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Check prices for these dates

Next weekend
26 Jun - 28 Jun
In two weeks
3 Jul - 5 Jul
In one month
17 Jul - 19 Jul
In two months
14 Aug - 16 Aug

Our top choices for Bailey Island bed & breakfast

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, (165 reviews)
"Vers Nice stay!"
Canada
Kateri
The price is AED 760
AED 829 total
includes taxes & fees
30 Jun - 1 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, (133 reviews)
"Breakfast was excellent! Very pet friendly. Room was lovely and clean. "
United States
Earlene
The price is AED 841
AED 917 total
includes taxes & fees
24 Jun - 25 Jun
Fleetwood House Bed & Breakfast
View from property

The Squire Tarbox Inn

The Squire Tarbox Inn
2.5 star property
Wiscasset
9.6 out of 10, Exceptional, (22 reviews)
"Lovely spot."
United States
Oona
The price is AED 773
AED 920 total
includes taxes & fees
23 Jun - 24 Jun
The Squire Tarbox Inn
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 AED 1,031
AED 1,124 total
includes taxes & fees
8 Jul - 9 Jul
The Nicholson Inn
Porch

Candlebay Inn

Candlebay Inn
3.0 star property
Freeport
9.6 out of 10, Exceptional, (463 reviews)
"Very nice owners and the place was clean food was great and location was excellent. Will tell are family and friends when they visit Maine."
United States
Barry
The price is AED 641
AED 699 total
includes taxes & fees
25 Jun - 26 Jun
Candlebay Inn
Sauna

Brewster House Bed & Breakfast

Brewster House Bed & Breakfast
4.0 star property
Freeport
9.8 out of 10, Exceptional, (118 reviews)
"The food was wonderful and the hospitality was great!"
United States
Olivia
The price is AED 640
AED 698 total
includes taxes & fees
23 Jun - 24 Jun
Brewster House Bed & Breakfast
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, (1,130 reviews)
"great place"
United States
Kimberly
The price is AED 587
AED 639 total
includes taxes & fees
23 Jun - 24 Jun
Inn at St John Portland In-Town
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, (232 reviews)
"Good location."
United States
Abeer
The price is AED 1,209
AED 1,318 total
includes taxes & fees
28 Jun - 29 Jun
Harborage Inn on the Oceanfront
Interior entrance

The Kendall Inn

The Kendall Inn
3.5 star property
Freeport
9.8 out of 10, Exceptional, (146 reviews)
"Nice bed and breakfast in quiet area near all the shopping "
United States
Suan
The price is AED 853
AED 930 total
includes taxes & fees
23 Jun - 24 Jun
The Kendall Inn
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, (185 reviews)
"The place was totally amazing."
United States
Gary
The price is AED 1,344
AED 1,465 total
includes taxes & fees
5 Jul - 6 Jul
Blind Tiger Portland - Danforth Street.
Living area

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street
3.5 star property
West End
9.6 out of 10, Exceptional, (123 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 AED 1,095
AED 1,193 total
includes taxes & fees
28 Jun - 29 Jun
Blind Tiger Portland – Carleton Street
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 AED 1,116
AED 1,216 total
includes taxes & fees
23 Jun - 24 Jun
The James Place Inn B&B
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 AED 2,130
AED 2,654 total
includes taxes & fees
30 Jun - 1 Jul
Boothbay Harbor Penthouse Suite - Room 15 at AQ Inn - Fireplace, Ocean View
Terrace/patio

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 AED 1,947
AED 2,426 total
includes taxes & fees
30 Jun - 1 Jul
Boothbay Harbor King Suite - Room 3 at Greenleaf Inn - Balcony, Harbor Views!
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 AED 1,469
AED 1,826 total
includes taxes & fees
23 Jun - 24 Jun
Boothbay Harbor Queen Suite - Room 16 at AQ Inn - Ocean View
Smart TV, fireplace, books

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
The price is AED 1,543
AED 1,918 total
includes taxes & fees
23 Jun - 24 Jun
Boothbay Harbor King Suite - Room 11 at AQ Inn - Balcony, Fireplace, Harbor View
Smart TV, fireplace, books

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
The price is AED 2,130
AED 2,654 total
includes taxes & fees
5 Jul - 6 Jul
Boothbay Harbor King Suite - Room 13 at AQ Inn - Fireplace, Patio, Harbor 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
The price is AED 1,616
AED 2,010 total
includes taxes & fees
23 Jun - 24 Jun
Boothbay Harbor King Suite - Room 10 at AQ Inn - Harbor View!
Smart TV, fireplace, books

Boothbay Harbor Garden Suite - Room 9 at AQ Inn - Garden & Ocean Views!

Boothbay Harbor Garden Suite - Room 9 at AQ Inn - Garden & Ocean Views!
Boothbay Harbor
The price is AED 1,653
AED 2,054 total
includes taxes & fees
23 Jun - 24 Jun
Boothbay Harbor Garden Suite - Room 9 at AQ Inn - Garden & Ocean Views!
Property grounds

Boothbay Harbor King Suite - Room 5 at Greenleaf Inn - Harbor Views!

Boothbay Harbor King Suite - Room 5 at Greenleaf Inn - Harbor Views!
Boothbay Harbor
The price is AED 1,983
AED 2,470 total
includes taxes & fees
24 Jun - 25 Jun
Boothbay Harbor King Suite - Room 5 at Greenleaf Inn - 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

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

10/10 Excellent
"Clean property. Comfy beds and pleasant staff"
Neal 1-night trip
Posted 1 hour ago
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

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?
Here 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.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. The Orchard House: Inn & Cafe: 5 rooms. 10.6 mi (17 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.

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