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
24 Jul - 26 Jul
In two weeks
31 Jul - 2 Aug
In one month
14 Aug - 16 Aug
In two months
11 Sep - 13 Sep

Our top choices for Bailey Island bed & breakfast

Exterior

West End Collection at 146 Pine

West End Collection at 146 Pine
3.0 star property
West End
9.6 out of 10, Exceptional, (95 reviews)
"Wonderful staff and scrumptious breakfast "
United States
Elena
The price is SAR 927
SAR 1,011 total
includes taxes & fees
3 Aug - 4 Aug
West End Collection at 146 Pine
Front of property - evening/night

The Orchard House: Inn & Cafe

The Orchard House: Inn & Cafe
3.0 star property
Freeport
9.6 out of 10, Exceptional, (168 reviews)
"The Orchard Inn is very quaint and charming. The grounds were very quiet and peaceful. We especially enjoyed the great coffee and healthy continental breakfast that was provided. Would definitely recommend the Orchard Inn."
United States
Kathleen
The price is SAR 848
SAR 924 total
includes taxes & fees
15 Jul - 16 Jul
The Orchard House: Inn & Cafe
Exterior detail

Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast
3.0 star property
Rosemont
9.0 out of 10, Wonderful, (134 reviews)
"Breakfast was excellent! Very pet friendly. Room was lovely and clean. "
United States
Earlene
The price is SAR 860
SAR 937 total
includes taxes & fees
15 Jul - 16 Jul
Fleetwood House Bed & Breakfast
Porch

Candlebay Inn

Candlebay Inn
3.0 star property
Freeport
9.6 out of 10, Exceptional, (472 reviews)
"Breakfast was very good b"
United States
William
The price is SAR 656
SAR 715 total
includes taxes & fees
22 Jul - 23 Jul
Candlebay Inn
Front of property - evening/night

Inn at St John Portland In-Town

Inn at St John Portland In-Town
2.5 star property
Valley Street
8.8 out of 10, Excellent, (1,135 reviews)
"great place"
United States
Kimberly
The price is SAR 635
SAR 692 total
includes taxes & fees
15 Jul - 16 Jul
Inn at St John Portland In-Town
Front of property

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
The price is SAR 1,116
SAR 1,216 total
includes taxes & fees
28 Jul - 29 Jul
The Nicholson Inn
View from property

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 SAR 1,211
SAR 1,441 total
includes taxes & fees
15 Jul - 16 Jul
The Squire Tarbox Inn
Interior entrance

The Kendall Inn

The Kendall Inn
3.5 star property
Freeport
9.8 out of 10, Exceptional, (149 reviews)
"Nice bed and breakfast in quiet area near all the shopping "
United States
Suan
The price is SAR 862
SAR 939 total
includes taxes & fees
15 Jul - 16 Jul
The Kendall Inn
Front of property

The James Place Inn B&B

The James Place Inn B&B
3.5 star property
Freeport
10.0 out of 10, Exceptional, (184 reviews)
"Great place. Comfortable and welcoming. Great proprietors and great location. "
United States
Cecilia
The price is SAR 1,141
SAR 1,243 total
includes taxes & fees
15 Jul - 16 Jul
The James Place Inn B&B
Deluxe Room, 1 King Bed, Harbor View, Oceanfront | Water view

Harborage Inn on the Oceanfront

Harborage Inn on the Oceanfront
3.5 star property
Boothbay Harbor
9.6 out of 10, Exceptional, (233 reviews)
"Good location."
United States
Abeer
The price is SAR 1,280
SAR 1,396 total
includes taxes & fees
16 Jul - 17 Jul
Harborage Inn on the Oceanfront
Baxter | Premium bedding, individually decorated, individually furnished

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.
3.5 star property
West End
9.6 out of 10, Exceptional, (188 reviews)
"The place was totally amazing."
United States
Gary
The price is SAR 1,663
SAR 1,813 total
includes taxes & fees
5 Aug - 6 Aug
Blind Tiger Portland - Danforth Street.
Front of property

Harbour Towne Inn on the Waterfront

Harbour Towne Inn on the Waterfront
3.0 star property
Boothbay Harbor
9.6 out of 10, Exceptional, (81 reviews)
"Wonderful old home, small rooms, excellent breakfast! Felt like I was part of a Hallmark movie. Loved the gardens and wonderful hostess!"
United States
Laneau
The price is SAR 1,368
SAR 1,491 total
includes taxes & fees
16 Jul - 17 Jul
Harbour Towne Inn on the Waterfront
Living area

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street
3.5 star property
West End
9.6 out of 10, Exceptional, (125 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
The price is SAR 1,435
SAR 1,565 total
includes taxes & fees
9 Aug - 10 Aug
Blind Tiger Portland – Carleton Street
Smart TV, fireplace, books

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
10.0 out of 10, Exceptional, (1 review)
"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 SAR 2,189
SAR 2,726 total
includes taxes & fees
19 Jul - 20 Jul
Boothbay Harbor Penthouse Suite - Room 15 at AQ Inn - Fireplace, Ocean View
Smart TV, fireplace, books

Boothbay Harbor King Suite - Room 3 at Greenleaf Inn - Balcony, Harbor Views!

