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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, (384)
"Lovely place - stayed in Bowers 21 - large room, very nicely appointed, comfortable bed. Shower was tiny, but great water pressure, plenty of hot water. Included breakfast was very good. "
The price is AED 496
AED 555 total
includes taxes & fees
3 Feb - 4 Feb
Frederick House

The Crossroads Inn

4.5 star property
10.0 out of 10, Exceptional, (20)
"This was our second time here. It will definitely become an annual stay. Our favorite place to stay in Charlottesville and our favorite Virginia winery Pippin Hill. "
The price is AED 679
AED 776 total
includes taxes & fees
3 Feb - 4 Feb
The Crossroads Inn

The Farmhouse at Veritas

4.0 star property
9.8 out of 10, Exceptional, (28)
"An amazing experience, would definitely recommend."
The price is AED 808
AED 907 total
includes taxes & fees
3 Feb - 4 Feb
The Farmhouse at Veritas

Osceola Mill

2.0 star property
10.0 out of 10, Exceptional, (1)
The price is AED 515
AED 594 total
includes taxes & fees
6 Feb - 7 Feb
Osceola Mill

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
27 Feb - 28 Feb
Red Hill Bed and Breakfast

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 690
AED 796 total
includes taxes & fees
6 Feb - 7 Feb
Sugar Tree Inn

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 - Reopening!

10.0 out of 10, Exceptional, (1)
"My husband and I decided to take a short road trip to Natural Bridge for Thanksgiving, and boy there were no regrets! Linda and her family are absolutely lovely and personable. This cabin is a 1800 flour mill which was converted into a B&B. The architecture was preserved and the wood beans and accents are beautiful. Linda and her husband have done a great job preserving the history of this mill. Breakfast every morning was so delicious. I had the best homemade cinnamon rolls I’ve ever had in my...
The price is AED 545
AED 702 total
includes taxes & fees
6 Feb - 7 Feb
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

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
3 Feb - 4 Feb
Woodville Bed and Breakfast

Harmony Hill B&B

3.5 star property
9.4 out of 10, Exceptional, (257)
"Harmony Hill is in a very quiet, beautiful setting. It was convenient to our event nearby and the owners were very kind, accommodating, and hospitable. Everything was very clean and comfortable and the communication was excellent. We really enjoyed our stay. "
Harmony Hill B&B

"Mizpah" B&B Historic Farmhouse in the Blue Ridge Mountains of Nelson County, VA

"Mizpah" B&B Historic Farmhouse in the Blue Ridge Mountains of Nelson County, VA

Osceola Mill - Reopening!

The price is AED 545
AED 702 total
includes taxes & fees
6 Feb - 7 Feb
Osceola Mill - Reopening!

Osceola Mill Bed & Breakfast Inn & Cabin

The price is AED 1,151
AED 1,486 total
includes taxes & fees
9 Feb - 10 Feb
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 and Cabin

The price is AED 848
AED 1,096 total
includes taxes & fees
6 Feb - 7 Feb
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

Osceola Mill Dining & Lodging

3.5 star property
10.0 out of 10, Exceptional, (1)
"We had a great time! The cabin was so cozy and perfect for a weekend getaway in the mountains! The food was delicious!! We had both dinner and breakfast there! "
Osceola Mill Dining & Lodging

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, (291)
"Fun, fun times in a short stay. Location was perfect ! "
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

The Modern Mountain Condo

10.0 out of 10, Exceptional, (20)
"Everything was good. Could not get the tv in bedroom to work. Would like to have a Keurig type coffee maker"
The price is AED 353
AED 797 total
includes taxes & fees
27 Feb - 28 Feb
The Modern Mountain Condo

Modern Luxe Treetop Retreat w/ Hot Tub, Gas Fire Pit, Steps to Ski! 100% 5 Star!

10.0 out of 10, Exceptional, (44)
"What a great inviting space!We loved the setup and proximity to the slopes.We will be back for sure!!!"
Modern Luxe Treetop Retreat w/ Hot Tub, Gas Fire Pit, Steps to Ski! 100% 5 Star!
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 Crossroads Inn: 6 rooms. 14 mi (22.5 km) from the downtown core. Enjoy the free full breakfast and winery. The Farmhouse at Veritas: 8 rooms. Situated 9.5 mi (15.4 km) from the heart of Wintergreen. Enjoy the free full breakfast and massage services. “Mizpah” B&B Historic Farmhouse in the Blue Ridge Mountains of Nelson County, VA: 8.2 mi (13.2 km) from the heart of downtown. Sugar Tree Inn: 11 rooms. Located 14.4 mi (23.2 km) from the core of Wintergreen. Enjoy the free full breakfast and deli.
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.