Find a Bed and Breakfast in Bailey Island from CA $116

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Check prices for these dates

Next weekend
Feb 14 - Feb 16
In two weeks
Feb 21 - Feb 23
In one month
Mar 7 - Mar 9
In two months
Apr 4 - Apr 6

Browse Select Bailey Island B&B

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, (1031)
"Loved the victorian charm, and it was close to some great restaurants. It was also very clean, would love to stay again!"
The price is CA $116
CA $127 total
includes taxes & fees
Feb 4 - Feb 5
Inn at St John Portland In-Town
Blind Tiger Portland - Danforth Street.
Baxter

Blind Tiger Portland - Danforth Street.

3.5 star property
9.6 out of 10, Exceptional, (140)
"Very interesting property. Well maintained/restored property that is 200 years old. Comfortable room and great common areas. Staff was friendly and accomodating."
The price is CA $281
CA $306 total
includes taxes & fees
Feb 10 - Feb 11
Blind Tiger Portland - Danforth Street.
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 CA $333
CA $363 total
includes taxes & fees
Feb 4 - Feb 5
Fleetwood House Bed & Breakfast
Candlebay Inn
Porch

Candlebay Inn

3.0 star property
9.6 out of 10, Exceptional, (420)
"Room was equipped with sprinklers and other fire safety items. Owner graciously welcomed us."
The price is CA $217
CA $236 total
includes taxes & fees
Feb 4 - Feb 5
Candlebay Inn
Blind Tiger Portland – Carleton Street
Stovall | Living area

Blind Tiger Portland – Carleton Street

3.5 star property
9.8 out of 10, Exceptional, (109)
"Charming place to stay. "
The price is CA $331
CA $361 total
includes taxes & fees
Feb 17 - Feb 18
Blind Tiger Portland – Carleton Street
West End Inn
Classic Room, 1 King Bed, City View

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 CA $231
CA $252 total
includes taxes & fees
Feb 4 - Feb 5
West End Inn
Benjamin F. Packard House
Exterior

Benjamin F. Packard House

3.0 star property
10.0 out of 10, Exceptional, (94)
"Beautiful inn! Very comfortable and clean. The innkeepers Amy and Mark were super nice. Breakfast was absolutely delicious. We will definitely be back! "
The price is CA $333
CA $363 total
includes taxes & fees
Feb 14 - Feb 15
Benjamin F. Packard House
Harborage Inn on the Oceanfront
Deluxe Room, 1 King Bed, Harbour View, Oceanfront | Water view

Harborage Inn on the Oceanfront

3.5 star property
9.4 out of 10, Exceptional, (203)
" Great location to walk into town . Very quiet . Would stay again . "
The price is CA $301
CA $328 total
includes taxes & fees
Feb 19 - Feb 20
Harborage Inn on the Oceanfront
The Orchard House & Cafe
Front of property - evening/night

The Orchard House & Cafe

3.0 star property
9.6 out of 10, Exceptional, (142)
"It was a delightful experience "
The price is CA $243
CA $265 total
includes taxes & fees
Feb 9 - Feb 10
The Orchard House & Cafe
The Chadwick Bed & Breakfast
Exterior

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
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 CA $259
CA $283 total
includes taxes & fees
Feb 4 - Feb 5
The Kendall Inn
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 CA $318
CA $347 total
includes taxes & fees
Feb 4 - Feb 5
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)
"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 CA $300
CA $327 total
includes taxes & fees
Feb 4 - Feb 5
The James Place Inn B&B
Captain Sawyer's Bed & Breakfast
Heritage Room

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
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."
Harbour Towne Inn on the Waterfront
Kennebec Room - King Bed, Private Bath
Pet-friendly

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
"SABINO" 1 Bdrm Suite
Pet-friendly

"SABINO" 1 Bdrm Suite

10.0 out of 10, Exceptional, (12)
"Charming old place. Close to beaches and great shopping. "
"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
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
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
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
Terrace/patio

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
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
Exterior

Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

9.8 out of 10, Exceptional, (68)
"Great house very comfortable and well appointed. Very roomy for our entire family. Nice to have en suite bathrooms with all the bedrooms. The host was very good with communication. Located on a busy road and the driveway is on a curve which made it a little challenging entering and exiting the property. "
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
The Weldon Hotel
Deluxe Suite, 2 Bedrooms | Private kitchen

The Weldon Hotel

4.0 star property
9.4 out of 10, Exceptional, (35)
"The full kitchen and appliances were perfect for my stay so that I did not have to eat out while I was there and save money "
The price is CA $222
CA $243 total
includes taxes & fees
Feb 23 - Feb 24
The Weldon Hotel
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.Blind Tiger Portland - Danforth Street.: 9 rooms. 14.7 mi (23.7 km) from the downtown core. Fleetwood House Bed & Breakfast: 3 rooms. Situated 16.1 mi (25.9 km) from the heart of Bailey Island. Enjoy the free full breakfast and unique décor. Blind Tiger Portland – Carleton Street: 6 rooms. 15 mi (24.2 km) from the heart of downtown. Enjoy the unique décor and in-room fireplace.
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.