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 14 - Aug 16
In two weeks
Aug 21 - Aug 23
In one month
Sep 4 - Sep 6
In two months
Oct 2 - Oct 4

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, (138 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
The price is ￥36,026
￥39,268 total
includes taxes & fees
Aug 9 - Aug 10
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, (1,118 reviews)
"Room was clean, bed was comfortable, staff were helpful. Would stay here again!"
United States
Caleb
The price is ￥20,664
￥22,524 total
includes taxes & fees
Aug 6 - Aug 7
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, (172 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 ￥35,337
￥38,517 total
includes taxes & fees
Aug 24 - Aug 25
The Orchard House: Inn & Cafe
Porch

4. Candlebay Inn

Candlebay Inn
3.0 star property
Freeport
9.6 out of 10, Exceptional, (476 reviews)
"The place was perfect for our Freeport stay! Walkable location and her breakfasts were fantastic! Would definitely stay again:)"
United States
Craig
The price is ￥27,468
￥29,939 total
includes taxes & fees
Aug 12 - Aug 13
Candlebay Inn
Baxter | Premium bedding, iron/ironing board, WiFi (free), individually decorated

5. 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
The price is ￥60,726
￥66,191 total
includes taxes & fees
Sep 1 - Sep 2
Blind Tiger Portland - Danforth Street.
Books

6. 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
The price is ￥53,280
￥58,075 total
includes taxes & fees
Aug 31 - Sep 1
Blind Tiger Portland – Carleton Street
Front of property

7. 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 ￥27,790
￥30,291 total
includes taxes & fees
Aug 6 - Aug 7
The Jeremiah Mason House B & B
Suite (The Carriage) | View from room

8. 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
The price is ￥23,752
￥25,890 total
includes taxes & fees
Aug 6 - Aug 7
The Perkins House
Interior entrance

9. The Kendall Inn

The Kendall Inn
3.5 star property
Freeport
9.8 out of 10, Exceptional, (157 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
The price is ￥34,500
￥37,605 total
includes taxes & fees
Sep 1 - Sep 2
The Kendall Inn
Front of property

10. 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 ￥41,534
￥45,272 total
includes taxes & fees
Aug 9 - Aug 10
The Nicholson Inn
Exterior

11. Old Orchard Beach Inn

Old Orchard Beach Inn
2.5 star property
Old Orchard Beach
8.2 out of 10, Very Good, (1,014 reviews)
"Great stay."
United States
David
The price is ￥17,383
￥21,314 total
includes taxes & fees
Sep 3 - Sep 4
Old Orchard Beach 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
The price is ￥47,791
￥52,092 total
includes taxes & fees
Aug 9 - Aug 10
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, (123 reviews)
"👍"
United States
Vicki
The price is ￥26,018
￥28,359 total
includes taxes & fees
Aug 6 - Aug 7
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
The price is ￥31,307
￥34,125 total
includes taxes & fees
Aug 17 - Aug 18
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.
The price is ￥36,272
￥45,211 total
includes taxes & fees
Sep 4 - Sep 5
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.
The price is ￥39,585
￥49,166 total
includes taxes & fees
Aug 28 - Aug 29
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
The price is ￥35,334
￥38,514 total
includes taxes & fees
Aug 30 - Aug 31
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

Clarion Pointe South Portland

Clarion Pointe South Portland

8/10 Good
"Piscine et déjeuner"
Julien 2-night trip
Posted 1 hour ago
Clarion Pointe South Portland

Find out more about Windham

Windham B&B information

Number of reviews
2,646
Accommodation
35 B&B
Lowest Price
￥21,314
Highest Price
￥66,191

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. The Orchard House: Inn & Cafe: 5 rooms. Situated 17.3 mi (27.9 km) from the heart of Windham. Fleetwood House Bed & Breakfast: 3 rooms. 7.9 mi (12.8 km) from the heart of downtown. Enjoy the free full breakfast and unique décor. 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 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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