A white church with a steeple and red accents, surrounded by autumn trees.

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
10 Jul - 12 Jul
In two weeks
17 Jul - 19 Jul
In one month
31 Jul - 2 Aug
In two months
28 Aug - 30 Aug

Our top choices for Windham bed & breakfast

Front of property – evening/night

The Orchard House: Inn & Cafe

The Orchard House: Inn & Cafe
3.0 star property
Freeport
9.6 out of 10, Exceptional, (165 reviews)
"Vers Nice stay!"
Canada
Kateri
The price is HK$1,770
HK$1,929 total
includes taxes & fees
13 Jul - 14 Jul
The Orchard House: Inn & Cafe
Exterior detail

Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast
3.0 star property
Rosemont
9.0 out of 10, Wonderful, (133 reviews)
"Breakfast was excellent! Very pet friendly. Room was lovely and clean. "
United States
Earlene
The price is HK$1,796
HK$1,957 total
includes taxes & fees
13 Jul - 14 Jul
Fleetwood House Bed & Breakfast
Porch

Noble House Inn

Noble House Inn
3.5 star property
Bridgton
9.8 out of 10, Exceptional, (116 reviews)
"Very nice room, excellant breakfast."
United States
SANDRA
The price is HK$1,437
HK$1,567 total
includes taxes & fees
21 Jul - 22 Jul
Noble House Inn
Front of property

The Jeremiah Mason House B & B

The Jeremiah Mason House B & B
3.0 star property
Limerick
9.6 out of 10, Exceptional, (52 reviews)
"Excellent place to stay. Clean room and dining area, tasty breakfast, and very friendly host!"
United States
Kenneth
The price is HK$1,330
HK$1,450 total
includes taxes & fees
6 Jul - 7 Jul
The Jeremiah Mason House B & B
Porch

Candlebay Inn

Candlebay Inn
3.0 star property
Freeport
9.6 out of 10, Exceptional, (465 reviews)
"Very nice owners and the place was clean food was great and location was excellent. Will tell are family and friends when they visit Maine."
United States
Barry
The price is HK$1,369
HK$1,492 total
includes taxes & fees
12 Jul - 13 Jul
Candlebay Inn
Front of property

The Nicholson Inn

The Nicholson Inn
3.0 star property
Freeport
10.0 out of 10, Exceptional, (1 review)
"The owners were amazing and so kind. The location is perfect, and the amenities feel so hoy and great."
United States
Meaghan
The price is HK$2,390
HK$2,605 total
includes taxes & fees
8 Jul - 9 Jul
The Nicholson Inn
Exterior

The Munroe Inn

The Munroe Inn
3.5 star property
Auburn
9.2 out of 10, Wonderful, (73 reviews)
"Close to Bates. Gorgeous house. Easy-check, laid back, responsive, and attentive host. We had a great time."
United States
Ippei
The price is HK$1,560
HK$1,701 total
includes taxes & fees
14 Jul - 15 Jul
The Munroe Inn
View from room

The Perkins House

The Perkins House
3.0 star property
Cornish
9.8 out of 10, Exceptional, (115 reviews)
"Wonderful stay "
Belgium
Yvan
The price is HK$1,143
HK$1,246 total
includes taxes & fees
27 Jul - 28 Jul
The Perkins House
Interior entrance

The Kendall Inn

The Kendall Inn
3.5 star property
Freeport
9.8 out of 10, Exceptional, (148 reviews)
"Nice bed and breakfast in quiet area near all the shopping "
United States
Suan
The price is HK$1,905
HK$2,077 total
includes taxes & fees
12 Jul - 13 Jul
The Kendall Inn
Sauna

Brewster House Bed & Breakfast

Brewster House Bed & Breakfast
4.0 star property
Freeport
9.8 out of 10, Exceptional, (118 reviews)
"The food was wonderful and the hospitality was great!"
United States
Olivia
The price is HK$1,532
HK$1,670 total
includes taxes & fees
20 Jul - 21 Jul
Brewster House Bed & Breakfast
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, (184 reviews)
"Great place. Comfortable and welcoming. Great proprietors and great location. "
United States
Cecilia
The price is HK$2,382
HK$2,596 total
includes taxes & fees
12 Jul - 13 Jul
The James Place Inn B&B
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)
"Second time staying here…very nice and clean as well as convenient location."
United States
Teresa
The price is HK$1,207
HK$1,433 total
includes taxes & fees
8 Jul - 9 Jul
Old Orchard Beach Inn
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, (1,134 reviews)
"great place"
United States
Kimberly
The price is HK$1,327
HK$1,446 total
includes taxes & fees
5 Jul - 6 Jul
Inn at St John Portland In-Town
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, (188 reviews)
"The place was totally amazing."
United States
Gary
The price is HK$3,051
HK$3,325 total
includes taxes & fees
6 Jul - 7 Jul
Blind Tiger Portland - Danforth Street.
Living area

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street
3.5 star property
West End
9.6 out of 10, Exceptional, (124 reviews)
"Beautiful place to stay in the middle of a quiet street and walking distance to many spots. The rooms and common areas were clean and beautifully maintained. Staff was ready to answer any questions you had via phone or text. I loved this inn and would choose it again. Definitely recommend it !"
United States
Adriana Cecilia
The price is HK$2,839
HK$3,095 total
includes taxes & fees
6 Jul - 7 Jul
Blind Tiger Portland – Carleton Street
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

Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

8/10 Good
"Everything was great. The only thing wrong was that we learned there was no parking on site until AFTER we booked the room. Too late to change then. Valet parking added another $40.00 per day to our stay. I feel the charge should have been mentioned before booking (during advertising) or be added to the nightly fee just as part of the nightly fee without saying it's for parking. The hotel should be honest about the fee upfront. I understand street parking was free from 6pm to 9am, but that was not mentioned to us by the hotel. I heard it from someone in town on our last day. This withholding of information seems dishonest."
William 2-night trip
Posted less than an hour ago
Hampton Inn Portland Downtown - Waterfront

Find out more about Windham

Windham B&B information

Number of reviews
4,016
Accommodation
33 B&B
Lowest Price
HK$1,246
Highest Price
HK$3,325

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, Little Sebago Lake and 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. The Orchard House: Inn & Cafe: 5 rooms. Situated 17.3 mi (27.9 km) from the heart of Windham. Fleetwood House Bed & Breakfast: 3 rooms. 7.9 mi (12.8 km) from the city centre. Enjoy the free full breakfast and unique decor. 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 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 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, 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