Search B&B in Windham

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 27 B&B in Windham with updated reviews, rates, and availability.

Inn at St John Portland In-Town
2.5 star property
9.0 out of 10, Wonderful, (1005)
"Location was a little too far for us to walk downtown, it wasn't too far but there were some sketchy characters in the area. The staff were lovely, the room ideal. We worried about our car outside because the area looked sketchy, but we did not have any problems so perhaps we wrongly judged the area"
The price is AED 400
AED 436 total
includes taxes & fees
5 Jun - 6 Jun
Inn at St John Portland In-Town
Old Orchard Beach Inn
2.5 star property
8.4 out of 10, Very Good, (1009)
"Great quant inn, would definitely go back!!"
The price is AED 559
AED 609 total
includes taxes & fees
5 Jun - 6 Jun
Old Orchard Beach Inn
The Orchard House & Cafe
3.0 star property
9.6 out of 10, Exceptional, (99)
"We had an amazing stay at The Orchard House. The pictures do not do it justice. It is beautiful and special. We stayed in the Library Room. Very unique and spacious for 2 people. I am in love with the bed/mattress! The light breakfast served (coffee/tea, cereal, boiled eggs, juice, toast.etc) was perfect and a great way to start the day. The owner Bill (and his Mom Lynn owner of the vintage shop Folly) are fabulous. And the dogs, Bingo and Bay are the icing on the cake. Would definitely...
The price is AED 806
AED 879 total
includes taxes & fees
9 Jun - 10 Jun
The Orchard House & Cafe
Save an average of 15% on thousands of hotels when you're signed in
Candlebay Inn
3.0 star property
9.6 out of 10, Exceptional, (379)
"Very friendly host. The Inn is lovely. "
The price is AED 694
AED 757 total
includes taxes & fees
13 Jun - 14 Jun
Candlebay Inn
West End Inn
3.0 star property
9.6 out of 10, Exceptional, (76)
"We stayed for a get a way weekend . Breakfast each morning was wonderful. Plenty of parking right in front of inn . We walked all over town. It was the weekend of the eclipse and we did not have glasses but Milan so graciously gave us extras he had . Wonderful host "
The price is AED 1,245
AED 1,357 total
includes taxes & fees
10 Jun - 11 Jun
West End Inn
Blind Tiger Portland - Danforth Street.
3.5 star property
9.6 out of 10, Exceptional, (114)
"Perfect stay for a weekend getaway!!"
The price is AED 1,327
AED 1,447 total
includes taxes & fees
25 Jun - 26 Jun
Blind Tiger Portland - Danforth Street.
And. N B&B
2.0 star property
9.8 out of 10, Exceptional, (28)
"We enjoyed our overnight stay. The young owners were gracious and interesting to talk with. We would have liked to have directions printed out for use of the TV and heating/cooling system in our room. The bed was comfortable and the entire place was very clean. Breakfast was prepared well and very tasty. Very enjoyable stay."
The price is AED 748
AED 816 total
includes taxes & fees
9 Jun - 10 Jun
And. N B&B
Fleetwood House Bed & Breakfast
3.0 star property
8.8 out of 10, Excellent, (99)
"This is a lovely, quaint, family run B&B. Highly recommended."
The price is AED 804
AED 913 total
includes taxes & fees
5 Jun - 6 Jun
Fleetwood House Bed & Breakfast
The Munroe Inn
3.5 star property
9.0 out of 10, Wonderful, (58)
"We stayed at the Munroe Inn for 2 nights to watch the solar eclipse and it was phenomenal. Olga could not have been more helpful or responsive and Inn is so charming, clean, and comfortable. Safety is a concern of ours as well and the Inn is in a residential neighborhood and is well lit for evening arrivals. Highly recommend!"
The price is AED 760
AED 829 total
includes taxes & fees
13 Jun - 14 Jun
The Munroe Inn
Blind Tiger Portland – Carleton Street
3.5 star property
9.8 out of 10, Exceptional, (99)
"Rooms were absolutely beautiful. Great breakfast and lots of thoughtful touches including free snack bar, board games and local recommendations. Highly recommend!"
The price is AED 1,225
AED 1,336 total
includes taxes & fees
6 Jun - 7 Jun
Blind Tiger Portland – Carleton Street
Atlantic Birches Inn
2.5 star property
9.4 out of 10, Exceptional, (343)
"Nice place, great location."
Atlantic Birches Inn
Harpswell Inn
2.0 star property
10.0 out of 10, Exceptional, (3)
"Nice country inn, beautiful views. best wishes for the new ownwers."
Harpswell Inn
