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Book Chebeague Island Bed & Breakfast

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Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1
In one month
Nov 13 - Nov 15
In two months
Dec 11 - Dec 13

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, (497 reviews)
"Great stay in a historic home."
United States
Richard
$159 nightly
The price is $173
Nov 1 - Nov 2
Total with taxes and fees
Candlebay Inn
A multi-story building with a stone facade, multiple windows, and awnings.

2. 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, (1,161 reviews)
"We love to stay at historic places when we travel, and we were not disappointed with this one! So cute and cozy!"
United States
Vicki
$89 nightly
The price is $97
Nov 1 - Nov 2
Total with taxes and fees
Inn at St John Portland In-Town
A covered porch with white railings and a view of a well-maintained lawn and pathway.

3. The Kendall Inn

The Kendall Inn
3.5 star property
Freeport
9.8 out of 10, Exceptional, (164 reviews)
"I really enjoyed The Kendall Inn. Elegant and comfortable, super clean rooms, friendly staff and delicious breakfasts (and home baked cookies in the evening). Definitely would love to stay there again"
United States
Katherine
$193 nightly
The price is $211
Nov 17 - Nov 18
Total with taxes and fees
The Kendall Inn
A black front door with a light fixture above it, flanked by two potted evergreen trees.

4. The Orchard House: Inn & Cafe

The Orchard House: Inn & Cafe
3.0 star property
Freeport
9.6 out of 10, Exceptional, (184 reviews)
"Great place"
United States
Mark
$226 nightly
The price is $246
Oct 19 - Oct 20
Total with taxes and fees
The Orchard House: Inn & Cafe
A house with a sign for The James Place Inn, indicating a vacancy.

5. The James Place Inn B&B

The James Place Inn B&B
3.5 star property
Freeport
10.0 out of 10, Exceptional, (196 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
$251 nightly
The price is $273
Nov 9 - Nov 10
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.

6. The Nicholson Inn

The Nicholson Inn
3.0 star property
Freeport
10.0 out of 10, Exceptional, (4 reviews)
"We had a fantastic and lovely, although quick, stay. The Inn is very charming and John and Loretta are so kind and helpful. Would love to go back and stay with them again.."
United States
alexandre
$246 nightly
The price is $268
Nov 16 - Nov 17
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, (100 reviews)
"This was a super cute boutique inn and the location was ideal. The staff was super friendly!"
United States
Stephanie
$212 nightly
The price is $231
Nov 1 - Nov 2
Total with taxes and fees
West End Collection at 146 Pine
A garden with a stone wall, various plants, and flowers.

8. Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast
3.0 star property
Rosemont
9.0 out of 10, Wonderful, (148 reviews)
"Breakfast was wonderful!"
United States
Karen
$238 nightly
The price is $260
Oct 19 - Oct 20
Total with taxes and fees
Fleetwood House Bed & Breakfast
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, (136 reviews)
"Fantastic property, full of character in a great location. Walkable location, we will be back next time we are in Portland."
United States
Ryan
$208 nightly
The price is $227
Nov 17 - Nov 18
Total with taxes and fees
Blind Tiger Portland – Carleton Street
A four-poster bed with a chandelier, a bedside table with books, and a view of a brick building through the windows.

10. Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.
3.5 star property
West End
9.6 out of 10, Exceptional, (199 reviews)
"Place was charming and quirky. Very comfortable and well located."
United States
Mary
$258 nightly
The price is $281
Nov 11 - Nov 12
Total with taxes and fees
Blind Tiger Portland - Danforth Street.
A kitchen with a wooden table, bench, and a fireplace.

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

Experience the History of Portland - The Hope Island Room
West End
10.0 out of 10, Exceptional, (1 review)
"Really cool home and room was big and clean!"
United States
Daniel
$208 nightly
The price is $227
Nov 3 - Nov 4
Total with taxes and fees
Experience the History of Portland - The Hope Island Room
An outdoor patio with a covered seating area, a brick pathway, and potted plants.

12. Benjamin F. Packard House

Benjamin F. Packard House
3.0 star property
Bath
10.0 out of 10, Exceptional, (117 reviews)
"This is a wonderful bed and breakfast! I highly recommend and I would stay here again and again!"
United States
Tina
$197 nightly
The price is $215
Nov 1 - Nov 2
Total with taxes and fees
Benjamin F. Packard House
A covered patio with wicker furniture and a mosaic table, surrounded by greenery and a white building.

13. Old Orchard Beach Inn

Old Orchard Beach Inn
2.5 star property
Old Orchard Beach
8.2 out of 10, Very good, (1,005 reviews)
"Really nice hotel"
United States
James
$136 nightly
The price is $148
Nov 9 - Nov 10
Total with taxes and fees
Old Orchard Beach Inn
A bedroom with a large bed, a wooden wardrobe, and a bench.

14. The Diamond Island Suite - Suite in Historic Home

The Diamond Island Suite - Suite in Historic Home
West End
$253 nightly
The price is $276
Nov 1 - Nov 2
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.

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

Experience the History of Portland - The Hope Island Room
West End
$266 nightly
The price is $290
Oct 27 - Oct 28
Total with taxes and fees
Experience the History of Portland - The Hope Island Room
An outdoor dining setup with a table set for two, featuring candles, glassware, and a vase of flowers.

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

Experience the History of Portland - Two Room Suite w/Private Bath
West End
$361 nightly
The price is $393
Nov 1 - Nov 2
Total with taxes and fees
Experience the History of Portland - Two Room Suite w/Private Bath
A staircase with a wooden handrail and black steps, leading to a room with patterned wallpaper and a chandelier.

17. The Loft - private suite in historic home

The Loft - private suite in historic home
West End
$445 nightly
The price is $485
Nov 8 - Nov 9
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

Clarion Pointe South Portland

Clarion Pointe South Portland

8/10 Good
"The price was very reasonable for the season and compared to other hotels in the area."
Karen 1-night trip
Posted 3 hours ago
Clarion Pointe South Portland

Find out more about Chebeague Island

Chebeague Island B&B information

Number of reviews
2,963
Accommodation
30 B&B
Lowest Price
$97
Highest Price
$485

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 $97 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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