Book Windham Bed & Breakfast

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Nov 14 - Nov 16
In two weeks
Nov 21 - Nov 23
In one month
Dec 5 - Dec 7
In two months
Jan 2 - Jan 4

B&B in Windham

Lounge
Bromley View Inn

Bromley View Inn

3.5 star property
Bondville
9.0 out of 10, Wonderful, (399)
"Breakfast , beverages and hot tub were nice in addition to the family game room area. "
United States
Lynn
$89 nightly
The price is $97
Nov 9 - Nov 10
Total with taxes and fees
Bromley View Inn
Porch
Harvest Barn Inn

Harvest Barn Inn

3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (243)
"Gourmet breakfast, quiet and beautiful scenery. Loved it!!!!!"
United States
RICHARD
$166 nightly
The price is $181
Nov 24 - Nov 25
Total with taxes and fees
Harvest Barn Inn
Dining
Four Columns Inn

Four Columns Inn

4.0 star property
Newfane
9.6 out of 10, Exceptional, (9)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
$170 nightly
The price is $186
Nov 19 - Nov 20
Total with taxes and fees
Four Columns 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, (147)
"Lovely place to stay Jack and Maryann excellent hosts"
United States
Lenny
$179 nightly
The price is $197
Nov 9 - Nov 10
Total with taxes and fees
The Inn at Ormsby Hill
Front of property
Colonel Williams Inn

Colonel Williams Inn

3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (338)
"Very charming place. Breakfast was really good, made fresh, very accommodating with food intolerances. Very much enjoyed my stay."
Canada
Carolyn
$150 nightly
The price is $166
Nov 20 - Nov 21
Total with taxes and fees
Colonel Williams Inn
Front of property
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3.0 star property
Chester
9.2 out of 10, Wonderful, (105)
"Room was super quiet and clean. "
United States
Ernest
$200 nightly
The price is $219
Dec 8 - Dec 9
Total with taxes and fees
Stone Hearth Inn and Eatery
Exterior
Deerfield Valley Inn

Deerfield Valley Inn

3.0 star property
West Dover
9.6 out of 10, Exceptional, (83)
"We had a lovely time staying here. "
United States
Jeff
$94 nightly
The price is $104
Nov 16 - Nov 17
Total with taxes and fees
Deerfield Valley Inn
Property grounds
The Inn at Manchester

The Inn at Manchester

3.5 star property
Manchester
10.0 out of 10, Exceptional, (275)
"The staff was so friendly and helpful. Would definitely recommend. "
United States
Christine
$165 nightly
The price is $182
Nov 9 - Nov 10
Total with taxes and fees
The Inn at Manchester
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, (17)
"Our stay was outstanding. The room was spacious, comfy and clean. The Inn was very quiet during our stay. We made friends with the local chipmunk who is extremely tame. We love having a place so cozy to stay when we are in the area. "
United States
Nevets
$149 nightly
The price is $167
Nov 9 - Nov 10
Total with taxes and fees
Room in Historic Inn! 20 Minutes to Okemo!
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)
"Yes, wonderful location and stay"
United States
Sharon
$144 nightly
The price is $161
Nov 10 - Nov 11
Total with taxes and fees
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Garden
Big Bears Lodge

Big Bears Lodge

3.0 star property
West Dover
9.0 out of 10, Wonderful, (185)
"The property is conveniently located in close proximity to Mt Snow and local restaurants. The staff is friendly. There's a big screen tv room with fireplace and a small sitting room to read or just converse. Rooms are a little dated but clean. Would stay again."
United States
Jonathan
$167 nightly
The price is $183
Dec 1 - Dec 2
Total with taxes and fees
Big Bears Lodge
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
$200 nightly
The price is $219
Nov 10 - Nov 11
Total with taxes and fees
Windham Hill Inn
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)
"Family ran business and a beautiful view "
United States
Tom
$177 nightly
The price is $195
Nov 9 - Nov 10
Total with taxes and fees
North Shire Lodge
Front of property
Hill Farm Inn

Hill Farm Inn

4.0 star property
Arlington
9.6 out of 10, Exceptional, (170)
"Beautiful property in a beautiful place. Staff were lovely. D food was great!"
United States
Andrea
$435 nightly
The price is $475
Nov 9 - Nov 10
Total with taxes and fees
Hill Farm 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.
$144 nightly
The price is $159
Nov 9 - Nov 10
Total with taxes and fees
Zen 10, relax and retreat in the heart of Vermont
Outdoor pool
Echo Lake Inn

Echo Lake Inn

2.5 star property
Plymouth
8.6 out of 10, Excellent, (98)
"The staff was super friendly, and welcoming "
United States
Janet
$271 nightly
The price is $296
Dec 8 - Dec 9
Total with taxes and fees
Echo Lake Inn
Exterior
Deerhill Inn

Deerhill Inn

3.5 star property
West Dover
9.6 out of 10, Exceptional, (223)
"An excellent stay! Warm and accommodating and helpful in every way. Wonderful breakfast too!"
United States
Clarence
$193 nightly
The price is $213
Nov 20 - Nov 21
Total with taxes and fees
Deerhill Inn
Lobby
Chesterfield Inn

Chesterfield Inn

4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (104)
"This is a genuine five star property, an ideal of what a country inn should be. Beautifully designed and decorated, comfortable and welcoming, charming staff. One of the nicest places we’ve ever stayed."
United States
Susan
$301 nightly
The price is $327
Nov 9 - Nov 10
Total with taxes and fees
Chesterfield Inn
Interior
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)
"The property has new owners and they clearly are working very hard to establish their business. The Inn was spotless, and they were very accommodating."
United States
Jean
$202 nightly
The price is $226
Nov 11 - Nov 12
Total with taxes and fees
King & Queen Suite in Historic Inn Circa 1780
1 bedroom, desk, iron/ironing board, free WiFi
Honeymoon Suite with Jacuzzi Tub in Historic Inn

Honeymoon Suite with Jacuzzi Tub in Historic Inn

Chester Depot
8.6 out of 10, Excellent, (7)
"We had a fantastic time staying in the Chester House. It was a short drive to Okemo Mountain, which was our main reason for booking, but the town of Chester, like the room we stayed in, was incredibly charming!"
United States
Jonathan G.
$159 nightly
The price is $178
Nov 9 - Nov 10
Total with taxes and fees
Honeymoon Suite with Jacuzzi Tub in Historic 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windham Hotel Reviews

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Nice clean room and friendly staff. I was there off season (early November) so some restaurants weren’t open but there were still plenty of options. "
Andrew 1-night trip
Posted 2 days ago
Pointe at Castle Hill Resort

Find out more about Windham

Windham B&B information

Number of reviews
2,361
Accommodation
40 B&B
Lowest Price
$97
Highest Price
$475

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 $97 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.

Explore a world of travel with Expedia