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Compare 36 B&B in Windham with updated reviews, rates, and availability.

Bromley View Inn

3.5 star property
9.2 out of 10, Wonderful, (326)
"My son and his friends stayed here to ski and snowboard for a few days in the area. The basic accommodations were sufficient for them. They were happy with their stay."
The price is SAR 438
SAR 482 total
includes taxes & fees
23 Jan - 24 Jan
Bromley View Inn

Big Bears Lodge

3.0 star property
8.8 out of 10, Excellent, (164)
"The property is well taken care of, rooms nicely decorated and beds comfortable. The area has many options for tasty food and although a bit expensive for what and where they are, still a lot more reasonable than the food at Mt Snow ($10 pizza slices, really! Bring your lunches). My suggestions for the property: add electric outlets in the room (we all have phones, tablets and laptops) and towel racks in the bathroom (lots of ski gear to hang dry)."
The price is SAR 626
SAR 688 total
includes taxes & fees
27 Jan - 28 Jan
Big Bears Lodge

Deerfield Valley Inn

3.0 star property
9.8 out of 10, Exceptional, (43)
"Super friendly host, location is next to the local main road. Don't need to worry about snow too much. "
The price is SAR 698
SAR 871 total
includes taxes & fees
30 Jan - 31 Jan
Deerfield Valley Inn

The Inn at Manchester

3.5 star property
10.0 out of 10, Exceptional, (225)
"Nice and quaint bed and breakfast. one of the best in the area. "
The price is SAR 619
SAR 681 total
includes taxes & fees
23 Jan - 24 Jan
The Inn at Manchester

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (79)
"Wonderful old building with tons of character and charm. Loved the stay, the food was terrific, and the owner couldn't have been more inviting and helpful!"
The price is SAR 1,244
SAR 1,356 total
includes taxes & fees
27 Jan - 28 Jan
Stone Hearth Inn and Eatery

Colonel Williams Inn

3.0 star property
9.6 out of 10, Exceptional, (290)
"Ooh - this was a gem of a B and B! Comfy, quiet room, delicious breakfast and very kind, accommodating hosts - we hope to return soon! I was hoping to hear a ghost or two - no luck this time !"
The price is SAR 567
SAR 618 total
includes taxes & fees
26 Jan - 27 Jan
Colonel Williams Inn

Deerhill Inn

3.5 star property
9.6 out of 10, Exceptional, (212)
"The innkeepers were such nice, friendly, helpful people, going out of their way to see that we had a delicious breakfast before our early departure. We loved everything about this inn! "
The price is SAR 717
SAR 789 total
includes taxes & fees
5 Feb - 6 Feb
Deerhill Inn

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 709
SAR 1,617 total
includes taxes & fees
23 Jan - 24 Jan
Hill Farm Inn

Echo Lake Inn

2.5 star property
8.6 out of 10, Excellent, (94)
"Old fashioned inn with wonderful hosts."
The price is SAR 951
SAR 1,037 total
includes taxes & fees
28 Jan - 29 Jan
Echo Lake Inn

The Ira Allen House

3.5 star property
9.8 out of 10, Exceptional, (182)
"Very comfortable and homey..nice fireplace, breakfast was extraordinary! Michael and Tim were wonderful hosts!"
The price is SAR 657
SAR 716 total
includes taxes & fees
23 Jan - 24 Jan
The Ira Allen House

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (200)
"good"
The price is SAR 591
SAR 644 total
includes taxes & fees
30 Jan - 31 Jan
Harvest Barn Inn

Windham Hill Inn

3.0 star property
8.2 out of 10, Very Good, (32)
"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
5 Feb - 6 Feb
Windham Hill Inn

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 1,106
SAR 1,217 total
includes taxes & fees
26 Jan - 27 Jan
The Inn at Ormsby Hill

Blue Gentian Lodge at Magic Mountain

2.5 star property
9.2 out of 10, Wonderful, (93)
"Very welcoming host."
Blue Gentian Lodge at Magic Mountain

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 SAR 1,153
SAR 1,251 total
includes taxes & fees
29 Jan - 30 Jan
Chesterfield Inn

North Shire Lodge

3.0 star property
9.4 out of 10, Exceptional, (146)
"Beautiful view from the room!"
North Shire Lodge

Four Columns Inn

3.0 star property
8.8 out of 10, Excellent, (3)
"Friendliest Staff Ever!"
Four Columns Inn

Golden Stage Inn B&B

3.5 star property
10.0 out of 10, Exceptional, (23)
"Very beautiful place and excellent service "
Golden Stage Inn B&B

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 634
SAR 979 total
includes taxes & fees
27 Jan - 28 Jan
King & Queen Suite in Historic Inn Circa 1780

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 559
SAR 857 total
includes taxes & fees
27 Jan - 28 Jan
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

Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.

10.0 out of 10, Exceptional, (39)
"This property was beautiful, clean, well maintained, had everything we needed. Wish we could have stayed longer! Thank you for a weekend we’ll never forget! We hope to rent this house again in the future. "
Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.

Long Trail House at Stratton Mountain Resort

3.0 star property
8.4 out of 10, Very Good, (72)
"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 SAR 1,467
SAR 1,823 total
includes taxes & fees
28 Jan - 29 Jan
Long Trail House at Stratton Mountain Resort

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

9.6 out of 10, Exceptional, (35)
"Convenient to Okemo. Has everything you need for a ski week or weekend! "
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
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: Big Bears Lodge: 24 rooms. 16.9 mi (27.1 km) from the heart of Windham. Enjoy the free cooked breakfast and outdoor pool. Bromley View Inn: 16 rooms. 10.5 mi (16.9 km) from the downtown core. Enjoy the unique décor and fireplace in the lobby. Deerfield Valley Inn: 9 rooms. Situated 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 heart of downtown. Enjoy the free cooked breakfast and outdoor pool. Stone Hearth Inn and Eatery: 8 rooms. Located 8.4 mi (13.5 km) from the core of Windham. Enjoy the free buffet breakfast 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.