Search B&B in Bailey Island

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

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

Inn at St John Portland In-Town
2.5 star property
Valley Street
8.8 out of 10, Excellent, (1139)
"Always a great stay from staff to cleanliness and comforts "
United States
Rachel
The price is HK$622
HK$678 total
includes taxes & fees
30 Dec - 31 Dec
Inn at St John Portland In-Town
Garden
Brewster House Bed & Breakfast

Brewster House Bed & Breakfast

Brewster House Bed & Breakfast
4.0 star property
Freeport
9.8 out of 10, Exceptional, (114)
"The food was wonderful and the hospitality was great!"
United States
Olivia
The price is HK$1,203
HK$1,311 total
includes taxes & fees
4 Jan - 5 Jan 2026
Brewster House Bed & Breakfast
Exterior
The Kendall Inn

The Kendall Inn

The Kendall Inn
3.5 star property
Freeport
9.8 out of 10, Exceptional, (145)
"Quaint stay. Enjoyed our stay. "
United States
Linda
The price is HK$1,301
HK$1,418 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Kendall Inn
Water view
Harborage Inn on the Oceanfront

Harborage Inn on the Oceanfront

Harborage Inn on the Oceanfront
3.5 star property
Boothbay Harbor
9.6 out of 10, Exceptional, (223)
"Yes, the room was spotless and comfortable. Check in was easy. Breakfast was delicious and appeared right on time!"
United States
Valerie
The price is HK$1,713
HK$1,868 total
includes taxes & fees
1 Jan - 2 Jan 2026
Harborage Inn on the Oceanfront
Front of property
Harbour Towne Inn on the Waterfront

Harbour Towne Inn on the Waterfront

Harbour Towne Inn on the Waterfront
3.0 star property
Boothbay Harbor
9.6 out of 10, Exceptional, (78)
"Very nice comfortable room with friendly staff and excellent breakfast."
United States
Robert
The price is HK$1,733
HK$1,889 total
includes taxes & fees
30 Dec - 31 Dec
Harbour Towne Inn on the Waterfront
Premium bedding, individually decorated, individually furnished
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.
3.5 star property
West End
9.6 out of 10, Exceptional, (167)
"The property is beautiful, the staff is kind, and the rooms are spacious and clean. It was great to have a safe place to park the car while having so many things to do within walking distance. Being able to grab a quick breakfast before heading out was great too! We loved our stay here!"
United States
Darby
The price is HK$1,601
HK$1,745 total
includes taxes & fees
4 Jan - 5 Jan 2026
Blind Tiger Portland - Danforth Street.
Porch
Candlebay Inn

Candlebay Inn

Candlebay Inn
3.0 star property
Freeport
9.6 out of 10, Exceptional, (460)
"The Candlebay Inn was a great stay! Staff was wonderful and the place was super cute and clean. "
United States
Paige
The price is HK$1,197
HK$1,304 total
includes taxes & fees
30 Dec - 31 Dec
Candlebay Inn
Living area
Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street
3.5 star property
West End
9.6 out of 10, Exceptional, (120)
"Loved the place "
United States
Stephen
The price is HK$1,391
HK$1,516 total
includes taxes & fees
11 Jan - 12 Jan 2026
Blind Tiger Portland – Carleton Street
Property entrance
Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast
3.0 star property
Rosemont
9.0 out of 10, Wonderful, (132)
"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 HK$1,780
HK$1,940 total
includes taxes & fees
30 Dec - 31 Dec
Fleetwood House Bed & Breakfast
Outdoor dining
The James Place Inn B&B

The James Place Inn B&B

The James Place Inn B&B
3.5 star property
Freeport
10.0 out of 10, Exceptional, (182)
"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 HK$1,697
HK$1,850 total
includes taxes & fees
30 Dec - 31 Dec
The James Place Inn B&B
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 King Suite - Room 2 at Greenleaf Inn - Balcony, Harbor Views!
2.0 star property
Boothbay Harbor
The price is HK$1,943
HK$2,363 total
includes taxes & fees
30 Dec - 31 Dec
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Bailey Island Hotel Reviews

Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent
"We were very pleased with our room (size, comfort and cleanliness)! The parking situation is easy, too."
Deborah 1-night trip
Posted 2 days ago
Holiday Inn Portland-By the Bay by IHG

Find out more about Bailey Island

Bailey Island B&B information

Number of reviews
2,735
Accommodation
28 B&B
Lowest Price
HK$678
Highest Price
HK$1,940

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. The Orchard House: Inn, Ice Cream, Cafe: 5 rooms. 10.6 mi (17 km) from the city centre. Blind Tiger Portland - Danforth Street.: 9 rooms. Situated 14.7 mi (23.7 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 Land's End Gift Shop 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.

Explore a world of travel with Expedia