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

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Check prices for these dates

Next weekend
21 Aug - 23 Aug
In two weeks
28 Aug - 30 Aug
In one month
11 Sept - 13 Sept
In two months
9 Oct - 11 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, (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
The price is HK$1,797
HK$1,959 total
includes taxes & fees
24 Aug - 25 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, (1,112 reviews)
"Room was clean, bed was comfortable, staff were helpful. Would stay here again!"
United States
Caleb
The price is HK$1,327
HK$1,447 total
includes taxes & fees
17 Aug - 18 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, (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
The price is HK$1,771
HK$1,931 total
includes taxes & fees
17 Aug - 18 Aug
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
The price is HK$2,867
HK$3,125 total
includes taxes & fees
15 Sept - 16 Sept
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
The price is HK$1,370
HK$1,493 total
includes taxes & fees
20 Aug - 21 Aug
Candlebay Inn
Premium bedding, iron/ironing board, free WiFi, 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
The price is HK$3,395
HK$3,700 total
includes taxes & fees
1 Sept - 2 Sept
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
The price is HK$1,721
HK$1,876 total
includes taxes & fees
1 Sept - 2 Sept
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
The price is HK$911
HK$1,111 total
includes taxes & fees
30 Aug - 31 Aug
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
The price is HK$1,322
HK$1,441 total
includes taxes & fees
17 Aug - 18 Aug
The Jeremiah Mason House B & B
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
The price is HK$1,130
HK$1,232 total
includes taxes & fees
7 Sept - 8 Sept
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
The price is HK$2,152
HK$2,346 total
includes taxes & fees
25 Aug - 26 Aug
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
The price is HK$2,384
HK$2,598 total
includes taxes & fees
21 Aug - 22 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, (125 reviews)
"👍"
United States
Vicki
The price is HK$1,251
HK$1,364 total
includes taxes & fees
20 Aug - 21 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 HK$1,562
HK$1,702 total
includes taxes & fees
17 Aug - 18 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 HK$1,475
HK$1,839 total
includes taxes & fees
4 Sept - 5 Sept
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 HK$1,365
HK$1,701 total
includes taxes & fees
11 Sept - 12 Sept
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 HK$1,734
HK$1,890 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

HomeAwhile

HomeAwhile

10/10 Excellent
"Amazing"
Mary 2-night trip
Posted 3 hours ago
HomeAwhile

Find out more about Windham

Windham B&B information

Number of reviews
3,915
Accommodation
33 B&B
Lowest Price
HK$1,111
Highest Price
HK$3,700

Frequently asked questions

Searching for B&Bs in Windham?
If you're hoping for something a little more offbeat than the traditional hotel experience, a bed and breakfast could be a great option for your holiday. When you want to explore some attractions in town, Little Sebago Lake and Sebago Lake are worth a stop.
Are you interested in an apartment instead of a traditional hotel?
With attentive service, opportunities to mingle with other guests and tasty breakfasts, B&Bs provide a unique 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 city centre. Enjoy the outdoor pool and unique decor. 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 city centre. Enjoy the free full breakfast and unique decor. 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 temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Windham are January, March, February and December, with each month seeing an average of 19 cm of snowfall.
What is there to do in Windham?
Travellers 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 should put Sebago Lake Basin and Forest Lake 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, ME (PWM-Portland Intl. Jetport), which is located 8.9 mi (14.3 km) away. Otherwise, look 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 a rental car for your journey.

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