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

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Check prices for these dates

Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct
In one month
6 Nov - 8 Nov
In two months
4 Dec - 6 Dec

Our top choices for Windham bed & breakfast

A multi-story building with a stone facade, multiple windows, and awnings.

1. 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, (1,156 reviews)
"It was a cool place to stay. Plenty of space in the room. Would stay here again."
United States
Steven
The price is AU$118
includes taxes & fees
25 Oct - 26 Oct
Inn at St John Portland In-Town
A garden with a stone wall, various plants, and flowers.

2. Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast
3.0 star property
Rosemont
9.0 out of 10, Wonderful, (148 reviews)
"A wonderful experience with Jim and Linda. Fantastic breakfast every morning, in the cutest old house just outside of the city. Definitely recommend!"
United States
Tyler
The price is AU$372
includes taxes & fees
13 Oct - 14 Oct
Fleetwood House Bed & Breakfast
A well-lit living room with a fireplace, comfortable seating, and a large mirror.

3. Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street
3.5 star property
West End
9.6 out of 10, Exceptional, (135 reviews)
"Fantastic property, full of character in a great location. Walkable location, we will be back next time we are in Portland."
United States
Ryan
The price is AU$383
includes taxes & fees
1 Nov - 2 Nov
Blind Tiger Portland – Carleton Street
An outdoor deck with a stone fireplace, a sofa with American flag cushions, and a wicker chair.

4. The Perkins House

The Perkins House
3.0 star property
Cornish
9.8 out of 10, Exceptional, (131 reviews)
"Nice rooms and decorations, easy parking"
United States
Lan
The price is AU$205
includes taxes & fees
18 Oct - 19 Oct
The Perkins House
Exterior

5. 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 AU$342
includes taxes & fees
1 Nov - 2 Nov
West End Collection at 146 Pine
A porch with white wicker chairs and a red cushion, a wooden deck, and a sign for the Noble House Inn in the background.

6. Noble House Inn

Noble House Inn
3.5 star property
Bridgton
9.6 out of 10, Exceptional, (131 reviews)
"All the staff, and even the lodgers were extremely nice. Very clean, cozy, and pleasant stay. I will make sure all my friends and family lodge at the Noble House after my move."
United States
Michael
The price is AU$223
includes taxes & fees
27 Oct - 28 Oct
Noble House Inn
A covered porch with white railings and a view of a well-maintained lawn and pathway.

7. The Kendall Inn

The Kendall Inn
3.5 star property
Freeport
9.8 out of 10, Exceptional, (164 reviews)
"I really enjoyed The Kendall Inn. Elegant and comfortable, super clean rooms, friendly staff and delicious breakfasts (and home baked cookies in the evening). Definitely would love to stay there again"
United States
Katherine
The price is AU$302
includes taxes & fees
1 Nov - 2 Nov
The Kendall Inn
A white building with a red roof, a sign indicating a vacancy at Candlebay Inn, and an American flag.

8. Candlebay Inn

Candlebay Inn
3.0 star property
Freeport
9.6 out of 10, Exceptional, (495 reviews)
"Great stay in a historic home."
United States
Richard
The price is AU$223
includes taxes & fees
1 Nov - 2 Nov
Candlebay 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, (198 reviews)
"Place was charming and quirky. Very comfortable and well located."
United States
Mary
The price is AU$412
includes taxes & fees
9 Nov - 10 Nov
Blind Tiger Portland - Danforth Street.
A black front door with a light fixture above it, flanked by two potted evergreen trees.

10. The Orchard House: Inn & Cafe

The Orchard House: Inn & Cafe
3.0 star property
Freeport
9.6 out of 10, Exceptional, (184 reviews)
"Great place"
United States
Mark
The price is AU$328
includes taxes & fees
21 Oct - 22 Oct
The Orchard House: Inn & Cafe
A covered patio with wicker furniture and a mosaic table, surrounded by greenery and a white building.

11. Old Orchard Beach Inn

Old Orchard Beach Inn
2.5 star property
Old Orchard Beach
8.2 out of 10, Very good, (1,005 reviews)
"Really nice hotel"
United States
James
The price is AU$197
includes taxes & fees
13 Oct - 14 Oct
Old Orchard Beach Inn
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, (63 reviews)
"Cute historic bed and breakfast. I had a very comfortable stay."
United States
Carrie
The price is AU$267
includes taxes & fees
13 Oct - 14 Oct
The Jeremiah Mason House B & B
A two-story house with a balcony, a front porch, and a snow-covered landscape.

13. The Nicholson Inn

The Nicholson Inn
3.0 star property
Freeport
10.0 out of 10, Exceptional, (4 reviews)
"We had a fantastic and lovely, although quick, stay. The Inn is very charming and John and Loretta are so kind and helpful. Would love to go back and stay with them again.."
United States
alexandre
The price is AU$402
includes taxes & fees
13 Oct - 14 Oct
The Nicholson Inn
A house with a sign for The James Place Inn, indicating a vacancy.

14. The James Place Inn B&B

The James Place Inn B&B
3.5 star property
Freeport
10.0 out of 10, Exceptional, (195 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 AU$391
includes taxes & fees
9 Nov - 10 Nov
The James Place Inn B&B
A kitchen with a wooden table, bench, and a fireplace.

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

Experience the History of Portland - The Hope Island Room
West End
10.0 out of 10, Exceptional, (1 review)
"Really cool home and room was big and clean!"
United States
Daniel
The price is AU$338
includes taxes & fees
1 Nov - 2 Nov
Experience the History of Portland - The Hope Island Room
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 AU$278
includes taxes & fees
13 Oct - 14 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 AU$395
includes taxes & fees
1 Nov - 2 Nov
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 AU$481
includes taxes & fees
1 Nov - 2 Nov
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 AU$553
includes taxes & fees
1 Nov - 2 Nov
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 AU$679
includes taxes & fees
8 Nov - 9 Nov
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

Clarion Pointe South Portland

Clarion Pointe South Portland

8/10 Good
"The hotel was good overall and a convenient option for our needs. We only stayed one night, but it was a good choice for a short stay. I would consider staying here again."
Eduardo 1-night trip
Posted less than an hour ago
Clarion Pointe South Portland

Find out more about Windham

Windham B&B information

Number of reviews
4,188
Accommodation
41 B&B
Lowest Price
AU$118
Highest Price
AU$679

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.

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