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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Windham bed & breakfast

Lounge
Bromley View Inn

Bromley View Inn

3.5 star property
Bondville
9.0 out of 10, Wonderful, (402)
"Overall a decent stay."
United States
Libin
Bromley View Inn
Garden
Four Columns Inn

Four Columns Inn

4.0 star property
Newfane
9.8 out of 10, Exceptional, (14)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
Four Columns Inn
Porch
Harvest Barn Inn

Harvest Barn Inn

3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (244)
"Gourmet breakfast, quiet and beautiful scenery. Loved it!!!!!"
United States
RICHARD
Harvest Barn Inn
Property grounds
The Inn at Manchester

The Inn at Manchester

3.5 star property
Manchester
10.0 out of 10, Exceptional, (280)
"Great establishment "
United States
Brenda
The price is AED 606
AED 667 total
includes taxes & fees
4 Jan - 5 January 2026
The Inn at Manchester
Front of property
Colonel Williams Inn

Colonel Williams Inn

3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (340)
"Very nice historic inn. We enjoyed our stay. Breakfast was exceptional."
United States
scott
The price is AED 538
AED 592 total
includes taxes & fees
10 Dec - 11 Dec
Colonel Williams Inn
Front of property
The Inn at Ormsby Hill

The Inn at Ormsby Hill

3.5 star property
Manchester Center
9.8 out of 10, Exceptional, (150)
"Lovely place to stay Jack and Maryann excellent hosts"
United States
Lenny
The price is AED 731
AED 804 total
includes taxes & fees
10 Dec - 11 Dec
The Inn at Ormsby Hill
Garden
Big Bears Lodge

Big Bears Lodge

3.0 star property
West Dover
9.0 out of 10, Wonderful, (185)
"The owners were wonderful: kind, interesting to talk to, and very hospitable."
United States
Margaret
The price is AED 612
AED 674 total
includes taxes & fees
10 Dec - 11 Dec
Big Bears Lodge
Terrace/patio
Room in Historic Inn! 20 Minutes to Okemo!

Room in Historic Inn! 20 Minutes to Okemo!

Chester Depot
9.2 out of 10, Wonderful, (18)
"The Chester Inn was beautiful and located in downtown Chester. "
United States
Peter C.
The price is AED 441
AED 708 total
includes taxes & fees
11 Dec - 12 Dec
Room in Historic Inn! 20 Minutes to Okemo!
Front of property
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3.0 star property
Chester
9.2 out of 10, Wonderful, (107)
"Good breakfast and dinner options. Great location for hiking."
United States
Paul
The price is AED 713
AED 778 total
includes taxes & fees
10 Dec - 11 Dec
Stone Hearth Inn and Eatery
Kayaking
Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain

2.5 star property
Londonderry
9.2 out of 10, Wonderful, (112)
"Lovely pleasant stay. "
United States
Heather
The price is AED 657
AED 723 total
includes taxes & fees
4 Jan - 5 January 2026
Blue Gentian Lodge at Magic Mountain
Front of property
Hill Farm Inn

Hill Farm Inn

4.0 star property
Arlington
9.6 out of 10, Exceptional, (173)
"This Inn is spectacular! The rooms, grounds, decor, staff and restaurant all were the best for stops on our vacation."
United States
Kenneth
The price is AED 625
AED 1,507 total
includes taxes & fees
4 Jan - 5 January 2026
Hill Farm Inn
Mountain view
Windham Hill Inn

Windham Hill Inn

4.0 star property
West Townshend
8.6 out of 10, Excellent, (37)
"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. "
United States
Brandon
The price is AED 694
AED 757 total
includes taxes & fees
10 Dec - 11 Dec
Windham Hill Inn
Property grounds
Zen 10, relax and retreat in the heart of Vermont

Zen 10, relax and retreat in the heart of Vermont

Manchester
10.0 out of 10, Exceptional, (1)
"Very nice and relaxing location"
United States
Jennifer C.
The price is AED 266
AED 477 total
includes taxes & fees
16 Dec - 17 Dec
Zen 10, relax and retreat in the heart of Vermont
Standard Room, 1 King Bed, Mountain View | Mountain view
North Shire Lodge

North Shire Lodge

3.0 star property
Manchester Center
9.4 out of 10, Exceptional, (156)
"Loved our stay at North Shire Lodge.."
United States
Mary
The price is AED 756
AED 832 total
includes taxes & fees
12 Dec - 13 Dec
North Shire Lodge
Dining
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

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

Chester Depot
9.0 out of 10, Wonderful, (2)
"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. "
United States
Jacque
The price is AED 437
AED 724 total
includes taxes & fees
10 Dec - 11 Dec
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Exterior
Deerfield Valley Inn

Deerfield Valley Inn

3.0 star property
West Dover
9.6 out of 10, Exceptional, (86)
"We had a lovely time staying here. "
United States
Jeff
Deerfield Valley Inn
Lobby
Chesterfield Inn

Chesterfield Inn

4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (104)
"Great stay"
United States
Wayne
The price is AED 1,106
AED 1,200 total
includes taxes & fees
10 Dec - 11 Dec
Chesterfield Inn
Outdoor pool
Echo Lake Inn

Echo Lake Inn

2.5 star property
Plymouth
8.6 out of 10, Excellent, (98)
"Old fashioned inn with wonderful hosts."
United States
James
The price is AED 996
AED 1,085 total
includes taxes & fees
17 Dec - 18 Dec
Echo Lake Inn
Exterior
Deerhill Inn

Deerhill Inn

3.5 star property
West Dover
9.6 out of 10, Exceptional, (224)
"Our hosts Arianne and Scott were very welcoming! The room was very comfortable and the breakfast and our server Cindy were amazing! Definitely recommend Deerhill Inn! "
United States
David
The price is AED 738
AED 812 total
includes taxes & fees
21 Dec - 22 Dec
Deerhill Inn
Property grounds
Room 7 - family room sleeps 4

Room 7 - family room sleeps 4

Manchester
The price is AED 251
AED 460 total
includes taxes & fees
10 Dec - 11 Dec
Room 7 - family room sleeps 4
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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Top Windham Hotel Reviews

The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

10/10 Excellent
"Nice staff, big room, comfortable bed, walking distance to downtown-overall great stay! "
Amanda 1-night trip
Posted 2 days ago
The Palmer House Resort, an Ascend Collection Hotel

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 Mount Snow 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. Four Columns Inn: 15 rooms. Situated 13.3 mi (21.5 km) from the heart of Windham. Enjoy the unique décor and coffee shop. Bromley View Inn: 16 rooms. 10.5 mi (16.9 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.
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.