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Check prices for these dates

Next weekend
21 Saf. - 23 Saf.
In two weeks
28 Saf. - 2 Rab. I
In one month
14 Rab. I - 16 Rab. I
In two months
11 Rab. II - 13 Rab. II

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

Frederick House
Terrace/patio

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 SAR 478
SAR 536 total
includes taxes & fees
18 Feb - 19 Feb
Frederick House
The Crossroads Inn
Front of property

The Crossroads Inn

4.5 star property
10.0 out of 10, Exceptional, (21)
"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 SAR 693
SAR 792 total
includes taxes & fees
17 Feb - 18 Feb
The Crossroads Inn
The Farmhouse at Veritas
Porch

The Farmhouse at Veritas

4.0 star property
9.8 out of 10, Exceptional, (29)
"An amazing experience, would definitely recommend."
The price is SAR 825
SAR 927 total
includes taxes & fees
19 Feb - 20 Feb
The Farmhouse at Veritas
Osceola Mill
Front of property

Osceola Mill

2.0 star property
10.0 out of 10, Exceptional, (1)
The price is SAR 526
SAR 606 total
includes taxes & fees
14 Mar - 15 Mar
Osceola Mill
Red Hill Bed and Breakfast
Exterior

Red Hill Bed and Breakfast

3.0 star property
8.2 out of 10, Very Good, (21)
"Wonderful stay! "
The price is SAR 1,125
SAR 1,263 total
includes taxes & fees
27 Feb - 28 Feb
Red Hill Bed and Breakfast
Sugar Tree Inn
Exterior

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 SAR 705
SAR 813 total
includes taxes & fees
15 Feb - 16 Feb
Sugar Tree Inn
Steeles Tavern Manor
Front of property

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!
Vesuvius Suite - Bathroom

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 SAR 557
SAR 717 total
includes taxes & fees
14 Feb - 15 Feb
Osceola Mill - Reopening!
Orchard House B&B
Front of property - evening/night

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
Front of property

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 SAR 934
SAR 1,067 total
includes taxes & fees
16 Feb - 17 Feb
Woodville Bed and Breakfast
Harmony Hill B&B
Front of property

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
Artist's Historic Farmhouse + Mountain Cideries + Bed & Breakfast, Fire pit
A moonlit dinner party on the western veranda

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

Artist's Historic Farmhouse + Mountain Cideries + Bed & Breakfast, Fire pit
Osceola Mill - Reopening!
The Mill house front porch

Osceola Mill - Reopening!

The price is SAR 557
SAR 717 total
includes taxes & fees
14 Feb - 15 Feb
Osceola Mill - Reopening!
Osceola Mill Bed & Breakfast Inn & Cabin
McCormick Cabin Exterior

Osceola Mill Bed & Breakfast Inn & Cabin

The price is SAR 1,176
SAR 1,517 total
includes taxes & fees
16 Feb - 17 Feb
Osceola Mill Bed & Breakfast Inn & Cabin
Fenton Inn
Exterior

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
Nettie Suite Bedroom

Osceola Mill Bed & Breakfast Inn and Cabin

The price is SAR 866
SAR 1,111 total
includes taxes & fees
14 Feb - 15 Feb
Osceola Mill Bed & Breakfast Inn and Cabin
The Mark Addy Bed & Breakfast
Front of property

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
Exterior

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
Front of property

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
Exterior

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.
Fresh Private Hot Tub Lower Deck Relaxing Location in woods with Beautiful Views

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

9.6 out of 10, Exceptional, (293)
"This home was everything we needed. Large pantry for storing food, well stocked kitchen supplies, outdoor areas to sit and relax, several sleeping options. The 2 floors gave us privacy and space, yet the closeness for a family or 2 if traveling with friends. Scott is very responsive to any questions or needs. "
The price is SAR 559
SAR 1,432 total
includes taxes & fees
19 Feb - 20 Feb
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
Modern Luxe Treetop Retreat w/ Hot Tub, Gas Fire Pit, Steps to Ski! 100% 5 Star!
Gorgeous retreat with hot tub, seasonal views, fire pit, pizza oven, and more!

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

10.0 out of 10, Exceptional, (46)
"Nice property, great location, good communication with owner management."
Modern Luxe Treetop Retreat w/ Hot Tub, Gas Fire Pit, Steps to Ski! 100% 5 Star!
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Our upper-floor condo is just steps to the car & firewood, provided nearby

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

10.0 out of 10, Exceptional, (307)
"Heather’s place was cozy, well-stocked with every detail considered. Heather was communicative and helpful. Great stay."
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
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.