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 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
$194 nightly
The price is $211
Sep 28 - Sep 29
Total with taxes and fees
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
$226 nightly
The price is $246
Sep 27 - Sep 28
Total with taxes and fees
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, (1,141 reviews)
"Cute spot and very affordable."
United States
Tess
$127 nightly
The price is $138
Sep 28 - Sep 29
Total with taxes and fees
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, (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 two-story house with a balcony, a front porch, and a snow-covered landscape.

5. 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
$291 nightly
The price is $317
Oct 4 - Oct 5
Total with taxes and fees
The Nicholson Inn
A covered porch with white railings and a view of a well-maintained lawn and pathway.

6. 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
$258 nightly
The price is $288
Sep 27 - Sep 28
Total with taxes and fees
The Kendall 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
$238 nightly
The price is $260
Sep 28 - Sep 29
Total with taxes and fees
Fleetwood House Bed & Breakfast

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, (99 reviews)
"Lovely property"
United States
Mary
$302 nightly
The price is $329
Oct 26 - Oct 27
Total with taxes and fees
West End Collection at 146 Pine
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
$324 nightly
The price is $353
Oct 26 - Oct 27
Total with taxes and fees
Blind Tiger Portland – Carleton Street
A kitchen with a wooden table, bench, and a fireplace.

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

Experience the History of Portland - The Hope Island Room
West End
$263 nightly
The price is $287
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
$528 nightly
The price is $576
Oct 26 - Oct 27
Total with taxes and fees
Blind Tiger Portland - Danforth Street.
A bedroom with a large bed, a wooden wardrobe, and a bench.

12. The Diamond Island Suite - Suite in Historic Home

The Diamond Island Suite - Suite in Historic Home
West End
$317 nightly
The price is $346
Sep 27 - Sep 28
Total with taxes and fees
The Diamond Island Suite - Suite in Historic Home
A dining area with a round table, six chairs, and a floral centerpiece.

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

Experience the History of Portland - The Hope Island Room
West End
$371 nightly
The price is $404
Sep 27 - Sep 28
Total with taxes and fees
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.

14. The Loft - private suite in historic home

The Loft - private suite in historic home
West End
$535 nightly
The price is $583
Sep 29 - Sep 30
Total with taxes and fees
The Loft - private suite in historic home
An outdoor dining setup with a table set for two, featuring candles, glassware, and a vase of flowers.

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

Experience the History of Portland - Two Room Suite w/Private Bath
West End
$400 nightly
The price is $436
Sep 27 - Sep 28
Total with taxes and fees
Experience the History of Portland - Two Room Suite w/Private Bath
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, (1,003 reviews)
"Beautiful property a short walk from the beach and all the attractions make it an ideal place to stay"
United States
James
$129 nightly
The price is $141
Sep 29 - Sep 30
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

Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

10/10 Excellent
"The room was spacious. We asked for a view and received a room with a water view."
Debra 2-night trip
Posted 10 hours ago
Hampton Inn Portland Downtown - Waterfront

Find out more about Chebeague Island

Chebeague Island B&B information

Number of reviews
2,737
Accommodation
24 B&B
Lowest Price
$138
Highest Price
$583

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 $138 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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