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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
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, (1040)
"Quaint and fun old style place to stay. "
$139 nightly
The price is $152
Sep 1 - Sep 2
Total includes taxes and fees
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, (1002)
"The property was gorgeous, quaint, and a home away from home. "
$183 nightly
The price is $200
Sep 4 - Sep 5
Total includes taxes and fees
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! "
$229 nightly
The price is $250
Aug 12 - Aug 13
Total includes taxes and fees
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 "
$199 nightly
The price is $217
Aug 11 - Aug 12
Total includes taxes and fees
Candlebay Inn
The Kendall Inn
Charming two-story house with a welcoming porch and a beautifully manicured lawn.

The Kendall Inn

3.5 star property
9.8 out of 10, Exceptional, (131)
"Quaint stay. Enjoyed our stay. "
$234 nightly
The price is $255
Aug 10 - Aug 11
Total includes taxes and fees
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"
$209 nightly
The price is $228
Aug 10 - Aug 11
Total includes taxes and fees
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."
$399 nightly
The price is $435
Aug 18 - Aug 19
Total includes taxes and fees
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!"
$394 nightly
The price is $430
Sep 3 - Sep 4
Total includes taxes and fees
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, (65)
"Lovely place to stay. Sweet staff and delicious breakfast. "
$176 nightly
The price is $192
Sep 3 - Sep 4
Total includes taxes and fees
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!"
$284 nightly
The price is $309
Sep 1 - Sep 2
Total includes taxes and fees
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 "
$152 nightly
The price is $166
Aug 31 - Sep 1
Total includes taxes and fees
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."
$129 nightly
The price is $140
Sep 7 - Sep 8
Total includes taxes and fees
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. "
$304 nightly
The price is $331
Aug 10 - Aug 11
Total includes taxes and fees
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"
$182 nightly
The price is $198
Aug 11 - Aug 12
Total includes taxes and fees
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."
$184 nightly
The price is $201
Aug 10 - Aug 11
Total includes taxes and fees
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."
$299 nightly
The price is $326
Aug 10 - Aug 11
Total includes taxes and fees
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

Casco Bay Hotel Portland Airport - Maine Mall, Ascend Hotel Collection

Casco Bay Hotel Portland Airport - Maine Mall, Ascend Hotel Collection

10/10 Excellent
"It’s clean and new"
Nudrat 1-night trip
Posted 11 hours ago
Casco Bay Hotel Portland Airport - Maine Mall, Ascend Hotel Collection

Frequently asked questions

What is the nightly rate for a B&B in Windham?
Prices for B&Bs in Windham often vary, but you can find a great deal from $140 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Windham B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed & Breakfast in Windham?
The best time to book a B&B in Windham is during the vibrant fall season, particularly from September to October. This period is favored by travelers seeking a picturesque escape amid the stunning autumn foliage. As the leaves change, Windham transforms into a canvas of brilliant reds, oranges, and yellows, providing a breathtaking backdrop for outdoor activities and leisurely strolls.

September offers mild temperatures, typically ranging from the low 50s to mid-70s Fahrenheit, making it ideal for hiking and exploring the scenic trails in the Catskill Mountains. The comfortable climate invites visitors to engage in outdoor adventures, whether it's a hike to the summit of Windham Mountain or a bike ride through the charming countryside.

If you are considering a more budget-friendly option, late October can be particularly appealing. This month often features fewer crowds, allowing for a peaceful retreat where you can enjoy the lingering fall beauty without the hustle and bustle. Plus, many local businesses offer seasonal promotions, giving you the opportunity to enjoy quality experiences at a great value.
What is the difference between a Windham Bed & Breakfast and a hotel?
Every Windham B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Windham B&Bs.