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

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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

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, (1,174 reviews)
"Great location and exactly what we needed for our time in Portland"
United States
Darbi
The price is AED 244
AED 266 total
includes taxes & fees
22 Nov - 23 Nov
Inn at St John Portland In-Town
A two-story house with a porch and a sign reading "Fleetwork House."

2. Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast
3.0 star property
Rosemont
9.0 out of 10, Wonderful, (150 reviews)
"Close location to airport. Sweet Neighbhorhood Good shower and breakfast was delish. Loved eating on the houses China"
United States
caia
The price is AED 841
AED 954 total
includes taxes & fees
5 Nov - 6 Nov
Fleetwood House Bed & Breakfast
A porch with white wicker chairs and a red cushion, a wooden deck, and a sign for the Noble House Inn in the background.

3. Noble House Inn

Noble House Inn
3.5 star property
Bridgton
9.6 out of 10, Exceptional, (136 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 AED 459
AED 500 total
includes taxes & fees
23 Nov - 24 Nov
Noble House Inn
A well-lit living room with a fireplace, comfortable seating, and a large mirror.

4. Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street
3.5 star property
West End
9.6 out of 10, Exceptional, (137 reviews)
"Beautiful place"
United States
Samuel
The price is AED 766
AED 835 total
includes taxes & fees
10 Nov - 11 Nov
Blind Tiger Portland – Carleton Street
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 AED 801
AED 873 total
includes taxes & fees
30 Nov - 1 Dec
West End Collection at 146 Pine
An outdoor deck with a stone fireplace, a sofa with American flag cushions, and a wicker chair.

6. The Perkins House

The Perkins House
3.0 star property
Cornish
9.8 out of 10, Exceptional, (132 reviews)
"Nice rooms and decorations, easy parking"
United States
Lan
The price is AED 441
AED 480 total
includes taxes & fees
5 Nov - 6 Nov
The Perkins House
A four-poster bed with a chandelier, a bedside table with books, and a view of a brick building through the windows.

7. Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.
3.5 star property
West End
9.6 out of 10, Exceptional, (204 reviews)
"Very helpful and friendly staff"
United States
paul k
The price is AED 896
AED 977 total
includes taxes & fees
8 Nov - 9 Nov
Blind Tiger Portland - Danforth Street.
A black front door with a light fixture above it, flanked by two potted evergreen trees.

8. The Orchard House: Inn & Cafe

The Orchard House: Inn & Cafe
3.0 star property
Freeport
9.6 out of 10, Exceptional, (185 reviews)
"Great place"
United States
Mark
The price is AED 575
AED 626 total
includes taxes & fees
1 Dec - 2 Dec
The Orchard House: Inn & Cafe
A covered patio with wicker furniture and a mosaic table, surrounded by greenery and a white building.

9. Old Orchard Beach Inn

Old Orchard Beach Inn
2.5 star property
Old Orchard Beach
8.2 out of 10, Very good, (1,000 reviews)
"Really nice hotel"
United States
James
The price is AED 458
AED 554 total
includes taxes & fees
5 Nov - 6 Nov
Old Orchard Beach Inn
A white building with a red roof, a sign indicating a vacancy at Candlebay Inn, and an American flag.

10. Candlebay Inn

Candlebay Inn
3.0 star property
Freeport
9.6 out of 10, Exceptional, (497 reviews)
"Great stay in a historic home."
United States
Richard
The price is AED 526
AED 573 total
includes taxes & fees
5 Nov - 6 Nov
Candlebay Inn
A covered porch with white railings and a view of a well-maintained lawn and pathway.

11. The Kendall Inn

The Kendall Inn
3.5 star property
Freeport
9.8 out of 10, Exceptional, (169 reviews)
"The breakfasts were so tasty! The Inn is so charming! We loved our stay and hope to return next year!"
United States
Justin Terry
The price is AED 694
AED 757 total
includes taxes & fees
5 Nov - 6 Nov
The Kendall 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, (67 reviews)
"Beautiful Bed & Breakfast. Owner was great!! Super breakfast!!"
United States
Michael
The price is AED 606
AED 661 total
includes taxes & fees
1 Dec - 2 Dec
The Jeremiah Mason House B & B
A two-story house with a stone staircase leading to a front door, surrounded by a garden with potted plants and a seating area with chairs.

13. 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 AED 650
AED 773 total
includes taxes & fees
18 Nov - 19 Nov
Experience the History of Portland - The Hope Island Room
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, (196 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 AED 920
AED 1,003 total
includes taxes & fees
9 Nov - 10 Nov
The James Place Inn B&B
A two-story house with a balcony, a front porch, and a snow-covered landscape.

15. The Nicholson Inn

The Nicholson Inn
3.0 star property
Freeport
10.0 out of 10, Exceptional, (5 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 AED 989
AED 1,078 total
includes taxes & fees
12 Nov - 13 Nov
The Nicholson Inn
A large, historic house with a prominent turret and bay windows, surrounded by a well-maintained garden with various flowers and a stone pathway.

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 AED 654
AED 713 total
includes taxes & fees
17 Nov - 18 Nov
The Munroe Inn
A two-story house with a stone staircase leading to a front door, surrounded by a garden with potted plants and a seating area with chairs.

17. Diamond Island | King Room with Private Ensuite

Diamond Island | King Room with Private Ensuite
West End
The price is AED 687
AED 777 total
includes taxes & fees
8 Nov - 9 Nov
Diamond Island | King Room with Private Ensuite
A two-story house with a stone staircase leading to a front door, surrounded by a garden with potted plants and a seating area with chairs.

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

Experience the History of Portland - The Hope Island Room
West End
The price is AED 837
AED 993 total
includes taxes & fees
15 Nov - 16 Nov
Experience the History of Portland - The Hope Island Room
A two-story house with a stone staircase leading to a front door, surrounded by a garden with potted plants and a seating area with chairs.

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 AED 973
AED 1,101 total
includes taxes & fees
8 Nov - 9 Nov
Experience the History of Portland - Two Room Suite w/Private Bath
A two-story house with a stone staircase leading to a front door, surrounded by a garden with potted plants and a seating area with chairs.

20. The Loft - private suite in historic home

The Loft - private suite in historic home
West End
The price is AED 1,190
AED 1,653 total
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

Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

8/10 Good
"Good location."
Jing 1-night trip
Posted 1 hour ago
Fireside Inn & Suites Portland

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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