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12 Sep - 14 Sep
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19 Sep - 21 Sep
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3 Oct - 5 Oct
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31 Oct - 2 Nov

B&B in Windham

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, (1085)
"Very nice staff. Clean and charming hotel."
The price is AED 400
AED 436 total
includes taxes & fees
4 Sep - 5 Sep
Inn at St John Portland In-Town
Old Orchard Beach Inn
Exterior

Old Orchard Beach Inn

2.5 star property
8.4 out of 10, Very Good, (1001)
"Great stay, close to everything!"
Old Orchard Beach Inn
Fleetwood House Bed & Breakfast
Property entrance

Fleetwood House Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (125)
"The breakfasts and friendly conversations were amazing. We thoroughly enjoyed our stay at the Fleetwood Bed and Breakfast "
The price is AED 841
AED 917 total
includes taxes & fees
7 Sep - 8 Sep
Fleetwood House Bed & Breakfast
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, (150)
"Everything was wonderful, we highly recommend staying here to anyone considering it."
The price is AED 1,399
AED 1,525 total
includes taxes & fees
15 Sep - 16 Sep
Blind Tiger Portland - Danforth Street.
Candlebay Inn
Porch

Candlebay Inn

3.0 star property
9.6 out of 10, Exceptional, (441)
"Great location and hospitality."
The price is AED 731
AED 797 total
includes taxes & fees
4 Sep - 5 Sep
Candlebay Inn
Blind Tiger Portland – Carleton Street
Stovall | Living area | Fireplace

Blind Tiger Portland – Carleton Street

3.5 star property
9.8 out of 10, Exceptional, (115)
"Loved the place "
The price is AED 1,814
AED 1,978 total
includes taxes & fees
25 Sep - 26 Sep
Blind Tiger Portland – Carleton Street
Lakeview Inn
Superior Room, 1 King Bed | Individually decorated, individually furnished, free WiFi, bed sheets

Lakeview Inn

3.5 star property
9.4 out of 10, Exceptional, (51)
"We would definitely stay here again!"
Lakeview Inn
The Orchard House & Cafe
Front of property - evening/night

The Orchard House & Cafe

3.0 star property
9.6 out of 10, Exceptional, (154)
"Lovely facility! We enjoyed the ice cream."
The price is AED 767
AED 837 total
includes taxes & fees
4 Sep - 5 Sep
The Orchard House & Cafe
The Kendall Inn
Exterior

The Kendall Inn

3.5 star property
9.8 out of 10, Exceptional, (135)
"Quaint stay. Enjoyed our stay. "
The price is AED 774
AED 843 total
includes taxes & fees
4 Sep - 5 Sep
The Kendall Inn
And. N B&B
Front of property

And. N B&B

3.0 star property
9.8 out of 10, Exceptional, (72)
"Really lovely place and great hospitality from the owners!"
The price is AED 706
AED 770 total
includes taxes & fees
2 Oct - 3 Oct
And. N B&B
Noble House Inn
Porch

Noble House Inn

3.5 star property
9.8 out of 10, Exceptional, (93)
"A very well maintained B&B. The folks that run it really go all out to provide an excellent stay."
The price is AED 507
AED 552 total
includes taxes & fees
4 Sep - 5 Sep
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, (105)
"Wonderful stay "
The Perkins House
The James Place Inn B&B
Outdoor dining

The James Place Inn B&B

3.5 star property
10.0 out of 10, Exceptional, (177)
"Great place. Comfortable and welcoming. Great proprietors and great location. "
The price is AED 1,116
AED 1,216 total
includes taxes & fees
4 Sep - 5 Sep
The James Place Inn B&B
Brewster House Bed & Breakfast
Garden

Brewster House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (112)
"Wonderful hosts. Enjoyed quiet evening and lovely gourmet breakfast. Truly memorable stay. We look forward to returning in the future."
The price is AED 1,098
AED 1,197 total
includes taxes & fees
7 Sep - 8 Sep
Brewster House Bed & Breakfast
West End Inn
Exterior

West End Inn

3.0 star property
9.6 out of 10, Exceptional, (90)
"Extremely cozy and clean, perfect bed and breakfast in the West End for those looking for walkable access to the Old Port and downtown as well as a quiet retreat at night in the historic West End District. "
West End Inn
The Jeremiah Mason House B & B
Comfort Single Room, Non Smoking (Room 1, Second Floor) | Individually decorated, individually furnished, iron/ironing board

The Jeremiah Mason House B & B

3.0 star property
9.6 out of 10, Exceptional, (46)
"Great charming place to stay"
The price is AED 881
AED 961 total
includes taxes & fees
3 Oct - 4 Oct
The Jeremiah Mason House B & B
The Munroe Inn
Courtyard view

The Munroe Inn

3.5 star property
9.2 out of 10, Wonderful, (63)
"We had a lovely stay and were very comfortable."
The price is AED 549
AED 599 total
includes taxes & fees
7 Sep - 8 Sep
The Munroe Inn
PineCrest Inn
Street view

PineCrest Inn

4.0 star property
9.8 out of 10, Exceptional, (103)
"Lovely home, great breakfast. Kathy is a very gracious hostess and really helped us to thoroughly enjoy the Portland area."
PineCrest Inn
Wolf Cove Inn
Sauna

Wolf Cove Inn

4.0 star property
10.0 out of 10, Exceptional, (1)
Wolf Cove Inn
Picturesque bed and breakfast, nestled in the foothills of the white mountains.
Exterior detail

Picturesque bed and breakfast, nestled in the foothills of the white mountains.

10.0 out of 10, Exceptional, (1)
"The property is well maintained. The room was comfortable and tastefully decorated. The hostess was accommodating and helpful"
Picturesque bed and breakfast, nestled in the foothills of the white mountains.
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

Portland Harbor Hotel

Portland Harbor Hotel

10/10 Excellent
"Nice hotel basically in the center of the Harbor district. Staff is very professional and friendly. I would recommend. "
Joseph 1-night trip
Posted 3 days ago
Portland Harbor Hotel

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. Fleetwood House Bed & Breakfast: 3 rooms. Situated 7.9 mi (12.7 km) from the heart of Windham. Enjoy the free full breakfast and unique décor. The Orchard House & Cafe: 5 rooms. 17.3 mi (27.9 km) from the heart of downtown.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 Maine Wildlife Park and Sebago Lake Basin 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.