Search B&B in Bailey Island

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct
Inn at St John Portland In-Town
Classic building with a stone facade and commercial establishments on the ground floor.

Inn at St John Portland In-Town

2.5 star property
8.8 out of 10, Excellent, (1045)
"Quaint and fun old style place to stay. "
The price is HK$1,091
HK$1,189 total
includes taxes & fees
1 Sept - 2 Sept
Inn at St John Portland In-Town
Fleetwood House Bed & Breakfast
Step up to the charming Fleecwood House, featuring a traditional facade with a welcoming porch and beautiful tree-lined surroundings.

Fleetwood House Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (121)
"We had a great time! The breakfast was wonderful! "
The price is HK$1,798
HK$1,959 total
includes taxes & fees
12 Aug - 13 Aug
Fleetwood House Bed & Breakfast
Candlebay Inn
Welcome to Candlebay Inn, a charming hotel surrounded by lush greenery and a well-manicured lawn.

Candlebay Inn

3.0 star property
9.6 out of 10, Exceptional, (435)
"The Inn was great and the staff was very hospitable "
The price is HK$1,562
HK$1,703 total
includes taxes & fees
17 Aug - 18 Aug
Candlebay Inn
The Kendall Inn
Charming two-story house with a welcoming porch and a beautifully manicured lawn.

The Kendall Inn

3.5 star property
9.8 out of 10, Exceptional, (133)
"Quaint stay. Enjoyed our stay. "
The price is HK$1,653
HK$1,802 total
includes taxes & fees
12 Aug - 13 Aug
The Kendall Inn
The Orchard House & Cafe
Stylish entrance with a central door and potted evergreen trees.

The Orchard House & Cafe

3.0 star property
9.6 out of 10, Exceptional, (150)
"The place was perfect"
The price is HK$1,640
HK$1,788 total
includes taxes & fees
12 Aug - 13 Aug
The Orchard House & Cafe
Blind Tiger Portland - Danforth Street.
Relax in a serene room with a four-poster canopy bed, featuring a table for reading and a decorative vase.

Blind Tiger Portland - Danforth Street.

3.5 star property
9.6 out of 10, Exceptional, (149)
"Everything was wonderful, we highly recommend staying here to anyone considering it."
The price is HK$2,819
HK$3,073 total
includes taxes & fees
26 Aug - 27 Aug
Blind Tiger Portland - Danforth Street.
Blind Tiger Portland – Carleton Street
Relax in a stylish living room with a sofa, side table, and artwork, perfect for reading and unwinding.

Blind Tiger Portland – Carleton Street

3.5 star property
9.8 out of 10, Exceptional, (114)
"The Blind Tiger was a gem. It was convenient and private enough to enjoy with staff available 24/7 with and questions. The room, lobby and all areas were immaculate and brilliantly arranged. I would definitely go again!"
The price is HK$3,878
HK$4,227 total
includes taxes & fees
7 Sept - 8 Sept
Blind Tiger Portland – Carleton Street
Captain Sawyer's Bed & Breakfast
Enjoy a classic view from the large window, featuring a building with a green roof and a starfish decoration.

Captain Sawyer's Bed & Breakfast

3.0 star property
9.2 out of 10, Wonderful, (119)
"Comfortable bed, walkable, free parking, good breakfast, but the hosts were the best part. "
Captain Sawyer's Bed & Breakfast
The James Place Inn B&B
Enjoy a romantic meal for two on the deck, surrounded by the house's charming facade.

The James Place Inn B&B

3.5 star property
10.0 out of 10, Exceptional, (173)
"Location to the busy areas of Freeport is steps away from this quiet oasis. Very nice innkeepers and staff will be there to make your stay pleasant while allowing you the privacy of a hotel guest. We stayed one night on our way home from mid coastal Maine and enjoyed our stay. "
The price is HK$2,385
HK$2,599 total
includes taxes & fees
13 Aug - 14 Aug
The James Place Inn B&B
Harbour Towne Inn on the Waterfront
Stunning corner building with a turret and balcony, surrounded by lush greenery and symmetrical architecture.

Harbour Towne Inn on the Waterfront

3.0 star property
9.6 out of 10, Exceptional, (68)
"Very nice bed and breakfast, close to shopping."
The price is HK$3,010
HK$3,281 total
includes taxes & fees
11 Aug - 12 Aug
Harbour Towne Inn on the Waterfront
West End Inn
Enjoy the view from this cozy corner bay window with a porch and brick facade.

West End Inn

3.0 star property
9.6 out of 10, Exceptional, (90)
"Extremely cozy and clean, perfect bed and breakfast in the West End for those looking for walkable access to the Old Port and downtown as well as a quiet retreat at night in the historic West End District. "
West End Inn
Benjamin F. Packard House
Enjoy dining or socializing in this charming patio area with a small table and two chairs under a pergola with string lights.

