Search B&B in Windham

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 35 B&B in Windham with updated reviews, rates, and availability.

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

Inn at St John Portland In-Town

2.5 star property
8.8 out of 10, Excellent, (1008)
"Always a great stay!!!"
The price is AED 364
AED 396 total
includes taxes & fees
5 Jun - 6 Jun
Inn at St John Portland In-Town
Old Orchard Beach Inn
Exterior

Old Orchard Beach Inn

2.5 star property
8.4 out of 10, Very Good, (1004)
"Beautiful old inn, beds not comfortable."
The price is AED 400
AED 436 total
includes taxes & fees
4 Jun - 5 Jun
Old Orchard Beach Inn
Candlebay Inn
Porch

Candlebay Inn

3.0 star property
9.6 out of 10, Exceptional, (423)
"Connie was very welcoming, and offered advice about the area. The Inn was quaint and comfortable, the breakfast delicious! We would definitely stay again!"
The price is AED 731
AED 797 total
includes taxes & fees
4 Jun - 5 Jun
Candlebay Inn
Blind Tiger Portland - Danforth Street.
Baxter | Premium bedding, individually decorated, individually furnished

Blind Tiger Portland - Danforth Street.

3.5 star property
9.6 out of 10, Exceptional, (145)
"Great, enjoyed our stay."
The price is AED 1,638
AED 1,786 total
includes taxes & fees
9 Jun - 10 Jun
Blind Tiger Portland - Danforth Street.
The Orchard House & Cafe
Front of property - evening/night

The Orchard House & Cafe

3.0 star property
9.6 out of 10, Exceptional, (144)
"This is the second time I've stayed here. It's a very charming, old house with tastefully decorated, comfortable rooms. The continental breakfast is very good and served in a cute and cozy dining room. The bed was a bit hard for me, but I'm pretty picky. Just a few minutes drive to the outlet stores and restaurants in town, but far enough away that it's nice and quiet. "
The price is AED 806
AED 879 total
includes taxes & fees
8 Jun - 9 Jun
The Orchard House & Cafe
Fleetwood House Bed & Breakfast
Property entrance

Fleetwood House Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (115)
"It was a really great place to stay! Everyone was very friendly and parking was super easy! I would stay again! "
The price is AED 841
AED 917 total
includes taxes & fees
4 Jun - 5 Jun
Fleetwood House Bed & Breakfast
And. N B&B
Front of property

And. N B&B

3.0 star property
9.8 out of 10, Exceptional, (59)
"Nice place, cute little town"
The price is AED 660
AED 720 total
includes taxes & fees
18 Jun - 19 Jun
And. N B&B
The Perkins House
Suite (The Carriage) | View from room

The Perkins House

3.0 star property
9.8 out of 10, Exceptional, (103)
"Wonderful stay "
The price is AED 621
AED 677 total
includes taxes & fees
11 Jun - 12 Jun
The Perkins House
Blind Tiger Portland – Carleton Street
Stovall | Living area | Fireplace

Blind Tiger Portland – Carleton Street

3.5 star property
9.8 out of 10, Exceptional, (112)
"We loved our stay at Blind Tiger! So many thoughtful touches."
The price is AED 1,690
AED 1,842 total
includes taxes & fees
9 Jun - 10 Jun
Blind Tiger Portland – Carleton Street
Lakeview Inn
Exterior

Lakeview Inn

3.5 star property
9.2 out of 10, Wonderful, (47)
"Absolutely amazing stay! My girlfriend absolutely adored the place! She felt super comfortable and loved the cozy atmosphere as well as the hospitality of the hosts."
The price is AED 933
AED 1,017 total
includes taxes & fees
4 Jun - 5 Jun
Lakeview Inn
West End Inn
Classic Room, 1 King Bed, City View | Individually decorated, individually furnished, iron/ironing board

West End Inn

3.0 star property
9.6 out of 10, Exceptional, (89)
"Beautiful building, great location and the breakfast was amazing!! "
The price is AED 1,172
AED 1,277 total
includes taxes & fees
5 Jun - 6 Jun
West End Inn
Noble House Inn
Porch

Noble House Inn

3.5 star property
9.8 out of 10, Exceptional, (88)
"You won't be sorry you stayed here! Clean, easy check-in, Great Breakfast, etc."
The price is AED 372
AED 405 total
includes taxes & fees
10 Jun - 11 Jun
Noble House Inn
The Kendall Inn
Exterior

The Kendall Inn

3.5 star property
9.8 out of 10, Exceptional, (123)
"What a fantastic stay!"
The price is AED 761
AED 829 total
includes taxes & fees
4 Jun - 5 Jun
The Kendall Inn
Brewster House Bed & Breakfast
Exterior

Brewster House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (110)
"The food was wonderful and the hospitality was great!"
The price is AED 878
AED 957 total
includes taxes & fees
13 Jun - 14 Jun
Brewster House Bed & Breakfast
The Jeremiah Mason House B & B
Comfort Single Room, Non Smoking (Room 1, Second Floor) | Individually decorated, individually furnished, iron/ironing board

The Jeremiah Mason House B & B

3.0 star property
9.6 out of 10, Exceptional, (44)
"Great charming place to stay"
The price is AED 668
AED 729 total
includes taxes & fees
4 Jun - 5 Jun
The Jeremiah Mason House B & B
The James Place Inn B&B
Outdoor dining

The James Place Inn B&B

3.5 star property
10.0 out of 10, Exceptional, (171)
"The food was great and the owners lovely."
The price is AED 1,116
AED 1,216 total
includes taxes & fees
4 Jun - 5 Jun
The James Place Inn B&B
Wolf Cove Inn
Dock

Wolf Cove Inn

3.0 star property
10.0 out of 10, Exceptional, (1)
Wolf Cove Inn
The Munroe Inn
Courtyard view

The Munroe Inn

3.5 star property
9.0 out of 10, Wonderful, (61)
"We had a lovely stay and were very comfortable."
The price is AED 634
AED 691 total
includes taxes & fees
6 Jun - 7 Jun
The Munroe Inn
PineCrest Inn
Street view

PineCrest Inn

4.0 star property
9.8 out of 10, Exceptional, (102)
"Kathy, the owner, was very professional and runs a very nice Inn (B & B)."
PineCrest Inn
Picturesque bed and breakfast, nestled in the foothills of the white mountains.
Exterior detail

Picturesque bed and breakfast, nestled in the foothills of the white mountains.

10.0 out of 10, Exceptional, (1)
"The property is well maintained. The room was comfortable and tastefully decorated. The hostess was accommodating and helpful"
Picturesque bed and breakfast, nestled in the foothills of the white mountains.
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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, Sebago Lake Basin 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. Fleetwood House Bed & Breakfast: 3 rooms. Situated 7.9 mi (12.7 km) from the heart of Windham. Enjoy the free full breakfast and unique décor. Blind Tiger Portland - Danforth Street.: 9 rooms. 10.2 mi (16.3 km) from the heart of downtown.The Orchard House & Cafe: 5 rooms. Located 17.3 mi (27.9 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, Sebago Lake Basin and Little Sebago Lake are some notable spots. You might put Sebago Lake and Maine Wildlife Park 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.