A rocky shoreline with a boat, a house, and a forest in the background.

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  • Upfront pricing

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

Check prices for these dates

Next weekend
Nov 6 - Nov 8
In two weeks
Nov 13 - Nov 15
In one month
Nov 27 - Nov 29
In two months
Dec 25 - Dec 27

Our top choices for Bailey 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 black front door with a light fixture above it, flanked by two potted evergreen trees.

2. 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
$187 nightly
The price is $204
Nov 4 - Nov 5
Total with taxes and fees
The Orchard House: Inn & Cafe
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, (166 reviews)
"The breakfasts were so tasty! The Inn is so charming! We loved our stay and hope to return next year!"
United States
Justin Terry
$193 nightly
The price is $211
Nov 27 - Nov 28
Total with taxes and fees
The Kendall Inn
A multi-story building with a stone facade, multiple windows, and awnings.

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, (1,171 reviews)
"Great location . Staff was awesome"
United States
Shad
$98 nightly
The price is $107
Nov 4 - Nov 5
Total with taxes and fees
Inn at St John Portland In-Town
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, (5 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
$255 nightly
The price is $278
Nov 4 - Nov 5
Total with taxes and fees
The Nicholson Inn
An outdoor patio with a covered seating area, a brick pathway, and potted plants.

7. 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
$220 nightly
The price is $240
Nov 3 - Nov 4
Total with taxes and fees
Benjamin F. Packard House
A well-lit living room with a fireplace, comfortable seating, and a large mirror.

8. Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street
3.5 star property
West End
9.6 out of 10, Exceptional, (137 reviews)
"Beautiful place"
United States
Samuel
$207 nightly
The price is $226
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.

9. Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.
3.5 star property
West End
9.6 out of 10, Exceptional, (201 reviews)
"Place was charming and quirky. Very comfortable and well located."
United States
Mary
$244 nightly
The price is $266
Nov 8 - Nov 9
Total with taxes and fees
Blind Tiger Portland - Danforth Street.
A balcony with two wooden chairs and a small table, overlooking a body of water with houses in the background.

10. Harborage Inn on the Oceanfront

Harborage Inn on the Oceanfront
3.5 star property
Boothbay Harbor
9.6 out of 10, Exceptional, (241 reviews)
"This little place was excellent! Great views, very convenient to walk everywhere. The morning breakfasts were delicious! Would definitely stay again!"
United States
Michele
$188 nightly
The price is $205
Oct 28 - Oct 29
Total with taxes and fees
Harborage Inn on the Oceanfront
Exterior

11. 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
$219 nightly
The price is $239
Nov 1 - Nov 2
Total with taxes and fees
West End Collection at 146 Pine
A two-story house with a porch and a sign reading "Fleetwork House."

12. Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast
3.0 star property
Rosemont
9.0 out of 10, Wonderful, (149 reviews)
"Breakfast was wonderful!"
United States
Karen
$238 nightly
The price is $260
Oct 28 - Oct 29
Total with taxes and fees
Fleetwood House Bed & Breakfast
A two-story house with a stone staircase leading to a front door, surrounded by a garden with potted plants and a seating area with chairs.

13. 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
$189 nightly
The price is $206
Nov 1 - Nov 2
Total with taxes and fees
Experience the History of Portland - The Hope Island Room
A large house with multiple sections, surrounded by lush greenery and trees.

14. The Squire Tarbox Inn

The Squire Tarbox Inn
2.5 star property
Wiscasset
9.6 out of 10, Exceptional, (23 reviews)
"Lovely spot."
United States
Oona
$334 nightly
The price is $361
Oct 30 - Oct 31
Total with taxes and fees
The Squire Tarbox Inn
A serene lakeside setting with two rocking chairs, a fire pit, and a view of boats on the water.

15. The Snug: Cozy Ground-Floor Queen at Admiral's Quarters, Boothbay Harbor

The Snug: Cozy Ground-Floor Queen at Admiral's Quarters, Boothbay Harbor
Boothbay Harbor
10.0 out of 10, Exceptional, (6 reviews)
"Our host, Jersey, was awesome. He goes out of his way to satisfy his customers. Can't say enough good things about the property!"
United States
Robert
$245 nightly
The price is $267
Oct 28 - Oct 29
Total with taxes and fees
The Snug: Cozy Ground-Floor Queen at Admiral's Quarters, Boothbay Harbor
A serene lakeside setting with two rocking chairs facing a calm body of water, a fire pit in the center, and a clear view of boats and distant land.

16. Your Own Deck Over the Harbor: Second-Floor King at Greenleaf Inn, Boothbay

Your Own Deck Over the Harbor: Second-Floor King at Greenleaf Inn, Boothbay
Boothbay Harbor
8.0 out of 10, Very good, (1 review)
$301 nightly
The price is $328
Oct 28 - Oct 29
Total with taxes and fees
Your Own Deck Over the Harbor: Second-Floor King at Greenleaf Inn, Boothbay
A wooden deck with three chairs and a table, overlooking a marina with boats and a lighthouse.

17. Ground-Level King with a Harbor-View Deck, Greenleaf Inn, Boothbay Harbor

Ground-Level King with a Harbor-View Deck, Greenleaf Inn, Boothbay Harbor
Boothbay Harbor
10.0 out of 10, Exceptional, (2 reviews)
"Jersey gave us a tour of the property, got us a reservation for dinner and made us feel right at home! 10/10 we will absolutely be here booking again. Clean room, comfy bed, couldn’t ask for a better stay."
United States
Kaitlyn H.
$288 nightly
The price is $314
Oct 28 - Oct 29
Total with taxes and fees
Ground-Level King with a Harbor-View Deck, Greenleaf Inn, Boothbay Harbor
A deck with three chairs and a table, overlooking a marina with boats and a lighthouse.

18. Second-Floor King Suite with a Deck Toward the Harbor, Greenleaf Inn, Boothbay

Second-Floor King Suite with a Deck Toward the Harbor, Greenleaf Inn, Boothbay
Boothbay Harbor
8.0 out of 10, Very good, (1 review)
"Friendly"
United States
Amy
$290 nightly
The price is $316
Oct 28 - Oct 29
Total with taxes and fees
Second-Floor King Suite with a Deck Toward the Harbor, Greenleaf Inn, Boothbay
A two-story house with a stone staircase leading to a front door, surrounded by a garden with potted plants and a seating area with chairs.

19. The Diamond Island Suite - Suite in Historic Home

The Diamond Island Suite - Suite in Historic Home
West End
$241 nightly
The price is $263
Oct 28 - Oct 29
Total with taxes and fees
The Diamond Island Suite - Suite in Historic Home
A two-story house with a stone staircase leading to a front door, surrounded by a garden with potted plants and a seating area with chairs.

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

Experience the History of Portland - The Hope Island Room
West End
$262 nightly
The price is $286
Nov 1 - Nov 2
Total with taxes and fees
Experience the History of Portland - The Hope Island Room
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 Bailey Island Hotel Reviews

Inn at St John Portland In-Town

Inn at St John Portland In-Town

8/10 Good
"Staff was great and room was clean"
Amanda 1-night trip
Posted 2 hours ago
Inn at St John Portland In-Town

Find out more about Bailey Island

Bailey Island B&B information

Number of reviews
2,359
Accommodation
55 B&B
Lowest Price
$107
Highest Price
$361

Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Bailey Island?
Prices for B&Bs in Bailey Island often vary, but you can find a great deal from $107 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Bailey 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.
What is the difference between a Bailey Island Bed & Breakfast and a hotel?
Every Bailey 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 Bailey Island B&Bs.

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