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Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 30 B&B in Bailey Island with updated reviews, rates, and availability.

Inn at St John Portland In-Town
Front of property - evening/night

Inn at St John Portland In-Town

2.5 star property
8.8 out of 10, Excellent, (1003)
"Always a great stay!!!"
The price is AED 364
AED 396 total
includes taxes & fees
1 Jun - 2 Jun
Inn at St John Portland In-Town
Candlebay Inn
Porch

Candlebay Inn

3.0 star property
9.6 out of 10, Exceptional, (423)
"Connie was very welcoming, and offered advice about the area. The Inn was quaint and comfortable, the breakfast delicious! We would definitely stay again!"
The price is AED 731
AED 797 total
includes taxes & fees
31 May - 1 Jun
Candlebay Inn
Blind Tiger Portland - Danforth Street.
Baxter | Premium bedding, individually decorated, individually furnished

Blind Tiger Portland - Danforth Street.

3.5 star property
9.6 out of 10, Exceptional, (144)
"Great, enjoyed our stay."
The price is AED 1,543
AED 1,681 total
includes taxes & fees
9 Jun - 10 Jun
Blind Tiger Portland - Danforth Street.
The Orchard House & Cafe
Front of property - evening/night

The Orchard House & Cafe

3.0 star property
9.6 out of 10, Exceptional, (144)
"This is the second time I've stayed here. It's a very charming, old house with tastefully decorated, comfortable rooms. The continental breakfast is very good and served in a cute and cozy dining room. The bed was a bit hard for me, but I'm pretty picky. Just a few minutes drive to the outlet stores and restaurants in town, but far enough away that it's nice and quiet. "
The price is AED 806
AED 879 total
includes taxes & fees
1 Jun - 2 Jun
The Orchard House & Cafe
Harborage Inn on the Oceanfront
Deluxe Room, 1 King Bed, Harbor View, Oceanfront | Water view

Harborage Inn on the Oceanfront

3.5 star property
9.4 out of 10, Exceptional, (208)
"We loved this place. Beautiful new rooms with full fridge/freezer and k-cup coffee machine. Porch all around the building was so nice to have to breakfast and take-out dinner. The breakfast at this b&b were fantastic. You have a choice of three things the night before and they deliver to your room in the morning. We ate on the porch overlooking the harbor. 2 minute walk to town and shops and restaurants. No car needed once you’re there. Loved it. mark who took care of us was fantastic!"
The price is AED 783
AED 853 total
includes taxes & fees
3 Jun - 4 Jun
Harborage Inn on the Oceanfront
Fleetwood House Bed & Breakfast
Property entrance

Fleetwood House Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (114)
"It was a really great place to stay! Everyone was very friendly and parking was super easy! I would stay again! "
The price is AED 841
AED 917 total
includes taxes & fees
31 May - 1 Jun
Fleetwood House Bed & Breakfast
Captain Sawyer's Bed & Breakfast
Heritage Room | 1 bedroom, premium bedding, bed sheets

Captain Sawyer's Bed & Breakfast

3.0 star property
9.2 out of 10, Wonderful, (115)
"Great place and people."
Captain Sawyer's Bed & Breakfast
Blind Tiger Portland – Carleton Street
Stovall | Living area | Fireplace

Blind Tiger Portland – Carleton Street

3.5 star property
9.8 out of 10, Exceptional, (112)
"We loved our stay at Blind Tiger! So many thoughtful touches."
The price is AED 1,333
AED 1,453 total
includes taxes & fees
4 Jun - 5 Jun
Blind Tiger Portland – Carleton Street
Harbour Towne Inn on the Waterfront
Front of property

Harbour Towne Inn on the Waterfront

3.0 star property
9.6 out of 10, Exceptional, (64)
"Awesome!"
Harbour Towne Inn on the Waterfront
Benjamin F. Packard House
Exterior

Benjamin F. Packard House

3.0 star property
10.0 out of 10, Exceptional, (95)
"Great!"
The price is AED 915
AED 997 total
includes taxes & fees
8 Jun - 9 Jun
Benjamin F. Packard House
West End Inn
Classic Room, 1 King Bed, City View | Individually decorated, individually furnished, iron/ironing board

West End Inn

3.0 star property
9.6 out of 10, Exceptional, (89)
"Beautiful building, great location and the breakfast was amazing!! "
The price is AED 1,172
AED 1,277 total
includes taxes & fees
5 Jun - 6 Jun
West End Inn
The Kendall Inn
Exterior

The Kendall Inn

3.5 star property
9.8 out of 10, Exceptional, (123)
"What a fantastic stay!"
The price is AED 761
AED 829 total
includes taxes & fees
31 May - 1 Jun
The Kendall Inn
Brewster House Bed & Breakfast
Exterior

Brewster House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (110)
"The food was wonderful and the hospitality was great!"
The price is AED 1,025
AED 1,117 total
includes taxes & fees
31 May - 1 Jun
Brewster House Bed & Breakfast
The James Place Inn B&B
Outdoor dining

The James Place Inn B&B

3.5 star property
10.0 out of 10, Exceptional, (171)
"The food was great and the owners lovely."
The price is AED 1,116
AED 1,216 total
includes taxes & fees
1 Jun - 2 Jun
The James Place Inn B&B
Blue Heron Seaside Inn
Front of property

Blue Heron Seaside Inn

3.0 star property
9.8 out of 10, Exceptional, (25)
"This property was beautiful, comfortable and clean, centrally located but out of the main street crowds. Everything we wanted to do was within walking distance so it worked out well. We would go back in a minute!! Carol is the ultimate hostess, and serves an amazing breakfast!!!!"
Blue Heron Seaside Inn
The Chadwick Bed & Breakfast
Exterior

The Chadwick Bed & Breakfast

3.5 star property
9.8 out of 10, Exceptional, (48)
"Great location for seeing Portland. "
The Chadwick Bed & Breakfast
Kennebec Room - King Bed, Private Bath
Pet-friendly

Kennebec Room - King Bed, Private Bath

8.4 out of 10, Very Good, (5)
"What a lovely place. My wife and I were able to relax and recharge. The home and property are an experience themselves. Then the beach right here for long walks was so rejuvenating. Rachel our host was a picture of hospitality and breakfast was so yummy. Thanks for the loving care, just what we needed!"
Kennebec Room - King Bed, Private Bath
"SABINO" 1 Bdrm Suite
Pet-friendly

"SABINO" 1 Bdrm Suite

10.0 out of 10, Exceptional, (12)
"Will definitely stay again."
"SABINO" 1 Bdrm Suite
Lake View Suite - Large King, Ensuite Bath
Pet-friendly

Lake View Suite - Large King, Ensuite Bath

8.0 out of 10, Very Good, (1)
"Clean and enjoyable"
Lake View Suite - Large King, Ensuite Bath
Harpswell Inn
Exterior

Harpswell Inn

2.0 star property
10.0 out of 10, Exceptional, (3)
"Had a great stay. The owner was SO welcoming. The setting is beautiful!!!!"
Harpswell Inn
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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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.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 - Danforth Street.: 9 rooms. Situated 14.7 mi (23.7 km) from the heart of Bailey Island. The Orchard House & Cafe: 5 rooms. 10.6 mi (17 km) from the heart of downtown.Candlebay Inn: 6 rooms. Located 10.2 mi (16.4 km) from the core of Bailey Island. Enjoy the free full breakfast and in-room dining.
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 explore some things to do in town, Bailey Island Bridge and Land’s End Gift Shop are some notable sights to visit. You might put Ragged Island 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.