Search B&B in Bailey Island

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 25 B&B in Bailey Island with updated reviews, rates, and availability.

Inn at St John Portland In-Town

2.5 star property
8.8 out of 10, Excellent, (1046)
"I enjoyed my third visit here. I was, however, very disappointed Friday evening by the young man at the desk not breaking a ten bill. He made like he was checking BUT I fully doubt he actually checked. Very disappointing. "
The price is AED 294
AED 320 total
includes taxes & fees
23 Dec - 24 Dec
Inn at St John Portland In-Town

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 AED 547
AED 597 total
includes taxes & fees
23 Dec - 24 Dec
Candlebay Inn

Blind Tiger Portland - Danforth Street.

3.5 star property
9.6 out of 10, Exceptional, (136)
"Blind Tiger on Danforth was perfect locale for San overnight in Portland. Walkable to Old Port, yet quiet & relaxing place to spend some time quiet in between all of the activities;)"
The price is AED 709
AED 773 total
includes taxes & fees
12 Jan - 13 January 2025
Blind Tiger Portland - Danforth Street.

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 AED 694
AED 757 total
includes taxes & fees
29 Dec - 30 Dec
West End Inn

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! "
Benjamin F. Packard House

Harborage Inn on the Oceanfront

3.5 star property
9.4 out of 10, Exceptional, (202)
" Great location to walk into town . Very quiet . Would stay again . "
The price is AED 696
AED 758 total
includes taxes & fees
24 Dec - 25 Dec
Harborage Inn on the Oceanfront

Blind Tiger Portland – Carleton Street

3.5 star property
9.8 out of 10, Exceptional, (109)
"Charming place to stay. "
The price is AED 874
AED 953 total
includes taxes & fees
7 Jan - 8 January 2025
Blind Tiger Portland – Carleton Street

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 804
AED 877 total
includes taxes & fees
23 Dec - 24 Dec
Fleetwood House Bed & Breakfast

The Orchard House & Cafe

3.0 star property
9.6 out of 10, Exceptional, (142)
"It was a delightful experience "
The price is AED 613
AED 668 total
includes taxes & fees
2 Jan - 3 January 2025
The Orchard House & Cafe

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 AED 1,079
AED 1,176 total
includes taxes & fees
23 Dec - 24 Dec
Harbour Towne Inn on the Waterfront

The Kendall Inn

3.5 star property
9.8 out of 10, Exceptional, (121)
"What a fantastic stay!"
The price is AED 655
AED 714 total
includes taxes & fees
2 Jan - 3 January 2025
The Kendall Inn

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 AED 757
AED 825 total
includes taxes & fees
28 Dec - 29 Dec
The James Place Inn B&B

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

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

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 AED 768
AED 837 total
includes taxes & fees
3 Jan - 4 January 2025
Brewster House Bed & Breakfast

"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

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

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

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

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.
Don't see what you're looking for?
See all available properties in Bailey Island
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Bailey Island

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

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

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

9.2 out of 10, Wonderful, (30)
"We had a great time. Nate made check in/check out very easy and the location is great. Would recommend staying here!"
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
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. Candlebay Inn: 6 rooms. Situated 10.2 mi (16.4 km) from the heart of Bailey Island. Enjoy the free full breakfast and in-room dining. Fleetwood House Bed & Breakfast: 3 rooms. 16.1 mi (25.9 km) from the heart of downtown. Enjoy the free full breakfast and unique décor.
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 Cobwork Bridge are some notable sights to visit. You might put Land’s End Gift Shop and Ragged Island 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.