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Our top choices for Chebeague Island bed & breakfast

1. The Orchard House: Inn & Cafe
The Orchard House: Inn & CafeFreeport
9.6 out of 10, Exceptional, (185 reviews)
$139 nightly
The price is $152
Dec 1 - Dec 2
Total with taxes and fees

2. Candlebay Inn
Candlebay InnFreeport
9.6 out of 10, Exceptional, (500 reviews)
$159 nightly
The price is $173
Nov 12 - Nov 13
Total with taxes and fees

3. Inn at St John Portland In-Town
Inn at St John Portland In-TownValley Street
8.6 out of 10, Excellent, (1,179 reviews)
$83 nightly
The price is $90
Nov 22 - Nov 23
Total with taxes and fees

4. The Kendall Inn
The Kendall InnFreeport
9.8 out of 10, Exceptional, (170 reviews)
$210 nightly
The price is $229
Nov 12 - Nov 13
Total with taxes and fees

5. The Nicholson Inn
The Nicholson InnFreeport
10.0 out of 10, Exceptional, (5 reviews)
$233 nightly
The price is $254
Nov 19 - Nov 20
Total with taxes and fees

6. The James Place Inn B&B
The James Place Inn B&BFreeport
10.0 out of 10, Exceptional, (196 reviews)
$251 nightly
The price is $273
Nov 12 - Nov 13
Total with taxes and fees

7. Blind Tiger Portland – Carleton Street
Blind Tiger Portland – Carleton StreetWest End
9.6 out of 10, Exceptional, (137 reviews)
$146 nightly
The price is $159
Nov 30 - Dec 1
Total with taxes and fees

8. Blind Tiger Portland - Danforth Street.
Blind Tiger Portland - Danforth Street.West End
9.6 out of 10, Exceptional, (206 reviews)
$244 nightly
The price is $266
Nov 16 - Nov 17
Total with taxes and fees

9. Fleetwood House Bed & Breakfast
Fleetwood House Bed & BreakfastRosemont
9.0 out of 10, Wonderful, (150 reviews)
$238 nightly
The price is $260
Nov 12 - Nov 13
Total with taxes and fees

10. West End Collection at 146 Pine
West End Collection at 146 PineWest End
9.6 out of 10, Exceptional, (101 reviews)
$216 nightly
The price is $235
Nov 30 - Dec 1
Total with taxes and fees

11. Experience the History of Portland - The Hope Island Room
Experience the History of Portland - The Hope Island RoomWest End
10.0 out of 10, Exceptional, (1 review)
$192 nightly
The price is $209
Nov 16 - Nov 17
Total with taxes and fees

12. Benjamin F. Packard House
Benjamin F. Packard HouseBath
10.0 out of 10, Exceptional, (118 reviews)
$204 nightly
The price is $222
Nov 13 - Nov 14
Total with taxes and fees

13. Old Orchard Beach Inn
Old Orchard Beach InnOld Orchard Beach
8.2 out of 10, Very good, (1,000 reviews)
$137 nightly
The price is $150
Nov 21 - Nov 22
Total with taxes and fees

14. Diamond Island | King Room with Private Ensuite
Diamond Island | King Room with Private EnsuiteWest End
$221 nightly
The price is $241
Nov 15 - Nov 16
Total with taxes and fees

15. Experience the History of Portland - The Hope Island Room
Experience the History of Portland - The Hope Island RoomWest End
$255 nightly
The price is $278
Nov 16 - Nov 17
Total with taxes and fees

16. Experience the History of Portland - Two Room Suite w/Private Bath
Experience the History of Portland - Two Room Suite w/Private BathWest End
$308 nightly
The price is $336
Nov 15 - Nov 16
Total with taxes and fees

17. The Loft - private suite in historic home
The Loft - private suite in historic homeWest End
$426 nightly
The price is $464
Nov 15 - Nov 16
Total with taxes and fees
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.
Learn more about Chebeague Island
Rent bikes to explore this peaceful island's rocky beaches and historic 1920s inn, where fresh lobster awaits. Take the passenger ferry from Cousins Island for a day trip, then kayak along the quiet coastline or hike wooded trails.




















































