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

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Check prices for these dates

Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18
In one month
Oct 30 - Nov 1
In two months
Nov 27 - Nov 29

Our top choices for Windham bed & breakfast

A garden with a stone wall, various plants, and flowers.

1. Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast
3.0 star property
Rosemont
9.0 out of 10, Wonderful, (147 reviews)
"Breakfast was wonderful!"
United States
Karen
$238 nightly
The price is $260
Oct 1 - Oct 2
Total with taxes and fees
Fleetwood House Bed & Breakfast
A multi-story building with a stone facade, multiple windows, and awnings.

2. Inn at St John Portland In-Town

Inn at St John Portland In-Town
2.5 star property
Valley Street
8.6 out of 10, Excellent, (1,149 reviews)
"Cute spot and very affordable."
United States
Tess
$144 nightly
The price is $157
Oct 5 - Oct 6
Total with taxes and fees
Inn at St John Portland In-Town
A black front door with a light fixture above it, flanked by two potted evergreen trees.

3. The Orchard House: Inn & Cafe

The Orchard House: Inn & Cafe
3.0 star property
Freeport
9.6 out of 10, Exceptional, (181 reviews)
"Amazing stay in a perfect location! Would absolutely recommend to family and friends and will likely stay again!"
United States
Megan
$199 nightly
The price is $217
Oct 20 - Oct 21
Total with taxes and fees
The Orchard House: Inn & Cafe
Exterior

4. West End Collection at 146 Pine

West End Collection at 146 Pine
3.0 star property
West End
9.6 out of 10, Exceptional, (100 reviews)
"This was a super cute boutique inn and the location was ideal. The staff was super friendly!"
United States
Stephanie
$245 nightly
The price is $267
Oct 29 - Oct 30
Total with taxes and fees
West End Collection at 146 Pine
A white building with a red roof, a sign indicating a vacancy at Candlebay Inn, and an American flag.

5. Candlebay Inn

Candlebay Inn
3.0 star property
Freeport
9.6 out of 10, Exceptional, (490 reviews)
"Great stay in a historic home."
United States
Richard
$194 nightly
The price is $211
Oct 1 - Oct 2
Total with taxes and fees
Candlebay Inn
A two-story house with a balcony, a front porch, and a snow-covered landscape.

6. The Nicholson Inn

The Nicholson Inn
3.0 star property
Freeport
10.0 out of 10, Exceptional, (3 reviews)
"The owners were amazing and so kind. The location is perfect, and the amenities feel so hoy and great."
United States
Meaghan
$275 nightly
The price is $300
Oct 5 - Oct 6
Total with taxes and fees
The Nicholson Inn
A well-lit living room with a fireplace, comfortable seating, and a large mirror.

7. Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street
3.5 star property
West End
9.6 out of 10, Exceptional, (133 reviews)
"Beautiful place"
United States
Samuel
$342 nightly
The price is $372
Oct 31 - Nov 1
Total with taxes and fees
Blind Tiger Portland – Carleton Street
A covered porch with white railings and a view of a well-maintained lawn and pathway.

8. The Kendall Inn

The Kendall Inn
3.5 star property
Freeport
9.8 out of 10, Exceptional, (162 reviews)
"The room was lovely and comfortable, including easy-to-adjust air conditioning. Breakfast was delicious as were the homemade cookies available each evening. Coffee and tea were available all the time."
United States
Kenneth and
$258 nightly
The price is $281
Oct 1 - Oct 2
Total with taxes and fees
The Kendall Inn
A four-poster bed with a chandelier, a bedside table with books, and a view of a brick building through the windows.

9. Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.
3.5 star property
West End
9.6 out of 10, Exceptional, (195 reviews)
"Place was charming and quirky. Very comfortable and well located."
United States
Mary
$342 nightly
The price is $373
Oct 31 - Nov 1
Total with taxes and fees
Blind Tiger Portland - Danforth Street.
A house with a sign for The James Place Inn, indicating a vacancy.

10. The James Place Inn B&B

The James Place Inn B&B
3.5 star property
Freeport
10.0 out of 10, Exceptional, (194 reviews)
"Sean was amazingly helpful and friendly. The house itself is so well maintained, and the blue room was adorable. Loved the fact that we were within walking distance of all the shops. Would definitely recommend and will plan on staying again the next time we’re in town."
United States
Kim
$237 nightly
The price is $258
Oct 5 - Oct 6
Total with taxes and fees
The James Place Inn B&B
An outdoor deck with a stone fireplace, a sofa with American flag cushions, and a wicker chair.

