Book Chebeague Island Bed & Breakfast

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4
In one month
Jan 16 - Jan 18
In two months
Feb 13 - Feb 15

Our top choices for Chebeague Island bed & breakfast

Front of property - evening/night
Inn at St John Portland In-Town

Inn at St John Portland In-Town

Inn at St John Portland In-Town
2.5 star property
Valley Street
8.8 out of 10, Excellent, (1142)
"Friendly helpful staff and a nice independent location "
United States
Robert
$80 nightly
The price is $87
Dec 21 - Dec 22
Total with taxes and fees
Inn at St John Portland In-Town
Exterior
Old Orchard Beach Inn

Old Orchard Beach Inn

Old Orchard Beach Inn
2.5 star property
Old Orchard Beach
8.2 out of 10, Very Good, (1001)
"A beautiful place to stay!!! First time at a B&B and it did not disappoint."
United States
Kristian
$109 nightly
The price is $119
Dec 20 - Dec 21
Total with taxes and fees
Old Orchard Beach Inn
Garden
Brewster House Bed & Breakfast

Brewster House Bed & Breakfast

Brewster House Bed & Breakfast
4.0 star property
Freeport
9.8 out of 10, Exceptional, (114)
"The food was wonderful and the hospitality was great!"
United States
Olivia
$167 nightly
The price is $182
Jan 4 - Jan 5, 2026
Total with taxes and fees
Brewster House Bed & Breakfast
Front of property
And. N B&B

And. N B&B

And. N B&B
3.0 star property
Gray
9.8 out of 10, Exceptional, (77)
"Really lovely place and great hospitality from the owners!"
United States
Hunter
$103 nightly
The price is $113
Jan 3 - Jan 4, 2026
Total with taxes and fees
And. N B&B
Baxter | Premium bedding, individually decorated, individually furnished
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.
3.5 star property
West End
9.6 out of 10, Exceptional, (167)
"The property is beautiful, the staff is kind, and the rooms are spacious and clean. It was great to have a safe place to park the car while having so many things to do within walking distance. Being able to grab a quick breakfast before heading out was great too! We loved our stay here!"
United States
Darby
$206 nightly
The price is $225
Jan 4 - Jan 5, 2026
Total with taxes and fees
Blind Tiger Portland - Danforth Street.
Stovall | Living area
Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street
3.5 star property
West End
9.6 out of 10, Exceptional, (120)
"Loved the place "
United States
Stephen
$171 nightly
The price is $186
Jan 4 - Jan 5, 2026
Total with taxes and fees
Blind Tiger Portland – Carleton Street
Exterior
The Kendall Inn

The Kendall Inn

The Kendall Inn
3.5 star property
Freeport
9.8 out of 10, Exceptional, (145)
"Quaint stay. Enjoyed our stay. "
United States
Linda
$167 nightly
The price is $182
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Kendall Inn
Porch
Candlebay Inn

Candlebay Inn

Candlebay Inn
3.0 star property
Freeport
9.6 out of 10, Exceptional, (460)
"The Candlebay Inn was a great stay! Staff was wonderful and the place was super cute and clean. "
United States
Paige
$154 nightly
The price is $168
Dec 20 - Dec 21
Total with taxes and fees
Candlebay Inn
Property entrance
Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast
3.0 star property
Rosemont
9.0 out of 10, Wonderful, (132)
"Lovely, comfortable stay! So welcoming and accommodating. We only stayed one night but will keep this in mind next time we are in the area :)"
United States
Sadie
$229 nightly
The price is $250
Dec 20 - Dec 21
Total with taxes and fees
Fleetwood House Bed & Breakfast
Outdoor dining
The James Place Inn B&B

The James Place Inn B&B

The James Place Inn B&B
3.5 star property
Freeport
10.0 out of 10, Exceptional, (182)
"Wish we could have stayed longer. It has the ambiance of an older inn but the rooms are very clean and well maintained. "
United States
Melissa
$218 nightly
The price is $238
Dec 27 - Dec 28
Total with taxes and fees
The James Place Inn B&B
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chebeague Island Hotel Reviews

Portland Harbor Hotel

Portland Harbor Hotel

10/10 Excellent
"The staff were amazing, the room was clean, and the valet parking was hassle free. "
Renee 2-night trip
Posted 2 days ago
Portland Harbor Hotel

Find out more about Chebeague Island

Chebeague Island B&B information

Number of reviews
3,493
Accommodation
24 B&B
Lowest Price
$87
Highest Price
$250

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 $87 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.

Explore a world of travel with Expedia