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Check prices for these dates

Next weekend
Jul 4 - Jul 6
In two weeks
Jul 11 - Jul 13
In one month
Jul 25 - Jul 27
In two months
Aug 22 - Aug 24

Compare 34 B&B in Windham with updated reviews, rates, and availability.

The Orchard House & Cafe
Front of property - evening/night

The Orchard House & Cafe

3.0 star property
9.6 out of 10, Exceptional, (144)
"Orchard House was very calm, relaxing, clean, and cozy; however, I would not consider it a typical bed and breakfast in a sense that there isn’t a home-cooked breakfast in the morning. They do provide granola and boiled eggs and a very small table with four seat seats, but it’s clear that most people including us go out to eat breakfast which isn’t necessarily a bad thing as there is plenty to do in the area just not what I’m typically used to. "
$209 nightly
The price is $228
Jun 25 - Jun 26
Total includes taxes and fees
The Orchard House & Cafe
Brewster House Bed & Breakfast
Exterior

Brewster House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (110)
"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
Jul 14 - Jul 15
Total includes taxes and fees
Brewster House Bed & Breakfast
The Kendall Inn
Exterior

The Kendall Inn

3.5 star property
9.8 out of 10, Exceptional, (124)
"We loved meeting the hosts. Stephanie was gracious to let us check in early so we could change our clothes before heading to a funeral. Then Matthew served warm cookies and milk in the kitchen in the evening when we returned. We enjoyed hearing about his thru-hike in the Appalachian trail. "
$207 nightly
The price is $226
Jun 25 - Jun 26
Total includes taxes and fees
The Kendall Inn
Candlebay Inn
Porch

Candlebay Inn

3.0 star property
9.6 out of 10, Exceptional, (428)
"Connie was a wonderful host!!! So attentive to our needs and just makes you feel at home. The king bed was super comfortable! Easy walk to shopping and restaurants. Highly recommend! "
$199 nightly
The price is $217
Jun 25 - Jun 26
Total includes taxes and fees
Candlebay Inn
The James Place Inn B&B
Outdoor dining

The James Place Inn B&B

3.5 star property
10.0 out of 10, Exceptional, (172)
"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
Jun 25 - Jun 26
Total includes taxes and fees
The James Place Inn B&B
Blind Tiger Portland - Danforth Street.
Baxter | 1 bedroom, premium bedding, individually decorated

Blind Tiger Portland - Danforth Street.

3.5 star property
9.6 out of 10, Exceptional, (147)
"Everything was wonderful, we highly recommend staying here to anyone considering it."
$387 nightly
The price is $422
Jul 1 - Jul 2
Total includes taxes and fees
Blind Tiger Portland - Danforth Street.
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."
$384 nightly
The price is $419
Jun 30 - Jul 1
Total includes taxes and fees
Blind Tiger Portland – Carleton Street
West End Inn
Classic Room, 1 King Bed, City View | 1 bedroom, individually decorated, individually furnished

West End Inn

3.0 star property
9.6 out of 10, Exceptional, (89)
"Beautiful building, great location and the breakfast was amazing!! "
$409 nightly
The price is $446
Jun 26 - Jun 27
Total includes taxes and fees
West End Inn
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, (1020)
"Always a great stay!!!"
$99 nightly
The price is $108
Jul 1 - Jul 2
Total includes taxes and fees
Inn at St John Portland In-Town
Fleetwood House Bed & Breakfast
Property entrance

Fleetwood House Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (116)
"Wonderful breakfast, nice hosts, beautiful home."
$229 nightly
The price is $250
Jun 25 - Jun 26
Total includes taxes and fees
Fleetwood House Bed & Breakfast
Old Orchard Beach Inn
Exterior

Old Orchard Beach Inn

2.5 star property
8.4 out of 10, Very Good, (1004)
"We stayed at the atlantic "
$118 nightly
The price is $129
Jun 26 - Jun 27
Total includes taxes and fees
Old Orchard Beach 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."
$155 nightly
The price is $169
Jun 25 - Jun 26
Total includes taxes and fees
The Munroe Inn
And. N B&B
Front of property

And. N B&B

3.0 star property
9.8 out of 10, Exceptional, (61)
"Very friendly owners, comfortable and clean room, bathroom, dining and sitting area, great breakfast. HIGHLY recommended!"
$172 nightly
The price is $188
Jul 13 - Jul 14
Total includes taxes and fees
And. N B&B
Lakeview Inn
Exterior

Lakeview Inn

3.5 star property
9.2 out of 10, Wonderful, (48)
"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."
$254 nightly
The price is $277
Jun 25 - Jun 26
Total includes taxes and fees
Lakeview Inn
The Jeremiah Mason House B & B
Comfort Single Room, Non Smoking (Room 1, Second Floor) | 1 bedroom, individually decorated, individually furnished

The Jeremiah Mason House B & B

3.0 star property
9.6 out of 10, Exceptional, (44)
"Great charming place to stay"
$164 nightly
The price is $179
Jun 25 - Jun 26
Total includes taxes and fees
The Jeremiah Mason House B & B
Noble House Inn
Porch

Noble House Inn

3.5 star property
9.8 out of 10, Exceptional, (89)
"You won't be sorry you stayed here! Clean, easy check-in, Great Breakfast, etc."
$169 nightly
The price is $184
Jun 29 - Jun 30
Total includes taxes and fees
Noble House Inn
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 "
$149 nightly
The price is $162
Jul 7 - Jul 8
Total includes taxes and fees
The Perkins House
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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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 $108 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.