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Compare 37 B&B in Windham with updated reviews, rates, and availability.

Deerfield Valley Inn
Front of property

Deerfield Valley Inn

3.0 star property
9.8 out of 10, Exceptional, (33)
"What a great place to stay! To spend a few nights away! From the hustle and bustle."
The price is AED 269
AED 397 total
includes taxes & fees
26 Nov - 27 Nov
Deerfield Valley Inn
The Inn at Manchester
Exterior

The Inn at Manchester

3.5 star property
10.0 out of 10, Exceptional, (218)
"Great place. Excellent hosts. Great location. Very well kept. "
The price is AED 569
AED 626 total
includes taxes & fees
26 Nov - 27 Nov
The Inn at Manchester
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 AED 716
AED 788 total
includes taxes & fees
27 Nov - 28 Nov
Deerhill Inn
Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.6 out of 10, Exceptional, (283)
"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 AED 515
AED 561 total
includes taxes & fees
2 Dec - 3 Dec
Colonel Williams Inn
The Ira Allen House
Exterior

The Ira Allen House

3.5 star property
9.8 out of 10, Exceptional, (178)
"Always enjoyable visit. Kevin and Mike are very friendly and the breakfast is always delicious!"
The price is AED 643
AED 701 total
includes taxes & fees
26 Nov - 27 Nov
The Ira Allen House
Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (194)
"Such an excellent stay. Beautiful view, felt safe and quiet. Blessing was kind enough to make us breakfast in the morning, highly recommended "
The price is AED 579
AED 631 total
includes taxes & fees
1 Dec - 2 Dec
Harvest Barn Inn
Big Bears Lodge
Front of property

Big Bears Lodge

3.0 star property
8.8 out of 10, Excellent, (153)
"Very quaint place to stay; the owners are sweet and considerate! They make the place feel like a safe get-away to somewhere nostalgic. I will definitely be booking a stay here again! "
The price is AED 591
AED 650 total
includes taxes & fees
26 Nov - 27 Nov
Big Bears Lodge
Stone Hearth Inn and Eatery
Front of property

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (73)
"My husband and I stayed here for a night. Communication was great. Beautiful old inn. The best part was the owners daughter/husband are chefs! Like...gourmet chefs! I think I had the best breakfast I've ever had in my life here. Just a lovely family owned - beautiful VT Inn. Would stay again in a heartbeat!"
The price is AED 658
AED 717 total
includes taxes & fees
27 Nov - 28 Nov
Stone Hearth Inn and Eatery
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 AED 951
AED 1,863 total
includes taxes & fees
26 Nov - 27 Nov
Hill Farm Inn
Bromley View Inn
Restaurant

Bromley View Inn

3.5 star property
9.2 out of 10, Wonderful, (322)
"Very nice stay. Cozy and comfortable."
Bromley View 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."
The price is AED 657
AED 723 total
includes taxes & fees
26 Nov - 27 Nov
Blue Gentian Lodge at Magic Mountain
The Inn at Ormsby Hill
Terrace/patio

The Inn at Ormsby Hill

3.5 star property
9.8 out of 10, Exceptional, (113)
"What a beautiful B&B! The staff was super kind and friendly. Loved my room and how it was so nicely decorated. Cozy and comfortable. Breakfast was great and town was just a 5 minute drive away. So glad my last minute decision to visit Vermont turned out so perfect. ❤️"
The price is AED 1,061
AED 1,167 total
includes taxes & fees
1 Dec - 2 Dec
The Inn at Ormsby Hill
King & Queen Suite in Historic Inn Circa 1780
Room

King & Queen Suite in Historic Inn Circa 1780

9.6 out of 10, Exceptional, (13)
"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 AED 437
AED 736 total
includes taxes & fees
1 Dec - 2 Dec
King & Queen Suite in Historic Inn Circa 1780
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 AED 650
AED 716 total
includes taxes & fees
26 Nov - 27 Nov
North Shire Lodge
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 AED 899
AED 980 total
includes taxes & fees
11 Dec - 12 Dec
Echo Lake Inn
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 AED 1,106
AED 1,200 total
includes taxes & fees
26 Nov - 27 Nov
Chesterfield Inn
Four Columns Inn
Garden

Four Columns Inn

3.0 star property
8.6 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 AED 760
AED 829 total
includes taxes & fees
8 Dec - 9 Dec
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 AED 437
AED 699 total
includes taxes & fees
26 Nov - 27 Nov
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 AED 400
AED 654 total
includes taxes & fees
26 Nov - 27 Nov
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.
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Outdoor spa tub

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (196)
"It was a wonderful little cabin that was clean and decorated comfortably. It had everything we needed. The hot tub was delightful! "
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool
Located in the Okemo Mt. Community, a mile to the base lodge

Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool

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 "
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool
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: Deerfield Valley Inn: 9 rooms. 17.4 mi (28.1 km) from the heart of Windham. Enjoy the unique décor and fireplace in the lobby. The Inn at Manchester: 18 rooms. 17.4 mi (28 km) from the downtown core. Enjoy the free cooked breakfast and outdoor pool. Big Bears Lodge: 24 rooms. Situated 16.9 mi (27.1 km) from the heart of Windham. Enjoy the free cooked breakfast and outdoor pool. Deerhill Inn: 14 rooms. 17.4 mi (27.9 km) from the heart of downtown. Enjoy the free full breakfast and designer toiletries.
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.