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Check prices for these dates

Next weekend
25 Apr - 27 Apr
In two weeks
2 May - 4 May
In one month
16 May - 18 May
In two months
13 Jun - 15 Jun

Compare 35 B&B in Windham with updated reviews, rates, and availability.

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, (1020)
"I’ve stayed at the Inn on St John many times. I have a long commute from home to Portland. I stay when the weather is bad and the travel is dangerous. I like to stay at the inn because the it very affordable, comfortable and very easy to check in, find food nearby and relax in my room. I’ve stayed in many of the rooms large and small and I’ve never had a bad night. Staff are super friendly. The parking is easy. It s also a nostalgic place as I grew up in Portland and My dad was friends with the...
The price is AED 294
AED 320 total
includes taxes & fees
27 Apr - 28 Apr
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, (1000)
"Amazing location, so much beauty and charm at this inn. Have stayed twice and can’t wait to return!"
The price is AED 584
AED 637 total
includes taxes & fees
15 Apr - 16 Apr
Old Orchard Beach Inn
Blind Tiger Portland - Danforth Street.
Baxter | Premium bedding, individually decorated, individually furnished

Blind Tiger Portland - Danforth Street.

3.5 star property
9.6 out of 10, Exceptional, (143)
"Love The Blind Tiger. Fantastic accommodations, lovely staff. Can't wait to go back!"
The price is AED 1,098
AED 1,197 total
includes taxes & fees
21 Apr - 22 Apr
Blind Tiger Portland - Danforth Street.
Blind Tiger Portland – Carleton Street
Stovall | Living area | Fireplace

Blind Tiger Portland – Carleton Street

3.5 star property
9.8 out of 10, Exceptional, (110)
"One of the best hotel/bnb experiences I’ve had in my past year of travels. Would recommend to anyone going to Maine. "
The price is AED 857
AED 934 total
includes taxes & fees
23 Apr - 24 Apr
Blind Tiger Portland – Carleton Street
And. N B&B
Front of property

And. N B&B

3.0 star property
9.8 out of 10, Exceptional, (58)
"Nice place, cute little town"
The price is AED 456
AED 497 total
includes taxes & fees
15 Apr - 16 Apr
And. N B&B
The Orchard House & Cafe
Front of property - evening/night

The Orchard House & Cafe

3.0 star property
9.6 out of 10, Exceptional, (142)
"It was a delightful experience "
The price is AED 613
AED 668 total
includes taxes & fees
15 Apr - 16 Apr
The Orchard House & Cafe
Noble House Inn
Porch

Noble House Inn

3.5 star property
9.8 out of 10, Exceptional, (85)
"Vert quaint, clean and comfortable. Owner is friendly."
The price is AED 674
AED 735 total
includes taxes & fees
15 Apr - 16 Apr
Noble House Inn
West End Inn
Classic Room, 1 King Bed, City View | Individually decorated, individually furnished, iron/ironing board

West End Inn

3.0 star property
9.6 out of 10, Exceptional, (89)
"Beautiful building, great location and the breakfast was amazing!! "
The price is AED 694
AED 757 total
includes taxes & fees
15 Apr - 16 Apr
West End Inn
The Kendall Inn
Exterior

The Kendall Inn

3.5 star property
9.8 out of 10, Exceptional, (123)
"This bed and breakfast was absolutely charming. The common space was well equipped with all types of entertainment, puzzles, games, tea/coffee, and a self service honor system minibar. The full breakfast was delicious with plenty of options and the hosts seem to really enjoy sharing their home. The bedroom and bathroom were spotless and comfortable. We will definitely recommend this bed and breakfast."
The price is AED 607
AED 661 total
includes taxes & fees
15 Apr - 16 Apr
The Kendall Inn
Candlebay Inn
Porch

Candlebay Inn

3.0 star property
9.6 out of 10, Exceptional, (420)
"Room was equipped with sprinklers and other fire safety items. Owner graciously welcomed us."
The price is AED 566
AED 617 total
includes taxes & fees
15 Apr - 16 Apr
Candlebay 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, (43)
"The homemade breakfast was wonderful and the host is very nice. "
The price is AED 668
AED 729 total
includes taxes & fees
15 Apr - 16 Apr
The Jeremiah Mason House B & B
Lakeview Inn
Exterior

