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Compare 21 B&B in Wintergreen with updated reviews, rates, and availability.

Frederick House

3.5 star property
9.4 out of 10, Exceptional, (387)
"Beautiful and charming old home with large rooms and nice decor. Clean and well kept. Breakfast was tasty with several interesting choices and a side of fresh fruit. Perfectly located to enjoy and explore Staunton's fun downtown. "
The price is AED 591
AED 661 total
includes taxes & fees
9 Mar - 10 Mar
Frederick House

The Farmhouse at Veritas

4.0 star property
9.8 out of 10, Exceptional, (29)
"An amazing experience, would definitely recommend."
The price is AED 1,194
AED 1,340 total
includes taxes & fees
12 Mar - 13 Mar
The Farmhouse at Veritas

The Crossroads Inn

4.5 star property
10.0 out of 10, Exceptional, (22)
"Our stay was wonderful! Accommodations were beautiful and the breakfast spread was delicious. We usually are not motivated to return to a bed and breakfast, but this one would be worth repeating. "
The price is AED 755
AED 862 total
includes taxes & fees
9 Mar - 10 Mar
The Crossroads Inn

Sugar Tree Inn

3.5 star property
9.4 out of 10, Exceptional, (96)
"The property is really unique. We liked it and highly recommend."
The price is AED 621
AED 717 total
includes taxes & fees
20 Mar - 21 Mar
Sugar Tree Inn

Woodville Bed and Breakfast

4.0 star property
10.0 out of 10, Exceptional, (50)
"Excellent stay. Typical Virginia style but modern amenities. Awesome host. The best breakfast. "
The price is AED 915
AED 1,045 total
includes taxes & fees
9 Mar - 10 Mar
Woodville Bed and Breakfast

Red Hill Bed and Breakfast

3.0 star property
8.2 out of 10, Very Good, (21)
"Wonderful stay! "
The price is AED 1,102
AED 1,237 total
includes taxes & fees
7 Mar - 8 Mar
Red Hill Bed and Breakfast

Osceola Mill

2.0 star property
10.0 out of 10, Exceptional, (1)
The price is AED 575
AED 663 total
includes taxes & fees
7 Mar - 8 Mar
Osceola Mill

Osceola Mill - Reopening!

10.0 out of 10, Exceptional, (2)
"Linda is creating a true gem in her property and experiences for guest stays. We were the only couple staying the night we were there and treated to a beautiful and delicious breakfast spread in the morning. She gave us space but was also very personable and delightful to talk with. I wish we had more time to spend there and would love to go back as the property and guest experiences continue to evolve!"
The price is AED 639
AED 834 total
includes taxes & fees
7 Mar - 8 Mar
Osceola Mill - Reopening!

Osceola Mill - Reopening!

The price is AED 639
AED 834 total
includes taxes & fees
7 Mar - 8 Mar
Osceola Mill - Reopening!

Orchard House B&B

3.5 star property
9.2 out of 10, Wonderful, (261)
"Friendly staff and the breakfasts were exceptional. "
Orchard House B&B

Steeles Tavern Manor

4.0 star property
9.6 out of 10, Exceptional, (137)
"Wonderful visit. Beautiful, clean room, delicious breakfast, friendly and accommodating hosts. Lovely property to explore!"
Steeles Tavern Manor

Osceola Mill Bed & Breakfast Inn & Cabin

The price is AED 639
AED 834 total
includes taxes & fees
7 Mar - 8 Mar
Osceola Mill Bed & Breakfast Inn & Cabin

Fenton Inn

3.5 star property
9.8 out of 10, Exceptional, (82)
"Fenton Inn is a cute little bed and breakfast. The service and food were both great. Our room was comfortable and exactly as described. I would highly recommend it for anyone who wants to get away for a weekend."
Fenton Inn

Osceola Mill Bed & Breakfast Inn & Cabin

The price is AED 1,212
AED 1,596 total
includes taxes & fees
13 Mar - 14 Mar
Osceola Mill Bed & Breakfast Inn & Cabin

Artist's Historic Farmhouse + Mountain Cideries + Bed & Breakfast, Fire pit

Artist's Historic Farmhouse + Mountain Cideries + Bed & Breakfast, Fire pit

Osceola Mill Bed & Breakfast Inn and Cabin

The price is AED 926
AED 1,211 total
includes taxes & fees
8 Mar - 9 Mar
Osceola Mill Bed & Breakfast Inn and Cabin

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

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

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
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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Other property types in Wintergreen

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

9.6 out of 10, Exceptional, (294)
"Perfect ski weekend rental. Great communication with Scott. Kitchen is nicely equipped. Hot tub is hot and was perfect for soaking and relaxing after a great day of skiing."
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

10.0 out of 10, Exceptional, (309)
"Clean, cozy,and convenient!"
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Wintergreen Condo -Steps to Ski and restaurants

9.8 out of 10, Exceptional, (10)
"Perfect location. Easy to walk to the resort. Clean, cozy, and quiet. Thanks for a great stay!"
The price is AED 349
AED 874 total
includes taxes & fees
9 Mar - 10 Mar
Wintergreen Condo -Steps to Ski and restaurants
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.

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 looking to hit the slopes on your trip to Wintergreen, Wintergreen Resort is worth a visit.
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 Farmhouse at Veritas: 8 rooms. 9.5 mi (15.4 km) from the downtown core. Enjoy the free full breakfast and massage services. The Crossroads Inn: 6 rooms. Situated 14 mi (22.5 km) from the heart of Wintergreen. Enjoy the free full breakfast and winery. Sugar Tree Inn: 11 rooms. 14.4 mi (23.2 km) from the heart of downtown. Enjoy the free full breakfast and deli. Woodville Bed and Breakfast: 5 rooms. Located 16.9 mi (27.2 km) from the core of Wintergreen. Enjoy the free cooked breakfast and winery.
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?
When you want to check out some attractions in town, you might consider a visit to Wintergreen Resort and George Washington National Forest. Bold Rock Hard Cider Nellysford Cidery and Stoney Creek Golf Course are also some sites to visit 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.