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Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

B&B in Bailey Island

Front of property - evening/night
Inn at St John Portland In-Town
Inn at St John Portland In-Town
2.5 star property
8.8 out of 10, Excellent, (1142)
"Enjoyed our stay."
United States
Heather
The price is AED 217
AED 236 total
includes taxes & fees
26 Oct - 27 Oct
Inn at St John Portland In-Town
Deluxe Room, 1 King Bed, Harbor View, Oceanfront | Water view
Harborage Inn on the Oceanfront
Harborage Inn on the Oceanfront
3.5 star property
9.4 out of 10, Exceptional, (216)
"Beautiful "
United States
Sherry
The price is AED 734
AED 800 total
includes taxes & fees
3 Nov - 4 Nov
Harborage Inn on the Oceanfront
Front of property - evening/night
The Orchard House & Cafe
The Orchard House & Cafe
3.0 star property
9.6 out of 10, Exceptional, (160)
"Very nice room in well renovated historic home. The hotel and grounds would be a nice spot for a small wedding. "
United States
Stacey
The price is AED 613
AED 668 total
includes taxes & fees
2 Nov - 3 Nov
The Orchard House & Cafe
Front of property
Harbour Towne Inn on the Waterfront
Harbour Towne Inn on the Waterfront
3.0 star property
9.6 out of 10, Exceptional, (75)
"The property was beautiful, breakfast was sumptuous, the area was scenic. "
United States
Glenn
The price is AED 819
AED 893 total
includes taxes & fees
26 Oct - 27 Oct
Harbour Towne Inn on the Waterfront
Exterior
The Kendall Inn
The Kendall Inn
3.5 star property
9.8 out of 10, Exceptional, (143)
"Quaint stay. Enjoyed our stay. "
United States
Linda
The price is AED 694
AED 757 total
includes taxes & fees
1 Nov - 2 Nov
The Kendall Inn
Baxter | 1 bedroom, premium bedding, individually decorated
Blind Tiger Portland - Danforth Street.
Blind Tiger Portland - Danforth Street.
3.5 star property
9.6 out of 10, Exceptional, (157)
" Beautiful historic building. The common areas and our room were stunning! Breakfast in the morning was great. Make sure to go to the widow’s walk in the evening for a view. "
United States
John
The price is AED 841
AED 917 total
includes taxes & fees
18 Nov - 19 Nov
Blind Tiger Portland - Danforth Street.
Porch
Candlebay Inn
Candlebay Inn
3.0 star property
9.6 out of 10, Exceptional, (455)
"Great location and hospitality."
United States
Brandon
The price is AED 566
AED 617 total
includes taxes & fees
2 Nov - 3 Nov
Candlebay Inn
Property entrance
Fleetwood House Bed & Breakfast
Fleetwood House Bed & Breakfast
3.0 star property
9.0 out of 10, Wonderful, (131)
"Lovely, comfortable stay! So welcoming and accommodating. We only stayed one night but will keep this in mind next time we are in the area :)"
United States
Sadie
The price is AED 841
AED 917 total
includes taxes & fees
26 Oct - 27 Oct
Fleetwood House Bed & Breakfast
Exterior
Benjamin F. Packard House
Benjamin F. Packard House
3.0 star property
10.0 out of 10, Exceptional, (102)
"Beautiful house, the breakfast food was amazing, and the owners were so personable and welcoming. "
United States
Jennifer
The price is AED 841
AED 917 total
includes taxes & fees
4 Nov - 5 Nov
Benjamin F. Packard House
Stovall | Living area
Blind Tiger Portland – Carleton Street
Blind Tiger Portland – Carleton Street
3.5 star property
9.6 out of 10, Exceptional, (117)
"Loved the place "
United States
Stephen
The price is AED 863
AED 941 total
includes taxes & fees
18 Nov - 19 Nov
Blind Tiger Portland – Carleton Street
Garden
Brewster House Bed & Breakfast
Brewster House Bed & Breakfast
4.0 star property
9.8 out of 10, Exceptional, (114)
"Wonderful hosts. Enjoyed quiet evening and lovely gourmet breakfast. Truly memorable stay. We look forward to returning in the future."
United States
Peter
The price is AED 1,135
AED 1,237 total
includes taxes & fees
25 Oct - 26 Oct
Brewster House Bed & Breakfast
Outdoor dining
The James Place Inn B&B
The James Place Inn B&B
3.5 star property
10.0 out of 10, Exceptional, (181)
"Wish we could have stayed longer. It has the ambiance of an older inn but the rooms are very clean and well maintained. "
United States
Melissa
The price is AED 959
AED 1,045 total
includes taxes & fees
2 Nov - 3 Nov
The James Place Inn B&B
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

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

10/10 Excellent
"Shuttle was easy and punctual. "
Erin 3-night trip
Posted 2 days ago
Portland Regency Hotel & Spa

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 – Carleton Street: 6 rooms. 15 mi (24.2 km) from the heart of downtown. Enjoy the unique décor and patio area. 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.