A wooden pier leading to a marina with boats docked.

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Our top choices for Chebeague Island bed & breakfast

1. West End Collection at 146 Pine

West End Collection at 146 Pine
3.0 star property
West End
9.6 out of 10, Exceptional, (96 reviews)
"Wonderful staff and scrumptious breakfast "
United States
Elena
$219 nightly
The price is $239
Aug 30 - Aug 31
Total with taxes and fees
West End Collection at 146 Pine

2. Candlebay Inn

Candlebay Inn
3.0 star property
Freeport
9.6 out of 10, Exceptional, (482 reviews)
"Great location, quiet room, great breakfast......"
United States
Keith
$173 nightly
The price is $188
Aug 24 - Aug 25
Total with taxes and fees
Candlebay Inn

3. The Orchard House: Inn & Cafe

The Orchard House: Inn & Cafe
3.0 star property
Freeport
9.6 out of 10, Exceptional, (178 reviews)
"Amazing stay in a perfect location! Would absolutely recommend to family and friends and will likely stay again!"
United States
Megan
$212 nightly
The price is $231
Sep 3 - Sep 4
Total with taxes and fees
The Orchard House: Inn & Cafe

4. The Kendall Inn

The Kendall Inn
3.5 star property
Freeport
9.8 out of 10, Exceptional, (159 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
$219 nightly
The price is $239
Sep 1 - Sep 2
Total with taxes and fees
The Kendall Inn

5. 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)
"Room was clean, bed was comfortable, staff were helpful. Would stay here again!"
United States
Caleb
$167 nightly
The price is $182
Aug 24 - Aug 25
Total with taxes and fees
Inn at St John Portland In-Town

6. The Nicholson Inn

The Nicholson Inn
3.0 star property
Freeport
10.0 out of 10, Exceptional, (1 review)
"The owners were amazing and so kind. The location is perfect, and the amenities feel so hoy and great."
United States
Meaghan
$298 nightly
The price is $325
Sep 3 - Sep 4
Total with taxes and fees
The Nicholson Inn

7. The James Place Inn B&B

The James Place Inn B&B
3.5 star property
Freeport
10.0 out of 10, Exceptional, (188 reviews)
"Fabulous hosts, beautiful property, excellent breakfast, walking distance to the main street of Freeport but still quiet. Highly recommend!"
United States
Carol
$304 nightly
The price is $331
Sep 6 - Sep 7
Total with taxes and fees
The James Place Inn B&B

8. Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast
3.0 star property
Rosemont
9.0 out of 10, Wonderful, (142 reviews)
"Breakfast was wonderful!"
United States
Karen
$238 nightly
The price is $260
Aug 24 - Aug 25
Total with taxes and fees
Fleetwood House Bed & Breakfast

9. Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street
3.5 star property
West End
9.6 out of 10, Exceptional, (129 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
$297 nightly
The price is $324
Sep 1 - Sep 2
Total with taxes and fees
Blind Tiger Portland – Carleton Street

10. Old Orchard Beach Inn

Old Orchard Beach Inn
2.5 star property
Old Orchard Beach
8.2 out of 10, Very Good, (1,016 reviews)
"This place was amazing. The staff were so friendly and the breakfast was delicious!"
United States
Samantha
$128 nightly
The price is $139
Aug 30 - Aug 31
Total with taxes and fees
Old Orchard Beach Inn

11. Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.
3.5 star property
West End
9.6 out of 10, Exceptional, (190 reviews)
"The place was totally amazing."
United States
Gary
$450 nightly
The price is $491
Sep 1 - Sep 2
Total with taxes and fees
Blind Tiger Portland - Danforth Street.

12. Charming Top-Floor Queen Room with Sloped Ceilings, Walk to the Beach

Charming Top-Floor Queen Room with Sloped Ceilings, Walk to the Beach
Old Orchard Beach
10.0 out of 10, Exceptional, (1 review)
"Definitely worth a visit! Beach just down the road!"
United States
Matt S.
$203 nightly
The price is $222
Sep 18 - Sep 19
Total with taxes and fees
Charming Top-Floor Queen Room with Sloped Ceilings, Walk to the Beach

13. Bright Character Studio Near the Beach with Outdoor Seating & Parking

Bright Character Studio Near the Beach with Outdoor Seating & Parking
Old Orchard Beach
8.0 out of 10, Very Good, (1 review)
"served its purpose as between residences; nice place with all necessities; time of year issue was not enough heat; host attentive to any questions"
United States
Beth W.
$238 nightly
The price is $259
Aug 28 - Aug 29
Total with taxes and fees
Bright Character Studio Near the Beach with Outdoor Seating & Parking
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

Find out more about Chebeague Island

Chebeague Island B&B information

Number of reviews
2,276
Accommodation
24 B&B
Lowest Price
$139
Highest Price
$491

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 $139 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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