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Check prices for these dates

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Aug 15 - Aug 17
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Sep 5 - Sep 7
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Oct 3 - Oct 5

B&B in Windham

Inn at St John Portland In-Town
Classic building with a stone facade and commercial establishments on the ground floor.

Inn at St John Portland In-Town

2.5 star property
8.8 out of 10, Excellent, (1044)
"Quaint and fun old style place to stay. "
The price is ￥20,536
￥22,385 total
includes taxes & fees
Sep 1 - Sep 2
Inn at St John Portland In-Town
Old Orchard Beach Inn
Relax in a serene outdoor setting surrounded by lush greenery and comfortable seating.

Old Orchard Beach Inn

2.5 star property
8.2 out of 10, Very Good, (1005)
"The property was gorgeous, quaint, and a home away from home. "
Old Orchard Beach Inn
Fleetwood House Bed & Breakfast
Step up to the charming Fleecwood House, featuring a traditional facade with a welcoming porch and beautiful tree-lined surroundings.

Fleetwood House Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (121)
"We had a great time! The breakfast was wonderful! "
The price is ￥33,649
￥36,677 total
includes taxes & fees
Aug 12 - Aug 13
Fleetwood House Bed & Breakfast
Candlebay Inn
Welcome to Candlebay Inn, a charming hotel surrounded by lush greenery and a well-manicured lawn.

Candlebay Inn

3.0 star property
9.6 out of 10, Exceptional, (434)
"The Inn was great and the staff was very hospitable "
The price is ￥29,241
￥31,873 total
includes taxes & fees
Aug 11 - Aug 12
Candlebay Inn
The Kendall Inn
Kendall Tavern Inn offers Bed & Breakfast services from its charming two-story building.

The Kendall Inn

3.5 star property
9.8 out of 10, Exceptional, (132)
"Quaint stay. Enjoyed our stay. "
The price is ￥30,946
￥33,731 total
includes taxes & fees
Aug 10 - Aug 11
The Kendall Inn
The Orchard House & Cafe
Stylish entrance with a central door and potted evergreen trees.

The Orchard House & Cafe

3.0 star property
9.6 out of 10, Exceptional, (150)
"The place was perfect"
The price is ￥30,703
￥33,466 total
includes taxes & fees
Aug 10 - Aug 11
The Orchard House & Cafe
Blind Tiger Portland - Danforth Street.
Relax in a serene room with a four-poster canopy bed, featuring a table for reading and a decorative vase.

Blind Tiger Portland - Danforth Street.

3.5 star property
9.6 out of 10, Exceptional, (149)
"Everything was wonderful, we highly recommend staying here to anyone considering it."
The price is ￥52,766
￥57,515 total
includes taxes & fees
Aug 18 - Aug 19
Blind Tiger Portland - Danforth Street.
Blind Tiger Portland – Carleton Street
Relax in a stylish living room with a sofa, side table, and artwork, perfect for reading and unwinding.

Blind Tiger Portland – Carleton Street

3.5 star property
9.8 out of 10, Exceptional, (114)
"The Blind Tiger was a gem. It was convenient and private enough to enjoy with staff available 24/7 with and questions. The room, lobby and all areas were immaculate and brilliantly arranged. I would definitely go again!"
The price is ￥72,588
￥79,121 total
includes taxes & fees
Sep 7 - Sep 8
Blind Tiger Portland – Carleton Street
And. N B&B
Stroll up to the central entrance of this charming two-story house, featuring a gabled roof and a cozy porch.

And. N B&B

3.0 star property
9.8 out of 10, Exceptional, (66)
"Lovely place to stay. Sweet staff and delicious breakfast. "
The price is ￥25,063
￥27,319 total
includes taxes & fees
Aug 27 - Aug 28
And. N B&B
Lakeview Inn
Enjoy a restful stay in this inviting room, featuring a comfortable bed, a breakfast tray, and a beautiful floral arrangement.

Lakeview Inn

3.5 star property
9.2 out of 10, Wonderful, (50)
"Super friendly staff with fantastic breakfasts and games to boot!"
Lakeview Inn
The Perkins House
Relax by the stone fireplace in a cozy outdoor setting surrounded by comfortable seating and lush trees.

