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Compare 23 B&B in Chebeague Island with updated reviews, rates, and availability.

Inn at St John Portland In-Town
2.5 star property
9.0 out of 10, Wonderful, (1001)
"Would stay here again! "
The price is AED 400
AED 436 total
includes taxes & fees
2 Jun - 3 Jun
Inn at St John Portland In-Town
Old Orchard Beach Inn
2.5 star property
8.4 out of 10, Very Good, (1004)
"Quick walk to the shops and beach. "
The price is AED 592
AED 645 total
includes taxes & fees
3 Jun - 4 Jun
Old Orchard Beach Inn
The Orchard House & Cafe
3.0 star property
9.6 out of 10, Exceptional, (99)
"We had an amazing stay at The Orchard House. The pictures do not do it justice. It is beautiful and special. We stayed in the Library Room. Very unique and spacious for 2 people. I am in love with the bed/mattress! The light breakfast served (coffee/tea, cereal, boiled eggs, juice, toast.etc) was perfect and a great way to start the day. The owner Bill (and his Mom Lynn owner of the vintage shop Folly) are fabulous. And the dogs, Bingo and Bay are the icing on the cake. Would definitely...
The price is AED 806
AED 879 total
includes taxes & fees
11 Jun - 12 Jun
The Orchard House & Cafe
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Blind Tiger Portland - Danforth Street.
3.5 star property
9.6 out of 10, Exceptional, (114)
"Perfect stay for a weekend getaway!!"
The price is AED 1,354
AED 1,476 total
includes taxes & fees
25 Jun - 26 Jun
Blind Tiger Portland - Danforth Street.
West End Inn
3.0 star property
9.6 out of 10, Exceptional, (75)
"We stayed for a get a way weekend . Breakfast each morning was wonderful. Plenty of parking right in front of inn . We walked all over town. It was the weekend of the eclipse and we did not have glasses but Milan so graciously gave us extras he had . Wonderful host "
The price is AED 1,172
AED 1,277 total
includes taxes & fees
3 Jun - 4 Jun
West End Inn
Candlebay Inn
3.0 star property
9.6 out of 10, Exceptional, (379)
"Very friendly host. The Inn is lovely. "
The price is AED 694
AED 757 total
includes taxes & fees
13 Jun - 14 Jun
Candlebay Inn
And. N B&B
2.0 star property
9.8 out of 10, Exceptional, (28)
"We enjoyed our overnight stay. The young owners were gracious and interesting to talk with. We would have liked to have directions printed out for use of the TV and heating/cooling system in our room. The bed was comfortable and the entire place was very clean. Breakfast was prepared well and very tasty. Very enjoyable stay."
The price is AED 741
AED 808 total
includes taxes & fees
6 Jun - 7 Jun
And. N B&B
Fleetwood House Bed & Breakfast
3.0 star property
8.8 out of 10, Excellent, (98)
"Charming house with great hospitality and hosts who were very accommodating. Very good breakfast. "
The price is AED 804
AED 914 total
includes taxes & fees
1 Jun - 2 Jun
Fleetwood House Bed & Breakfast
Blind Tiger Portland – Carleton Street
3.5 star property
9.8 out of 10, Exceptional, (98)
"Best place to stay in Portland! The decor, service and location are awesome, this is my second time staying here!"
The price is AED 1,774
AED 1,933 total
includes taxes & fees
1 Jul - 2 Jul
Blind Tiger Portland – Carleton Street
Atlantic Birches Inn
2.5 star property
9.4 out of 10, Exceptional, (343)
"Nice place, great location."
Atlantic Birches Inn
Harpswell Inn
2.0 star property
10.0 out of 10, Exceptional, (3)
"Nice country inn, beautiful views. best wishes for the new ownwers."
Harpswell Inn
The James Place Inn B&B
3.5 star property
10.0 out of 10, Exceptional, (165)
"I had a lovely stay at the James Inn; the hosts were great and the breakfast was delicious!! Anne"
The price is AED 1,071
AED 1,167 total
includes taxes & fees
1 Jun - 2 Jun
The James Place Inn B&B
Benjamin F. Packard House
3.0 star property
10.0 out of 10, Exceptional, (79)
