A rocky shoreline with a boat, a house, and a forest in the background.

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Check prices for these dates

Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct
In one month
23 Oct - 25 Oct
In two months
20 Nov - 22 Nov

Our top choices for Bailey Island bed & breakfast

Porch

1. Candlebay Inn

Candlebay Inn
3.0 star property
Freeport
9.6 out of 10, Exceptional, (489 reviews)
"Great location, quiet room, great breakfast......"
United States
Keith
The price is AED 641
AED 699 total
includes taxes & fees
28 Sep - 29 Sep
Candlebay Inn
Front of property - evening/night

2. The Orchard House: Inn & Cafe

The Orchard House: Inn & Cafe
3.0 star property
Freeport
9.6 out of 10, Exceptional, (181 reviews)
"Amazing stay in a perfect location! Would absolutely recommend to family and friends and will likely stay again!"
United States
Megan
The price is AED 821
AED 895 total
includes taxes & fees
23 Sep - 24 Sep
The Orchard House: Inn & Cafe
Interior entrance

3. The Kendall Inn

The Kendall Inn
3.5 star property
Freeport
9.8 out of 10, Exceptional, (162 reviews)
"The room was lovely and comfortable, including easy-to-adjust air conditioning. Breakfast was delicious as were the homemade cookies available each evening. Coffee and tea were available all the time."
United States
Kenneth and
The price is AED 836
AED 911 total
includes taxes & fees
23 Sep - 24 Sep
The Kendall Inn
Front of property

4. The Nicholson Inn

The Nicholson Inn
3.0 star property
Freeport
10.0 out of 10, Exceptional, (2 reviews)
"The owners were amazing and so kind. The location is perfect, and the amenities feel so hoy and great."
United States
Meaghan
The price is AED 1,035
AED 1,128 total
includes taxes & fees
28 Sep - 29 Sep
The Nicholson Inn
Front of property - evening/night

5. Inn at St John Portland In-Town

Inn at St John Portland In-Town
2.5 star property
Valley Street
8.6 out of 10, Excellent, (1,122 reviews)
"Great place to stay, affordable,clean with walking access to to port area!"
United States
Steve Robert
The price is AED 466
AED 507 total
includes taxes & fees
28 Sep - 29 Sep
Inn at St John Portland In-Town
Front of property

6. The James Place Inn B&B

The James Place Inn B&B
3.5 star property
Freeport
10.0 out of 10, Exceptional, (193 reviews)
"Sean was amazingly helpful and friendly. The house itself is so well maintained, and the blue room was adorable. Loved the fact that we were within walking distance of all the shops. Would definitely recommend and will plan on staying again the next time we’re in town."
United States
Kim
The price is AED 839
AED 914 total
includes taxes & fees
5 Oct - 6 Oct
The James Place Inn B&B
Exterior detail

7. Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast
3.0 star property
Rosemont
9.0 out of 10, Wonderful, (147 reviews)
"Breakfast was wonderful!"
United States
Karen
The price is AED 841
AED 954 total
includes taxes & fees
23 Sep - 24 Sep
Fleetwood House Bed & Breakfast
Exterior

8. West End Collection at 146 Pine

West End Collection at 146 Pine
3.0 star property
West End
9.6 out of 10, Exceptional, (98 reviews)
"It was wonderful staying. Beautiful old house with all amenities and"
United States
Svetlana
The price is AED 1,197
AED 1,305 total
includes taxes & fees
13 Oct - 14 Oct
West End Collection at 146 Pine
View from property

9. The Squire Tarbox Inn

The Squire Tarbox Inn
2.5 star property
Wiscasset
9.6 out of 10, Exceptional, (23 reviews)
"Lovely spot."
United States
Oona
The price is AED 1,031
AED 1,226 total
includes taxes & fees
16 Oct - 17 Oct
The Squire Tarbox Inn
Deluxe Room, 1 King Bed, Harbor View, Oceanfront | Water view

10. Harborage Inn on the Oceanfront

Harborage Inn on the Oceanfront
3.5 star property
Boothbay Harbor
9.6 out of 10, Exceptional, (235 reviews)
"Good location."
United States
Abeer
The price is AED 1,209
AED 1,318 total
includes taxes & fees
13 Oct - 14 Oct
Harborage Inn on the Oceanfront
Books

11. Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street
3.5 star property
West End
9.6 out of 10, Exceptional, (132 reviews)
"Beautiful place"
United States
Samuel
The price is AED 1,380
AED 1,505 total
includes taxes & fees
29 Sep - 30 Sep
Blind Tiger Portland – Carleton Street
Baxter | Premium bedding, iron/ironing board, WiFi (free), individually decorated

12. Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.
3.5 star property
West End
9.6 out of 10, Exceptional, (193 reviews)
"Place was charming and quirky. Very comfortable and well located."
United States
Mary
The price is AED 1,693
AED 1,846 total
includes taxes & fees
27 Sep - 28 Sep
Blind Tiger Portland - Danforth Street.
Exterior

