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Check prices for these dates

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

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 HK$1,123
HK$1,224 total
includes taxes & fees
1 Nov - 2 Nov
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 HK$1,771
HK$1,931 total
includes taxes & fees
19 Oct - 20 Oct
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, (1,129 reviews)
"Cute spot and very affordable."
United States
Tess
The price is HK$700
HK$763 total
includes taxes & fees
2 Nov - 3 Nov
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 HK$1,858
HK$2,025 total
includes taxes & fees
19 Oct - 20 Oct
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 HK$1,483
HK$1,657 total
includes taxes & fees
1 Nov - 2 Nov
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 HK$2,233
HK$2,434 total
includes taxes & fees
4 Oct - 5 Oct
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 HK$1,797
HK$2,037 total
includes taxes & fees
4 Oct - 5 Oct
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 HK$1,718
HK$1,873 total
includes taxes & fees
1 Nov - 2 Nov
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 HK$2,299
HK$2,506 total
includes taxes & fees
1 Nov - 2 Nov
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 HK$2,461
HK$2,682 total
includes taxes & fees
1 Nov - 2 Nov
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 HK$982
HK$1,188 total
includes taxes & fees
4 Oct - 5 Oct
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 HK$1,530
HK$1,839 total
includes taxes & fees
1 Nov - 2 Nov
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 HK$1,781
HK$2,164 total
includes taxes & fees
1 Nov - 2 Nov
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 HK$2,542
HK$3,087 total
includes taxes & fees
1 Nov - 2 Nov
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 HK$2,040
HK$2,480 total
includes taxes & fees
1 Nov - 2 Nov
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 HK$3,178
HK$4,575 total
includes taxes & fees
5 Oct - 6 Oct
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

Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine

8/10 Good
"The furniture in the rooms was worn down draperies need cleaning"
pya 1-night trip
Posted less than an hour ago
Embassy Suites by Hilton Portland Maine

Find out more about Chebeague Island

Chebeague Island B&B information

Number of reviews
2,345
Accommodation
30 B&B
Lowest Price
HK$763
Highest Price
HK$4,575

Frequently asked questions

Searching for B&Bs in Chebeague Island?
If you're looking for something a little quirkier than your standard hotel experience, a bed and breakfast might be the perfect option for your trip.
Why would you choose B&Bs instead of traditional hotels?
With attentive service, opportunities to interact with the owner and tasty breakfasts, B&Bs provide 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 city centre. Blind Tiger Portland – Carleton Street: 6 rooms. Located 10.3 mi (16.5 km) from the core of Chebeague Island. Enjoy the unique decor and patio area.
When is the best time to stay at a B&B in Chebeague Island?
When you're dreaming of a getaway 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 temperature of 18°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Chebeague Island are January, March, February and December, with each month seeing an average of 19 cm of snowfall.
How can I get to and around Chebeague Island?
You can plan your excursions in and around Chebeague Island ahead of time with these transportation options. Fly into Portland, ME (PWM-Portland Intl. Jetport), which is located 12.1 mi (19.4 km) away from the heart of the city. Otherwise, you can search for flights to 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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