Search B&B in Bailey Island

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Compare 26 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, (1075)
"The whole building is very unique. It’s almost like a maze. It’s very bright there’s a lot of art in the hallways. The bathrooms are extremely clean."
The price is SAR 342
SAR 372 total
includes taxes & fees
24 Nov - 25 Nov
Inn at St John Portland In-Town
Blind Tiger Portland - Danforth Street.
Lobby sitting area

Blind Tiger Portland - Danforth Street.

3.5 star property
9.6 out of 10, Exceptional, (132)
"Great except for the billing. "
The price is SAR 858
SAR 935 total
includes taxes & fees
10 Dec - 11 Dec
Blind Tiger Portland - Danforth Street.
Candlebay Inn
Porch

Candlebay Inn

3.0 star property
9.6 out of 10, Exceptional, (418)
"Wonderful Bed & Breakfast"
The price is SAR 559
SAR 610 total
includes taxes & fees
24 Nov - 25 Nov
Candlebay Inn
Harborage Inn on the Oceanfront
Water view

Harborage Inn on the Oceanfront

3.5 star property
9.4 out of 10, Exceptional, (200)
"Inn mgrs Mark and Brooke were awesome. Accommodated all our needs. Inn was beautiful, relaxing, and quiet. Breakfast by Brooke was delicious every day. This was our first visit to Maine, and specifically Boothbay Harbor, and it definitely made a fantastic first impression on us about how great Mainers are. Will definitely plan more trips to Maine. "
The price is SAR 711
SAR 775 total
includes taxes & fees
4 Dec - 5 Dec
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 SAR 822
SAR 896 total
includes taxes & fees
24 Nov - 25 Nov
Fleetwood House Bed & Breakfast
Blind Tiger Portland – Carleton Street
Reception

Blind Tiger Portland – Carleton Street

3.5 star property
9.8 out of 10, Exceptional, (108)
"WOW! What an amazing hotel! We had such a beautiful stay and LOVED Portland. The room was so comfortable and quiet. Beautifully appointed too. As an interior designer, I kept taking pictures and videos of all the beautiful details. The hotel company left the most amazing list of restaurants and things to do and we’re so glad we took their advice. We found spots we would never have known about otherwise. The Japanese restaurant they recommend was OUT OF THIS WORLD!"
The price is SAR 948
SAR 1,034 total
includes taxes & fees
11 Dec - 12 Dec
Blind Tiger Portland – Carleton Street
The Orchard House & Cafe
Front of property

The Orchard House & Cafe

3.0 star property
9.6 out of 10, Exceptional, (142)
"It was a delightful experience "
The price is SAR 745
SAR 812 total
includes taxes & fees
1 Dec - 2 Dec
The Orchard House & Cafe
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, (63)
"Last minute find for us to spend the night. The breakfast was wonderful. Beautiful view of the harbor. Enjoyed sitting in the chairs down on the dock in the morning."
The price is SAR 1,103
SAR 1,202 total
includes taxes & fees
1 Dec - 2 Dec
Harbour Towne Inn on the Waterfront
West End Inn
Breakfast area

West End Inn

3.0 star property
9.6 out of 10, Exceptional, (88)
"Truly wonderful staff and space. The breakfasts offered are also phenomenal."
The price is SAR 860
SAR 937 total
includes taxes & fees
24 Nov - 25 Nov
West End Inn
The James Place Inn B&B
Front of property

The James Place Inn B&B

3.5 star property
10.0 out of 10, Exceptional, (171)
"This B and B was outstanding for attention to detail, immaculate condition and cleanliness. Their breakfast was delicious with a start of fresh fruit and scones, and a great breakfast burrito that day. A short walk to LLBean, it’s near all the attractions in Freeport. The hosts were very friendly and accommodating. It was a real pleasure to stay there!"
The price is SAR 774
SAR 844 total
includes taxes & fees
1 Dec - 2 Dec
The James Place Inn B&B
Benjamin F. Packard House
Front of property

