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Check prices for these dates

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12 Dec - 14 Dec
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2 Jan - 4 Jan
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30 Jan - 1 Feb

B&B in Chebeague Island

Front of property - evening/night
Inn at St John Portland In-Town

Inn at St John Portland In-Town

2.5 star property
Valley Street
8.8 out of 10, Excellent, (1151)
"Enjoyed our stay."
United States
Heather
The price is SAR 300
SAR 327 total
includes taxes & fees
7 Dec - 8 Dec
Inn at St John Portland In-Town
Front of property
And. N B&B

And. N B&B

3.0 star property
Gray
9.8 out of 10, Exceptional, (77)
"Really lovely place and great hospitality from the owners!"
United States
Hunter
The price is SAR 402
SAR 438 total
includes taxes & fees
17 Dec - 18 Dec
And. N B&B
Exterior
Old Orchard Beach Inn

Old Orchard Beach Inn

2.5 star property
Old Orchard Beach
8.2 out of 10, Very Good, (1001)
"A beautiful place to stay!!! First time at a B&B and it did not disappoint."
United States
Kristian
Old Orchard Beach Inn
Front of property - evening/night
The Orchard House: Inn, Ice Cream, Cafe

The Orchard House: Inn, Ice Cream, Cafe

3.0 star property
Freeport
9.6 out of 10, Exceptional, (162)
"Wonderful place to stay! The room was very clean and the beds super comfortable. Will most definitely be returning for another visit in Maine."
United States
Shannon
The Orchard House: Inn, Ice Cream, Cafe
Exterior
Benjamin F. Packard House

Benjamin F. Packard House

3.0 star property
Bath
10.0 out of 10, Exceptional, (102)
"Beautiful house, the breakfast food was amazing, and the owners were so personable and welcoming. "
United States
Jennifer
The price is SAR 859
SAR 936 total
includes taxes & fees
6 Dec - 7 Dec
Benjamin F. Packard House
Porch
Candlebay Inn

Candlebay Inn

3.0 star property
Freeport
9.6 out of 10, Exceptional, (457)
"Great location and hospitality."
United States
Brandon
The price is SAR 578
SAR 630 total
includes taxes & fees
10 Dec - 11 Dec
Candlebay Inn
Exterior
The Kendall Inn

The Kendall Inn

3.5 star property
Freeport
9.8 out of 10, Exceptional, (145)
"Quaint stay. Enjoyed our stay. "
United States
Linda
The price is SAR 628
SAR 685 total
includes taxes & fees
1 Jan - 2 January 2026
The Kendall Inn
Baxter | Premium bedding, individually decorated, individually furnished
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 star property
West End
9.6 out of 10, Exceptional, (166)
"The property is beautiful, the staff is kind, and the rooms are spacious and clean. It was great to have a safe place to park the car while having so many things to do within walking distance. Being able to grab a quick breakfast before heading out was great too! We loved our stay here!"
United States
Darby
The price is SAR 649
SAR 708 total
includes taxes & fees
9 Dec - 10 Dec
Blind Tiger Portland - Danforth Street.
Stovall | Living area
Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 star property
West End
9.6 out of 10, Exceptional, (120)
"Loved the place "
United States
Stephen
The price is SAR 615
SAR 670 total
includes taxes & fees
9 Dec - 10 Dec
Blind Tiger Portland – Carleton Street
Garden
Brewster House Bed & Breakfast

Brewster House Bed & Breakfast

4.0 star property
Freeport
9.8 out of 10, Exceptional, (114)
"The food was wonderful and the hospitality was great!"
United States
Olivia
The price is SAR 784
SAR 855 total
includes taxes & fees
11 Dec - 12 Dec
Brewster House Bed & Breakfast
Property entrance
Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast

3.0 star property
Rosemont
9.0 out of 10, Wonderful, (132)
"Lovely, comfortable stay! So welcoming and accommodating. We only stayed one night but will keep this in mind next time we are in the area :)"
United States
Sadie
The price is SAR 859
SAR 936 total
includes taxes & fees
12 Dec - 13 Dec
Fleetwood House Bed & Breakfast
Outdoor dining
The James Place Inn B&B

The James Place Inn B&B

3.5 star property
Freeport
10.0 out of 10, Exceptional, (182)
"Wish we could have stayed longer. It has the ambiance of an older inn but the rooms are very clean and well maintained. "
United States
Melissa
The price is SAR 819
SAR 893 total
includes taxes & fees
11 Dec - 12 Dec
The James Place Inn B&B
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 Chebeague Island Hotel Reviews

Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

10/10 Excellent
"Easy check in, cozy and clean 👍"
Kathryn 2-night trip
Posted 1 day ago
Fireside Inn & Suites Portland

Frequently asked questions

Searching for B&Bs in Chebeague Island?
If you're looking for something a little different than your standard hotel, a bed and breakfast could be the perfect alternative for your trip.
Why would you choose a B&B over a traditional hotel room?
With attentive service, an atmosphere suited to mingling with other guests, and top-rated breakfasts, B&Bs all have a truly one-of-a-kind environment.
What are the best B&Bs in Chebeague Island?
Here are some well-liked B&Bs in the surrounding area: Inn at St John Portland In-Town: 10.5 mi (16.9 km) from the heart of Chebeague Island.Blind Tiger Portland – Carleton Street: 6 rooms. Situated 10.3 mi (16.5 km) from the heart of Chebeague Island. Enjoy the unique décor and patio area. The Orchard House: Inn, Ice Cream, Cafe: 5 rooms. 9.1 mi (14.7 km) from the heart of downtown.Blind Tiger Portland - Danforth Street.: 9 rooms. Located 10 mi (16.1 km) from the core of Chebeague Island.
When should I stay at a B&B in Chebeague Island?
When you're dreaming of a escape to Chebeague Island, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Chebeague Island are January, March, February, and December, with each month seeing an average of 7 inches of snowfall.
How can I get to and around Chebeague Island?
Planning your excursions in and around Chebeague Island is easier with these transportation options. Fly into Portland Intl. Jetport Airport (PWM), which is located 12.1 mi (19.4 km) away from the city center. You can also search for flights into Auburn, ME (LEW-Auburn - Lewiston Municipal), which is 23 mi (37.1 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.