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Compare 36 B&B in Windham with updated reviews, rates, and availability.

Big Bears Lodge
Front of property

Big Bears Lodge

3.0 star property
8.8 out of 10, Excellent, (155)
"So close to Mount snow it’s a great place to stay "
The price is SAR 626
SAR 689 total
includes taxes & fees
5 Jan - 6 January 2025
Big Bears Lodge
The Inn at Manchester
Exterior

The Inn at Manchester

3.5 star property
10.0 out of 10, Exceptional, (223)
"Amazing friendly service. "
The price is SAR 582
SAR 640 total
includes taxes & fees
5 Jan - 6 January 2025
The Inn at Manchester
Stone Hearth Inn and Eatery
Front of property

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (75)
"Breakfast was great. The owner is super nice"
The price is SAR 841
SAR 916 total
includes taxes & fees
30 Dec - 31 Dec
Stone Hearth Inn and Eatery
Bromley View Inn
Restaurant

Bromley View Inn

3.5 star property
9.2 out of 10, Wonderful, (322)
"Very nice stay. Cozy and comfortable."
The price is SAR 443
SAR 488 total
includes taxes & fees
5 Jan - 6 January 2025
Bromley View Inn
Echo Lake Inn
Front of property

Echo Lake Inn

2.5 star property
8.6 out of 10, Excellent, (94)
"Old fashioned inn with wonderful hosts."
The price is SAR 942
SAR 1,026 total
includes taxes & fees
8 Jan - 9 January 2025
Echo Lake Inn
Deerfield Valley Inn
Front of property

Deerfield Valley Inn

3.0 star property
9.8 out of 10, Exceptional, (38)
"no frills, but convenient, clean, attentive staff, "
The price is SAR 632
SAR 798 total
includes taxes & fees
25 Dec - 26 Dec
Deerfield Valley Inn
Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.6 out of 10, Exceptional, (284)
"Great New England hospitality!....delicious breakfast and comfortable bedding. The location was great - between the small town of Wilmington, Mt. Snow and Brattleboro. Victoria and Brian could not have been more accommodating and friendly! Would definitely stay again when in the area. "
The price is SAR 491
SAR 535 total
includes taxes & fees
24 Dec - 25 Dec
Colonel Williams Inn
Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (197)
"No Complaints, Excellent breakfast "
The price is SAR 708
SAR 772 total
includes taxes & fees
3 Jan - 4 January 2025
Harvest Barn Inn
Hill Farm Inn
Front of property

Hill Farm Inn

4.0 star property
9.6 out of 10, Exceptional, (165)
"Its exactly what you think of when you think of a Vermont Inn. "
The price is SAR 710
SAR 1,619 total
includes taxes & fees
5 Jan - 6 January 2025
Hill Farm Inn
Deerhill Inn
Exterior

Deerhill Inn

3.5 star property
9.6 out of 10, Exceptional, (211)
"The innkeepers were such nice, friendly, helpful people, going out of their way to see that we had a delicious breakfast before our early departure. We loved everything about this inn! "
The price is SAR 733
SAR 806 total
includes taxes & fees
5 Jan - 6 January 2025
Deerhill Inn
Blue Gentian Lodge at Magic Mountain
Property entrance

Blue Gentian Lodge at Magic Mountain

2.5 star property
9.0 out of 10, Wonderful, (92)
"Very welcoming host."
Blue Gentian Lodge at Magic Mountain
King & Queen Suite in Historic Inn Circa 1780
Room

King & Queen Suite in Historic Inn Circa 1780

9.6 out of 10, Exceptional, (14)
"This is a fine place to stay. Everything is thoughtfully provided to make guests comfortable. The bed was very high quality, too. There were snacks, breakfast options, and good coffee available in the morning. Nothing fancy, but very useful and much appreciated."
The price is SAR 635
SAR 985 total
includes taxes & fees
5 Jan - 6 January 2025
King & Queen Suite in Historic Inn Circa 1780
The Inn at Ormsby Hill
Terrace/patio

The Inn at Ormsby Hill

3.5 star property
9.8 out of 10, Exceptional, (115)
"Really liked the beautiful interior of the inn."
The price is SAR 977
SAR 1,075 total
includes taxes & fees
24 Dec - 25 Dec
The Inn at Ormsby Hill
North Shire Lodge
Front of property

North Shire Lodge

3.0 star property
9.4 out of 10, Exceptional, (146)
"Beautiful view from the room!"
The price is SAR 773
SAR 851 total
includes taxes & fees
31 Dec - 1 January 2025
North Shire Lodge
The Ira Allen House
Exterior

The Ira Allen House

3.5 star property
9.8 out of 10, Exceptional, (180)
"Our second stay at Ira Allen House. Got to see finished renovation and enjoyed sitting around large fireplace and chatting with other guests. Mike and Kevin are wonderful hosts."
The price is SAR 657
SAR 717 total
includes taxes & fees
5 Jan - 6 January 2025
The Ira Allen House
Chesterfield Inn
Lobby

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (101)
"Lots of things were lovely; fantastic room service food (unbelievably fresh and delicious, better than anywhere I’ve ever eaten in a hotel while traveling), beautiful serene natural setting, and wonderful design of the buildings plus COOKIES and tea in the afternoon. The service was also fantastic. The paint could use freshening and the bathroom grout needs redoing (or consider retiling). A piece of one window pane, a wood bit, fell off… so I stuck it back, obviously needs a proper repair. With...
The price is SAR 1,155
SAR 1,253 total
includes taxes & fees
7 Jan - 8 January 2025
Chesterfield Inn
Four Columns Inn
Garden

