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Check prices for these dates

Next weekend
4 Rab. II - 6 Rab. II
In two weeks
11 Rab. II - 13 Rab. II
In one month
25 Rab. II - 27 Rab. II
In two months
23 Jum. I - 25 Jum. I

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, (338)
"Very cool room. Looking out towards the ski area."
The price is SAR 376
SAR 414 total
includes taxes & fees
1 Apr - 2 Apr
Bromley View Inn
Big Bears Lodge
Outdoor spa tub

Big Bears Lodge

3.0 star property
9.0 out of 10, Wonderful, (179)
"It was very close to the ski resort. "
The price is SAR 626
SAR 688 total
includes taxes & fees
1 Apr - 2 Apr
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, (117)
"Great inn. Very warm and friendly. Perfect for a getaway. Close proximity to town and restaurants. "
The price is SAR 671
SAR 739 total
includes taxes & fees
1 Apr - 2 Apr
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, (233)
"From ease of parking and check-in, the spacious room, comfortable bed and delicious breakfasts, we loved our stay at at the Inn at Manchester. The hosts were charming and helpful and the on-site pub was a fun place to meet other guests. Conveniently walkable to most of Manchester's historic area and dining. Highly recommended!"
The price is SAR 544
SAR 598 total
includes taxes & fees
1 Apr - 2 Apr
The Inn at Manchester
Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (302)
"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 SAR 538
SAR 586 total
includes taxes & fees
13 Apr - 14 Apr
Colonel Williams Inn
Deerfield Valley Inn
Exterior

Deerfield Valley Inn

3.0 star property
9.6 out of 10, Exceptional, (48)
"Accommodating staff. Nice old Inn convenient to Mt. Snow and restaurants. Had a great stay. Would stay here again."
The price is SAR 319
SAR 454 total
includes taxes & fees
1 Apr - 2 Apr
Deerfield Valley Inn
Deerhill Inn
Exterior

Deerhill Inn

3.5 star property
9.6 out of 10, Exceptional, (217)
"Charming Inn! My daughter and I loved it here. We stayed in the Magnolia and the room was very clean, beautiful and comfortable. Everyone at the Inn was just lovely to talk to and the breakfast was delish! "
The price is SAR 769
SAR 846 total
includes taxes & fees
17 Apr - 18 Apr
Deerhill Inn
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 SAR 679
SAR 741 total
includes taxes & fees
13 Apr - 14 Apr
Windham Hill Inn
The Ira Allen House
Exterior

The Ira Allen House

3.5 star property
9.8 out of 10, Exceptional, (189)
"Absolutely love! Such great history and charm. Wonderful service! Thoroughly enjoyed the stay. "
The price is SAR 656
SAR 716 total
includes taxes & fees
1 Apr - 2 Apr
The Ira Allen House
Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (208)
"Nice and comfortable great breakfast"
The price is SAR 591
SAR 644 total
includes taxes & fees
2 Apr - 3 Apr
Harvest Barn 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 SAR 897
SAR 1,821 total
includes taxes & fees
1 Apr - 2 Apr
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, (88)
"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 SAR 1,244
SAR 1,356 total
includes taxes & fees
1 Apr - 2 Apr
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 SAR 1,017
SAR 1,108 total
includes taxes & fees
7 Apr - 8 Apr
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)
"Amazing "
The price is SAR 634
SAR 697 total
includes taxes & fees
1 Apr - 2 Apr
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 SAR 664
SAR 731 total
includes taxes & fees
1 Apr - 2 Apr
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)
"I was enchanted to be staying in a beautiful antique decorated place. And the jacuzzi tub was large, comfortable, and easily accessed by a step."
The price is SAR 371
SAR 626 total
includes taxes & fees
6 Apr - 7 Apr
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 SAR 319
SAR 588 total
includes taxes & fees
1 Apr - 2 Apr
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 SAR 334
SAR 618 total
includes taxes & fees
7 Apr - 8 Apr
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)
"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 334
SAR 584 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, (47)
"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
8.6 out of 10, Excellent, (74)
"Nice, clean room in prime location"
The price is SAR 1,268
SAR 1,576 total
includes taxes & fees
13 Apr - 14 Apr
Long Trail House at Stratton Mountain Resort
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Outdoor dining

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (203)
"Very clean. Well equipped. Close to the ski slope."
Cozy Hideaway near Ludlow/Okemo. 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. Big Bears Lodge: 24 rooms. 16.9 mi (27.1 km) from the downtown core. Enjoy the free cooked breakfast and outdoor pool. The Inn at Manchester: 18 rooms. Situated 17.4 mi (28 km) from the heart of Windham. Enjoy the free cooked breakfast and outdoor pool. 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.