A white church with a steeple and red accents, surrounded by autumn trees.

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Our top choices for Windham bed & breakfast

The Orchard House: Inn & Cafe

The Orchard House: Inn & Cafe
3.0 star property
Freeport
9.6 out of 10, Exceptional, (165 reviews)
"Vers Nice stay!"
Canada
Kateri
$214 nightly
The price is $234
Jul 2 - Jul 3
Total with taxes and fees
The Orchard House: Inn & Cafe

Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast
3.0 star property
Rosemont
9.0 out of 10, Wonderful, (133 reviews)
"Breakfast was excellent! Very pet friendly. Room was lovely and clean. "
United States
Earlene
$229 nightly
The price is $250
Jul 2 - Jul 3
Total with taxes and fees
Fleetwood House Bed & Breakfast

Noble House Inn

Noble House Inn
3.5 star property
Bridgton
9.8 out of 10, Exceptional, (116 reviews)
"Very nice room, excellant breakfast."
United States
SANDRA
$183 nightly
The price is $200
Jul 2 - Jul 3
Total with taxes and fees
Noble House Inn

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
$189 nightly
The price is $205
Jul 2 - Jul 3
Total with taxes and fees
The Jeremiah Mason House B & B

Candlebay Inn

Candlebay Inn
3.0 star property
Freeport
9.6 out of 10, Exceptional, (466 reviews)
"Very nice owners and the place was clean food was great and location was excellent. Will tell are family and friends when they visit Maine."
United States
Barry
$194 nightly
The price is $211
Jul 2 - Jul 3
Total with taxes and fees
Candlebay Inn

The Nicholson Inn

The Nicholson Inn
3.0 star property
Freeport
10.0 out of 10, Exceptional, (1 review)
"The owners were amazing and so kind. The location is perfect, and the amenities feel so hoy and great."
United States
Meaghan
$290 nightly
The price is $316
Jul 9 - Jul 10
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, (73 reviews)
"Close to Bates. Gorgeous house. Easy-check, laid back, responsive, and attentive host. We had a great time."
United States
Ippei
$199 nightly
The price is $217
Jul 6 - Jul 7
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, (115 reviews)
"Wonderful stay "
Belgium
Yvan
$154 nightly
The price is $168
Jul 7 - Jul 8
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, (148 reviews)
"Nice bed and breakfast in quiet area near all the shopping "
United States
Suan
$270 nightly
The price is $294
Jul 2 - Jul 3
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, (118 reviews)
"The food was wonderful and the hospitality was great!"
United States
Olivia
$224 nightly
The price is $244
Jul 20 - Jul 21
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, (184 reviews)
"Great place. Comfortable and welcoming. Great proprietors and great location. "
United States
Cecilia
$304 nightly
The price is $331
Jul 2 - Jul 3
Total with taxes and fees
The James Place Inn B&B

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)
"Second time staying here…very nice and clean as well as convenient location."
United States
Teresa
$180 nightly
The price is $196
Jul 2 - Jul 3
Total with taxes and fees
Old Orchard Beach Inn

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, (1,134 reviews)
"great place"
United States
Kimberly
$183 nightly
The price is $199
Jul 6 - Jul 7
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, (188 reviews)
"The place was totally amazing."
United States
Gary
$438 nightly
The price is $478
Jul 6 - Jul 7
Total with taxes and fees
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street
3.5 star property
West End
9.6 out of 10, Exceptional, (124 reviews)
"Beautiful place to stay in the middle of a quiet street and walking distance to many spots. The rooms and common areas were clean and beautifully maintained. Staff was ready to answer any questions you had via phone or text. I loved this inn and would choose it again. Definitely recommend it !"
United States
Adriana Cecilia
$416 nightly
The price is $454
Jul 6 - Jul 7
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
4,017
Accommodation
33 B&B
Lowest Price
$168
Highest Price
$478

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 $168 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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