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Jan 2 - Jan 4
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Jan 23 - Jan 25
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Feb 20 - Feb 22

Our top choices for Windham bed & breakfast

Lounge
Bromley View Inn

Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (405)
"Clean and great location with fun lounge area."
United States
Marshall
$137 nightly
The price is $151
Jan 19 - Jan 20, 2026
Total with taxes and fees
Bromley View Inn
Land view from property
Four Columns Inn

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
$129 nightly
The price is $141
Dec 30 - Dec 31
Total with taxes and fees
Four Columns Inn
Porch
Harvest Barn Inn

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
$140 nightly
The price is $153
Jan 5 - Jan 6, 2026
Total with taxes and fees
Harvest Barn Inn
Property grounds
The Inn at Manchester

The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (281)
"Charming bed and breakfast found on a whim. Captures New England charm and the owners are so nice and hospitable. Really liked the bar as well to mingle with locals. Will definitely be returning again!"
United States
Amy
$165 nightly
The price is $182
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Inn at Manchester
Front of property
Colonel Williams Inn

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
$143 nightly
The price is $158
Jan 1 - Jan 2, 2026
Total with taxes and fees
Colonel Williams Inn
Front of property - evening/night
The Inn at Ormsby Hill

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
$194 nightly
The price is $214
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Inn at Ormsby Hill
Kayaking
Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
2.5 star property
Londonderry
9.2 out of 10, Wonderful, (113)
"Lovely pleasant stay. "
United States
Heather
$177 nightly
The price is $195
Jan 4 - Jan 5, 2026
Total with taxes and fees
Blue Gentian Lodge at Magic Mountain
Room, 1 Queen Bed, Garden View | Mountain view
Windham Hill Inn

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
$181 nightly
The price is $198
Jan 1 - Jan 2, 2026
Total with taxes and fees
Windham Hill Inn
Outdoor pool, sun loungers
Hill Farm Inn

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
$395 nightly
The price is $431
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hill Farm Inn
Front of property
Stone Hearth Inn and Eatery

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
$223 nightly
The price is $244
Dec 30 - Dec 31
Total with taxes and fees
Stone Hearth Inn and Eatery
Garden
Big Bears Lodge

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
$178 nightly
The price is $196
Jan 1 - Jan 2, 2026
Total with taxes and fees
Big Bears Lodge
Property grounds
Room 7 - family room sleeps 4

Room 7 - family room sleeps 4

Room 7 - family room sleeps 4
Manchester
10.0 out of 10, Exceptional, (1)
"Nice spot, good location. Towels could be better, but overall a great spot. "
United States
Kuan-Chung
$124 nightly
The price is $137
Jan 4 - Jan 5, 2026
Total with taxes and fees
Room 7 - family room sleeps 4
Dining
King & Queen Suite in Historic Inn Circa 1780

King & Queen Suite in Historic Inn Circa 1780

King & Queen Suite in Historic Inn Circa 1780
Chester Depot
9.8 out of 10, Exceptional, (16)
"Central for our needs. easy check in process. Lovely large room with comfy beds. "
United States
HIlary H.
$221 nightly
The price is $248
Jan 4 - Jan 5, 2026
Total with taxes and fees
King & Queen Suite in Historic Inn Circa 1780
Exterior
Deerfield Valley Inn

Deerfield Valley Inn

Deerfield Valley Inn
3.0 star property
West Dover
9.6 out of 10, Exceptional, (88)
"We had a lovely time staying here. "
United States
Jeff
$176 nightly
The price is $194
Jan 22 - Jan 23, 2026
Total with taxes and fees
Deerfield Valley Inn
Front of property - evening/night
Chesterfield Inn

Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (104)
"Great stay"
United States
Wayne
$307 nightly
The price is $334
Jan 13 - Jan 14, 2026
Total with taxes and fees
Chesterfield Inn
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!

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
$198 nightly
The price is $222
Jan 4 - Jan 5, 2026
Total with taxes and fees
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Exterior
Echo Lake Inn

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
$259 nightly
The price is $283
Jan 5 - Jan 6, 2026
Total with taxes and fees
Echo Lake Inn
Exterior
Deerhill Inn

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
$189 nightly
The price is $208
Jan 4 - Jan 5, 2026
Total with taxes and fees
Deerhill Inn
Property grounds
Zen 10, relax and retreat in the heart of Vermont

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.
$124 nightly
The price is $137
Jan 5 - Jan 6, 2026
Total with taxes and fees
Zen 10, relax and retreat in the heart of Vermont
Dining
Room in Historic Inn! 20 Minutes to Okemo!

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.
$181 nightly
The price is $203
Jan 4 - Jan 5, 2026
Total with taxes and fees
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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Top Windham Hotel Reviews

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent
"Comfort and cleanliness. Nice fireplace with comfortable couches. Very nice staff. Pretty Christmas decorations."
Nancy 2-night trip
Posted 3 days ago
Kimpton Taconic Hotel by IHG

Find out more about Windham

Windham B&B information

Number of reviews
2,353
Accommodation
48 B&B
Lowest Price
$137
Highest Price
$431

Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Windham?
Prices for B&Bs in Windham often vary, but you can find a great deal from $137 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Windham B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed and Breakfast in Windham?
The best time to book a B&B in Windham is during the picturesque fall months, particularly in September. This time of year showcases the stunning autumn foliage, making it a superb backdrop for outdoor activities such as hiking the scenic trails or enjoying leisurely strolls through charming local towns.

While September marks the beginning of the high tourist season, it also offers a comfortable climate with temperatures generally ranging from the mid-50s to low 70s Fahrenheit. This pleasant weather makes it an ideal month for sightseeing, whether you're exploring the area's beautiful landscapes or taking part in local festivals that celebrate the harvest season.

For those who prefer a quieter experience, consider visiting in December. This month not only features a peaceful atmosphere but also offers a unique charm as the region transforms into a winter wonderland, superb for cozy getaways.
What is the difference between a Windham B&B and a hotel?
Every Windham B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Windham B&Bs.

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