Benjamin F. Packard House

3.0 star property
10.0 out of 10, Exceptional, (93)
"The first BnB we've experienced that emphasized recycling of paper, plastic, and toiletries. Thank you Mark, Amy and Picco for a memorable stay. Hope to see you again soon. "
The price is SAR 747
SAR 814 total
includes taxes & fees
22 Dec - 23 Dec
Benjamin F. Packard House
Captain Sawyer's Bed & Breakfast
Front of property

Captain Sawyer's Bed & Breakfast

3.0 star property
9.2 out of 10, Wonderful, (115)
"The inn keepers were very very nice and accommodating. Nice old historic bed and breakfast right in downtown Boothbay. Everything about this stay was excellent. "
Captain Sawyer's Bed & Breakfast
Brewster House Bed & Breakfast
Exterior

Brewster House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (110)
"Nice inn - a bit noisy as it's on a main street and I had a front facing room. "
The price is SAR 1,119
SAR 1,220 total
includes taxes & fees
24 Nov - 25 Nov
Brewster House Bed & Breakfast
The Chadwick Bed & Breakfast
View from room

The Chadwick Bed & Breakfast

3.5 star property
9.8 out of 10, Exceptional, (48)
"The Innkeepers were friendly and wonderful communicators. Breakfast was DELICIOUS! The rooms were cozy and the area was easy to commute on foot"
The Chadwick Bed & Breakfast
"SABINO" 1 Bdrm Suite
"Sabino Suite" King Bed, Sitting Area, South westerly exposure, water view

"SABINO" 1 Bdrm Suite

10.0 out of 10, Exceptional, (12)
"Charming old place. Close to beaches and great shopping. "
"SABINO" 1 Bdrm Suite
Kennebec Room - King Bed, Private Bath
Room

Kennebec Room - King Bed, Private Bath

8.4 out of 10, Very Good, (5)
"We had a very pleasant stay for two nights at the Stonehouse Manor late season at Popham Beach. Our room had a beautiful view of the mouth of the Kennebunk River. In the morning we lay in bed watching the sun rise on the autumn colored hillside by Fort Popham through the large bay window. It was quiet. We strolled the expansive grounds with our coffee admiring the botanical variation particularly the huge old copper beech in front of the manor. A homemade breakfast of Rachels blueberry...
Kennebec Room - King Bed, Private Bath
Harpswell Inn
Exterior

Harpswell Inn

2.0 star property
10.0 out of 10, Exceptional, (3)
"Nice country inn, beautiful views. best wishes for the new ownwers."
Harpswell Inn
Lake View Suite - Large King, Ensuite Bath
Master Suite with 4 poster King Size bed and comfortable seating & ensuite bath

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
The Kendall Inn
Exterior

The Kendall Inn

3.5 star property
9.8 out of 10, Exceptional, (121)
"What a fantastic stay!"
The price is SAR 756
SAR 824 total
includes taxes & fees
24 Nov - 25 Nov
The Kendall Inn
Blue Heron Seaside Inn
Room

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
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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Other property types in Bailey Island

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
THE GILLS GROUP has two additional cottages available for larger groups

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

10.0 out of 10, Exceptional, (99)
"This property is stunning, and the view is spectacular. If this were my house, I’d never leave! We had a fabulous time. "
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage

Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage

9.8 out of 10, Exceptional, (6)
"Overall this location is a great spot for those that dont need many amenities. There is no tv and no ac but the view and the breeze from the water make up for that! The space was clean and there was a grill plus Cooks Lobster house was a quick walk down the street! "
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist

Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist

10.0 out of 10, Exceptional, (35)
"What a great place! Located in the arts district, this refurbished brownstone has every modern convenience within walking distance of restaurants and museums. Windows on both sides of the apartment provide street views, one active and bustling, one quiet with a view of Casco Bay and sunrises. And the rooftop patio is a dream - we loved being part of Portland history with an up close view of the florist's ad mural!"
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
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.

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. Candlebay Inn: 6 rooms. 10.2 mi (16.4 km) from the heart of downtown. 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, April, March, and February, with each month seeing an average of 9 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.