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

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Check prices for these dates

Next weekend
31 Jul - 2 Aug
In two weeks
7 Aug - 9 Aug
In one month
21 Aug - 23 Aug
In two months
18 Sep - 20 Sep

Our top choices for Windham bed & breakfast

Exterior detail

Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast
3.0 star property
Rosemont
9.0 out of 10, Wonderful, (134 reviews)
"Breakfast was excellent! Very pet friendly. Room was lovely and clean. "
United States
Earlene
The price is AED 841
AED 917 total
includes taxes & fees
26 Jul - 27 Jul
Fleetwood House 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, (1,121 reviews)
"great place"
United States
Kimberly
The price is AED 621
AED 677 total
includes taxes & fees
26 Jul - 27 Jul
Inn at St John Portland In-Town
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, (169 reviews)
"The Orchard Inn is very quaint and charming. The grounds were very quiet and peaceful. We especially enjoyed the great coffee and healthy continental breakfast that was provided. Would definitely recommend the Orchard Inn."
United States
Kathleen
The price is AED 829
AED 904 total
includes taxes & fees
23 Jul - 24 Jul
The Orchard House: Inn & Cafe
Porch

Candlebay Inn

Candlebay Inn
3.0 star property
Freeport
9.6 out of 10, Exceptional, (473 reviews)
"Perfect Inn for a getaway to Freeport. Connie was extremely welcoming and the location is perfect to explore Freeport."
United States
Gabrielle
The price is AED 641
AED 699 total
includes taxes & fees
27 Jul - 28 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 AED 1,080
AED 1,177 total
includes taxes & fees
28 Jul - 29 Jul
The Nicholson Inn
Baxter | Premium bedding, iron/ironing board, WiFi (free), individually decorated

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 AED 1,425
AED 1,553 total
includes taxes & fees
28 Jul - 29 Jul
Blind Tiger Portland - Danforth Street.
Suite (The Carriage) | View from room

The Perkins House

The Perkins House
3.0 star property
Cornish
9.8 out of 10, Exceptional, (119 reviews)
"Wonderful stay "
Belgium
Yvan
The price is AED 529
AED 577 total
includes taxes & fees
5 Aug - 6 Aug
The Perkins House
Living area

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street
3.5 star property
West End
9.6 out of 10, Exceptional, (127 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 AED 1,104
AED 1,203 total
includes taxes & fees
28 Jul - 29 Jul
Blind Tiger Portland – Carleton Street
Interior entrance

The Kendall Inn

The Kendall Inn
3.5 star property
Freeport
9.8 out of 10, Exceptional, (152 reviews)
"Nice bed and breakfast in quiet area near all the shopping "
United States
Suan
The price is AED 843
AED 919 total
includes taxes & fees
23 Jul - 24 Jul
The Kendall 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, (53 reviews)
"Absolutely amazing host and yummy breakfast!!"
United States
andy
The price is AED 647
AED 705 total
includes taxes & fees
23 Jul - 24 Jul
The Jeremiah Mason House B & B
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, (185 reviews)
"Fabulous hosts, beautiful property, excellent breakfast, walking distance to the main street of Freeport but still quiet. Highly recommend!"
United States
Carol
The price is AED 1,116
AED 1,216 total
includes taxes & fees
23 Jul - 24 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)
"Great location, nice staff and good amenities."
United States
Erica
The price is AED 622
AED 733 total
includes taxes & fees
30 Jul - 31 Jul
Old Orchard Beach Inn
Porch

Noble House Inn

Noble House Inn
3.5 star property
Bridgton
9.6 out of 10, Exceptional, (121 reviews)
"👍"
United States
Vicki
The price is AED 586
AED 638 total
includes taxes & fees
16 Aug - 17 Aug
Noble House 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 AED 731
AED 797 total
includes taxes & fees
29 Jul - 30 Jul
The Munroe Inn
Room

Bright Character Studio Near the Beach with Outdoor Seating & Parking

Bright Character Studio Near the Beach with Outdoor Seating & Parking
Old Orchard Beach
8.0 out of 10, Very Good, (1 review)
"served its purpose as between residences; nice place with all necessities; time of year issue was not enough heat; host attentive to any questions"
United States
Beth W.
The price is AED 922
AED 1,145 total
includes taxes & fees
22 Aug - 23 Aug
Bright Character Studio Near the Beach with Outdoor Seating & Parking
Exterior

West End Collection at 146 Pine

West End Collection at 146 Pine
3.0 star property
West End
9.6 out of 10, Exceptional, (96 reviews)
"Wonderful staff and scrumptious breakfast "
United States
Elena
The price is AED 1,032
AED 1,125 total
includes taxes & fees
18 Aug - 19 Aug
West End Collection at 146 Pine
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.
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Top Windham Hotel Reviews

Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

8/10 Good
"The hotel is in a super convenient location (close to Old Port). Everything we wanted to do was in walking distance (most being 25 minutes. The room was very spacious and updated. The only downsides are there is only valet parking for $40 a day ( I was sent a message from the hotel saying we could self-park for $30, but that wasn't an option). Secondly- you're charged $25 daily resort fee, which they say you can use as a food & beverage credit. The only on-site restaurant was only open 7 AM-10AM (with one person working so it was always too busy to east at) then reopens at 5 PM. It was just inconvenient to our iteniary. Overall, I did enjoy the hotel."
Nina 2-night trip
Posted 1 hour ago
Cambria Hotel Portland Downtown-Old Port

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, Little Sebago Lake and 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: Old Orchard Beach Inn: 16.7 mi (26.8 km) from the heart of Windham. Enjoy the outdoor pool and unique décor. Inn at St John Portland In-Town: 9.4 mi (15.2 km) from the downtown core. The Orchard House: Inn & Cafe: 5 rooms. Situated 17.3 mi (27.9 km) from the heart of Windham. Blind Tiger Portland - Danforth Street.: 9 rooms. 10.2 mi (16.3 km) from the heart of downtown.Fleetwood House Bed & Breakfast: 3 rooms. Located 7.9 mi (12.8 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 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 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.

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