A wooden pier leading to a marina with boats docked.

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Check prices for these dates

Next weekend
Sep 25 - Sep 27
In two weeks
Oct 2 - Oct 4
In one month
Oct 16 - Oct 18
In two months
Nov 13 - Nov 15

Our top choices for Chebeague Island bed & breakfast

Porch

1. Candlebay Inn

Candlebay Inn
3.0 star property
Freeport
9.6 out of 10, Exceptional, (488 reviews)
"Great location, quiet room, great breakfast......"
United States
Keith
$194 nightly
The price is $211
Sep 20 - Sep 21
Total with taxes and fees
Candlebay Inn
Front of property - evening/night

2. The Orchard House: Inn & Cafe

The Orchard House: Inn & Cafe
3.0 star property
Freeport
9.6 out of 10, Exceptional, (179 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 17 - Sep 18
Total with taxes and fees
The Orchard House: Inn & Cafe
Front of property

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
Sep 20 - Sep 21
Total with taxes and fees
The James Place Inn B&B
Front of property - evening/night

4. 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, (1,124 reviews)
"Great place to stay, affordable,clean with walking access to to port area!"
United States
Steve Robert
$152 nightly
The price is $166
Sep 20 - Sep 21
Total with taxes and fees
Inn at St John Portland In-Town
Interior entrance

5. The Kendall Inn

The Kendall Inn
3.5 star property
Freeport
9.8 out of 10, Exceptional, (160 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
$222 nightly
The price is $248
Sep 17 - Sep 18
Total with taxes and fees
The Kendall Inn
Front of property

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
$316 nightly
The price is $345
Sep 28 - Sep 29
Total with taxes and fees
The Nicholson Inn
Exterior

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, (97 reviews)
"It was wonderful staying. Beautiful old house with all amenities and"
United States
Svetlana
$269 nightly
The price is $293
Sep 30 - Oct 1
Total with taxes and fees
West End Collection at 146 Pine
Exterior detail

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 17 - Sep 18
Total with taxes and fees
Fleetwood House Bed & Breakfast
Books

9. Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street
3.5 star property
West End
9.6 out of 10, Exceptional, (130 reviews)
"Beautiful place to stay in the middle of a quiet street and walking distance to many spots. The rooms and common areas were clean and beautifully maintained. Staff was ready to answer any questions you had via phone or text. I loved this inn and would choose it again. Definitely recommend it !"
United States
Adriana Cecilia
$309 nightly
The price is $336
Oct 1 - Oct 2
Total with taxes and fees
Blind Tiger Portland – Carleton Street
Fireplace, offices

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

Experience the History of Portland - The Hope Island Room
West End
$264 nightly
The price is $288
Sep 20 - Sep 21
Total with taxes and fees
Experience the History of Portland - The Hope Island Room
Baxter | Premium bedding, iron/ironing board, WiFi (free), individually decorated

11. Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.
3.5 star property
West End
9.6 out of 10, Exceptional, (192 reviews)
"Enjoyable"
Canada
Lawrence
$491 nightly
The price is $536
Sep 27 - Sep 28
Total with taxes and fees
Blind Tiger Portland - Danforth Street.
Fireplace, offices

12. The Diamond Island Suite - Suite in Historic Home

The Diamond Island Suite - Suite in Historic Home
West End
$331 nightly
The price is $361
Sep 20 - Sep 21
Total with taxes and fees
The Diamond Island Suite - Suite in Historic Home
Dining

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

Experience the History of Portland - The Hope Island Room
West End
$361 nightly
The price is $393
Sep 20 - Sep 21
Total with taxes and fees
Experience the History of Portland - The Hope Island Room
Exterior

14. Old Orchard Beach Inn

Old Orchard Beach Inn
2.5 star property
Old Orchard Beach
8.2 out of 10, Very good, (1,001 reviews)
"Beautiful property a short walk from the beach and all the attractions make it an ideal place to stay"
United States
James
$137 nightly
The price is $150
Oct 17 - Oct 18
Total with taxes and fees
Old Orchard Beach Inn
TV, fireplace, offices

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
$452 nightly
The price is $493
Sep 20 - Sep 21
Total with taxes and fees
Experience the History of Portland - Two Room Suite w/Private Bath
Outdoor dining

16. The Loft - private suite in historic home

The Loft - private suite in historic home
West End
$557 nightly
The price is $607
Sep 20 - Sep 21
Total with taxes and fees
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 Harbor Hotel

Portland Harbor Hotel

10/10 Excellent
"Everything"
Diane 1-night trip
Posted 1 hour ago
Portland Harbor Hotel

Find out more about Chebeague Island

Chebeague Island B&B information

Number of reviews
2,401
Accommodation
24 B&B
Lowest Price
$150
Highest Price
$607

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 $150 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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