads Inn
Patrick-27 | Iron/ironing board, free WiFi, bed sheets
Frederick House

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
$123 nightly
The price is $138
Jan 11 - Jan 12, 2026
Total with taxes and fees
Frederick House
Exterior
Osceola Mill

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
$154 nightly
The price is $178
Dec 30 - Dec 31
Total with taxes and fees
Osceola Mill
Porch
The Farmhouse at Veritas

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
$220 nightly
The price is $247
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Farmhouse at Veritas
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

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.
$199 nightly
The price is $221
Dec 24 - Dec 25
Total with taxes and fees
Stay in a 1795 Log Cabin on a working farm, George Washington Swoope, Jr Suite
Room, Private Bathroom (Sugar Tree Country) | Deep soaking bathtub
Sugar Tree Inn

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
$223 nightly
The price is $257
Dec 26 - Dec 27
Total with taxes and fees
Sugar Tree Inn
Property entrance
Steeles Tavern Manor

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
$235 nightly
The price is $271
Jan 4 - Jan 5, 2026
Total with taxes and fees
Steeles Tavern Manor
Free daily local cuisine breakfast
Harmony Haill Bed and Breakfast

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
$194 nightly
The price is $218
Dec 25 - Dec 26
Total with taxes and fees
Harmony Haill Bed and Breakfast
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

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
$228 nightly
The price is $254
Dec 24 - Dec 25
Total with taxes and fees
Bed & Breakfast in a 1795 Log Cabin on working farm, Eliza Trent Swoope Suite
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

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
$199 nightly
The price is $221
Dec 24 - Dec 25
Total with taxes and fees
Bed&Breakfast in a 1795 Log Cabin on working farm, Margaret Baylor-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

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.
$336 nightly
The price is $374
Dec 24 - Dec 25
Total with taxes and fees
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

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.
$426 nightly
The price is $474
Dec 24 - Dec 25
Total with taxes and fees
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

Wintergreen. Sunset Vista Villa - Sea of Mountains

Wintergreen. Sunset Vista Villa - Sea of Mountains

10/10 Excellent
"Great stay with a fabulous view! Very cozy and comfortable! We had a wonderful little getaway!"
Vicki E. 1-night trip
Posted 3 days ago
Wintergreen. Sunset Vista Villa - Sea of Mountains

Find out more about Wintergreen

Wintergreen B&B information

Number of reviews
692
Accommodation
0 B&B
Lowest Price
$138
Highest Price
$474

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 $138 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.

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