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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
18 Apr - 20 Apr
In two weeks
25 Apr - 27 Apr
In one month
9 May - 11 May
In two months
6 Jun - 8 Jun

Compare 30 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, (1018)
"I’ve stayed at the Inn on St John many times. I have a long commute from home to Portland. I stay when the weather is bad and the travel is dangerous. I like to stay at the inn because the it very affordable, comfortable and very easy to check in, find food nearby and relax in my room. I’ve stayed in many of the rooms large and small and I’ve never had a bad night. Staff are super friendly. The parking is easy. It s also a nostalgic place as I grew up in Portland and My dad was friends with the...
The price is AED 294
AED 320 total
includes taxes & fees
27 Apr - 28 Apr
Inn at St John Portland In-Town
Blind Tiger Portland - Danforth Street.
Baxter | Premium bedding, individually decorated, individually furnished

Blind Tiger Portland - Danforth Street.

3.5 star property
9.6 out of 10, Exceptional, (143)
"Love The Blind Tiger. Fantastic accommodations, lovely staff. Can't wait to go back!"
The price is AED 1,022
AED 1,114 total
includes taxes & fees
14 Apr - 15 Apr
Blind Tiger Portland - Danforth Street.
Blind Tiger Portland – Carleton Street
Stovall | Living area | Fireplace

Blind Tiger Portland – Carleton Street

3.5 star property
9.8 out of 10, Exceptional, (110)
"One of the best hotel/bnb experiences I’ve had in my past year of travels. Would recommend to anyone going to Maine. "
The price is AED 893
AED 973 total
includes taxes & fees
23 Apr - 24 Apr
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, (142)
"It was a delightful experience "
The price is AED 613
AED 668 total
includes taxes & fees
14 Apr - 15 Apr
The Orchard House & Cafe
West End Inn
Classic Room, 1 King Bed, City View | Individually decorated, individually furnished, iron/ironing board

West End Inn

3.0 star property
9.6 out of 10, Exceptional, (89)
"Beautiful building, great location and the breakfast was amazing!! "
The price is AED 694
AED 757 total
includes taxes & fees
14 Apr - 15 Apr
West End Inn
The Kendall Inn
Exterior

The Kendall Inn

3.5 star property
9.8 out of 10, Exceptional, (123)
"This bed and breakfast was absolutely charming. The common space was well equipped with all types of entertainment, puzzles, games, tea/coffee, and a self service honor system minibar. The full breakfast was delicious with plenty of options and the hosts seem to really enjoy sharing their home. The bedroom and bathroom were spotless and comfortable. We will definitely recommend this bed and breakfast."
The price is AED 607
AED 661 total
includes taxes & fees
14 Apr - 15 Apr
The Kendall Inn
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 AED 566
AED 617 total
includes taxes & fees
14 Apr - 15 Apr
Candlebay 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 AED 841
AED 917 total
includes taxes & fees
17 Apr - 18 Apr
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, (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
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 AED 841
AED 917 total
includes taxes & fees
14 Apr - 15 Apr
Fleetwood House Bed & Breakfast
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, (206)
"Absolutely comfortable stay! Fresh and clean. Free breakfast choices every morning! Highly recommend!! Will plan to make future visits here!"
The price is AED 609
AED 664 total
includes taxes & fees
14 Apr - 15 Apr
Harborage Inn on the Oceanfront
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 AED 959
AED 1,045 total
includes taxes & fees
14 Apr - 15 Apr
The James Place Inn B&B
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 AED 804
AED 877 total
includes taxes & fees
14 Apr - 15 Apr
Brewster House 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."
The price is AED 776
AED 846 total
includes taxes & fees
14 Apr - 15 Apr
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
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
"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.
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
Sign in
Sign up, it's free

Other property types in Bailey Island

Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage
Property grounds

Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage

9.4 out of 10, Exceptional, (16)
"Loved the location."
Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage
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
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
On the beach

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

10.0 out of 10, Exceptional, (212)
"We had a peaceful time at this home. It served as a home base for exploring. When my daughter left her most priced possession, her stuffed otter, the lovely hosts found it and shipped it back to us. We're so grateful for the thoughtfulness. "
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
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. West End Inn: 6 rooms. 15.1 mi (24.4 km) from the heart of downtown. Enjoy the local cuisine breakfast and deli. Blind Tiger Portland – Carleton Street: 6 rooms. Located 15 mi (24.2 km) from the core of Bailey Island. 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.