The Perkins House

3.0 star property
9.8 out of 10, Exceptional, (103)
"Wonderful stay "
The price is ￥23,090
￥25,168 total
includes taxes & fees
Aug 10 - Aug 11
The Perkins House
Noble House Inn
Relax on the porch with comfortable wicker furniture and enjoy the serene surroundings.

Noble House Inn

3.5 star property
9.8 out of 10, Exceptional, (92)
"You won't be sorry you stayed here! Clean, easy check-in, Great Breakfast, etc."
The price is ￥19,029
￥20,741 total
includes taxes & fees
Sep 9 - Sep 10
Noble House Inn
The James Place Inn B&B
Enjoy a romantic meal for two on the deck, surrounded by the house's charming facade.

The James Place Inn B&B

3.5 star property
10.0 out of 10, Exceptional, (173)
"Location to the busy areas of Freeport is steps away from this quiet oasis. Very nice innkeepers and staff will be there to make your stay pleasant while allowing you the privacy of a hotel guest. We stayed one night on our way home from mid coastal Maine and enjoyed our stay. "
The price is ￥44,637
￥48,654 total
includes taxes & fees
Aug 13 - Aug 14
The James Place Inn B&B
The Jeremiah Mason House B & B
Relax in this inviting living room with a sofa, armchair, and ottoman, surrounded by floral patterns and a view of the outside.

The Jeremiah Mason House B & B

3.0 star property
9.6 out of 10, Exceptional, (45)
"Great charming place to stay"
The price is ￥26,743
￥29,150 total
includes taxes & fees
Aug 11 - Aug 12
The Jeremiah Mason House B & B
West End Inn
Enjoy the view from this cozy corner bay window with a porch and brick facade.

West End Inn

3.0 star property
9.6 out of 10, Exceptional, (90)
"Extremely cozy and clean, perfect bed and breakfast in the West End for those looking for walkable access to the Old Port and downtown as well as a quiet retreat at night in the historic West End District. "
West End Inn
The Munroe Inn
Experience the charm of Munroe Inn, a historic building with a wrap-around porch and beautifully maintained gardens.

The Munroe Inn

3.5 star property
9.0 out of 10, Wonderful, (62)
"We had a lovely stay and were very comfortable."
The price is ￥27,037
￥29,470 total
includes taxes & fees
Aug 10 - Aug 11
The Munroe Inn
PineCrest Inn
Experience the charm of this traditional bed and breakfast, featuring a welcoming front porch and beautifully maintained grounds.

PineCrest Inn

4.0 star property
9.8 out of 10, Exceptional, (103)
"Lovely home, great breakfast. Kathy is a very gracious hostess and really helped us to thoroughly enjoy the Portland area."
PineCrest Inn
Brewster House Bed & Breakfast
Escape to a serene garden oasis with a charming cottage nestled among vibrant flowers and lush greenery.

Brewster House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (112)
"Wonderful hosts. Enjoyed quiet evening and lovely gourmet breakfast. Truly memorable stay. We look forward to returning in the future."
The price is ￥43,935
￥47,889 total
includes taxes & fees
Aug 10 - Aug 11
Brewster House Bed & Breakfast
Wolf Cove Inn
Relax by the fire pit in a serene natural setting surrounded by benches and trees.

Wolf Cove Inn

4.0 star property
10.0 out of 10, Exceptional, (1)
Wolf Cove Inn
Picturesque bed and breakfast, nestled in the foothills of the white mountains.
Experience a traditional bed and breakfast at Jeremiah Mason House, featuring a classic facade, welcoming front porch, and balcony.

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.
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Top Windham Hotel Reviews

Grand Beach Inn

Grand Beach Inn

10/10 Excellent
"Staff was helpful, food was great, good entertainment, trolly was available right at the location, clean and the heated pool was a great bonus! Was a great stay! "
Shauna 2-night trip
Posted 1 day ago
Grand Beach Inn

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: 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. The Orchard House & Cafe: 5 rooms. 17.3 mi (27.9 km) from the heart of downtown.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 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 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.