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Dec 5 - Dec 7
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Dec 26 - Dec 28
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Jan 23 - Jan 25

B&B in Windham

Lounge
Bromley View Inn

Bromley View Inn

3.5 star property
Bondville
9.0 out of 10, Wonderful, (401)
"Overall a decent stay."
United States
Libin
$90 nightly
The price is $99
Nov 30 - Dec 1
Total with taxes and fees
Bromley View Inn
Garden
Four Columns Inn

Four Columns Inn

4.0 star property
Newfane
9.8 out of 10, Exceptional, (12)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
$125 nightly
The price is $137
Dec 2 - Dec 3
Total with taxes and fees
Four Columns Inn
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
$148 nightly
The price is $163
Dec 2 - Dec 3
Total with taxes and fees
Colonel Williams Inn
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
$95 nightly
The price is $105
Nov 30 - Dec 1
Total with taxes and fees
Deerfield Valley 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, (149)
"Lovely place to stay Jack and Maryann excellent hosts"
United States
Lenny
$187 nightly
The price is $206
Dec 3 - Dec 4
Total with taxes and fees
The Inn at Ormsby Hill
Front of property
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3.0 star property
Chester
9.2 out of 10, Wonderful, (106)
"Good breakfast and dinner options. Great location for hiking."
United States
Paul
$202 nightly
The price is $221
Dec 22 - Dec 23
Total with taxes and fees
Stone Hearth Inn and Eatery
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
$165 nightly
The price is $182
Nov 30 - Dec 1
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, (18)
"The Chester Inn was beautiful and located in downtown Chester. "
United States
Peter C.
$149 nightly
The price is $167
Nov 30 - Dec 1
Total with taxes and fees
Room in Historic Inn! 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 owners were wonderful: kind, interesting to talk to, and very hospitable."
United States
Margaret
$167 nightly
The price is $183
Dec 1 - Dec 2
Total with taxes and fees
Big Bears 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
$144 nightly
The price is $161
Nov 30 - Dec 1
Total with taxes and fees
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
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
Dec 8 - Dec 9
Total with taxes and fees
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.
$139 nightly
The price is $153
Nov 30 - Dec 1
Total with taxes and fees
Zen 10, relax and retreat in the heart of Vermont
Front of property
Hill Farm Inn

Hill Farm Inn

4.0 star property
Arlington
9.6 out of 10, Exceptional, (172)
"This Inn is spectacular! The rooms, grounds, decor, staff and restaurant all were the best for stops on our vacation."
United States
Kenneth
$435 nightly
The price is $475
Nov 30 - Dec 1
Total with taxes and fees
Hill Farm Inn
Lobby
Chesterfield Inn

Chesterfield Inn

4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (104)
"Great stay"
United States
Wayne
$301 nightly
The price is $327
Nov 27 - Nov 28
Total with taxes and fees
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
$274 nightly
The price is $299
Dec 2 - Dec 3
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, (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
$193 nightly
The price is $213
Dec 22 - Dec 23
Total with taxes and fees
Deerhill Inn
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)
"Charming place, hope to go back soon."
United States
Sharon S.
$194 nightly
The price is $217
Nov 30 - Dec 1
Total with taxes and fees
Honeymoon Suite with Jacuzzi Tub in Historic Inn
Property grounds
Room 7 - family room sleeps 4

Room 7 - family room sleeps 4

Manchester
$139 nightly
The price is $153
Nov 30 - Dec 1
Total with taxes and fees
Room 7 - family room sleeps 4
TV
Alpine 5, cozy Vermont retreat

Alpine 5, cozy Vermont retreat

Manchester
$139 nightly
The price is $153
Nov 30 - Dec 1
Total with taxes and fees
Alpine 5, cozy Vermont retreat
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)
"Central for our needs. easy check in process. Lovely large room with comfy beds. "
United States
HIlary H.
$363 nightly
The price is $407
Nov 30 - Dec 1
Total with taxes and fees
King & Queen Suite in Historic Inn Circa 1780
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

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"It was great. The room was wonderful and the staff great."
Constance 2-night trip
Posted 4 days ago
Hampton Inn and Suites Manchester

Find out more about Windham

Windham B&B information

Number of reviews
1,980
Accommodation
48 B&B
Lowest Price
$99
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 $99 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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