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
The price is CA $325
CA $368 total
includes taxes & fees
Oct 1 - Oct 2
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
The price is CA $180
CA $196 total
includes taxes & fees
Oct 5 - Oct 6
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
The price is CA $295
CA $321 total
includes taxes & fees
Oct 20 - Oct 21
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
The price is CA $348
CA $379 total
includes taxes & fees
Oct 29 - Oct 30
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
The price is CA $248
CA $270 total
includes taxes & fees
Oct 1 - Oct 2
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
The price is CA $384
CA $418 total
includes taxes & fees
Oct 5 - Oct 6
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
The price is CA $517
CA $564 total
includes taxes & fees
Oct 31 - Nov 1
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
The price is CA $330
CA $379 total
includes taxes & fees
Oct 1 - Oct 2
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
The price is CA $523
CA $570 total
includes taxes & fees
Oct 30 - Oct 31
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
The price is CA $336
CA $366 total
includes taxes & fees
Oct 5 - Oct 6
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
The price is CA $196
CA $214 total
includes taxes & fees
Oct 7 - Oct 8
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
The price is CA $239
CA $261 total
includes taxes & fees
Oct 23 - Oct 24
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
The price is CA $383
CA $455 total
includes taxes & fees
Oct 6 - Oct 7
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
The price is CA $162
CA $197 total
includes taxes & fees
Oct 4 - Oct 5
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
The price is CA $184
CA $201 total
includes taxes & fees
Oct 29 - Oct 30
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
The price is CA $253
CA $275 total
includes taxes & fees
Oct 5 - Oct 6
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
The price is CA $422
CA $514 total
includes taxes & fees
Oct 6 - Oct 7
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
The price is CA $498
CA $608 total
includes taxes & fees
Oct 6 - Oct 7
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
The price is CA $536
CA $654 total
includes taxes & fees
Oct 6 - Oct 7
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
The price is CA $575
CA $825 total
includes taxes & fees
Oct 4 - Oct 5
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

The Westin Portland Harborview

The Westin Portland Harborview

8/10 Good
"Very nice property. Front desk staff could have been more attentive to guests checking in."
Sheryll 1-night trip
Posted less than an hour ago
The Westin Portland Harborview

Find out more about Windham

Windham B&B information

Number of reviews
2,614
Accommodation
35 B&B
Lowest Price
CA $196
Highest Price
CA $825

Frequently asked questions

Searching for B&Bs in Windham?
If you're looking for something a little different than your standard hotel experience, a bed and breakfast could be a great option for your trip. When you want to explore some attractions in town, Little Sebago Lake and Sebago Lake are worth a stop.
Are you thinking about a B&B instead of a traditional hotel?
With attentive service, opportunities to meet other guests, and hearty breakfasts, B&Bs provide a one-of-a-kind environment.
What are the best B&Bs in Windham?
Here are some well-liked B&Bs in the surrounding area: Inn at St John Portland In-Town: 9.4 mi (15.2 km) from the heart of Windham.Old Orchard Beach Inn: 16.7 mi (26.8 km) from the downtown core. Enjoy the outdoor pool and unique décor. Blind Tiger Portland - Danforth Street.: 9 rooms. Situated 10.2 mi (16.3 km) from the heart of Windham. The Orchard House: Inn & Cafe: 5 rooms. 17.3 mi (27.9 km) from the heart of downtown.Blind Tiger Portland – Carleton Street: 6 rooms. Located 9.8 mi (15.8 km) from the core of Windham. Enjoy the unique décor and patio area.
What's the best time of year to stay at a B&B in Windham?
When you're dreaming of a stay in Windham, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Windham are January, March, February, and December, with each month seeing an average of 7 inches of snowfall.
What is there to do in Windham?
Travelers enjoy Windham for its lakeside setting and restaurants. When you want to spend some time in the great outdoors, Little Sebago Lake and Sebago Lake are some notable spots. You might put Sebago Lake Basin and Seacoast Adventure on your list if you want to see more of the area.
How can I get to and around Windham?
Mapping out your trip in and around Windham is easy with these transportation options. Fly into Portland Intl. Jetport Airport (PWM), which is located 8.9 mi (14.3 km) away from the heart of the city. You can also search for flights into Auburn, ME (LEW-Auburn - Lewiston Municipal), which is 20.8 mi (33.5 km) away. If you'd like to explore around the area, you may want to rent a car for your trip.

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