Lakeview Inn

3.5 star property
9.2 out of 10, Wonderful, (46)
"Nice staff, ample parking, nice room. Conveniently located. Breakfast and coffee was great. Bed is very comfortable. "
The price is AED 885
AED 964 total
includes taxes & fees
15 Apr - 16 Apr
Lakeview Inn
The Perkins House
Suite (The Carriage) | View from room

The Perkins House

3.0 star property
9.8 out of 10, Exceptional, (103)
"Adorably decorated place and friendly service "
The Perkins House
Fleetwood House Bed & Breakfast
Property entrance

Fleetwood House Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (114)
"It was a really great place to stay! Everyone was very friendly and parking was super easy! I would stay again! "
The price is AED 841
AED 917 total
includes taxes & fees
15 Apr - 16 Apr
Fleetwood House Bed & Breakfast
The James Place Inn B&B
Outdoor dining

The James Place Inn B&B

3.5 star property
10.0 out of 10, Exceptional, (171)
"This B and B was outstanding for attention to detail, immaculate condition and cleanliness. Their breakfast was delicious with a start of fresh fruit and scones, and a great breakfast burrito that day. A short walk to LLBean, it’s near all the attractions in Freeport. The hosts were very friendly and accommodating. It was a real pleasure to stay there!"
The price is AED 959
AED 1,045 total
includes taxes & fees
15 Apr - 16 Apr
The James Place Inn B&B
Wolf Cove Inn
Dock

Wolf Cove Inn

3.0 star property
10.0 out of 10, Exceptional, (1)
Wolf Cove Inn
Brewster House Bed & Breakfast
Exterior

Brewster House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (110)
"Nice inn - a bit noisy as it's on a main street and I had a front facing room. "
The price is AED 804
AED 877 total
includes taxes & fees
28 Apr - 29 Apr
Brewster House Bed & Breakfast
PineCrest Inn
Street view

PineCrest Inn

4.0 star property
9.8 out of 10, Exceptional, (102)
"Lovely home, great breakfast. Kathy is a very gracious hostess and really helped us to thoroughly enjoy the Portland area."
PineCrest Inn
The Munroe Inn
Exterior

The Munroe Inn

3.5 star property
9.0 out of 10, Wonderful, (61)
"This is a great historic home. The owner was very friendly and kind. Only complaints were no tissue in the bathroom, and house was quite cold."
The price is AED 570
AED 622 total
includes taxes & fees
15 Apr - 16 Apr
The Munroe Inn
The Chadwick Bed & Breakfast
Exterior

The Chadwick Bed & Breakfast

3.5 star property
9.8 out of 10, Exceptional, (48)
"The Innkeepers were friendly and wonderful communicators. Breakfast was DELICIOUS! The rooms were cozy and the area was easy to commute on foot"
The Chadwick Bed & Breakfast
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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Other property types in Windham

The Weldon Hotel
Deluxe Suite, 2 Bedrooms | Private kitchen | Full-size fridge, microwave, oven, stovetop

The Weldon Hotel

4.0 star property
9.6 out of 10, Exceptional, (54)
"A great place to stay if you’re in town for several days. Felt like my own apt and loved the extra living space to chill after a busy week of work travels. "
The price is AED 574
AED 901 total
includes taxes & fees
27 Apr - 28 Apr
The Weldon Hotel
Gorgeous ocean-front home with stunning beach views
On the beach

Gorgeous ocean-front home with stunning beach views

9.6 out of 10, Exceptional, (103)
"Loved the property, location and views"
Gorgeous ocean-front home with stunning beach views
Oceanfront Condo! Spectacular Views From Private Large Balcony
On the beach

Oceanfront Condo! Spectacular Views From Private Large Balcony

9.0 out of 10, Wonderful, (124)
"Great location! If you are looking for quiet time during the evening hours this isn’t the place for you as The Brunswick restaurant is directly below. If you like music and a great view, it’s an amazing spot! "
The price is AED 551
AED 1,121 total
includes taxes & fees
16 Apr - 17 Apr
Oceanfront Condo! Spectacular Views From Private Large Balcony
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.

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. Blind Tiger Portland - Danforth Street.: 9 rooms. Situated 10.2 mi (16.3 km) from the heart of Windham. Fleetwood House Bed & Breakfast: 3 rooms. 7.9 mi (12.7 km) from the heart of downtown. Enjoy the free full breakfast and unique décor. West End Inn: 6 rooms. Located 9.9 mi (15.9 km) from the core of Windham. Enjoy the local cuisine breakfast and deli.
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.