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Check prices for these dates

Next weekend
7 Feb - 9 Feb
In two weeks
14 Feb - 16 Feb
In one month
28 Feb - 2 Mar
In two months
28 Mar - 30 Mar

Compare 23 B&B in Chebeague Island 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, (1035)
"This is a lovely in-town hotel, very clean and very helpful and friendly staff. We especially appreciated the nice touch of cookies in the evening and breakfast which started at 6:00 am because we had a very early doctor appointment to get to. "
The price is AED 294
AED 320 total
includes taxes & fees
28 Jan - 29 Jan
Inn at St John Portland In-Town
Old Orchard Beach Inn
Front of property

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 621
AED 677 total
includes taxes & fees
29 Jan - 30 Jan
Old Orchard Beach Inn
Blind Tiger Portland - Danforth Street.
Lobby sitting area

Blind Tiger Portland - Danforth Street.

3.5 star property
9.6 out of 10, Exceptional, (139)
"Very interesting property. Well maintained/restored property that is 200 years old. Comfortable room and great common areas. Staff was friendly and accomodating."
The price is AED 666
AED 726 total
includes taxes & fees
28 Jan - 29 Jan
Blind Tiger Portland - Danforth Street.
Atlantic Birches Inn
Exterior

Atlantic Birches Inn

2.5 star property
9.4 out of 10, Exceptional, (343)
"-Had been taken over by Old Orchard Inn, we were not notified. Wifi for Atlantic Birches did not work (ever), no one in the inn to ask questions of, even during the day. -No breakfast in the inn, had to walk down the street to Old Orchard Inn with wet hair for what was a woeful breakfast. First morning was kid's cereal (literally only choice), stale bagels, hard boiled eggs, bad coffee. Another guest told us about yogurt (all sweet) in a small refridg. No one ever came into the dining room to...
Atlantic Birches Inn
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
28 Jan - 29 Jan
Fleetwood House Bed & Breakfast
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 547
AED 597 total
includes taxes & fees
28 Jan - 29 Jan
Candlebay Inn
West End Inn
Breakfast area

West End Inn

3.0 star property
9.6 out of 10, Exceptional, (88)
"Truly wonderful staff and space. The breakfasts offered are also phenomenal."
The price is AED 694
AED 757 total
includes taxes & fees
28 Jan - 29 Jan
West End Inn
And. N B&B
Front of property

And. N B&B

3.0 star property
9.8 out of 10, Exceptional, (56)
"It's winter, house has central and each room has a split heatpump soooo nice and comfy. Located on not-so-traveled road yet central to village makes it pretty quiet. Definitely Dog Lovers - pet friendly ice-melt/couple waste bags/bowls/mat/doggy bed!!!! Thanks "
The price is AED 415
AED 452 total
includes taxes & fees
10 Feb - 11 Feb
And. N B&B
Blind Tiger Portland – Carleton Street
Reception

Blind Tiger Portland – Carleton Street

3.5 star property
9.8 out of 10, Exceptional, (109)
"Charming place to stay. "
The price is AED 874
AED 953 total
includes taxes & fees
3 Feb - 4 Feb
Blind Tiger Portland – Carleton Street
Benjamin F. Packard House
Front of property

Benjamin F. Packard House

3.0 star property
10.0 out of 10, Exceptional, (94)
"The first BnB we've experienced that emphasized recycling of paper, plastic, and toiletries. Thank you Mark, Amy and Picco for a memorable stay. Hope to see you again soon. "
The price is AED 841
AED 917 total
includes taxes & fees
14 Feb - 15 Feb
Benjamin F. Packard House
The Orchard House & Cafe
Front of property

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
28 Jan - 29 Jan
The Orchard House & Cafe
The James Place Inn B&B
Front of property

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 757
AED 825 total
includes taxes & fees
28 Jan - 29 Jan
The James Place Inn B&B
The Chadwick Bed & Breakfast
View from room

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
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 657
AED 717 total
includes taxes & fees
31 Jan - 1 Feb
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
"SABINO" 1 Bdrm Suite
"Sabino Suite" King Bed, Sitting Area, South westerly exposure, water view

"SABINO" 1 Bdrm Suite

10.0 out of 10, Exceptional, (12)
"Charming old place. Close to beaches and great shopping. "
"SABINO" 1 Bdrm Suite
Kennebec Room - King Bed, Private Bath
Room

Kennebec Room - King Bed, Private Bath

8.4 out of 10, Very Good, (5)
"We had a very pleasant stay for two nights at the Stonehouse Manor late season at Popham Beach. Our room had a beautiful view of the mouth of the Kennebunk River. In the morning we lay in bed watching the sun rise on the autumn colored hillside by Fort Popham through the large bay window. It was quiet. We strolled the expansive grounds with our coffee admiring the botanical variation particularly the huge old copper beech in front of the manor. A homemade breakfast of Rachels blueberry...
Kennebec Room - King Bed, Private Bath
Harpswell Inn
Exterior

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
Lake View Suite - Large King, Ensuite Bath
Master Suite with 4 poster King Size bed and comfortable seating & ensuite bath

Lake View Suite - Large King, Ensuite Bath

8.0 out of 10, Very Good, (1)
"Clean and enjoyable"
Lake View Suite - Large King, Ensuite Bath
The Kendall Inn
Exterior

The Kendall Inn

3.5 star property
9.8 out of 10, Exceptional, (121)
"What a fantastic stay!"
The price is AED 524
AED 571 total
includes taxes & fees
28 Jan - 29 Jan
The Kendall Inn
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 Chebeague Island

The Weldon Hotel
Front of property

The Weldon Hotel

4.0 star property
9.4 out of 10, Exceptional, (35)
"The full kitchen and appliances were perfect for my stay so that I did not have to eat out while I was there and save money "
The price is AED 562
AED 613 total
includes taxes & fees
4 Feb - 5 Feb
The Weldon Hotel
Gorgeous ocean-front home with stunning beach views

Gorgeous ocean-front home with stunning beach views

9.6 out of 10, Exceptional, (100)
"The view and location are amazing. The house was very comfortable for the three adults on our trip. It’s also very suitable for a family with kids as one of the rooms has two bunk bed sets. It’s comfortable, cozy, and completely relaxing. Within walking distance of the pier and entertainment. Great place to stay. "
Gorgeous ocean-front home with stunning beach views
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Spectacular oceanfront view from your private newly built expansive balcony!!

Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

9.8 out of 10, Exceptional, (197)
"Great codo unit, very close to everything "
The price is AED 643
AED 1,249 total
includes taxes & fees
29 Jan - 30 Jan
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
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.
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 - Danforth Street.: 9 rooms. Situated 10 mi (16.1 km) from the heart of Chebeague Island. Fleetwood House Bed & Breakfast: 3 rooms. 10.9 mi (17.6 km) from the heart of downtown. Enjoy the free full breakfast and unique décor. Candlebay Inn: 6 rooms. Located 8.3 mi (13.3 km) from the core of Chebeague Island. Enjoy the free full breakfast and in-room dining.
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.
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.