A dense forest with a variety of coniferous trees and a small clearing with grass and a few scattered trees.

Book Wintergreen Bed & Breakfast

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18
In one month
Oct 30 - Nov 1
In two months
Nov 27 - Nov 29

Our top choices for Wintergreen bed & breakfast

A wooden porch with two rocking chairs and a white fence.

1. The Farmhouse at Veritas

The Farmhouse at Veritas
4.0 star property
Afton
9.8 out of 10, Exceptional, (37 reviews)
"We are very grateful for the stay and for all the kind treatment and the beautiful place."
United States
Carlos
$463 nightly
The price is $515
Oct 14 - Oct 15
Total with taxes and fees
The Farmhouse at Veritas
A gravel path leading to a large house surrounded by lush greenery and white hydrangea bushes.

2. The Crossroads Inn

The Crossroads Inn
5.0 star property
North Garden
9.8 out of 10, Exceptional, (70 reviews)
"Would stay there again, excellent place."
United States
William
$205 nightly
The price is $235
Oct 7 - Oct 8
Total with taxes and fees
The Crossroads Inn
A cozy room with a wooden interior, a bookshelf, a dining table with chairs, and a view of a grassy area with trees.

3. 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
$197 nightly
The price is $221
Oct 2 - Oct 3
Total with taxes and fees
Harmony Haill Bed and Breakfast
A room with a large window, a bathtub, a wine bottle, and a glass of wine on a wooden tray.

4. Sugar Tree Inn

Sugar Tree Inn
3.5 star property
Vesuvius
9.6 out of 10, Exceptional, (111 reviews)
"The food was fresh and delicious. Brenda and Kevin made our stay the perfect getaway!"
United States
Jessica
$263 nightly
The price is $303
Oct 5 - Oct 6
Total with taxes and fees
Sugar Tree Inn
A spacious room with a large window, a round table with a lace tablecloth, and a chandelier.

5. Steeles Tavern Manor

Steeles Tavern Manor
4.0 star property
Raphine
9.6 out of 10, Exceptional, (146 reviews)
"The staff, the food, the room and the attention to details and little touches made my stay exceptional. We WILL be back! The staff really go above and beyond to accommodate their guests and make them feel welcome."
United States
Maureen
$232 nightly
The price is $267
Oct 26 - Oct 27
Total with taxes and fees
Steeles Tavern Manor
A living room with a sofa, a table, a chair, a fireplace, and curtains.

6. Frederick House

Frederick House
3.5 star property
Staunton
9.4 out of 10, Exceptional, (490 reviews)
"Great location! Helpful staff, delicious breakfast and the quietest room we have stayed in."
United States
Leigh
$159 nightly
The price is $178
Oct 5 - Oct 6
Total with taxes and fees
Frederick House
A balcony with a table set for a meal, two chairs, and a scenic view of a vineyard.

7. Woodville Bed and Breakfast

Woodville Bed and Breakfast
4.0 star property
Esmont
10.0 out of 10, Exceptional, (57 reviews)
"Awesome place to stay and the people there are so friendly and welcoming! I’d definitely recommend visiting again "
United States
Patrick
$249 nightly
The price is $285
Oct 4 - Oct 5
Total with taxes and fees
Woodville Bed and Breakfast
A log cabin-style building with a central entrance, surrounded by a well-maintained lawn and trees.

8. 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, (47 reviews)
"Clean, out of the way, quiet. Owner was great. The history is amazing"
United States
heather
$200 nightly
The price is $223
Oct 4 - Oct 5
Total with taxes and fees
Bed&Breakfast in a 1795 Log Cabin on working farm, Margaret Baylor-Swoope suite
A log cabin-style building with a central entrance, surrounded by a well-maintained lawn and trees.

9. 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, (11 reviews)
"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.
$198 nightly
The price is $220
Oct 4 - Oct 5
Total with taxes and fees
Stay in a 1795 Log Cabin on a working farm, George Washington Swoope, Jr Suite
A log cabin-style building with a central entrance, surrounded by a well-maintained lawn and trees.

10. 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, (12 reviews)
"it was a quiet weekend, host was genial and had some great stories at breakfast. "
United States
Tom C.
$243 nightly
The price is $270
Oct 5 - Oct 6
Total with taxes and fees
Bed & Breakfast in a 1795 Log Cabin on working farm, Eliza Trent Swoope Suite
A cozy outdoor seating area with a stone fireplace, metal tables, and blue and white patterned tableware.

11. 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.
$337 nightly
The price is $375
Oct 4 - Oct 5
Total with taxes and fees
Bed & Breakfast in a 1795 Log Cabin on working farm, George Washington, Sr 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Wintergreen Hotel Reviews

Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants

10/10 Excellent
"This well-equipped condo was central to the market and restaurants. We enjoyed the fireplace and the deck."
Lynne F. 4-night trip
Posted 2 days ago
Wintergreen Condo -Steps to Ski and restaurants

Find out more about Wintergreen

Wintergreen B&B information

Number of reviews
948
Accommodation
0 B&B
Lowest Price
$178
Highest Price
$515

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 $178 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.

Explore a world of travel with Expedia