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

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Check prices for these dates

Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct
In one month
23 Oct - 25 Oct
In two months
20 Nov - 22 Nov

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, (489 reviews)
"Great location, quiet room, great breakfast......"
United States
Keith
The price is HK$1,370
HK$1,493 total
includes taxes & fees
5 Oct - 6 Oct
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, (181 reviews)
"Amazing stay in a perfect location! Would absolutely recommend to family and friends and will likely stay again!"
United States
Megan
The price is HK$1,771
HK$1,930 total
includes taxes & fees
24 Sept - 25 Sept
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, (162 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
The price is HK$1,619
HK$1,809 total
includes taxes & fees
15 Oct - 16 Oct
The Kendall Inn
A two-story house with a balcony, a front porch, and a snow-covered landscape.

4. The Nicholson Inn

The Nicholson Inn
3.0 star property
Freeport
10.0 out of 10, Exceptional, (2 reviews)
"The owners were amazing and so kind. The location is perfect, and the amenities feel so hoy and great."
United States
Meaghan
The price is HK$2,233
HK$2,434 total
includes taxes & fees
28 Sept - 29 Sept
The Nicholson Inn
A multi-story building with a stone facade, multiple windows, and awnings.

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, (1,122 reviews)
"Great place to stay, affordable,clean with walking access to to port area!"
United States
Steve Robert
The price is HK$994
HK$1,084 total
includes taxes & fees
28 Sept - 29 Sept
Inn at St John Portland In-Town
A house with a sign for The James Place Inn, indicating a vacancy.

6. The James Place Inn B&B

The James Place Inn B&B
3.5 star property
Freeport
10.0 out of 10, Exceptional, (193 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
The price is HK$1,791
HK$1,953 total
includes taxes & fees
5 Oct - 6 Oct
The James Place Inn B&B
A garden with a stone wall, various plants, and flowers.

7. Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast
3.0 star property
Rosemont
9.0 out of 10, Wonderful, (147 reviews)
"Breakfast was wonderful!"
United States
Karen
The price is HK$1,796
HK$2,037 total
includes taxes & fees
5 Oct - 6 Oct
Fleetwood House Bed & Breakfast

8. West End Collection at 146 Pine

West End Collection at 146 Pine
3.0 star property
West End
9.6 out of 10, Exceptional, (98 reviews)
"It was wonderful staying. Beautiful old house with all amenities and"
United States
Svetlana
The price is HK$2,557
HK$2,788 total
includes taxes & fees
13 Oct - 14 Oct
West End Collection at 146 Pine
A large house with multiple sections, surrounded by lush greenery and trees.

9. 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
The price is HK$2,201
HK$2,619 total
includes taxes & fees
16 Oct - 17 Oct
The Squire Tarbox Inn
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, (235 reviews)
"Good location."
United States
Abeer
The price is HK$2,583
HK$2,816 total
includes taxes & fees
13 Oct - 14 Oct
Harborage Inn on the Oceanfront
A well-lit living room with a fireplace, comfortable seating, and a large mirror.

11. Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street
3.5 star property
West End
9.6 out of 10, Exceptional, (132 reviews)
"Beautiful place"
United States
Samuel
The price is HK$3,171
HK$3,456 total
includes taxes & fees
18 Oct - 19 Oct
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.

12. Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.
3.5 star property
West End
9.6 out of 10, Exceptional, (193 reviews)
"Place was charming and quirky. Very comfortable and well located."
United States
Mary
The price is HK$4,283
HK$4,669 total
includes taxes & fees
23 Sept - 24 Sept
Blind Tiger Portland - Danforth Street.
A large white house with multiple balconies, a porch, and a garage.

13. Boothbay Harbor 2-Story Suite - Room 12 at AQ Inn - Balconies, Harbor View

Boothbay Harbor 2-Story Suite - Room 12 at AQ Inn - Balconies, Harbor View
Boothbay Harbor
10.0 out of 10, Exceptional, (5 reviews)
The price is HK$2,228
HK$2,779 total
includes taxes & fees
23 Sept - 24 Sept
Boothbay Harbor 2-Story Suite - Room 12 at AQ Inn - Balconies, Harbor View
A wooden deck with three chairs and a table, overlooking a marina with boats and a lighthouse.

14. Boothbay Harbor King Suite - Room 7 at Greenleaf Inn - Balcony, Harbor Views!

Boothbay Harbor King Suite - Room 7 at Greenleaf Inn - Balcony, Harbor Views!
Boothbay Harbor
10.0 out of 10, Exceptional, (3 reviews)
"Loved the amenities and views! Great location… walking distance to everything. The staff was very friendly and accommodating!"
United States
Melissa
The price is HK$2,016
HK$2,514 total
includes taxes & fees
27 Sept - 28 Sept
Boothbay Harbor King Suite - Room 7 at Greenleaf Inn - Balcony, Harbor Views!
A spacious living room with a brown leather sofa, beige armchairs, and a round coffee table.

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

Experience the History of Portland - The Hope Island Room
West End
The price is HK$2,118
HK$2,506 total
includes taxes & fees
27 Sept - 28 Sept
Experience the History of Portland - The Hope Island Room
A balcony with two chairs and a small table, overlooking a marina with boats and a distant shoreline.

