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Check prices for these dates

Next weekend
5 Sep - 7 Sep
In two weeks
12 Sep - 14 Sep
In one month
26 Sep - 28 Sep
In two months
24 Oct - 26 Oct

B&B in Bailey Island

Our top choices for Bailey Island bed & breakfast

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, (1072)
"The tub with jets was very nice. Staff was very courteous and helpful."
The price is SAR 522
SAR 569 total
includes taxes & fees
1 Sep - 2 Sep
Inn at St John Portland In-Town
Fleetwood House Bed & Breakfast
Property entrance

Fleetwood House Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (125)
"The breakfasts and friendly conversations were amazing. We thoroughly enjoyed our stay at the Fleetwood Bed and Breakfast "
The price is SAR 859
SAR 937 total
includes taxes & fees
1 Sep - 2 Sep
Fleetwood House Bed & Breakfast
Blind Tiger Portland - Danforth Street.
Baxter | 1 bedroom, premium bedding, individually decorated

Blind Tiger Portland - Danforth Street.

3.5 star property
9.6 out of 10, Exceptional, (150)
"Everything was wonderful, we highly recommend staying here to anyone considering it."
The price is SAR 1,497
SAR 1,632 total
includes taxes & fees
1 Sep - 2 Sep
Blind Tiger Portland - Danforth Street.
Candlebay Inn
Porch

Candlebay Inn

3.0 star property
9.6 out of 10, Exceptional, (441)
"Great location and hospitality."
The price is SAR 747
SAR 814 total
includes taxes & fees
2 Sep - 3 Sep
Candlebay Inn
Blind Tiger Portland – Carleton Street
Stovall | Living area | Fireplace

Blind Tiger Portland – Carleton Street

3.5 star property
9.8 out of 10, Exceptional, (115)
"Loved the place "
The price is SAR 1,540
SAR 1,679 total
includes taxes & fees
9 Sep - 10 Sep
Blind Tiger Portland – Carleton Street
The Orchard House & Cafe
Front of property - evening/night

The Orchard House & Cafe

3.0 star property
9.6 out of 10, Exceptional, (154)
"Lovely facility! We enjoyed the ice cream."
The price is SAR 784
SAR 855 total
includes taxes & fees
31 Aug - 1 Sep
The Orchard House & Cafe
The Kendall Inn
Exterior

The Kendall Inn

3.5 star property
9.8 out of 10, Exceptional, (135)
"Quaint stay. Enjoyed our stay. "
The price is SAR 790
SAR 861 total
includes taxes & fees
11 Sep - 12 Sep
The Kendall Inn
Benjamin F. Packard House
Exterior

Benjamin F. Packard House

3.0 star property
10.0 out of 10, Exceptional, (100)
"Beautiful house, the breakfast food was amazing, and the owners were so personable and welcoming. "
The price is SAR 934
SAR 1,018 total
includes taxes & fees
29 Sep - 30 Sep
Benjamin F. Packard House
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, (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
Outdoor dining

The James Place Inn B&B

3.5 star property
10.0 out of 10, Exceptional, (177)
"Great place. Comfortable and welcoming. Great proprietors and great location. "
The price is SAR 1,140
SAR 1,242 total
includes taxes & fees
31 Aug - 1 Sep
The James Place Inn B&B
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, (71)
"Very nice bed and breakfast, close to shopping."
The price is SAR 1,147
SAR 1,250 total
includes taxes & fees
31 Aug - 1 Sep
Harbour Towne Inn on the Waterfront
Brewster House Bed & Breakfast
Garden

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 SAR 1,122
SAR 1,223 total
includes taxes & fees
7 Sep - 8 Sep
Brewster House Bed & Breakfast
West End Inn
Exterior

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
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, (210)
"Enjoyed staying here and electric was wonderful. Loved the made to order breakfast that we ate out on the deck."
The price is SAR 1,103
SAR 1,202 total
includes taxes & fees
31 Aug - 1 Sep
Harborage Inn on the Oceanfront
Blue Heron Seaside Inn
Garden

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

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
"SABINO" 1 Bdrm Suite
Property grounds

"SABINO" 1 Bdrm Suite

10.0 out of 10, Exceptional, (14)
"Will definitely stay again."
"SABINO" 1 Bdrm Suite
Lake View Suite - Large King, Ensuite Bath
Interior

Lake View Suite - Large King, Ensuite Bath

9.4 out of 10, Exceptional, (3)
"Clean and enjoyable"
Lake View Suite - Large King, Ensuite Bath
Kennebec Room - King Bed, Private Bath
Interior

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
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

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. 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 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 spend some time in the great outdoors, Ragged Island and Mackerel Cove are some notable spots. You might 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?
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.