"wonderful traditional house in a perfect location. homemade breakfast was the best! Thanks Amy. "
The price is AED 878
AED 957 total
includes taxes & fees
3 Jun - 4 Jun
Benjamin F. Packard House
The Chadwick Bed & Breakfast
3.5 star property
9.8 out of 10, Exceptional, (38)
"Great location for seeing Portland. "
The price is AED 951
AED 1,037 total
includes taxes & fees
5 Jun - 6 Jun
The Chadwick Bed & Breakfast
"SABINO" 1 Bdrm Suite
9.8 out of 10, Exceptional, (6)
"It was absolutely amazing. Gorgeous grounds and surroundings. The host Jane is wonderful. Her cooking is most delicious. Most tranquil vacation!"
"SABINO" 1 Bdrm Suite
Brewster House Bed & Breakfast
4.0 star property
9.8 out of 10, Exceptional, (105)
"The breakfasts are to die for. Freeport is a lovely place and easy to walk into from Brewster’s. Kelleigh and Dave are so welcoming. Would love to go back."
The price is AED 1,095
AED 1,193 total
includes taxes & fees
3 Jun - 4 Jun
Brewster House Bed & Breakfast
PineCrest Inn
4.0 star property
9.8 out of 10, Exceptional, (98)
"Our stay at the Pinecrest was wonderful. We would highly recommend staying and plan to visit again. The breakfasts were fantastic. The service was just right. We were very comfortable. Kathy was the perfect host!"
PineCrest Inn
Guest room with private bath and gourmet breakfast served daily
10.0 out of 10, Exceptional, (4)
"Book with the property (online or call) to avoid extra charges! John and Loretta are amazing people and inn keepers. The breakfast is delicious and the house itself is styled as it would have been almost 100 years ago. 10/10, we will be back! Thank you!"
Guest room with private bath and gourmet breakfast served daily
Charming rm w/king bed, w/sm ensuite w/shw. Sitting area, writing desk+chair.
6.0 out of 10, (2)
"The house is very beautiful and lovingly maintained. It is set on a peninsula with views of the water looking both ways. The owner/manger was wonderful. Breakfast was great and we sat and talked over breakfast with her and her husband for almost four hours one day. We have never done that before. Great people. Great place. By far the best stay we have ever had at a B and B."
Charming rm w/king bed, w/sm ensuite w/shw. Sitting area, writing desk+chair.
Kendall Tavern Inn
3.5 star property
9.8 out of 10, Exceptional, (121)
"What a fantastic stay!"
Kendall Tavern Inn
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See all available properties in Chebeague Island
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.

Other property types in Chebeague Island

2 duplex
3.0 star property
The price is AED 926
AED 1,376 total
includes taxes & fees
8 Jun - 9 Jun
2 duplex
Gorgeous ocean-front home with stunning beach views
9.6 out of 10, Exceptional, (75)
"Great little condo. Right on the beach! Balcony is wonderful, as is the view from the master. Second bedroom is definitely a “kids” room with the two bunk beds. Garage was great for a car, would not fit the height of a truck"
Gorgeous ocean-front home with stunning beach views
Rent a room in the gorgeous Holt House
8.4 out of 10, Very Good, (19)
"It was a great trip up to Portland and the property met our needs."
Rent a room in the gorgeous Holt House
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 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.
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, April, March, and February, with each month seeing an average of 9 inches of snowfall.
What is there to do in Chebeague Island?
When you want to spend some time in the great outdoors, Wolfe’s Neck Woods State Park and Casco Bay are some notable spots. You might put Sand Beach and East End Beach on your list if you want to see more of the area.
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.

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