16. Boothbay Harbor Penthouse Suite - Room 15 at AQ Inn - Fireplace, Ocean View

Boothbay Harbor Penthouse Suite - Room 15 at AQ Inn - Fireplace, Ocean View
Boothbay Harbor
9.8 out of 10, Exceptional, (9 reviews)
"Gracious and welcoming host, the property is all about the view. Nice relaxing get away. Beautiful ocean view with peace and quiet."
United States
Harrison S.
The price is HK$2,346
HK$2,908 total
includes taxes & fees
5 Oct - 6 Oct
Boothbay Harbor Penthouse Suite - Room 15 at AQ Inn - Fireplace, Ocean View
A living room with a wooden ceiling, a grey sofa, a wooden coffee table, and a chair.

17. Boothbay Harbor King Suite - Room 2 at Greenleaf Inn - Balcony, Harbor Views!

Boothbay Harbor King Suite - Room 2 at Greenleaf Inn - Balcony, Harbor Views!
Boothbay Harbor
10.0 out of 10, Exceptional, (1 review)
"The property was amazing! The staff are very helpful. This wasn't a very relaxing and enjoyable stay. We definitely would come back"
United States
Robert S.
The price is HK$2,150
HK$2,668 total
includes taxes & fees
15 Oct - 16 Oct
Boothbay Harbor King Suite - Room 2 at Greenleaf Inn - Balcony, Harbor Views!
A wooden deck with three white Adirondack chairs facing a marina with boats and houses in the background.

18. Boothbay Harbor - Room 10 at Greenleaf Inn - Balcony, Harbor Views!

Boothbay Harbor - Room 10 at Greenleaf Inn - Balcony, Harbor Views!
Boothbay Harbor
10.0 out of 10, Exceptional, (1 review)
"We had such a great time at The Greenleaf. Jersey is an incredible host and will make sure your visit is amazing."
United States
Karen G.
The price is HK$1,852
HK$2,309 total
includes taxes & fees
29 Sept - 30 Sept
Boothbay Harbor - Room 10 at Greenleaf Inn - Balcony, Harbor Views!
A large white house with multiple balconies, a porch, and a garage.

19. Boothbay Harbor King Suite - Room 11 at AQ Inn - Balcony, Fireplace, Harbor View

Boothbay Harbor King Suite - Room 11 at AQ Inn - Balcony, Fireplace, Harbor View
Boothbay Harbor
10.0 out of 10, Exceptional, (2 reviews)
"The service and attention was above and beyond and you could not ask for a better location. Five stars, hands down."
United States
Robbyn G.
The price is HK$2,048
HK$2,557 total
includes taxes & fees
27 Sept - 28 Sept
Boothbay Harbor King Suite - Room 11 at AQ Inn - Balcony, Fireplace, Harbor View
A large white house with multiple balconies, a porch, and a garage.

20. Boothbay Harbor King Suite - Room 16 at AQ Inn

Boothbay Harbor King Suite - Room 16 at AQ Inn
Boothbay Harbor
10.0 out of 10, Exceptional, (4 reviews)
"Great location. Shared spaces were comfortable and had beautiful harbor views. Very nice Inn. Would definitely stay here again."
United States
Rhonda L.
The price is HK$1,640
HK$2,044 total
includes taxes & fees
30 Sept - 1 Oct
Boothbay Harbor King Suite - Room 16 at AQ Inn
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

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

10/10 Excellent
"This hotel was right in the middle of Old Port and in such close proximity to all of the amazing restaurants and stores. The staff was incredibly attentive and so friendly. We never had to wait more than a couple minutes for anything. Even the restaurant and bar in the hotel was great and the food was delicious"
Brianne Renee 3-night trip
Posted 4 hours ago
Portland Regency Hotel & Spa

Find out more about Bailey Island

Bailey Island B&B information

Number of reviews
1,846
Accommodation
47 B&B
Lowest Price
HK$1,084
Highest Price
HK$4,669

Frequently asked questions

Searching for B&Bs in Bailey Island?
If you're interested in something a little different than the traditional hotel experience, a bed and breakfast might be the perfect option for your getaway. If you'd like to learn more about Bailey Island through its top sites and landmarks, Bailey Island Bridge and Cobwork Bridge are some notable monuments to visit.
Are you considering an apartment instead of a traditional hotel?
With attentive service, opportunities to meet other guests and breakfast served on site, B&Bs all have a one-of-a-kind setting.
What are the best bed and breakfasts in Bailey Island?
Below are some well-liked B&Bs in the surrounding area: Inn at St John Portland In-Town: 15.3 mi (24.7 km) from the heart of Bailey Island. Blind Tiger Portland - Danforth Street.: 9 rooms. 14.7 mi (23.7 km) from the city centre. The Orchard House: Inn & Cafe: 5 rooms. Situated 10.6 mi (17 km) from the heart of Bailey Island. Blind Tiger Portland – Carleton Street: 6 rooms. 15 mi (24.2 km) from the city centre. Enjoy the unique decor and patio area. Fleetwood House Bed & Breakfast: 3 rooms. Located 16.1 mi (25.9 km) from the core of Bailey Island. Enjoy the free full breakfast and unique decor.
When should I stay at a B&B in Bailey Island?
When you're dreaming of a getaway to Bailey Island, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Bailey Island are January, March, February and December, with each month seeing an average of 19 cm of snowfall.
What is there to do in Bailey Island?
When you want to spend some time in the great outdoors, Mackerel Cove and Ragged Island are some notable spots. You should put Bailey Island Bridge and Cobwork Bridge on your list if you want to see more of the area.
How can I get to and around Bailey Island?
Planning your excursions in and around Bailey Island is easier with these transportation options. Fly into Portland, ME (PWM-Portland Intl. Jetport), which is located 17 mi (27.3 km) away from the city centre. You can also search for flights into Wiscasset, ME (ISS), which is 21.1 mi (33.9 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.

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