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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

Front of property - evening/night
Inn at St John Portland In-Town
Inn at St John Portland In-Town
2.5 star property
8.8 out of 10, Excellent, (1129)
"Great place to stay. Would highly recommend "
United States
Benjamin
$80 nightly
The price is $87
Dec 1 - Dec 2
Total with taxes and fees
Inn at St John Portland In-Town
Front of property - evening/night
The Orchard House & Cafe
The Orchard House & Cafe
3.0 star property
9.6 out of 10, Exceptional, (161)
"Lovely home outside the congestion of Freeport but close for easy visit. Breakfast was perfect. "
United States
M. Karen
$167 nightly
The price is $182
Nov 9 - Nov 10
Total with taxes and fees
The Orchard House & Cafe
Porch
Noble House Inn
Noble House Inn
3.5 star property
9.8 out of 10, Exceptional, (100)
"Excellent accommodations, clean well provided for. Owners were very friendly. Recommend highly. "
United States
Victor
$120 nightly
The price is $130
Nov 18 - Nov 19
Total with taxes and fees
Noble House Inn
Exterior
Old Orchard Beach Inn
Old Orchard Beach Inn
2.5 star property
8.2 out of 10, Very Good, (1000)
"My family had a cozy and memorable stay. The staff was incredibly helpful and my daughter enjoyed the historical look and feel to the Inn."
United States
Christopher
$98 nightly
The price is $107
Nov 8 - Nov 9
Total with taxes and fees
Old Orchard Beach Inn
Porch
Candlebay Inn
Candlebay Inn
3.0 star property
9.6 out of 10, Exceptional, (456)
"The Inn was great and the staff was very hospitable "
United States
Timothy
$154 nightly
The price is $168
Nov 7 - Nov 8
Total with taxes and fees
Candlebay Inn
Suite (The Carriage) | View from room
The Perkins House
The Perkins House
3.0 star property
9.8 out of 10, Exceptional, (111)
"Wonderful stay "
Belgium
Yvan
$150 nightly
The price is $164
Nov 30 - Dec 1
Total with taxes and fees
The Perkins House
Exterior
The Kendall Inn
The Kendall Inn
3.5 star property
9.8 out of 10, Exceptional, (144)
"Quaint stay. Enjoyed our stay. "
United States
Linda
$210 nightly
The price is $229
Nov 7 - Nov 8
Total with taxes and fees
The Kendall Inn
Courtyard view
The Munroe Inn
The Munroe Inn
3.5 star property
9.2 out of 10, Wonderful, (68)
"Near downtown, restaurnts, beautiful old victorian, delicious breakfast."
United States
wilbur
$161 nightly
The price is $175
Nov 8 - Nov 9
Total with taxes and fees
The Munroe Inn
Property entrance
Fleetwood House Bed & Breakfast
Fleetwood House Bed & Breakfast
3.0 star property
9.0 out of 10, Wonderful, (132)
"This was a beautiful old house in excellent condition. The hosts were very nice. The breakfast was excellent. "
United States
Linda
$229 nightly
The price is $250
Nov 7 - Nov 8
Total with taxes and fees
Fleetwood House Bed & Breakfast
Baxter | 1 bedroom, premium bedding, individually decorated
Blind Tiger Portland - Danforth Street.
Blind Tiger Portland - Danforth Street.
3.5 star property
9.6 out of 10, Exceptional, (160)
" Beautiful historic building. The common areas and our room were stunning! Breakfast in the morning was great. Make sure to go to the widow’s walk in the evening for a view. "
United States
John
$224 nightly
The price is $245
Nov 16 - Nov 17
Total with taxes and fees
Blind Tiger Portland - Danforth Street.
Comfort Single Room, Non Smoking (Room 1, Second Floor) | Individually decorated, individually furnished, iron/ironing board
The Jeremiah Mason House B & B
The Jeremiah Mason House B & B
3.0 star property
9.6 out of 10, Exceptional, (51)
"Valerie was an excellent hostess. My room was cozy and comfortable. If I find myself in the area, I will definitely stay here, again. "
United States
Gina
$189 nightly
The price is $205
Nov 7 - Nov 8
Total with taxes and fees
The Jeremiah Mason House B & B
Stovall | Living area
Blind Tiger Portland – Carleton Street
Blind Tiger Portland – Carleton Street
3.5 star property
9.6 out of 10, Exceptional, (118)
"Great location and such an amazing day! The interiors are inspiring! "
United States
Riddhi
$222 nightly
The price is $242
Nov 17 - Nov 18
Total with taxes and fees
Blind Tiger Portland – Carleton Street
Outdoor dining
The James Place Inn B&B
The James Place Inn B&B
3.5 star property
10.0 out of 10, Exceptional, (182)
"Wish we could have stayed longer. It has the ambiance of an older inn but the rooms are very clean and well maintained. "
United States
Melissa
$218 nightly
The price is $238
Dec 1 - Dec 2
Total with taxes and fees
The James Place Inn B&B
Garden
Brewster House Bed & Breakfast
Brewster House Bed & Breakfast
4.0 star property
9.8 out of 10, Exceptional, (114)
"Nice inn - a bit noisy as it's on a main street and I had a front facing room. "
United States
lorna
$379 nightly
The price is $413
Dec 3 - Dec 4
Total with taxes and fees
Brewster House Bed & Breakfast
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

LivAway Suites Portland-Scarborough

LivAway Suites Portland-Scarborough

10/10 Excellent
"clean and check in and out was easy.Quality for that price is a steal."
Gershom 14-night trip
Posted 1 day ago
LivAway Suites Portland-Scarborough

Find out more about Windham

Windham B&B information

Number of reviews
3,901
Accommodation
34 B&B
Lowest Price
$87
Highest Price
$413

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 $87 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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