Boothbay Harbor King Suite - Room 3 at Greenleaf Inn - Balcony, Harbor Views!
Boothbay Harbor
The price is SAR 2,001
SAR 2,492 total
includes taxes & fees
15 Jul - 16 Jul
Boothbay Harbor King Suite - Room 3 at Greenleaf Inn - Balcony, Harbor Views!
Dining

Boothbay Harbor King Suite - Room 13 at AQ Inn - Fireplace, Patio, Harbor View!

Boothbay Harbor King Suite - Room 13 at AQ Inn - Fireplace, Patio, Harbor View!
Boothbay Harbor
10.0 out of 10, Exceptional, (1 review)
The price is SAR 2,189
SAR 2,726 total
includes taxes & fees
19 Jul - 20 Jul
Boothbay Harbor King Suite - Room 13 at AQ Inn - Fireplace, Patio, Harbor View!
Smart TV, fireplace, books

Boothbay Harbor Queen Suite - Room 16 at AQ Inn - Ocean View

Boothbay Harbor Queen Suite - Room 16 at AQ Inn - Ocean View
Boothbay Harbor
The price is SAR 1,427
SAR 1,772 total
includes taxes & fees
15 Jul - 16 Jul
Boothbay Harbor Queen Suite - Room 16 at AQ Inn - Ocean View
Smart TV, fireplace, books

Boothbay Harbor King Suite - Room 10 at AQ Inn - Harbor View!

Boothbay Harbor King Suite - Room 10 at AQ Inn - Harbor View!
Boothbay Harbor
8.0 out of 10, Very Good, (1 review)
"This is a great property. You have full access to a kitchen that is stocked with snacks and breakfast. There are lots of rocking chairs and outdoor chairs to lounge and look at the harbor. Jersey was great. He even lit a fire every evening. Everything is walkable from here. Would definitely stay here again."
United States
Kelli H.
The price is SAR 1,926
SAR 2,398 total
includes taxes & fees
15 Jul - 16 Jul
Boothbay Harbor King Suite - Room 10 at AQ Inn - Harbor View!
Smart TV, fireplace, books

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
The price is SAR 1,986
SAR 2,456 total
includes taxes & fees
28 Jul - 29 Jul
Boothbay Harbor 2-Story Suite - Room 12 at AQ Inn - Balconies, Harbor View
Smart TV, fireplace, books

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
The price is SAR 1,964
SAR 2,447 total
includes taxes & fees
22 Jul - 23 Jul
Boothbay Harbor King Suite - Room 2 at Greenleaf Inn - Balcony, Harbor Views!
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

Comfort Inn South Portland Airport

Comfort Inn South Portland Airport

8/10 Good
"Clean, a very nice stay. Had some problems with the shower, tho staff was helpful as could be, so 4 stars, but really 4.5"
Halina 1-night trip
Posted 1 hour ago
Comfort Inn South Portland Airport

Frequently asked questions

Searching for B&Bs in Bailey Island?
If you're looking for something a little more offbeat than the traditional hotel experience, a bed and breakfast could be a great option for your trip. 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 check out.
Are you thinking about a B&B for your stay?
With attentive service, opportunities to meet guests from other places, and of course a full breakfast, B&Bs provide 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.The Orchard House: Inn & Cafe: 5 rooms. 10.6 mi (17 km) from the downtown core. Fleetwood House Bed & Breakfast: 3 rooms. Situated 16.1 mi (25.9 km) from the heart of Bailey Island. Enjoy the free full breakfast and unique décor. Blind Tiger Portland - Danforth Street.: 9 rooms. 14.7 mi (23.7 km) from the heart of downtown.Blind Tiger Portland – Carleton Street: 6 rooms. Located 15 mi (24.2 km) from the core of Bailey Island. Enjoy the unique décor and patio area.
What's the best time of year to 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 temp of 65°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Bailey Island are January, March, February, and December, with each month seeing an average of 7 inches 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 might 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?
You can plan your excursions in and around Bailey Island ahead of time with these transportation options. Fly into Portland Intl. Jetport Airport (PWM), which is located 17 mi (27.3 km) away from the city center. Otherwise, you can search for flights to Wiscasset, ME (ISS), which is 21.1 mi (33.9 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights.