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Check prices for these dates

Next weekend
21 Nov - 23 Nov
In two weeks
28 Nov - 30 Nov
In one month
12 Dec - 14 Dec
In two months
9 Jan - 11 Jan

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, (1137)
"Great place to stay. Would highly recommend "
United States
Benjamin
The price is AED 294
AED 320 total
includes taxes & fees
16 Dec - 17 Dec
Inn at St John Portland In-Town
Exterior
Old Orchard Beach Inn

Old Orchard Beach Inn

2.5 star property
Old Orchard Beach
8.2 out of 10, Very Good, (1000)
"My family had a cozy and memorable stay. The staff was incredibly helpful and my daughter enjoyed the historical look and feel to the Inn."
United States
Christopher
Old Orchard Beach Inn
Porch
Candlebay Inn

Candlebay Inn

3.0 star property
Freeport
9.6 out of 10, Exceptional, (457)
"The Inn was great and the staff was very hospitable "
United States
Timothy
The price is AED 566
AED 617 total
includes taxes & fees
16 Dec - 17 Dec
Candlebay Inn
Front of property - evening/night
The Orchard House & Cafe

The Orchard House & Cafe

3.0 star property
Freeport
9.6 out of 10, Exceptional, (161)
"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 price is AED 613
AED 668 total
includes taxes & fees
16 Nov - 17 Nov
The Orchard House & Cafe
Exterior
Benjamin F. Packard House

Benjamin F. Packard House

3.0 star property
Bath
10.0 out of 10, Exceptional, (102)
"Wonderful place to stay in Bath. The breakfast is terrific!"
United States
William
The price is AED 841
AED 917 total
includes taxes & fees
15 Dec - 16 Dec
Benjamin F. Packard House
Exterior
The Kendall Inn

The Kendall Inn

3.5 star property
Freeport
9.8 out of 10, Exceptional, (144)
"Quaint stay. Enjoyed our stay. "
United States
Linda
The price is AED 694
AED 757 total
includes taxes & fees
28 Nov - 29 Nov
The Kendall Inn
Property entrance
Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast

3.0 star property
Rosemont
9.0 out of 10, Wonderful, (132)
"This was a beautiful old house in excellent condition. The hosts were very nice. The breakfast was excellent. "
United States
Linda
The price is AED 841
AED 917 total
includes taxes & fees
20 Nov - 21 Nov
Fleetwood House Bed & Breakfast
Baxter | 1 bedroom, premium bedding, individually decorated
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 star property
West End
9.6 out of 10, Exceptional, (161)
" Beautiful historic building. The common areas and our room were stunning! Breakfast in the morning was great. Make sure to go to the widow’s walk in the evening for a view. "
United States
John
The price is AED 967
AED 1,054 total
includes taxes & fees
27 Nov - 28 Nov
Blind Tiger Portland - Danforth Street.
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 AED 802
AED 874 total
includes taxes & fees
1 Dec - 2 Dec
The James Place Inn B&B
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, (119)
"One of the best hotel/bnb experiences I’ve had in my past year of travels. Would recommend to anyone going to Maine. "
United States
Cristian
The price is AED 986
AED 1,075 total
includes taxes & fees
15 Dec - 16 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)
"Nice inn - a bit noisy as it's on a main street and I had a front facing room. "
United States
lorna
The price is AED 1,392
AED 1,517 total
includes taxes & fees
3 Dec - 4 Dec
Brewster House 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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Top Chebeague Island Hotel Reviews

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

10/10 Excellent
"Lovely hotel, great location, great staff, valet parking."
Elizabeth 1-night trip
Posted 15 hours ago
Portland Regency Hotel & Spa

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. Blind Tiger Portland - Danforth Street.: 9 rooms. 10 mi (16.1 km) from the heart of downtown.Fleetwood House Bed & Breakfast: 3 rooms. Located 10.9 mi (17.6 km) from the core of Chebeague Island. Enjoy the free full breakfast and unique décor.
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.