A wooden pier leading to a marina with boats docked.

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Check prices for these dates

Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11
In one month
Oct 23 - Oct 25
In two months
Nov 20 - Nov 22

Our top choices for Chebeague Island bed & breakfast

A multi-story building with a stone facade, multiple windows, and awnings.

1. 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, (1,122 reviews)
"Great place to stay, affordable,clean with walking access to to port area!"
United States
Steve Robert
$144 nightly
The price is $157
Sep 28 - Sep 29
Total with taxes and fees
Inn at St John Portland In-Town
A white building with a red roof, a sign indicating a vacancy at Candlebay Inn, and an American flag.

2. Candlebay Inn

Candlebay Inn
3.0 star property
Freeport
9.6 out of 10, Exceptional, (489 reviews)
"Great location, quiet room, great breakfast......"
United States
Keith
$194 nightly
The price is $211
Sep 28 - Sep 29
Total with taxes and fees
Candlebay Inn
A house with a sign for The James Place Inn, indicating a vacancy.

3. The James Place Inn B&B

The James Place Inn B&B
3.5 star property
Freeport
10.0 out of 10, Exceptional, (193 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
$228 nightly
The price is $249
Oct 5 - Oct 6
Total with taxes and fees
The James Place Inn B&B
A black front door with a light fixture above it, flanked by two potted evergreen trees.

4. 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
$217 nightly
The price is $236
Sep 22 - Sep 23
Total with taxes and fees
The Orchard House: Inn & Cafe
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
$232 nightly
The price is $253
Sep 30 - Oct 1
Total with taxes and fees
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, (2 reviews)
"The owners were amazing and so kind. The location is perfect, and the amenities feel so hoy and great."
United States
Meaghan
$288 nightly
The price is $314
Oct 22 - Oct 23
Total with taxes and fees
The Nicholson Inn

7. West End Collection at 146 Pine

West End Collection at 146 Pine
3.0 star property
West End
9.6 out of 10, Exceptional, (98 reviews)
"It was wonderful staying. Beautiful old house with all amenities and"
United States
Svetlana
$330 nightly
The price is $360
Oct 13 - Oct 14
Total with taxes and fees
West End Collection at 146 Pine
A garden with a stone wall, various plants, and flowers.

8. 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
$238 nightly
The price is $260
Sep 22 - Sep 23
Total with taxes and fees
Fleetwood House Bed & Breakfast
A well-lit living room with a fireplace, comfortable seating, and a large mirror.

9. Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street
3.5 star property
West End
9.6 out of 10, Exceptional, (132 reviews)
"Beautiful place"
United States
Samuel
$338 nightly
The price is $368
Sep 22 - Sep 23
Total with taxes and fees
Blind Tiger Portland – Carleton Street
A spacious living room with a brown leather sofa, beige armchairs, and a round coffee table.

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

Experience the History of Portland - The Hope Island Room
West End
$293 nightly
The price is $319
Sep 27 - Sep 28
Total with taxes and fees
Experience the History of Portland - The Hope Island Room
A four-poster bed with a chandelier, a bedside table with books, and a view of a brick building through the windows.

11. Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.
3.5 star property
West End
9.6 out of 10, Exceptional, (193 reviews)
"Place was charming and quirky. Very comfortable and well located."
United States
Mary
$546 nightly
The price is $595
Sep 23 - Sep 24
Total with taxes and fees
Blind Tiger Portland - Danforth Street.
A living room with a fireplace, leather sofa, and a chandelier.

12. The Diamond Island Suite - Suite in Historic Home

The Diamond Island Suite - Suite in Historic Home
West End
$361 nightly
The price is $393
Sep 27 - Sep 28
Total with taxes and fees
The Diamond Island Suite - Suite in Historic Home
A living room with a fireplace, leather sofa, and a chandelier.

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

Experience the History of Portland - Two Room Suite w/Private Bath
West End
$452 nightly
The price is $493
Sep 27 - Sep 28
Total with taxes and fees
Experience the History of Portland - Two Room Suite w/Private Bath
A dining area with a round table, six chairs, and a floral centerpiece.

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

Experience the History of Portland - The Hope Island Room
West End
$391 nightly
The price is $426
Sep 27 - Sep 28
Total with taxes and fees
Experience the History of Portland - The Hope Island Room
A patio with outdoor furniture, a brick building, and a garden with shrubs and flowers.

15. The Loft - private suite in historic home

The Loft - private suite in historic home
West End
$535 nightly
The price is $583
Sep 22 - Sep 23
Total with taxes and fees
The Loft - private suite in historic home
A covered patio with wicker furniture and a mosaic table, surrounded by greenery and a white building.

16. Old Orchard Beach Inn

Old Orchard Beach Inn
2.5 star property
Old Orchard Beach
8.2 out of 10, Very good, (1,008 reviews)
"Beautiful property a short walk from the beach and all the attractions make it an ideal place to stay"
United States
James
$136 nightly
The price is $148
Sep 22 - Sep 23
Total with taxes and fees
Old Orchard Beach 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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Top Chebeague Island Hotel Reviews

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

10/10 Excellent
"We had a great stay. The room was clean and comfortable."
Destalia 1-night trip
Posted less than an hour ago
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Find out more about Chebeague Island

Chebeague Island B&B information

Number of reviews
2,603
Accommodation
24 B&B
Lowest Price
$148
Highest Price
$595

Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Chebeague Island?
Prices for B&Bs in Chebeague Island often vary, but you can find a great deal from $148 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Chebeague Island B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed and Breakfast in Chebeague Island?
The best time to book a B&B in Chebeague Island is during the summer months, particularly from June to August. This vibrant season draws visitors eager to enjoy the island's stunning coastal scenery, partake in water activities, and bask in the warm weather, with temperatures typically ranging from the mid-60s to low 80s Fahrenheit.

July stands out as the peak month, where the island comes alive with festivals, outdoor concerts, and bustling local markets. It's an ideal time for families and couples looking to soak in the lively atmosphere, as well as explore the picturesque beaches and charming walking trails that showcase the island's natural beauty.

For those seeking a more tranquil experience, consider visiting in September. During this time, you can still enjoy pleasant weather, along with the added bonus of fewer crowds. The summer bustle gives way to a quieter charm, allowing for leisurely walks along the shoreline and peaceful moments watching the sunset.
What is the difference between a Chebeague Island Bed & Breakfast and a hotel?
Every Chebeague Island B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Chebeague Island B&Bs.

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