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Check prices for these dates

Next weekend
6 Feb - 8 Feb
In two weeks
13 Feb - 15 Feb
In one month
27 Feb - 1 Mar
In two months
27 Mar - 29 Mar

Our top choices for Bailey Island 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, (1,138 reviews)
"Always a great stay from staff to cleanliness and comforts "
United States
Rachel
The price is AED 294
AED 320 total
includes taxes & fees
28 Jan - 29 Jan
Inn at St John Portland In-Town
Garden

Brewster House Bed & Breakfast

Brewster House Bed & Breakfast
4.0 star property
Freeport
9.8 out of 10, Exceptional, (115 reviews)
"The food was wonderful and the hospitality was great!"
United States
Olivia
The price is AED 613
AED 668 total
includes taxes & fees
5 Feb - 6 Feb
Brewster House Bed & Breakfast
Interior entrance

The Kendall Inn

The Kendall Inn
3.5 star property
Freeport
9.8 out of 10, Exceptional, (145 reviews)
"Quaint stay. Enjoyed our stay. "
United States
Linda
The price is AED 615
AED 670 total
includes taxes & fees
28 Jan - 29 Jan
The Kendall Inn
Porch

Candlebay Inn

Candlebay Inn
3.0 star property
Freeport
9.6 out of 10, Exceptional, (460 reviews)
"The Candlebay Inn was a great stay! Staff was wonderful and the place was super cute and clean. "
United States
Paige
The price is AED 566
AED 617 total
includes taxes & fees
28 Jan - 29 Jan
Candlebay 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, (169 reviews)
"The whole was cozy! Well curated style and knowledgeable staff."
United States
jeffrey c
The price is AED 757
AED 825 total
includes taxes & fees
25 Feb - 26 Feb
Blind Tiger Portland - Danforth Street.
Property grounds

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 AED 613
AED 749 total
includes taxes & fees
28 Jan - 29 Jan
Boothbay Harbor King Suite - Room 2 at Greenleaf Inn - Balcony, Harbor Views!
Living area

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street
3.5 star property
West End
9.6 out of 10, Exceptional, (120 reviews)
"Loved the place "
United States
Stephen
The price is AED 657
AED 717 total
includes taxes & fees
25 Feb - 26 Feb
Blind Tiger Portland – Carleton Street
Exterior detail

Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast
3.0 star property
Rosemont
9.0 out of 10, Wonderful, (132 reviews)
"Lovely, comfortable stay! So welcoming and accommodating. We only stayed one night but will keep this in mind next time we are in the area :)"
United States
Sadie
The price is AED 841
AED 917 total
includes taxes & fees
28 Jan - 29 Jan
Fleetwood House Bed & Breakfast
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, (182 reviews)
"Wish we could have stayed longer. It has the ambiance of an older inn but the rooms are very clean and well maintained. "
United States
Melissa
The price is AED 802
AED 874 total
includes taxes & fees
28 Jan - 29 Jan
The James Place Inn B&B
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

Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine

10/10 Excellent
"Fun hotel excellent and friendly staff"
Joseph 2-night trip
Posted 1 day ago
Embassy Suites by Hilton Portland Maine

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, Cobwork Bridge and Bailey Island 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.Fleetwood House Bed & Breakfast: 3 rooms. 16.1 mi (25.9 km) from the downtown core. Enjoy the free full breakfast and unique décor. Blind Tiger Portland – Carleton Street: 6 rooms. Situated 15 mi (24.2 km) from the heart of Bailey Island. Enjoy the unique décor and patio area. Blind Tiger Portland - Danforth Street.: 9 rooms. 14.7 mi (23.7 km) from the heart of downtown.Benjamin F. Packard House: 4 rooms. Located 15.6 mi (25 km) from the core of Bailey Island. Enjoy the free full breakfast and unique décor.
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 Cobwork Bridge and Bailey Island 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.