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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

B&B in Windham

Bromley View Inn
Lounge

Bromley View Inn

3.5 star property
9.2 out of 10, Wonderful, (359)
"Awesome view and a nice place to stargaze"
Bromley View Inn
The Inn at Manchester
Property grounds

The Inn at Manchester

3.5 star property
10.0 out of 10, Exceptional, (244)
"Third stay since Jan 2025 and continues to be such a pleasure to stay here! Wonderful Inn and fabulous staff!"
The price is AED 612
AED 673 total
includes taxes & fees
31 Jul - 1 Aug
The Inn at Manchester
The Inn at Ormsby Hill
Front of property

The Inn at Ormsby Hill

3.5 star property
9.8 out of 10, Exceptional, (127)
"Thank you for a wonderful stay!"
The price is AED 724
AED 796 total
includes taxes & fees
20 Jul - 21 Jul
The Inn at Ormsby Hill
Blue Gentian Lodge at Magic Mountain
Kayaking

Blue Gentian Lodge at Magic Mountain

2.5 star property
9.2 out of 10, Wonderful, (102)
"The most comfortable stay I have had in a long time. I look forward to visiting the Blue Gentian Lodge again!"
The price is AED 474
AED 521 total
includes taxes & fees
20 Jul - 21 Jul
Blue Gentian Lodge at Magic Mountain
Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (221)
"Very accommodating and wonderful people! Hoping to return!"
Harvest Barn Inn
The Ira Allen House
Exterior

The Ira Allen House

3.5 star property
10.0 out of 10, Exceptional, (193)
"Wonderful breakfast, comfortable bed, and space in quiet to read"
The price is AED 639
AED 697 total
includes taxes & fees
5 Aug - 6 Aug
The Ira Allen House
Stone Hearth Inn and Eatery
Front of property

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (90)
"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 740
AED 806 total
includes taxes & fees
31 Jul - 1 Aug
Stone Hearth Inn and Eatery
Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (307)
"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 509
AED 555 total
includes taxes & fees
23 Jul - 24 Jul
Colonel Williams Inn
Deerfield Valley Inn
Exterior

Deerfield Valley Inn

3.0 star property
9.4 out of 10, Exceptional, (51)
"Overall great spot!"
Deerfield Valley Inn
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, (151)
"Friendly, quiet, Excellent breakfast, clean, easy parking in front of your room."
North Shire Lodge
Windham Hill Inn
Mountain view

Windham Hill Inn

4.0 star property
8.4 out of 10, Very Good, (36)
"This place was amazing, beautiful and the staff was great. We will be coming back here again. Visit the waterfalls in the area, beautiful. Great romantic getaway. "
The price is AED 694
AED 757 total
includes taxes & fees
20 Jul - 21 Jul
Windham Hill Inn
Chesterfield Inn
Lobby

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (103)
"Great stay"
The price is AED 1,106
AED 1,200 total
includes taxes & fees
21 Jul - 22 Jul
Chesterfield Inn
Hill Farm Inn
Front of property

Hill Farm Inn

4.0 star property
9.6 out of 10, Exceptional, (168)
"Beautiful location, friendly staff, delicious breakfast and excellent accommodation."
The price is AED 790
AED 1,688 total
includes taxes & fees
31 Jul - 1 Aug
Hill Farm Inn
Big Bears Lodge
Garden

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
27 Jul - 28 Jul
Big Bears Lodge
Golden Stage Inn B&B
Seasonal outdoor pool

Golden Stage Inn B&B

3.5 star property
10.0 out of 10, Exceptional, (26)
"Very beautiful place and excellent service "
Golden Stage Inn B&B
Echo Lake Inn
Exterior

Echo Lake Inn

2.5 star property
8.6 out of 10, Excellent, (96)
"Charming place, the food was great, rooms clean, and service was excellent"
The price is AED 703
AED 766 total
includes taxes & fees
21 Jul - 22 Jul
Echo Lake 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
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 511
AED 794 total
includes taxes & fees
20 Jul - 21 Jul
Honeymoon Suite with Jacuzzi Tub in Historic Inn
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Dining

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 400
AED 675 total
includes taxes & fees
20 Jul - 21 Jul
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Deerhill Inn
Exterior

Deerhill Inn

3.5 star property
9.6 out of 10, Exceptional, (219)
"Never disappoints!"
The price is AED 700
AED 770 total
includes taxes & fees
21 Jul - 22 Jul
Deerhill 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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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. Blue Gentian Lodge at Magic Mountain: 13 rooms. Situated 3.3 mi (5.3 km) from the heart of Windham. Enjoy the free buffet breakfast and spa. 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 Ormsby Hill: 10 rooms. Located 18.6 mi (29.9 km) from the core of Windham. 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.