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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 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, (1142)
"Room was a great experience, felt like a proper inn with a lot of history "
United States
Armin
The price is AED 294
AED 320 total
includes taxes & fees
11 Dec - 12 Dec
Inn at St John Portland In-Town
Porch
Candlebay Inn

Candlebay Inn

Candlebay Inn
3.0 star property
Freeport
9.6 out of 10, Exceptional, (457)
"Great location and hospitality."
United States
Brandon
The price is AED 566
AED 617 total
includes taxes & fees
11 Dec - 12 Dec
Candlebay Inn
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 AED 615
AED 670 total
includes taxes & fees
1 Jan - 2 January 2026
The Kendall Inn
Deluxe Room, 1 King Bed, Harbor View, Oceanfront | 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, (220)
"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 AED 734
AED 800 total
includes taxes & fees
22 Dec - 23 Dec
Harborage Inn on the Oceanfront
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 AED 657
AED 716 total
includes taxes & fees
4 Jan - 5 January 2026
Brewster House Bed & Breakfast
Exterior
Benjamin F. Packard House

Benjamin F. Packard House

Benjamin F. Packard House
3.0 star property
Bath
10.0 out of 10, Exceptional, (102)
"Beautiful house, the breakfast food was amazing, and the owners were so personable and welcoming. "
United States
Jennifer
The price is AED 841
AED 917 total
includes taxes & fees
11 Dec - 12 Dec
Benjamin F. Packard House
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 AED 841
AED 917 total
includes taxes & fees
11 Dec - 12 Dec
Fleetwood House Bed & Breakfast
Baxter | 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 AED 790
AED 861 total
includes taxes & fees
4 Jan - 5 January 2026
Blind Tiger Portland - Danforth Street.
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, (77)
"Excellent location, easy to walk."
United States
Brian
The price is AED 968
AED 1,055 total
includes taxes & fees
14 Dec - 15 Dec
Harbour Towne Inn on the Waterfront
Stovall | 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 AED 881
AED 961 total
includes taxes & fees
15 Dec - 16 Dec
Blind Tiger Portland – Carleton Street
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 AED 802
AED 874 total
includes taxes & fees
11 Dec - 12 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 AED 918
AED 1,137 total
includes taxes & fees
11 Dec - 12 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.
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Top Bailey Island Hotel Reviews

Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

10/10 Excellent
"clean room, digital key wonderful, good breakfast selection, staff very accommodating. Pool water very, very cloudy (negative)"
geraldine 3-night trip
Posted 1 day ago
Hampton Inn Portland Downtown - Waterfront

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, Ice Cream, Cafe: 5 rooms. 10.6 mi (17 km) from the downtown core. Blind Tiger Portland - Danforth Street.: 9 rooms. Situated 14.7 mi (23.7 km) from the heart of Bailey Island. Fleetwood House Bed & Breakfast: 3 rooms. 16.1 mi (25.9 km) from the heart of downtown. Enjoy the free full breakfast and unique décor. 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 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?
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.