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

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Check prices for these dates

Next weekend
Aug 21 - Aug 23
In two weeks
Aug 28 - Aug 30
In one month
Sep 11 - Sep 13
In two months
Oct 9 - Oct 11

Our top choices for Windham bed & breakfast

Exterior detail

1. Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast
3.0 star property
Rosemont
9.0 out of 10, Wonderful, (139 reviews)
"Cozy room and a great breakfast from Linda in the morning! Short drive or bus ride to downtown Portland. Appreciate her flexibility with check-in (make sure to check your Expedia messages more often than I did) and meeting one of the resident cats."
United States
Sarah
$229 nightly
The price is $250
Aug 19 - Aug 20
Total with taxes and fees
Fleetwood House Bed & Breakfast
Front of property - evening/night

2. Inn at St John Portland In-Town

Inn at St John Portland In-Town
2.5 star property
Valley Street
8.6 out of 10, Excellent, (1,112 reviews)
"Room was clean, bed was comfortable, staff were helpful. Would stay here again!"
United States
Caleb
$188 nightly
The price is $205
Aug 17 - Aug 18
Total with taxes and fees
Inn at St John Portland In-Town
Front of property - evening/night

3. The Orchard House: Inn & Cafe

The Orchard House: Inn & Cafe
3.0 star property
Freeport
9.6 out of 10, Exceptional, (175 reviews)
"Such kind helpful owners and a beautiful area to check out! A little dusty in our room but overall we had a great experience."
United States
Brooke
$211 nightly
The price is $230
Sep 13 - Sep 14
Total with taxes and fees
The Orchard House: Inn & Cafe
Books

4. Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street
3.5 star property
West End
9.6 out of 10, Exceptional, (129 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
$365 nightly
The price is $398
Sep 15 - Sep 16
Total with taxes and fees
Blind Tiger Portland – Carleton Street
Porch

5. Candlebay Inn

Candlebay Inn
3.0 star property
Freeport
9.6 out of 10, Exceptional, (479 reviews)
"The place was perfect for our Freeport stay! Walkable location and her breakfasts were fantastic! Would definitely stay again:)"
United States
Craig
$175 nightly
The price is $190
Aug 27 - Aug 28
Total with taxes and fees
Candlebay Inn
Baxter | Premium bedding, iron/ironing board, WiFi (free), individually decorated

6. Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.
3.5 star property
West End
9.6 out of 10, Exceptional, (189 reviews)
"The place was totally amazing."
United States
Gary
$433 nightly
The price is $472
Sep 1 - Sep 2
Total with taxes and fees
Blind Tiger Portland - Danforth Street.
Interior entrance

7. The Kendall Inn

The Kendall Inn
3.5 star property
Freeport
9.8 out of 10, Exceptional, (158 reviews)
"This is a classic Maine B&B! Wonderful owners and delicious breakfast with always two options! Fresh homemade cookies at the end of the day! Rooms were very nice with nice sized private bathroom. A wonderful stay and will definitely be back. Why do the chain hotel when you can have this experience!"
United States
Joseph
$219 nightly
The price is $239
Sep 1 - Sep 2
Total with taxes and fees
The Kendall Inn
Exterior

8. Old Orchard Beach Inn

Old Orchard Beach Inn
2.5 star property
Old Orchard Beach
8.2 out of 10, Very Good, (1,004 reviews)
"Great stay."
United States
David
$130 nightly
The price is $142
Aug 30 - Aug 31
Total with taxes and fees
Old Orchard Beach Inn
Front of property

9. 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
$182 nightly
The price is $199
Aug 26 - Aug 27
Total with taxes and fees
The Jeremiah Mason House B & B
Suite (The Carriage) | View from room

10. The Perkins House

The Perkins House
3.0 star property
Cornish
9.8 out of 10, Exceptional, (121 reviews)
"Charming B&B with great owners. Delicious breakfast, comfortable bed, good size bathroom with amenities shared with one other bedroom. Would love to stay here again."
United States
Linda
$158 nightly
The price is $173
Sep 7 - Sep 8
Total with taxes and fees
The Perkins House
Front of property

11. 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
$298 nightly
The price is $325
Sep 10 - Sep 11
Total with taxes and fees
The Nicholson Inn
Front of property

12. The James Place Inn B&B

The James Place Inn B&B
3.5 star property
Freeport
10.0 out of 10, Exceptional, (187 reviews)
"Fabulous hosts, beautiful property, excellent breakfast, walking distance to the main street of Freeport but still quiet. Highly recommend!"
United States
Carol
$304 nightly
The price is $331
Aug 21 - Aug 22
Total with taxes and fees
The James Place Inn B&B
Porch

13. Noble House Inn

Noble House Inn
3.5 star property
Bridgton
9.6 out of 10, Exceptional, (125 reviews)
"👍"
United States
Vicki
$159 nightly
The price is $174
Aug 20 - Aug 21
Total with taxes and fees
Noble House Inn
Exterior

14. The Munroe Inn

The Munroe Inn
3.5 star property
Auburn
9.2 out of 10, Wonderful, (74 reviews)
"Wonderful place to stay. The rooms are so comfortable and the host was very accommodating. Breakfast was outstanding and the best cup of coffee in Auburn. Such a gem of a place!"
United States
Tristan
$199 nightly
The price is $217
Aug 17 - Aug 18
Total with taxes and fees
The Munroe Inn
Internet

15. Charming Top-Floor Queen Room with Sloped Ceilings, Walk to the Beach

Charming Top-Floor Queen Room with Sloped Ceilings, Walk to the Beach
Old Orchard Beach
10.0 out of 10, Exceptional, (1 review)
"Definitely worth a visit! Beach just down the road!"
United States
Matt S.
$239 nightly
The price is $260
Sep 4 - Sep 5
Total with taxes and fees
Charming Top-Floor Queen Room with Sloped Ceilings, Walk to the Beach
Room

16. 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.
$199 nightly
The price is $217
Sep 11 - Sep 12
Total with taxes and fees
Bright Character Studio Near the Beach with Outdoor Seating & Parking
Exterior

17. 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
$221 nightly
The price is $241
Aug 30 - Aug 31
Total with taxes and fees
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

HomeAwhile

HomeAwhile

10/10 Excellent
"Amazing"
Mary 2-night trip
Posted less than an hour ago
HomeAwhile

Find out more about Windham

Windham B&B information

Number of reviews
3,915
Accommodation
35 B&B
Lowest Price
$142
Highest Price
$472

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 $142 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.

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