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Check prices for these dates

Next weekend
27 Mar - 29 Mar
In two weeks
3 Apr - 5 Apr
In one month
17 Apr - 19 Apr
In two months
15 May - 17 May

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, (1,128 reviews)
"Great stay. Staff were very nice. Very dog friendly Inn."
United States
Stuart
The price is AED 294
AED 320 total
includes taxes & fees
19 Mar - 20 Mar
Inn at St John Portland In-Town
Exterior

Benjamin F. Packard House

Benjamin F. Packard House
3.0 star property
Bath
10.0 out of 10, Exceptional, (102 reviews)
"Beautiful house, the breakfast food was amazing, and the owners were so personable and welcoming. "
United States
Jennifer
The price is AED 799
AED 871 total
includes taxes & fees
22 Mar - 23 Mar
Benjamin F. Packard House
Exterior

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 584
AED 637 total
includes taxes & fees
21 Mar - 22 Mar
Candlebay Inn
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, (224 reviews)
"The room was spotless, the staff was courteous and the breakfast was very good."
United States
Manuel
The price is AED 734
AED 800 total
includes taxes & fees
1 Apr - 2 Apr
Harborage Inn on the Oceanfront
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
19 Mar - 20 Mar
The Kendall Inn
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
19 Mar - 20 Mar
Fleetwood House Bed & Breakfast
Lobby lounge

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.
3.5 star property
West End
9.6 out of 10, Exceptional, (177 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
29 Mar - 30 Mar
Blind Tiger Portland - Danforth Street.
Sauna

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 833
AED 908 total
includes taxes & fees
15 Apr - 16 Apr
Brewster 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
20 Mar - 21 Mar
The James Place Inn B&B
Living area

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street
3.5 star property
West End
9.6 out of 10, Exceptional, (121 reviews)
"Loved the place "
United States
Stephen
The price is AED 716
AED 781 total
includes taxes & fees
23 Mar - 24 Mar
Blind Tiger Portland – Carleton 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 765 total
includes taxes & fees
31 Mar - 1 Apr
Boothbay Harbor King Suite - Room 2 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 713
AED 889 total
includes taxes & fees
1 Apr - 2 Apr
Boothbay Harbor Queen Suite - Room 16 at AQ Inn - 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 907
AED 1,125 total
includes taxes & fees
17 Apr - 18 Apr
Boothbay Harbor King Suite - Room 3 at Greenleaf Inn - Balcony, Harbor 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 815
AED 997 total
includes taxes & fees
31 Mar - 1 Apr
Boothbay Harbor King Suite - Room 5 at Greenleaf Inn - Harbor Views!
Property grounds

Boothbay Harbor King Suite - Room 4 at Greenleaf Inn - Fireplace, Harbor Views!

Boothbay Harbor King Suite - Room 4 at Greenleaf Inn - Fireplace, Harbor Views!
Boothbay Harbor
The price is AED 815
AED 997 total
includes taxes & fees
31 Mar - 1 Apr
Boothbay Harbor King Suite - Room 4 at Greenleaf Inn - Fireplace, Harbor Views!
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 907
AED 1,109 total
includes taxes & fees
1 Apr - 2 Apr
Boothbay Harbor King Suite - Room 11 at AQ Inn - Balcony, Fireplace, 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 911
AED 1,113 total
includes taxes & fees
1 Apr - 2 Apr
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 948
AED 1,157 total
includes taxes & fees
1 Apr - 2 Apr
Boothbay Harbor Garden Suite - Room 9 at AQ Inn - Garden & Ocean Views!
Smart TV, fireplace, books

Boothbay Harbor Penthouse Suite - Room 14 at AQ Inn - Fireplace, Ocean View

Boothbay Harbor Penthouse Suite - Room 14 at AQ Inn - Fireplace, Ocean View
Boothbay Harbor
The price is AED 1,003
AED 1,217 total
includes taxes & fees
2 Apr - 3 Apr
Boothbay Harbor Penthouse Suite - Room 14 at AQ Inn - Fireplace, Ocean 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 1,017
AED 1,241 total
includes taxes & fees
1 Apr - 2 Apr
Boothbay Harbor King Suite - Room 13 at AQ Inn - Fireplace, Patio, Harbor View!
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

DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

8/10 Good
"Thanks "
Patrick 2-night trip
Posted 5 hours ago
DoubleTree by Hilton Hotel Portland

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.Blind Tiger Portland – Carleton Street: 6 rooms. 15 mi (24.2 km) from the downtown core. Enjoy the unique décor and patio area. 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. 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 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.

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