A wooden pier leading to a marina with boats docked.

Find a Bed and Breakfast in Chebeague Island from CA $139

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Check prices for these dates

Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18
In one month
Oct 30 - Nov 1
In two months
Nov 27 - Nov 29

Our top choices for Chebeague Island bed & breakfast

A white building with a red roof, a sign indicating a vacancy at Candlebay Inn, and an American flag.

1. Candlebay Inn

Candlebay Inn
3.0 star property
Freeport
9.6 out of 10, Exceptional, (490 reviews)
"Great stay in a historic home."
United States
Richard
The price is CA $204
CA $222 total
includes taxes & fees
Nov 1 - Nov 2
Candlebay Inn
A black front door with a light fixture above it, flanked by two potted evergreen trees.

2. The Orchard House: Inn & Cafe

The Orchard House: Inn & Cafe
3.0 star property
Freeport
9.6 out of 10, Exceptional, (181 reviews)
"Amazing stay in a perfect location! Would absolutely recommend to family and friends and will likely stay again!"
United States
Megan
The price is CA $295
CA $322 total
includes taxes & fees
Oct 20 - Oct 21
The Orchard House: Inn & Cafe
A multi-story building with a stone facade, multiple windows, and awnings.

3. Inn at St John Portland In-Town

Inn at St John Portland In-Town
2.5 star property
Valley Street
8.6 out of 10, Excellent, (1,133 reviews)
"Cute spot and very affordable."
United States
Tess
The price is CA $127
CA $139 total
includes taxes & fees
Nov 1 - Nov 2
Inn at St John Portland In-Town
A house with a sign for The James Place Inn, indicating a vacancy.

4. The James Place Inn B&B

The James Place Inn B&B
3.5 star property
Freeport
10.0 out of 10, Exceptional, (194 reviews)
"Sean was amazingly helpful and friendly. The house itself is so well maintained, and the blue room was adorable. Loved the fact that we were within walking distance of all the shops. Would definitely recommend and will plan on staying again the next time we’re in town."
United States
Kim
The price is CA $337
CA $367 total
includes taxes & fees
Oct 20 - Oct 21
The James Place Inn B&B
A covered porch with white railings and a view of a well-maintained lawn and pathway.

5. The Kendall Inn

The Kendall Inn
3.5 star property
Freeport
9.8 out of 10, Exceptional, (162 reviews)
"The room was lovely and comfortable, including easy-to-adjust air conditioning. Breakfast was delicious as were the homemade cookies available each evening. Coffee and tea were available all the time."
United States
Kenneth and
The price is CA $269
CA $310 total
includes taxes & fees
Nov 1 - Nov 2
The Kendall Inn
A two-story house with a balcony, a front porch, and a snow-covered landscape.

6. The Nicholson Inn

The Nicholson Inn
3.0 star property
Freeport
10.0 out of 10, Exceptional, (3 reviews)
"The owners were amazing and so kind. The location is perfect, and the amenities feel so hoy and great."
United States
Meaghan
The price is CA $405
CA $441 total
includes taxes & fees
Oct 20 - Oct 21
The Nicholson Inn
A garden with a stone wall, various plants, and flowers.

7. Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast
3.0 star property
Rosemont
9.0 out of 10, Wonderful, (147 reviews)
"Breakfast was wonderful!"
United States
Karen
The price is CA $326
CA $369 total
includes taxes & fees
Oct 5 - Oct 6
Fleetwood House Bed & Breakfast
Exterior

8. West End Collection at 146 Pine

West End Collection at 146 Pine
3.0 star property
West End
9.6 out of 10, Exceptional, (100 reviews)
"This was a super cute boutique inn and the location was ideal. The staff was super friendly!"
United States
Stephanie
The price is CA $302
CA $329 total
includes taxes & fees
Nov 3 - Nov 4
West End Collection at 146 Pine
A four-poster bed with a chandelier, a bedside table with books, and a view of a brick building through the windows.

9. Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.
3.5 star property
West End
9.6 out of 10, Exceptional, (195 reviews)
"Place was charming and quirky. Very comfortable and well located."
United States
Mary
The price is CA $418
CA $455 total
includes taxes & fees
Nov 1 - Nov 2
Blind Tiger Portland - Danforth Street.
A well-lit living room with a fireplace, comfortable seating, and a large mirror.

10. Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street
3.5 star property
West End
9.6 out of 10, Exceptional, (133 reviews)
"Beautiful place"
United States
Samuel
The price is CA $393
CA $429 total
includes taxes & fees
Nov 1 - Nov 2
Blind Tiger Portland – Carleton Street
A covered patio with wicker furniture and a mosaic table, surrounded by greenery and a white building.

11. Old Orchard Beach Inn

Old Orchard Beach Inn
2.5 star property
Old Orchard Beach
8.2 out of 10, Very good, (1,005 reviews)
"Beautiful property a short walk from the beach and all the attractions make it an ideal place to stay"
United States
James
The price is CA $160
CA $196 total
includes taxes & fees
Oct 11 - Oct 12
Old Orchard Beach Inn
A kitchen with a wooden table, bench, and a fireplace.

12. Experience the History of Portland - The Hope Island Room

Experience the History of Portland - The Hope Island Room
West End
The price is CA $278
CA $334 total
includes taxes & fees
Nov 1 - Nov 2
Experience the History of Portland - The Hope Island Room
A bedroom with a large bed, a wooden wardrobe, and a bench.

13. The Diamond Island Suite - Suite in Historic Home

The Diamond Island Suite - Suite in Historic Home
West End
The price is CA $324
CA $391 total
includes taxes & fees
Nov 1 - Nov 2
The Diamond Island Suite - Suite in Historic Home
An outdoor dining setup with a table set for two, featuring candles, glassware, and a vase of flowers.

14. Experience the History of Portland - Two Room Suite w/Private Bath

Experience the History of Portland - Two Room Suite w/Private Bath
West End
The price is CA $462
CA $558 total
includes taxes & fees
Nov 1 - Nov 2
Experience the History of Portland - Two Room Suite w/Private Bath
A dining area with a round table, six chairs, and a floral centerpiece.

15. Experience the History of Portland - The Hope Island Room

Experience the History of Portland - The Hope Island Room
West End
The price is CA $371
CA $447 total
includes taxes & fees
Nov 1 - Nov 2
Experience the History of Portland - The Hope Island Room
A staircase with a wooden handrail and black steps, leading to a room with patterned wallpaper and a chandelier.

16. The Loft - private suite in historic home

The Loft - private suite in historic home
West End
The price is CA $576
CA $826 total
includes taxes & fees
Oct 4 - Oct 5
The Loft - private suite in historic home
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
"This historic hotel was perfect for a vacation to Portland! Located in a historic building, this hotel has been beautifully maintained. Rooms were very clean and large for being at the center of town. Additionally, the location of the hotel was perfect for walkability. We didn't have to take a car anywhere. The spa amenities were a nice addition that helped us recover from all that cobblestone walking. Additionally, the free shuttle service to/from the airport was an added cost savings. When I first booked this hotel, I honestly thought it was overpriced. However, after having stayed there and taken advantage of the location and amenities, I can say it is a good value for the price!"
Paula 2-night trip
Posted less than an hour ago
Portland Regency Hotel & Spa

Find out more about Chebeague Island

Chebeague Island B&B information

Number of reviews
2,349
Accommodation
24 B&B
Lowest Price
CA $139
Highest Price
CA $826

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. The Orchard House: Inn & Cafe: 5 rooms. 9.1 mi (14.7 km) from the heart of downtown.Blind Tiger Portland – Carleton Street: 6 rooms. Located 10.3 mi (16.5 km) from the core of Chebeague Island. Enjoy the unique décor and patio area.
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.

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