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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)
"The deer valley inn was a cozy small guesthouse . The staff were very kind and helpful. Highly recommend the place . The staff manager was originally from turkey. Really sorry I forgot the name at this moment but he was wonderful . "
The price is SAR 314
SAR 448 total
includes taxes & fees
18 Nov - 19 Nov
Deerfield Valley Inn
Colonel Williams Inn
Front of property
Colonel Williams Inn
3.0 star property
9.6 out of 10, Exceptional, (282)
"We absolutely loved our stay! The property is beautiful, and Brian & Victoria were so sweet and accommodating. Not to mention that the breakfast spread was fabtastic! We can't wait to visit again."
The price is SAR 538
SAR 587 total
includes taxes & fees
18 Nov - 19 Nov
Colonel Williams Inn
Stone Hearth Inn and Eatery
Front of property
Stone Hearth Inn and Eatery
3.0 star property
9.2 out of 10, Wonderful, (73)
"If you’re looking for an authentic experience in a 200 year old home - with tons of wonderful history and true early American character - you’ll love this stay! This is NOT a shiny new hotel, with all the conveniences. You can forget your free “make-your-own hot breakfast” deal. This chef-curated breakfast was fresh, carefully crafted, and delicious! The eggs were light, fluffy and flavorful. The bacon was thick and cooked perfectly. And OMG, the homemade Belgian waffles were literally covered...
The price is SAR 840
SAR 916 total
includes taxes & fees
18 Nov - 19 Nov
Stone Hearth Inn and Eatery
The Inn at Manchester
Exterior
The Inn at Manchester
3.5 star property
10.0 out of 10, Exceptional, (218)
"Great stay to end out our Vermont honeymoon."
The price is SAR 582
SAR 640 total
includes taxes & fees
19 Nov - 20 Nov
The Inn at Manchester
The Ira Allen House
Exterior
The Ira Allen House
3.5 star property
9.8 out of 10, Exceptional, (177)
"Everything was perfect!!!"
The price is SAR 657
SAR 716 total
includes taxes & fees
18 Nov - 19 Nov
The Ira Allen House
Bromley View Inn
Restaurant
Bromley View Inn
3.5 star property
9.2 out of 10, Wonderful, (322)
"There is a contactless checkin and checkout. Very comfortable atmosphere. Lots of amenities, like jacquizi, lounge area, breakfast area, food to go. Area is kept clean and tidy. Wish my bedroom on the second floor had either curtains to close or blinds for the evening. Loved my pot belly stove in bedroom. Great television selections. Will definitely stay there again"
Bromley View 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 732
SAR 805 total
includes taxes & fees
21 Nov - 22 Nov
Deerhill Inn
Harvest Barn Inn
Porch
Harvest Barn Inn
3.0 star property
9.8 out of 10, Exceptional, (194)
"The young couple who own the Harvest Barn Inn are wonderful. The breakfasts were well thought out and excellent. Coffee and cookies were available in the afternoon and the cookies were delicious. The inn is located on a quiet road close to the VT Country Store and downtown Bellows Falls is unique and inviting. Beautiful views. Can’t say enough good things about this inn. "
The price is SAR 665
SAR 725 total
includes taxes & fees
24 Nov - 25 Nov
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 972
SAR 1,905 total
includes taxes & fees
18 Nov - 19 Nov
Hill Farm 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 SAR 604
SAR 665 total
includes taxes & fees
18 Dec - 19 Dec
Big Bears 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 SAR 996
SAR 1,085 total
includes taxes & fees
25 Nov - 26 Nov
Echo Lake 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 777
SAR 847 total
includes taxes & fees
1 Dec - 2 Dec
Windham Hill 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 SAR 672
SAR 739 total
includes taxes & fees
21 Nov - 22 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 SAR 1,085
SAR 1,193 total
includes taxes & fees
24 Nov - 25 Nov
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 751
SAR 826 total
includes taxes & fees
28 Nov - 29 Nov
North Shire Lodge
Golden Stage Inn B&B
Front of property
Golden Stage Inn B&B
3.5 star property
10.0 out of 10, Exceptional, (22)
"We chose this bed and breakfast based on others’ reviews- and you should, too! Our room was lovely and homey and had everything you’d want or need available. Mike and Julie are spectacularly thoughtful hosts. We felt welcomed, cared for, and a little bit spoiled :) during our three day stay. Will absolutely stay here again on our next visit to VT! "
Golden Stage Inn B&B
King & Queen Suite in Historic Inn Circa 1780
Room
King & Queen Suite in Historic Inn Circa 1780
9.6 out of 10, Exceptional, (13)
"SUCH a lovely, cozy stay in this beautiful VT town. Could not recommend more highly!"
The price is SAR 372
SAR 660 total
includes taxes & fees
18 Nov - 19 Nov
King & Queen Suite in Historic Inn Circa 1780
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 1,131
SAR 1,227 total
includes taxes & fees
19 Nov - 20 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
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 319
SAR 568 total
includes taxes & fees
18 Nov - 19 Nov
Room in Historic Inn! 20 Minutes to Okemo!
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)
"The unit was perfect for our ski race weekend. Very accessible, underground parking included (ski boxes on top of SUVs will not fit - thankfully we left ours at home), really nice place with everything we needed!"
The price is SAR 1,230
SAR 1,523 total
includes taxes & fees
18 Nov - 19 Nov
Long Trail House at Stratton Mountain Resort
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree!
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!
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!
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. Stone Hearth Inn and Eatery: 8 rooms. Situated 8.4 mi (13.5 km) from the heart of Windham. Enjoy the free buffet breakfast and unique décor. Deerfield Valley Inn: 9 rooms. 17.4 mi (28.1 km) from the heart of downtown. Enjoy the unique décor and fireplace in the lobby. The Inn at Manchester: 18 rooms. Located 17.4 mi (28 km) from the core of Windham. Enjoy the free cooked breakfast and outdoor pool.
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.