The James Place Inn B&B
3.5 star property
10.0 out of 10, Exceptional, (165)
"I had a lovely stay at the James Inn; the hosts were great and the breakfast was delicious!! Anne"
The price is AED 1,071
AED 1,167 total
includes taxes & fees
29 Jun - 30 Jun
The James Place Inn B&B
Noble House Inn
3.5 star property
9.8 out of 10, Exceptional, (75)
"Wonderful place, beautiful setting, convenient to town. Lovely breakfast!"
The price is AED 714
AED 778 total
includes taxes & fees
13 Jun - 14 Jun
Noble House Inn
The Perkins House
3.0 star property
9.8 out of 10, Exceptional, (85)
"The room was very comfortable, quiet and clean. There is a shared bathroom for the floor, which was fine for us since only one other room was occupied. (I don’t know how that goes when the inn is full.) We did not take advantage of any of the other common areas (living room w/TV, sitting room). The entire house is beautifully decorated in the Victorian style, with lots of furniture, busy wallpaper, and decorative items on the shelves, dressers and side tables. It looked great, but I was afraid...
The price is AED 573
AED 624 total
includes taxes & fees
17 Jun - 18 Jun
The Perkins House
The Chadwick Bed & Breakfast
3.5 star property
9.8 out of 10, Exceptional, (38)
"The Chadwick is beautiful, centrally located. Owners are great!"
The price is AED 1,098
AED 1,197 total
includes taxes & fees
11 Jun - 12 Jun
The Chadwick Bed & Breakfast
Brewster House Bed & Breakfast
4.0 star property
9.8 out of 10, Exceptional, (105)
"The breakfasts are to die for. Freeport is a lovely place and easy to walk into from Brewster’s. Kelleigh and Dave are so welcoming. Would love to go back."
The price is AED 1,095
AED 1,193 total
includes taxes & fees
5 Jun - 6 Jun
Brewster House Bed & Breakfast
Wolf Cove Inn
3.0 star property
10.0 out of 10, Exceptional, (1)
Wolf Cove Inn
PineCrest Inn
4.0 star property
9.8 out of 10, Exceptional, (98)
"Our stay at the Pinecrest was wonderful. We would highly recommend staying and plan to visit again. The breakfasts were fantastic. The service was just right. We were very comfortable. Kathy was the perfect host!"
PineCrest Inn
The Jeremiah Mason House B & B
3.0 star property
9.6 out of 10, Exceptional, (37)
"My mom and I had a small weekend getaway in Limerick, Maine. The reason for our trip, was to attend a maple syrup weekend event at Hilltop Boilers and hike on Sawyer Mountain. After doing research for a hotel stay, we decided to stay at The Jeremiah Mason Bed and Breakfast. I want to say that our stay was the highlight of the trip! The minute we walked in, Valerie treated us like we were family. She explained all the features of the inn, and asked us what we wanted for breakfast and if we had...
The price is AED 572
AED 623 total
includes taxes & fees
5 Jun - 6 Jun
The Jeremiah Mason House B & B
Don't see what you're looking for?
See all available properties in Windham
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.

Other property types in Windham

Pet-friendly! Modern and spacious 3-bedroom home on the Pleasant River.
Pet-friendly! Modern and spacious 3-bedroom home on the Pleasant River.
Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome
8.4 out of 10, Very Good, (21)
"The house was really great - plenty of room and a nice and serene. Older house with squeaky and uneven floors but the decor and some modern makeovers made it have great character! Communicating with property manager was very easy and we got prompt responses. The only thing worth mentioning that needs attention is the little bridge to go over to get to the driveway. Luckily we have a higher car but anyone with a regular sedan would have bottomed out and/or possibly got stuck. I’m sure it was...
Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome
2 duplex
3.0 star property
2 duplex
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.

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, Maine Wildlife Park 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'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, April, March, and February, with each month seeing an average of 9 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 Maine Wildlife Park 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.

Recent reviews of Windham hotels
Expedia verified reviews