Search B&B in Windham

Start date: Check-in selected.
To Date
End date: Check-out

  • 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 Jan - 11 Jan
In two weeks
16 Jan - 18 Jan
In one month
30 Jan - 1 Feb
In two months
27 Feb - 1 Mar

Our top choices for Windham bed & breakfast

Porch
Noble House Inn

Noble House Inn

Noble House Inn
3.5 star property
Bridgton
9.8 out of 10, Exceptional, (100)
"Comfortable, quiet, clean and included a delicious breakfast!"
United States
Jim
The price is HK$894
HK$974 total
includes taxes & fees
30 Dec - 31 Dec
Noble House Inn
Front of property – evening/night
Inn at St John Portland In-Town

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, (1141)
"Always a great stay from staff to cleanliness and comforts "
United States
Rachel
The price is HK$622
HK$678 total
includes taxes & fees
30 Dec - 31 Dec
Inn at St John Portland In-Town
Front of property
And. N B&B

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 HK$877
HK$956 total
includes taxes & fees
12 Jan - 13 Jan 2026
And. N B&B
Exterior
The Kendall Inn

The Kendall Inn

The Kendall Inn
3.5 star property
Freeport
9.8 out of 10, Exceptional, (145)
"Quaint stay. Enjoyed our stay. "
United States
Linda
The price is HK$1,301
HK$1,418 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Kendall Inn
Garden
Brewster House Bed & Breakfast

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 HK$1,203
HK$1,311 total
includes taxes & fees
4 Jan - 5 Jan 2026
Brewster House Bed & Breakfast
Exterior
Old Orchard Beach Inn

Old Orchard Beach Inn

Old Orchard Beach Inn
2.5 star property
Old Orchard Beach
8.2 out of 10, Very good, (1001)
"This inn was lovely, quiet, and inviting. "
United States
Jack
Old Orchard Beach Inn
Courtyard view
The Munroe Inn

The Munroe Inn

The Munroe Inn
3.5 star property
Auburn
9.2 out of 10, Wonderful, (69)
"The host is very helpful."
United States
philip
The price is HK$1,251
HK$1,364 total
includes taxes & fees
30 Dec - 31 Dec
The Munroe Inn
Porch
Candlebay Inn

Candlebay Inn

Candlebay Inn
3.0 star property
Freeport
9.6 out of 10, Exceptional, (460)
"The Candlebay Inn was a great stay! Staff was wonderful and the place was super cute and clean. "
United States
Paige
The price is HK$1,197
HK$1,304 total
includes taxes & fees
30 Dec - 31 Dec
Candlebay Inn
View from room
The Perkins House

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
Living area
Blind Tiger Portland – Carleton Street

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 HK$1,391
HK$1,516 total
includes taxes & fees
11 Jan - 12 Jan 2026
Blind Tiger Portland – Carleton Street
Property entrance
Fleetwood House Bed & Breakfast

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 HK$1,780
HK$1,940 total
includes taxes & fees
30 Dec - 31 Dec
Fleetwood House Bed & Breakfast
Premium bedding, individually decorated, individually furnished
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.
3.5 star property
West End
9.6 out of 10, Exceptional, (167)
"The property is beautiful, the staff is kind, and the rooms are spacious and clean. It was great to have a safe place to park the car while having so many things to do within walking distance. Being able to grab a quick breakfast before heading out was great too! We loved our stay here!"
United States
Darby
The price is HK$1,601
HK$1,745 total
includes taxes & fees
4 Jan - 5 Jan 2026
Blind Tiger Portland - Danforth Street.
Outdoor dining
The James Place Inn B&B

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 HK$1,697
HK$1,850 total
includes taxes & fees
30 Dec - 31 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.
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

Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent
"We were very pleased with our room (size, comfort and cleanliness)! The parking situation is easy, too."
Deborah 1-night trip
Posted 3 days ago
Holiday Inn Portland-By the Bay by IHG

Find out more about Windham

Windham B&B information

Number of reviews
3,774
Accommodation
34 B&B
Lowest Price
HK$678
Highest Price
HK$1,940

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, Seacoast Adventure and Little 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. Blind Tiger Portland – Carleton Street: 6 rooms. 9.8 mi (15.8 km) from the city centre. 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 Seacoast Adventure and Sebago Lake Basin 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