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Check prices for these dates

Next weekend
14 Mar - 16 Mar
In two weeks
21 Mar - 23 Mar
In one month
4 Apr - 6 Apr
In two months
2 May - 4 May

Compare 35 B&B in Windham with updated reviews, rates, and availability.

Bromley View Inn
Lounge

Bromley View Inn

3.5 star property
9.2 out of 10, Wonderful, (336)
"This was such a nice lodge! I appreciate how clean & comfortable the room was. It was a self check-in that provided easy access that came with a list of instructions & all of the things that are available at the lodge. The common room was large along in a cozy set-up with a fire place/ tv/ pool & plenty of couches. Even though the room came with a small fridge, there was two large refrigerators in the common room & dining area. To top it off, the hot tub was great! "
The price is AED 563
AED 620 total
includes taxes & fees
11 Mar - 12 Mar
Bromley View Inn
Big Bears Lodge
Outdoor spa tub

Big Bears Lodge

3.0 star property
9.0 out of 10, Wonderful, (179)
"Outdoor hot tub!"
The price is AED 612
AED 674 total
includes taxes & fees
9 Mar - 10 Mar
Big Bears Lodge
Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.6 out of 10, Exceptional, (300)
"It is about 30 mins from Mount Snow. The room was gorgeous and king bed so comfortable. Brian was welcoming and the breakfast tacos to go were amazing!"
The price is AED 497
AED 542 total
includes taxes & fees
6 Apr - 7 Apr
Colonel Williams Inn
Deerfield Valley Inn
Exterior

Deerfield Valley Inn

3.0 star property
9.6 out of 10, Exceptional, (45)
"Amazing stay. We really recommend this place for anyone with Pet. Thanks"
The price is AED 639
AED 804 total
includes taxes & fees
9 Mar - 10 Mar
Deerfield Valley Inn
Deerhill Inn
Exterior

Deerhill Inn

3.5 star property
9.6 out of 10, Exceptional, (214)
"Never disappoints!"
The price is AED 753
AED 828 total
includes taxes & fees
9 Mar - 10 Mar
Deerhill Inn
Blue Gentian Lodge at Magic Mountain
Kayaking

Blue Gentian Lodge at Magic Mountain

2.5 star property
9.2 out of 10, Wonderful, (96)
"Simple and convenient lodging for mountain activities, plus the hostess was very nice and the coffee was good!"
Blue Gentian Lodge at Magic Mountain
North Shire Lodge
Standard Room, 1 King Bed, Mountain View | Mountain view

North Shire Lodge

3.0 star property
9.4 out of 10, Exceptional, (149)
"After scrambling to find a place to stay for the night after the weather kept us longer than planned, I’m so glad we came across this place! You will not find better or kinder service, and the view is unbeatable and all for a very reasonable price! Breakfast was also excellent, and Otis is adorable! We will definitely be coming back here. "
The price is AED 773
AED 850 total
includes taxes & fees
7 Mar - 8 Mar
North Shire Lodge
The Ira Allen House
Exterior

The Ira Allen House

3.5 star property
9.8 out of 10, Exceptional, (187)
"We had a lovely stay at the Ira Allen House. Breakfast was hot and delicious and Mike accommodated our gluten free needs from fresh pancakes to homemade cookies. We will definitely be coming back on our next trip to Vermont. "
The price is AED 643
AED 701 total
includes taxes & fees
9 Mar - 10 Mar
The Ira Allen House
The Inn at Manchester
Property grounds

The Inn at Manchester

3.5 star property
10.0 out of 10, Exceptional, (229)
"Cozy, comfortable. Loved the Inn"
The price is AED 533
AED 586 total
includes taxes & fees
30 Mar - 31 Mar
The Inn at Manchester
Windham Hill Inn
Romantic Room, 1 King Bed | Mountain view

Windham Hill Inn

3.0 star property
8.4 out of 10, Very Good, (33)
"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 665
AED 725 total
includes taxes & fees
19 Mar - 20 Mar
Windham Hill Inn
Hill Farm Inn
Front of property

Hill Farm Inn

4.0 star property
9.6 out of 10, Exceptional, (167)
"We love the house itself, we love the location and love the farm animals. We love that we can relax at the property and drive to Manchester for shopping/things to do and Stratton Mountain for skiing/snowtubing."
The price is AED 694
AED 1,583 total
includes taxes & fees
9 Mar - 10 Mar
Hill Farm Inn
Stone Hearth Inn and Eatery
Front of property