13. Boothbay Harbor 2-Story Suite - Room 12 at AQ Inn - Balconies, Harbor View

Boothbay Harbor 2-Story Suite - Room 12 at AQ Inn - Balconies, Harbor View
Boothbay Harbor
10.0 out of 10, Exceptional, (5 reviews)
The price is AED 1,043
AED 1,301 total
includes taxes & fees
23 Sep - 24 Sep
Boothbay Harbor 2-Story Suite - Room 12 at AQ Inn - Balconies, Harbor View
Terrace/patio

14. Boothbay Harbor King Suite - Room 7 at Greenleaf Inn - Balcony, Harbor Views!

Boothbay Harbor King Suite - Room 7 at Greenleaf Inn - Balcony, Harbor Views!
Boothbay Harbor
10.0 out of 10, Exceptional, (3 reviews)
"Loved the amenities and views! Great location… walking distance to everything. The staff was very friendly and accommodating!"
United States
Melissa
The price is AED 944
AED 1,177 total
includes taxes & fees
27 Sep - 28 Sep
Boothbay Harbor King Suite - Room 7 at Greenleaf Inn - Balcony, Harbor Views!
Fireplace, offices

15. Experience the History of Portland - The Hope Island Room

Experience the History of Portland - The Hope Island Room
West End
The price is AED 992
AED 1,173 total
includes taxes & fees
27 Sep - 28 Sep
Experience the History of Portland - The Hope Island Room
Property grounds

16. Boothbay Harbor Penthouse Suite - Room 15 at AQ Inn - Fireplace, Ocean View

Boothbay Harbor Penthouse Suite - Room 15 at AQ Inn - Fireplace, Ocean View
Boothbay Harbor
9.8 out of 10, Exceptional, (9 reviews)
"Gracious and welcoming host, the property is all about the view. Nice relaxing get away. Beautiful ocean view with peace and quiet."
United States
Harrison S.
The price is AED 1,098
AED 1,361 total
includes taxes & fees
5 Oct - 6 Oct
Boothbay Harbor Penthouse Suite - Room 15 at AQ Inn - Fireplace, Ocean View
Smart TV, fireplace, books

17. Boothbay Harbor King Suite - Room 2 at Greenleaf Inn - Balcony, Harbor Views!

Boothbay Harbor King Suite - Room 2 at Greenleaf Inn - Balcony, Harbor Views!
Boothbay Harbor
10.0 out of 10, Exceptional, (1 review)
"The property was amazing! The staff are very helpful. This wasn't a very relaxing and enjoyable stay. We definitely would come back"
United States
Robert S.
The price is AED 1,006
AED 1,249 total
includes taxes & fees
15 Oct - 16 Oct
Boothbay Harbor King Suite - Room 2 at Greenleaf Inn - Balcony, Harbor Views!
Property grounds

18. Boothbay Harbor - Room 10 at Greenleaf Inn - Balcony, Harbor Views!

Boothbay Harbor - Room 10 at Greenleaf Inn - Balcony, Harbor Views!
Boothbay Harbor
10.0 out of 10, Exceptional, (1 review)
"We had such a great time at The Greenleaf. Jersey is an incredible host and will make sure your visit is amazing."
United States
Karen G.
The price is AED 871
AED 1,037 total
includes taxes & fees
24 Sep - 25 Sep
Boothbay Harbor - Room 10 at Greenleaf Inn - Balcony, Harbor Views!
Exterior

19. Boothbay Harbor King Suite - Room 11 at AQ Inn - Balcony, Fireplace, Harbor View

Boothbay Harbor King Suite - Room 11 at AQ Inn - Balcony, Fireplace, Harbor View
Boothbay Harbor
10.0 out of 10, Exceptional, (2 reviews)
"The service and attention was above and beyond and you could not ask for a better location. Five stars, hands down."
United States
Robbyn G.
The price is AED 959
AED 1,197 total
includes taxes & fees
27 Sep - 28 Sep
Boothbay Harbor King Suite - Room 11 at AQ Inn - Balcony, Fireplace, Harbor View
Exterior

20. Boothbay Harbor King Suite - Room 16 at AQ Inn

Boothbay Harbor King Suite - Room 16 at AQ Inn
Boothbay Harbor
10.0 out of 10, Exceptional, (4 reviews)
"Great location. Shared spaces were comfortable and had beautiful harbor views. Very nice Inn. Would definitely stay here again."
United States
Rhonda L.
The price is AED 768
AED 957 total
includes taxes & fees
30 Sep - 1 Oct
Boothbay Harbor King Suite - Room 16 at AQ 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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Top Bailey Island Hotel Reviews

Comfort Inn South Portland Airport

Comfort Inn South Portland Airport

8/10 Good
"No other comments"
Colleen 1-night trip
Posted 3 hours ago
Comfort Inn South Portland Airport

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. The Orchard House: Inn & Cafe: 5 rooms. Situated 10.6 mi (17 km) from the heart of Bailey Island. Blind Tiger Portland – Carleton Street: 6 rooms. 15 mi (24.2 km) from the heart of downtown. Enjoy the unique décor and patio area. Fleetwood House Bed & Breakfast: 3 rooms. Located 16.1 mi (25.9 km) from the core of Bailey Island. 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 spend some time in the great outdoors, Mackerel Cove and Ragged Island 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.

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