11. The Perkins House

The Perkins House
3.0 star property
Cornish
9.8 out of 10, Exceptional, (129 reviews)
"Nice rooms and decorations, easy parking"
United States
Lan
$135 nightly
The price is $147
Oct 25 - Oct 26
Total with taxes and fees
The Perkins House
A brick building with a white entrance, steps leading up to a door, and potted plants on either side.

12. The Jeremiah Mason House B & B

The Jeremiah Mason House B & B
3.0 star property
Limerick
9.6 out of 10, Exceptional, (60 reviews)
"Cute historic bed and breakfast. I had a very comfortable stay."
United States
Carrie
$169 nightly
The price is $184
Oct 1 - Oct 2
Total with taxes and fees
The Jeremiah Mason House B & B
A kitchen with a wooden table, bench, and a fireplace.

13. Experience the History of Portland - The Hope Island Room

Experience the History of Portland - The Hope Island Room
West End
$293 nightly
The price is $319
Oct 25 - Oct 26
Total with taxes and fees
Experience the History of Portland - The Hope Island Room
A covered patio with wicker furniture and a mosaic table, surrounded by greenery and a white building.

14. Old Orchard Beach Inn

Old Orchard Beach Inn
2.5 star property
Old Orchard Beach
8.2 out of 10, Very good, (1,001 reviews)
"Beautiful property a short walk from the beach and all the attractions make it an ideal place to stay"
United States
James
$129 nightly
The price is $141
Oct 4 - Oct 5
Total with taxes and fees
Old Orchard Beach Inn
A porch with white wicker chairs and a red cushion, a wooden deck, and a sign for the Noble House Inn in the background.

15. Noble House Inn

Noble House Inn
3.5 star property
Bridgton
9.6 out of 10, Exceptional, (130 reviews)
"Comfortable, lovely view of garden, clean."
United States
Virginia
$143 nightly
The price is $156
Oct 27 - Oct 28
Total with taxes and fees
Noble House Inn
A two-story house with a snow-covered roof and a porch.

16. The Munroe Inn

The Munroe Inn
3.5 star property
Auburn
9.2 out of 10, Wonderful, (78 reviews)
"Wonderful place to stay. The rooms are so comfortable and the host was very accommodating. Breakfast was outstanding and the best cup of coffee in Auburn. Such a gem of a place!"
United States
Tristan
$178 nightly
The price is $194
Oct 5 - Oct 6
Total with taxes and fees
The Munroe Inn
A bedroom with a large bed, a wooden wardrobe, and a bench.

17. The Diamond Island Suite - Suite in Historic Home

The Diamond Island Suite - Suite in Historic Home
West End
$330 nightly
The price is $360
Oct 6 - Oct 7
Total with taxes and fees
The Diamond Island Suite - Suite in Historic Home
A dining area with a round table, six chairs, and a floral centerpiece.

18. Experience the History of Portland - The Hope Island Room

Experience the History of Portland - The Hope Island Room
West End
$391 nightly
The price is $426
Oct 6 - Oct 7
Total with taxes and fees
Experience the History of Portland - The Hope Island Room
An outdoor dining setup with a table set for two, featuring candles, glassware, and a vase of flowers.

19. Experience the History of Portland - Two Room Suite w/Private Bath

Experience the History of Portland - Two Room Suite w/Private Bath
West End
$421 nightly
The price is $459
Oct 6 - Oct 7
Total with taxes and fees
Experience the History of Portland - Two Room Suite w/Private Bath
A staircase with a wooden handrail and black steps, leading to a room with patterned wallpaper and a chandelier.

20. The Loft - private suite in historic home

The Loft - private suite in historic home
West End
$535 nightly
The price is $583
Oct 4 - Oct 5
Total with taxes and fees
The Loft - private suite in historic home
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

Comfort Inn South Portland Airport

Comfort Inn South Portland Airport

8/10 Good
"There is a build up of people trying to get their breakfast the way it is designed. The rooms are smaller than I usually get."
Cynthia 1-night trip
Posted 1 hour ago
Comfort Inn South Portland Airport

Find out more about Windham

Windham B&B information

Number of reviews
2,614
Accommodation
35 B&B
Lowest Price
$141
Highest Price
$583

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 $141 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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