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Our top choices for Windham bed & breakfast

Noble House Inn

Noble House Inn
3.5 star property
Bridgton
9.8 out of 10, Exceptional, (110 reviews)
"Very nice room, excellant breakfast."
United States
SANDRA
$115 nightly
The price is $125
May 17 - May 18
Total with taxes and fees
Noble House Inn

The Orchard House: Inn & Cafe

The Orchard House: Inn & Cafe
3.0 star property
Freeport
9.6 out of 10, Exceptional, (162 reviews)
"Wonderful place to stay! The room was very clean and the beds super comfortable. Will most definitely be returning for another visit in Maine."
United States
Shannon
$156 nightly
The price is $171
May 12 - May 13
Total with taxes and fees
The Orchard House: Inn & Cafe

Lakeview Inn

Lakeview Inn
3.5 star property
Naples
9.2 out of 10, Wonderful, (57 reviews)
"Very good location, great host and a really good breakfast!"
United States
Andrew
$230 nightly
The price is $251
May 24 - May 25
Total with taxes and fees
Lakeview Inn

Candlebay Inn

Candlebay Inn
3.0 star property
Freeport
9.6 out of 10, Exceptional, (462 reviews)
"The room was extremely clean the owner very friendly and the breakfast delicious highly recommend."
United States
Dawn
$149 nightly
The price is $162
May 12 - May 13
Total with taxes and fees
Candlebay Inn

Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast
3.0 star property
Rosemont
9.0 out of 10, Wonderful, (132 reviews)
"Wonderful breakfast, nice hosts, beautiful home."
United States
Joan
$229 nightly
The price is $250
May 12 - May 13
Total with taxes and fees
Fleetwood House Bed & Breakfast

The Jeremiah Mason House B & B

The Jeremiah Mason House B & B
3.0 star property
Limerick
9.6 out of 10, Exceptional, (52 reviews)
"Excellent place to stay. Clean room and dining area, tasty breakfast, and very friendly host!"
United States
Kenneth
$167 nightly
The price is $182
May 13 - May 14
Total with taxes and fees
The Jeremiah Mason House B & B

The Nicholson Inn

The Nicholson Inn
3.0 star property
Freeport
$247 nightly
The price is $270
May 17 - May 18
Total with taxes and fees
The Nicholson Inn

The Munroe Inn

The Munroe Inn
3.5 star property
Auburn
9.2 out of 10, Wonderful, (72 reviews)
"Close to Bates. Gorgeous house. Easy-check, laid back, responsive, and attentive host. We had a great time."
United States
Ippei
$150 nightly
The price is $164
May 12 - May 13
Total with taxes and fees
The Munroe Inn

The Perkins House

The Perkins House
3.0 star property
Cornish
9.8 out of 10, Exceptional, (114 reviews)
"Carriage House was very nice and comfortable. "
United States
Susan
$152 nightly
The price is $166
May 18 - May 19
Total with taxes and fees
The Perkins House

The Kendall Inn

The Kendall Inn
3.5 star property
Freeport
9.8 out of 10, Exceptional, (145 reviews)
"Nice bed and breakfast in quiet area near all the shopping "
United States
Suan
$222 nightly
The price is $242
May 12 - May 13
Total with taxes and fees
The Kendall Inn

Brewster House Bed & Breakfast

Brewster House Bed & Breakfast
4.0 star property
Freeport
9.8 out of 10, Exceptional, (115 reviews)
"The food was wonderful and the hospitality was great!"
United States
Olivia
$167 nightly
The price is $182
May 13 - May 14
Total with taxes and fees
Brewster House Bed & Breakfast

The James Place Inn B&B

The James Place Inn B&B
3.5 star property
Freeport
10.0 out of 10, Exceptional, (183 reviews)
"Great place. Comfortable and welcoming. Great proprietors and great location. "
United States
Cecilia
$304 nightly
The price is $331
May 12 - May 13
Total with taxes and fees
The James Place Inn B&B

Inn at St John Portland In-Town

Inn at St John Portland In-Town
2.5 star property
Valley Street
8.8 out of 10, Excellent, (1,139 reviews)
"Fantastic place "
United States
Maybe
$115 nightly
The price is $125
May 12 - May 13
Total with taxes and fees
Inn at St John Portland In-Town

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.
3.5 star property
West End
9.6 out of 10, Exceptional, (182 reviews)
"The place was totally amazing."
United States
Gary
$328 nightly
The price is $357
May 27 - May 28
Total with taxes and fees
Blind Tiger Portland - Danforth Street.

Old Orchard Beach Inn

Old Orchard Beach Inn
2.5 star property
Old Orchard Beach
8.2 out of 10, Very Good, (1,000 reviews)
"decent stay for a short time Period."
United States
Dwayne
$146 nightly
The price is $159
Jun 10 - Jun 11
Total with taxes and fees
Old Orchard Beach Inn

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street
3.5 star property
West End
9.6 out of 10, Exceptional, (121 reviews)
"Great location and such an amazing day! The interiors are inspiring! "
United States
Riddhi
$251 nightly
The price is $274
May 19 - May 20
Total with taxes and fees
Blind Tiger Portland – Carleton Street
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

Find out more about Windham

Windham B&B information

Number of reviews
3,094
Accommodation
34 B&B
Lowest Price
$125
Highest Price
$357

Frequently asked questions

What is the nightly rate for a B&B in Windham?
Prices for B&Bs in Windham often vary, but you can find a great deal from $125 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 & Breakfast in Windham?
The best time to book a B&B in Windham is during the vibrant fall season, particularly from September to October. This period is favored by travelers seeking a picturesque escape amid the stunning autumn foliage. As the leaves change, Windham transforms into a canvas of brilliant reds, oranges, and yellows, providing a breathtaking backdrop for outdoor activities and leisurely strolls.

September offers mild temperatures, typically ranging from the low 50s to mid-70s Fahrenheit, making it ideal for hiking and exploring the scenic trails in the Catskill Mountains. The comfortable climate invites visitors to engage in outdoor adventures, whether it's a hike to the summit of Windham Mountain or a bike ride through the charming countryside.

If you are considering a more budget-friendly option, late October can be particularly appealing. This month often features fewer crowds, allowing for a peaceful retreat where you can enjoy the lingering fall beauty without the hustle and bustle. Plus, many local businesses offer seasonal promotions, giving you the opportunity to enjoy quality experiences at a great value.
What is the difference between a Windham Bed & Breakfast 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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