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

Search B&B in Windham

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

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 HK$1,797
HK$2,037 total
includes taxes & fees
1 Oct - 2 Oct
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 HK$995
HK$1,084 total
includes taxes & fees
5 Oct - 6 Oct
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 HK$1,771
HK$1,931 total
includes taxes & fees
7 Oct - 8 Oct
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 HK$1,930
HK$2,104 total
includes taxes & fees
29 Oct - 30 Oct
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 HK$1,370
HK$1,493 total
includes taxes & fees
5 Oct - 6 Oct
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 HK$2,233
HK$2,434 total
includes taxes & fees
5 Oct - 6 Oct
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 HK$2,434
HK$2,653 total
includes taxes & fees
26 Oct - 27 Oct
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 HK$1,822
HK$1,986 total
includes taxes & fees
5 Oct - 6 Oct
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 HK$3,492
HK$3,806 total
includes taxes & fees
30 Oct - 31 Oct
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 HK$1,858
HK$2,025 total
includes taxes & fees
5 Oct - 6 Oct
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 HK$1,165
HK$1,270 total
includes taxes & fees
8 Oct - 9 Oct
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 HK$1,324
HK$1,443 total
includes taxes & fees
9 Oct - 10 Oct
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 HK$2,118
HK$2,506 total
includes taxes & fees
25 Oct - 26 Oct
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 HK$982
HK$1,188 total
includes taxes & fees
4 Oct - 5 Oct
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 HK$1,020
HK$1,112 total
includes taxes & fees
29 Oct - 30 Oct
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 HK$1,397
HK$1,522 total
includes taxes & fees
5 Oct - 6 Oct
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 HK$2,330
HK$2,822 total
includes taxes & fees
6 Oct - 7 Oct
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 HK$2,966
HK$3,601 total
includes taxes & fees
25 Oct - 26 Oct
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 HK$2,966
HK$3,601 total
includes taxes & fees
6 Oct - 7 Oct
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 HK$3,178
HK$4,576 total
includes taxes & fees
4 Oct - 5 Oct
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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
HK$1,084
Highest Price
HK$4,576

Frequently asked questions

Searching for B&Bs in Windham?
If you're hoping for something a little more offbeat than the traditional hotel experience, a bed and breakfast could be a great option for your holiday. When you want to explore some attractions in town, Little Sebago Lake and Sebago Lake are worth a stop.
Are you interested in an apartment instead of a traditional hotel?
With attentive service, opportunities to mingle with other guests and tasty breakfasts, B&Bs provide a unique 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 city centre. Enjoy the outdoor pool and unique decor. 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 city centre. Blind Tiger Portland – Carleton Street: 6 rooms. Located 9.8 mi (15.8 km) from the core of Windham. Enjoy the unique decor 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 temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Windham are January, March, February and December, with each month seeing an average of 19 cm of snowfall.
What is there to do in Windham?
Travellers 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 should 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, ME (PWM-Portland Intl. Jetport), which is located 8.9 mi (14.3 km) away. Otherwise, look 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 a rental car for your journey.

Explore a world of travel with Expedia