Benjamin F. Packard House

3.0 star property
10.0 out of 10, Exceptional, (99)
"wonderful!!! great location, comfy bed, quiet and relaxing space, gorgeous decor, delicious breakfast."
The price is HK$1,955
HK$2,131 total
includes taxes & fees
14 Aug - 15 Aug
Benjamin F. Packard House
Harborage Inn on the Oceanfront
Enjoy serene views of the lake from this balcony with a bridge in the distance.

Harborage Inn on the Oceanfront

3.5 star property
9.4 out of 10, Exceptional, (208)
"Absolutely comfortable stay! Fresh and clean. Free breakfast choices every morning! Highly recommend!! Will plan to make future visits here!"
The price is HK$2,677
HK$2,918 total
includes taxes & fees
17 Aug - 18 Aug
Harborage Inn on the Oceanfront
Brewster House Bed & Breakfast
Escape to a serene garden oasis with a charming cottage nestled among vibrant flowers and lush greenery.

Brewster House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (112)
"Wonderful hosts. Enjoyed quiet evening and lovely gourmet breakfast. Truly memorable stay. We look forward to returning in the future."
The price is HK$2,347
HK$2,558 total
includes taxes & fees
13 Aug - 14 Aug
Brewster House Bed & Breakfast
"SABINO" 1 Bdrm Suite
Escape to a serene garden oasis with a charming thatched-roof pavilion surrounded by lush greenery and a tranquil body of water.

"SABINO" 1 Bdrm Suite

10.0 out of 10, Exceptional, (13)
"Will definitely stay again."
"SABINO" 1 Bdrm Suite
Stonehouse Manor -Popham Beach B&B - Pond Island Room
Experience the warmth of a traditional atmosphere, complete with a grand fireplace, ornate staircase, and elegant chandelier.

Stonehouse Manor -Popham Beach B&B - Pond Island Room

10.0 out of 10, Exceptional, (1)
"The place is quiet, breakfast was so good and Jane the host is a very kind, knowledgeable person. "
Stonehouse Manor -Popham Beach B&B - Pond Island Room
Blue Heron Seaside Inn
Step into the Blue Heron Seaside Inn's charming porch, adorned with lush flower baskets and a striped awning.

Blue Heron Seaside Inn

3.0 star property
9.8 out of 10, Exceptional, (25)
"This B&B is perfectly located and well run. The site Mgr is wonderful and serves an amazing daily breakfast. The room we had was spacious, quiet, and beautifully furnished. It is a very short walk to the center of Boothbay Harbor shopping and eating. My wife's favorite shop was only 5 doors away from the Blue Heron's front door. If we ever return to the Boothbay area we will definitely stay at the Blue Heron again."
Blue Heron Seaside Inn
Kennebec Room - King Bed, Private Bath
Experience traditional elegance in this beautifully designed space, featuring a grand fireplace, ornate staircase, and high ceilings.

Kennebec Room - King Bed, Private Bath

9.0 out of 10, Wonderful, (7)
"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
The Chadwick Bed & Breakfast
Terrace/patio

The Chadwick Bed & Breakfast

3.5 star property
9.8 out of 10, Exceptional, (48)
"Great getaway within Portland. The breakfast is first rate!"
The Chadwick Bed & Breakfast
Lake View Suite - Large King, Ensuite Bath
Cozy living area with a traditional fireplace, high ceiling, and large window offering a view of the outdoors.

Lake View Suite - Large King, Ensuite Bath

9.4 out of 10, Exceptional, (3)
"Clean and enjoyable"
Lake View Suite - Large King, Ensuite Bath
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.
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

Hyatt Place Portland Downtown - Old Port Square

Hyatt Place Portland Downtown - Old Port Square

10/10 Excellent
"Our only negative was the noise level from rooms above. The type of flooring conducts noise more easily than carpet. I do appreciate the ability to clean these floors over carpeting though."
Pamela 3-night trip
Posted 7 hours ago
Hyatt Place Portland Downtown - Old Port Square

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. Fleetwood House Bed & Breakfast: 3 rooms. 16.1 mi (25.9 km) from the city centre. Enjoy the free full breakfast and unique decor. The Orchard House & Cafe: 5 rooms. Situated 10.6 mi (17 km) from the heart of Bailey Island. Blind Tiger Portland - Danforth Street.: 9 rooms. 14.7 mi (23.7 km) from the city centre. Blind Tiger Portland – Carleton Street: 6 rooms. Located 15 mi (24.2 km) from the core of Bailey Island. Enjoy the local cuisine 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, Ragged Island and Mackerel Cove are some notable spots. You should put Bailey Island Bridge and Cobwork Bridge 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.