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
6 Feb - 8 Feb
In two weeks
13 Feb - 15 Feb
In one month
27 Feb - 1 Mar
In two months
27 Mar - 29 Mar

Our top choices for Windham bed & breakfast

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, (1,138 reviews)
"Always a great stay from staff to cleanliness and comforts "
United States
Rachel
The price is SAR 300
SAR 327 total
includes taxes & fees
31 Jan - 1 Feb
Inn at St John Portland In-Town
Porch

Noble House Inn

Noble House Inn
3.5 star property
Bridgton
9.8 out of 10, Exceptional, (104 reviews)
"We skied at Pleasant Mountain for 2 days and The Noble House was the perfect spot to spend the night as it is only 10 minutes away. The Inn was very inviting and our room was perfect for what we needed - very clean! We were not able to stay for the french toast in the morning, but it smelled amazing. We will definitely be staying there again!"
United States
Patrick
The price is SAR 449
SAR 489 total
includes taxes & fees
1 Mar - 2 Mar
Noble House Inn
Exterior

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)
"Beautiful quaint hotel. Clean rooms "
United States
John
Old Orchard Beach Inn
Interior entrance

The Kendall Inn

The Kendall Inn
3.5 star property
Freeport
9.8 out of 10, Exceptional, (145 reviews)
"Quaint stay. Enjoyed our stay. "
United States
Linda
The price is SAR 628
SAR 684 total
includes taxes & fees
31 Jan - 1 Feb
The Kendall Inn
Family Suite | Individually decorated, free WiFi

And. N B&B

And. N B&B
3.0 star property
Gray
9.8 out of 10, Exceptional, (77 reviews)
"Nice place, excellent breakfast! "
United States
Clarence
And. N B&B
Exterior

The Munroe Inn

The Munroe Inn
3.5 star property
Auburn
9.2 out of 10, Wonderful, (69 reviews)
"The host is very helpful."
United States
philip
The price is SAR 563
SAR 613 total
includes taxes & fees
30 Jan - 31 Jan
The Munroe Inn
Porch

Candlebay Inn

Candlebay Inn
3.0 star property
Freeport
9.6 out of 10, Exceptional, (460 reviews)
"The Candlebay Inn was a great stay! Staff was wonderful and the place was super cute and clean. "
United States
Paige
The price is SAR 578
SAR 629 total
includes taxes & fees
1 Feb - 2 Feb
Candlebay Inn
Suite (The Carriage) | View from room

The Perkins House

The Perkins House
3.0 star property
Cornish
9.8 out of 10, Exceptional, (114 reviews)
"Fun, hospitable hosts. Helpful with ideas for our itinerary. Great breakfast. "
United States
John
The Perkins House
Garden

Brewster House Bed & Breakfast

Brewster House Bed & Breakfast
4.0 star property
Freeport
9.8 out of 10, Exceptional, (115 reviews)
"The food was wonderful and the hospitality was great!"
United States
Olivia
The price is SAR 626
SAR 682 total
includes taxes & fees
5 Feb - 6 Feb
Brewster House Bed & Breakfast
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, (169 reviews)
"The whole was cozy! Well curated style and knowledgeable staff."
United States
jeffrey c
The price is SAR 742
SAR 808 total
includes taxes & fees
9 Feb - 10 Feb
Blind Tiger Portland - Danforth Street.
Exterior detail

Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast
3.0 star property
Rosemont
9.0 out of 10, Wonderful, (132 reviews)
"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
5 Feb - 6 Feb
Fleetwood House Bed & Breakfast
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 reviews)
"Loved the place "
United States
Stephen
The price is SAR 671
SAR 732 total
includes taxes & fees
12 Feb - 13 Feb
Blind Tiger Portland – Carleton Street
Front of property

The James Place Inn B&B

The James Place Inn B&B
3.5 star property
Freeport
10.0 out of 10, Exceptional, (182 reviews)
"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
31 Jan - 1 Feb
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

Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

10/10 Excellent
"Great staff, clean room."
Meghan 2-night trip
Posted 1 day ago
Tru by Hilton Portland Airport Area

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, Seacoast Adventure and Little 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. Blind Tiger Portland – Carleton Street: 6 rooms. 9.8 mi (15.8 km) from the heart of downtown. Enjoy the unique décor and patio area. Fleetwood House Bed & Breakfast: 3 rooms. Located 7.9 mi (12.7 km) from the core of Windham. Enjoy the free full breakfast and unique décor.
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 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 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.