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (86)
"The Inn was lovely. My grandchildren were welcomed with open arms ages 8 and 10. They loved our stay and asked for us to take them back. Breakfast specials were delicious and the attached restaurant was as well. We’ll be back!!"
The price is AED 1,218
AED 1,327 total
includes taxes & fees
10 Mar - 11 Mar
Stone Hearth Inn and Eatery
Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (207)
"We had a wonderful weekend stay at the Inn! The 3 course breakfast was fantastic, the bed was comfortable, the shower was amazing, and the space was homey and cute. We would absolutely stay again!"
The price is AED 579
AED 631 total
includes taxes & fees
16 Mar - 17 Mar
Harvest Barn Inn
Echo Lake Inn
Exterior

Echo Lake Inn

2.5 star property
8.6 out of 10, Excellent, (96)
"Old fashioned inn with wonderful hosts."
The price is AED 1,070
AED 1,167 total
includes taxes & fees
10 Mar - 11 Mar
Echo Lake Inn
The Inn at Ormsby Hill
Terrace/patio

The Inn at Ormsby Hill

3.5 star property
9.8 out of 10, Exceptional, (117)
"Great inn. Very warm and friendly. Perfect for a getaway. Close proximity to town and restaurants. "
The price is AED 823
AED 905 total
includes taxes & fees
10 Mar - 11 Mar
The Inn at Ormsby Hill
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Interior

Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

8.0 out of 10, Very Good, (1)
"Property seemed well-maintained and cared for. We were only there a short time, but it was well put together. The check-in process was a little hectic, check in time was 3pm, but our room wasn't ready. The caretaker was very friendly. We only had to wait about 20 minutes. We weren't aware this property was a VRBO, and not a regular Inn. "
The price is AED 312
AED 576 total
includes taxes & fees
30 Mar - 31 Mar
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
King & Queen Suite in Historic Inn Circa 1780
Interior

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 AED 327
AED 605 total
includes taxes & fees
1 Apr - 2 Apr
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 AED 1,129
AED 1,225 total
includes taxes & fees
9 Mar - 10 Mar
Chesterfield Inn
Four Columns Inn
Deluxe Room | Living area | 20-inch TV with cable channels

Four Columns Inn

3.0 star property
8.8 out of 10, Excellent, (3)
"Friendliest Staff Ever!"
Four Columns Inn
Room in Historic Inn! 20 Minutes to Okemo!
Terrace/patio

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 327
AED 572 total
includes taxes & fees
1 Apr - 2 Apr
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

Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.
Smart TV, fireplace, foosball, table tennis

Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.

10.0 out of 10, Exceptional, (46)
"We had a great stay at this property and every year a few families get together to spend a few days skiing and other winter activities. The house was a great layout for our group with plenty of spaces for all to sleep. Kids loved the downstairs while the adults love the game house. The property was well stocked with all needs if you forgot anything to make meal times easy. Host was great and if we had any questions they were answered right away. "
Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.
Long Trail House at Stratton Mountain Resort
Condo, 2 Bedrooms | Pool | Outdoor pool, open 10:00 AM to 10:00 PM, sun loungers

Long Trail House at Stratton Mountain Resort

3.0 star property
8.4 out of 10, Very Good, (73)
"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 AED 1,341
AED 1,666 total
includes taxes & fees
1 Apr - 2 Apr
Long Trail House at Stratton Mountain Resort
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Property grounds

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

9.2 out of 10, Wonderful, (67)
"Was supposed to be first floor but had to go up lots of stairs. The place was very clean but dated. Better for young people not good for old people."
The price is AED 367
AED 1,126 total
includes taxes & fees
9 Mar - 10 Mar
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
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: Bromley View Inn: 16 rooms. 10.5 mi (16.9 km) from the heart of Windham. Enjoy the unique décor and fireplace in the lobby. Big Bears Lodge: 24 rooms. 16.9 mi (27.1 km) from the downtown core. Enjoy the free cooked breakfast and outdoor pool. 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. Windham Hill Inn: 8 rooms. Located 5.2 mi (8.3 km) from the core of Windham. Enjoy the outdoor pool and unique décor.
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.