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12 Dec - 14 Dec
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30 Jan - 1 Feb

B&B in Windham

Front of property - evening/night
Inn at St John Portland In-Town

Inn at St John Portland In-Town

2.5 star property
Valley Street
8.8 out of 10, Excellent, (1151)
"Enjoyed our stay."
United States
Heather
The price is SAR 300
SAR 327 total
includes taxes & fees
2 Dec - 3 Dec
Inn at St John Portland In-Town
Front of property
And. N B&B

And. N B&B

3.0 star property
Gray
9.8 out of 10, Exceptional, (77)
"Really lovely place and great hospitality from the owners!"
United States
Hunter
The price is SAR 394
SAR 429 total
includes taxes & fees
1 Jan - 2 January 2026
And. N B&B
Porch
Noble House Inn

Noble House Inn

3.5 star property
Bridgton
9.8 out of 10, Exceptional, (100)
"A very well maintained B&B. The folks that run it really go all out to provide an excellent stay."
United States
Steve
The price is SAR 431
SAR 470 total
includes taxes & fees
28 Dec - 29 Dec
Noble House Inn
Front of property - evening/night
The Orchard House: Inn, Ice Cream, Cafe

The Orchard House: Inn, Ice Cream, Cafe

3.0 star property
Freeport
9.6 out of 10, Exceptional, (162)
"Wonderful place to stay! The room was very clean and the beds super comfortable. Will most definitely be returning for another visit in Maine."
United States
Shannon
The Orchard House: Inn, Ice Cream, Cafe
Exterior
Old Orchard Beach Inn

Old Orchard Beach Inn

2.5 star property
Old Orchard Beach
8.2 out of 10, Very Good, (1001)
"A beautiful place to stay!!! First time at a B&B and it did not disappoint."
United States
Kristian
Old Orchard Beach Inn
Exterior
The Kendall Inn

The Kendall Inn

3.5 star property
Freeport
9.8 out of 10, Exceptional, (144)
"Quaint stay. Enjoyed our stay. "
United States
Linda
The price is SAR 628
SAR 685 total
includes taxes & fees
1 Jan - 2 January 2026
The Kendall Inn
Porch
Candlebay Inn

Candlebay Inn

3.0 star property
Freeport
9.6 out of 10, Exceptional, (457)
"Great location and hospitality."
United States
Brandon
The price is SAR 578
SAR 630 total
includes taxes & fees
2 Dec - 3 Dec
Candlebay Inn
Courtyard view
The Munroe Inn

The Munroe Inn

3.5 star property
Auburn
9.2 out of 10, Wonderful, (68)
"The host is very helpful."
United States
philip
The price is SAR 604
SAR 658 total
includes taxes & fees
2 Dec - 3 Dec
The Munroe Inn
Baxter | Premium bedding, individually decorated, individually furnished
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 star property
West End
9.6 out of 10, Exceptional, (166)
" Beautiful historic building. The common areas and our room were stunning! Breakfast in the morning was great. Make sure to go to the widow’s walk in the evening for a view. "
United States
John
The price is SAR 740
SAR 807 total
includes taxes & fees
11 Dec - 12 Dec
Blind Tiger Portland - Danforth Street.
Suite (The Carriage) | View from room
The Perkins House

The Perkins House

3.0 star property
Cornish
9.8 out of 10, Exceptional, (114)
"Fun, hospitable hosts. Helpful with ideas for our itinerary. Great breakfast. "
United States
John
The Perkins House
Stovall | Living area
Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 star property
West End
9.6 out of 10, Exceptional, (120)
"Loved the place "
United States
Stephen
The price is SAR 621
SAR 677 total
includes taxes & fees
8 Dec - 9 Dec
Blind Tiger Portland – Carleton Street
Property entrance
Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast

3.0 star property
Rosemont
9.0 out of 10, Wonderful, (132)
"Lovely, comfortable stay! So welcoming and accommodating. We only stayed one night but will keep this in mind next time we are in the area :)"
United States
Sadie
The price is SAR 859
SAR 936 total
includes taxes & fees
2 Dec - 3 Dec
Fleetwood House Bed & Breakfast
Garden
Brewster House Bed & Breakfast

Brewster House Bed & Breakfast

4.0 star property
Freeport
9.8 out of 10, Exceptional, (114)
"The food was wonderful and the hospitality was great!"
United States
Olivia
The price is SAR 784
SAR 855 total
includes taxes & fees
7 Dec - 8 Dec
Brewster House Bed & Breakfast
Comfort Single Room, Non Smoking (Room 1, Second Floor) | Individually decorated, individually furnished, iron/ironing board
The Jeremiah Mason House B & B

The Jeremiah Mason House B & B

3.0 star property
Limerick
9.6 out of 10, Exceptional, (51)
"Great charming place to stay"
United States
Susan
The price is SAR 707
SAR 771 total
includes taxes & fees
2 Dec - 3 Dec
The Jeremiah Mason House B & B
Outdoor dining
The James Place Inn B&B

The James Place Inn B&B

3.5 star property
Freeport
10.0 out of 10, Exceptional, (182)
"Wish we could have stayed longer. It has the ambiance of an older inn but the rooms are very clean and well maintained. "
United States
Melissa
The price is SAR 819
SAR 893 total
includes taxes & fees
2 Dec - 3 Dec
The James Place Inn B&B
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

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

10/10 Excellent
"Excellent location "
maureen 2-night trip
Posted 14 hours ago
Portland Regency Hotel & Spa

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 – Carleton Street: 6 rooms. Situated 9.8 mi (15.8 km) from the heart of Windham. Enjoy the unique décor and patio area. The Orchard House & Cafe: 5 rooms. 17.3 mi (27.9 km) from the heart of downtown.Blind Tiger Portland - Danforth Street.: 9 rooms. Located 10.2 mi (16.3 km) from the core of Windham.
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.