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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 40 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, (343)
"It was nice that they had a pool table in the common area."
The price is AED 390
AED 429 total
includes taxes & fees
12 May - 13 May
Bromley View Inn
Big Bears Lodge
Outdoor spa tub

Big Bears Lodge

3.0 star property
9.0 out of 10, Wonderful, (179)
"So close to Mount snow it’s a great place to stay "
The price is AED 612
AED 674 total
includes taxes & fees
22 May - 23 May
Big Bears Lodge
The Inn at Ormsby Hill
Terrace/patio

The Inn at Ormsby Hill

3.5 star property
9.8 out of 10, Exceptional, (118)
"Really liked the beautiful interior of the inn."
The price is AED 579
AED 636 total
includes taxes & fees
13 May - 14 May
The Inn at Ormsby Hill
The Inn at Manchester
Property grounds

The Inn at Manchester

3.5 star property
10.0 out of 10, Exceptional, (238)
"Todd gave us the warmest welcome. Breakfast was delicious. Comfortable, cozy, lovely country inn! Staff is terrific!"
The price is AED 569
AED 626 total
includes taxes & fees
12 May - 13 May
The Inn at Manchester
Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (303)
"The inn keepers are always super friendly and the place is kept well. The breakfast is delicious. Great for families who prefer quiet and quaint."
The price is AED 579
AED 631 total
includes taxes & fees
19 May - 20 May
Colonel Williams Inn
Deerfield Valley Inn
Exterior

Deerfield Valley Inn

3.0 star property
9.4 out of 10, Exceptional, (50)
"Nice quiet bed and breakfast. Staff was great. Walking distance to three restaurants. "
The price is AED 306
AED 438 total
includes taxes & fees
19 May - 20 May
Deerfield Valley Inn
Deerhill Inn
Exterior

Deerhill Inn

3.5 star property
9.6 out of 10, Exceptional, (219)
"Amazing property! Absolutely will return again"
The price is AED 693
AED 762 total
includes taxes & fees
15 May - 16 May
Deerhill Inn
Windham Hill Inn
Romantic Room, 1 King Bed | Mountain view

Windham Hill Inn

4.0 star property
8.4 out of 10, Very Good, (33)
"Amazing trip. Beautiful property. Hope to return someday. "
The price is AED 665
AED 725 total
includes taxes & fees
29 May - 30 May
Windham Hill Inn
The Ira Allen House
Exterior

The Ira Allen House

3.5 star property
9.8 out of 10, Exceptional, (190)
"Absolutely love! Such great history and charm. Wonderful service! Thoroughly enjoyed the stay. "
The price is AED 643
AED 701 total
includes taxes & fees
18 May - 19 May
The Ira Allen House
Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (212)
"This was such a sweet little in the best part about it was that they cooked you a free breakfast in the morning and it was so good I can't wait to come back thank you so much"
The price is AED 625
AED 681 total
includes taxes & fees
13 May - 14 May
Harvest Barn Inn
Hill Farm Inn
Front of property

Hill Farm Inn

4.0 star property
9.6 out of 10, Exceptional, (167)
"Beautiful location, friendly staff, delicious breakfast and excellent accommodation."
The price is AED 694
AED 1,583 total
includes taxes & fees
15 May - 16 May
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, (89)
"A historic establishment ran by a family, this cozy place in the mountains is a nice retreat from the daily hustle and bustle. "
The price is AED 1,218
AED 1,327 total
includes taxes & fees
12 May - 13 May
Stone Hearth Inn and Eatery
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 703
AED 766 total
includes taxes & fees
27 May - 28 May
Echo Lake Inn
Blue Gentian Lodge at Magic Mountain
Kayaking

Blue Gentian Lodge at Magic Mountain

2.5 star property
9.2 out of 10, Wonderful, (98)
"A great room close to the slopes; warm and comfortable; breakfast that was included was simple but home cooked and amazing."
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)
"Great home base for ski adventures!! "
North Shire Lodge
Honeymoon Suite with Jacuzzi Tub in Historic Inn
1 bedroom, desk, iron/ironing board, free WiFi

Honeymoon Suite with Jacuzzi Tub in Historic Inn

8.6 out of 10, Excellent, (7)
"Charming place, hope to go back soon."
The price is AED 474
AED 740 total
includes taxes & fees
12 May - 13 May
Honeymoon Suite with Jacuzzi Tub in Historic 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
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 327
AED 592 total
includes taxes & fees
12 May - 13 May
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 437
AED 736 total
includes taxes & fees
12 May - 13 May
King & Queen Suite in Historic Inn Circa 1780
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)
"Our stay was outstanding. The room was spacious, comfy and clean. The Inn was very quiet during our stay. We made friends with the local chipmunk who is extremely tame. We love having a place so cozy to stay when we are in the area. "
The price is AED 441
AED 703 total
includes taxes & fees
12 May - 13 May
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, (47)
"Consistently great time at this place (3rd time there)"
Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Exterior

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

9.6 out of 10, Exceptional, (209)
"We absolutely loved our stay in the Honeymoon Cottage! Place was well stocked and clean. We loved the location, very private and close to the Appalachian Long Trail, which we enjoyed hiking. Location is close to Manchester for shopping, groceries and dining. Would happily return. Thank you for a lovely few romantic days."
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Outdoor spa tub

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

9.8 out of 10, Exceptional, (18)
"Family ski weekend. Our stay was very comfortable. Communication with host was phenomenal, always prompt and courteous Location is nice , very close to the ski resorts "
The price is AED 744
AED 2,365 total
includes taxes & fees
12 May - 13 May
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
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 could be the perfect alternative for your vacation.
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. The Inn at Manchester: 18 rooms. 17.4 mi (28 km) from the downtown core. Enjoy the free cooked breakfast and outdoor pool. The Inn at Ormsby Hill: 10 rooms. Situated 18.6 mi (29.9 km) from the heart of Windham. Enjoy the free full breakfast and designer toiletries. Big Bears Lodge: 24 rooms. 16.9 mi (27.1 km) from the heart of downtown. Enjoy the free cooked breakfast and outdoor pool. 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.