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

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Check prices for these dates

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

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 AED 841
AED 917 total
includes taxes & fees
9 Aug - 10 Aug
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 AED 482
AED 526 total
includes taxes & fees
6 Aug - 7 Aug
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, (171 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 AED 792
AED 863 total
includes taxes & fees
9 Aug - 10 Aug
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 AED 641
AED 699 total
includes taxes & fees
12 Aug - 13 Aug
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 AED 1,418
AED 1,545 total
includes taxes & fees
1 Sep - 2 Sep
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 AED 1,241
AED 1,352 total
includes taxes & fees
31 Aug - 1 Sep
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 AED 647
AED 705 total
includes taxes & fees
6 Aug - 7 Aug
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, (120 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 AED 553
AED 603 total
includes taxes & fees
6 Aug - 7 Aug
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 AED 805
AED 878 total
includes taxes & fees
1 Sep - 2 Sep
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 AED 977
AED 1,065 total
includes taxes & fees
13 Aug - 14 Aug
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, (1,012 reviews)
"Great stay."
United States
David
The price is AED 405
AED 496 total
includes taxes & fees
3 Sep - 4 Sep
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 AED 1,116
AED 1,216 total
includes taxes & fees
6 Aug - 7 Aug
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 AED 586
AED 638 total
includes taxes & fees
18 Aug - 19 Aug
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 AED 731
AED 797 total
includes taxes & fees
10 Aug - 11 Aug
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 AED 845
AED 1,053 total
includes taxes & fees
4 Sep - 5 Sep
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 AED 922
AED 1,145 total
includes taxes & fees
28 Aug - 29 Aug
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 AED 823
AED 897 total
includes taxes & fees
30 Aug - 31 Aug
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

Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

10/10 Excellent
"Parking was a little tight for my car-width. Breakfast could have been a little hotter, but was generally good. There was a little dirt build-up at the room floor/wall intersection, but it was generally clean."
Peter 1-night trip
Posted 10 hours ago
Quality Inn & Suites South Portland

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: Old Orchard Beach Inn: 16.7 mi (26.8 km) from the heart of Windham. Enjoy the outdoor pool and unique décor. Inn at St John Portland In-Town: 9.4 mi (15.2 km) from the downtown core. Blind Tiger Portland - Danforth Street.: 9 rooms. Situated 10.2 mi (16.3 km) from the heart of Windham. The Orchard House: Inn & Cafe: 5 rooms. 17.3 mi (27.9 km) from the heart of downtown.Fleetwood House Bed & Breakfast: 3 rooms. Located 7.9 mi (12.8 km) from the core of Windham. Enjoy the free full breakfast and unique décor.
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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