Four Columns Inn

3.0 star property
8.8 out of 10, Excellent, (3)
"Friendliest Staff Ever!"
Four Columns Inn
Windham Hill Inn
Exterior

Windham Hill Inn

3.0 star property
8.2 out of 10, Very Good, (32)
"The rustic charm of a beautifully renovated New England barn, with spacious rooms that provide quiet solitude and comfortable furnishings, wall to wall! The king size bed, the oversized bathroom with a giant jetted tub beneath a skylight…SO INCREDIBLY PEACEFUL!! And outdoors there are numerous trails and Adirondack chairs placed at scenic spots to take in the beauty of the land in front of you and to enjoy the star filled wide-open sky above at night, which we did and thoroughly enjoyed! We...
The price is SAR 778
SAR 848 total
includes taxes & fees
6 Jan - 7 January 2025
Windham Hill Inn
Room in Historic Inn! 20 Minutes to Okemo!
Room

Room in Historic Inn! 20 Minutes to Okemo!

9.4 out of 10, Exceptional, (13)
"I loved the room we stayed in. It was such a comfortable bed as well as the pillows. The bathroom was large and just about everything in our room was like a storybook. Loved skimming through some of the old books...so informative. The only thing I wished we knew is it was difficult to find a place to eat as we were there Monday thru Wednesday morning and no eateries on Main Street was opened. We drove a half our to eat breakfast. Perhaps it was the wrong season to go but the foliage was...
The price is SAR 560
SAR 858 total
includes taxes & fees
6 Jan - 7 January 2025
Room in Historic Inn! 20 Minutes to Okemo!
Honeymoon Suite with Jacuzzi Tub in Historic Inn
Living area

Honeymoon Suite with Jacuzzi Tub in Historic Inn

8.6 out of 10, Excellent, (7)
"I was enchanted to be staying in a beautiful antique decorated place. And the jacuzzi tub was large, comfortable, and easily accessed by a step."
The price is SAR 597
SAR 905 total
includes taxes & fees
6 Jan - 7 January 2025
Honeymoon Suite with Jacuzzi Tub in Historic Inn
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 Windham

Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.
Exterior

Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.

10.0 out of 10, Exceptional, (39)
"This property was beautiful, clean, well maintained, had everything we needed. Wish we could have stayed longer! Thank you for a weekend we’ll never forget! We hope to rent this house again in the future. "
Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.
Long Trail House at Stratton Mountain Resort
Living room

Long Trail House at Stratton Mountain Resort

3.0 star property
8.4 out of 10, Very Good, (72)
"Condo was great, cozy, and clean. Has access to the pool and hot tubs from back porch and has great Mountain View’s. The village had plenty of food, little expensive, but pretty good. Overall great place to stay and enjoy the mountain. "
The price is SAR 1,424
SAR 1,770 total
includes taxes & fees
6 Jan - 7 January 2025
Long Trail House at Stratton Mountain Resort
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Located in the Okemo Mt. Community, a mile to the base lodge

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

9.8 out of 10, Exceptional, (164)
"The property is exactly like the pictures indicate. The house is in a friendly neighborhood outside of town. The house is very comfortable and spacious. The host responds to your messages in timely manner, and, she is very workable. Would definitely stay there again "
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
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 Windham?
If you’re looking for something a little more offbeat than your standard hotel experience, a bed and breakfast might be the perfect option for your vacation. When you want to explore some top attractions, Stratton Mountain Resort and Okemo Mountain Resort are worth a stop.
Are you thinking about B&Bs over traditional hotel rooms?
With attentive service, opportunities to mingle with other guests, and of course a scrumptious breakfast, B&Bs all have a unique setting.
What are the best B&Bs in Windham?
Below are some well-liked B&Bs in the area: Big Bears Lodge: 24 rooms. 16.9 mi (27.1 km) from the heart of Windham. Enjoy the free cooked breakfast and outdoor pool. The Inn at Manchester: 18 rooms. 17.4 mi (28 km) from the downtown core. Enjoy the free cooked breakfast and outdoor pool. Bromley View Inn: 16 rooms. Situated 10.5 mi (16.9 km) from the heart of Windham. Enjoy the unique décor and fireplace in the lobby. Stone Hearth Inn and Eatery: 8 rooms. 8.4 mi (13.5 km) from the heart of downtown. Enjoy the free buffet breakfast and unique décor. Deerfield Valley Inn: 9 rooms. Located 17.4 mi (28.1 km) from the core of Windham. Enjoy the unique décor and fireplace in the lobby.
What's the best time of year to stay at a B&B in Windham?
When you’re dreaming of a getaway to Windham, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 64°F, while the coldest months are January and February with an average of 24°F. The snowiest months in Windham are January, March, November, and February, with each month seeing an average of 14 inches of snowfall.
What is there to do in Windham?
Spend some time exploring Jamaica State Park and Emerald Lake State Park if you’re hoping to see some of the area’s natural features. You might put Stratton Mountain Resort and Okemo Mountain Resort on your list if you want to see more of the area.
How can I get to and around Windham?
You can map out your trip in and around Windham ahead of time with these transportation options. Fly into Springfield, VT (VSF-Hartness State), which is located 15.5 mi (24.9 km) from the city center. Otherwise, look for flights into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 26.9 mi (43.3 km) away. If you’d like to explore around the area, consider renting a car to take in more sights.