Search B&B in Bailey Island

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Compare 27 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
9.0 out of 10, Wonderful, (1002)
"The people working at the hotel were excellent. There was someone at the desk 24 hours, including to let guests in after hours. I especially appreciated the afternoon cookies and having real plates and cups for the included breakfast. The property is listed as having off street parking but the lot is too small for all of the guests and some must park on the street. The feeling was definitely vintage European with the more economical rooms having private or shared bathrooms across the hall from...
The price is AED 547
AED 597 total
includes taxes & fees
24 Jun - 25 Jun
Inn at St John Portland In-Town
The Orchard House & Cafe
Front of property
The Orchard House & Cafe
3.0 star property
9.6 out of 10, Exceptional, (103)
"Bill has a beautiful property. The rooms are immaculate- clean, charming decor, lovely breakfast options in the morning, and you may be greeted on the property by his gorgeous and friendly yellow lab! He made us feel right at home, the Café is still under renovation but we hope he is able to open soon and wish him all the success. We will be returning to stay again. "
The price is AED 806
AED 879 total
includes taxes & fees
23 Jun - 24 Jun
The Orchard House & Cafe
Blind Tiger Portland - Danforth Street.
Lobby sitting area
Blind Tiger Portland - Danforth Street.
3.5 star property
9.6 out of 10, Exceptional, (116)
"Beautiful Victorian home with a great re-decoration. Very few amenities beyond breakfast. About a 15 minute walk to the Old Port. "
The price is AED 1,770
AED 1,930 total
includes taxes & fees
27 Jun - 28 Jun
Blind Tiger Portland - Danforth Street.
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Fleetwood House Bed & Breakfast
Property entrance
Fleetwood House Bed & Breakfast
3.0 star property
8.8 out of 10, Excellent, (99)
"This is a lovely, quaint, family run B&B. Highly recommended."
The price is AED 804
AED 914 total
includes taxes & fees
23 Jun - 24 Jun
Fleetwood House Bed & Breakfast
Candlebay Inn
Porch
Candlebay Inn
3.0 star property
9.6 out of 10, Exceptional, (382)
"A great bed and breakfast place to stay in Freeport, ME. "
The price is AED 713
AED 777 total
includes taxes & fees
1 Jul - 2 Jul
Candlebay Inn
West End Inn
Breakfast area
West End Inn
3.0 star property
9.6 out of 10, Exceptional, (76)
"We stayed for a get a way weekend . Breakfast each morning was wonderful. Plenty of parking right in front of inn . We walked all over town. It was the weekend of the eclipse and we did not have glasses but Milan so graciously gave us extras he had . Wonderful host "
The price is AED 1,466
AED 1,597 total
includes taxes & fees
2 Jul - 3 Jul
West End Inn
The James Place Inn B&B
Front of property
The James Place Inn B&B
3.5 star property
10.0 out of 10, Exceptional, (165)
"I had a lovely stay at the James Inn; the hosts were great and the breakfast was delicious!! Anne"
The price is AED 1,071
AED 1,167 total
includes taxes & fees
23 Jun - 24 Jun
The James Place Inn B&B
Captain Sawyer's Bed & Breakfast
Front of property
Captain Sawyer's Bed & Breakfast
3.0 star property
9.2 out of 10, Wonderful, (104)
"Very clean, food was delicious, owners were kind and helpful."
Captain Sawyer's Bed & Breakfast
Harborage Inn on the Oceanfront
Water view
Harborage Inn on the Oceanfront
3.5 star property
9.4 out of 10, Exceptional, (189)
"Lovely location, room was great, bed comfy and service fantastic!"
The price is AED 1,174
AED 1,280 total
includes taxes & fees
1 Jul - 2 Jul
Harborage Inn on the Oceanfront
Blind Tiger Portland – Carleton Street
Reception
Blind Tiger Portland – Carleton Street
3.5 star property
9.8 out of 10, Exceptional, (99)
"Rooms were absolutely beautiful. Great breakfast and lots of thoughtful touches including free snack bar, board games and local recommendations. Highly recommend!"
The price is AED 1,332
AED 1,452 total
includes taxes & fees
15 Jul - 16 Jul
Blind Tiger Portland – Carleton Street
Coveside Bed & Breakfast
Front of property - evening/night
Coveside Bed & Breakfast
4.0 star property
9.8 out of 10, Exceptional, (25)
"Amazing place, great breakfast. Peaceful, beautiful, charming. All the things you’re looking for in a B&B"
The price is AED 1,337
AED 1,457 total
includes taxes & fees
21 Jun - 22 Jun
Coveside Bed & Breakfast
Benjamin F. Packard House
Front of property
Benjamin F. Packard House
3.0 star property
10.0 out of 10, Exceptional, (79)
"wonderful traditional house in a perfect location. homemade breakfast was the best! Thanks Amy. "
The price is AED 878
AED 957 total
includes taxes & fees
23 Jun - 24 Jun
Benjamin F. Packard House
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, (36)
"This place is really beautiful. The garden is absolutely amazing! There are huge flower arrangements everywhere and I love it. It's a 5 minute walksuper to shopping and all the restaurants. "
The price is AED 776
AED 846 total
includes taxes & fees
22 Jun - 23 Jun
Harbour Towne Inn on the Waterfront
"SABINO" 1 Bdrm Suite
"Sabino Suite" King Bed, Sitting Area, South westerly exposure, water view
"SABINO" 1 Bdrm Suite
9.8 out of 10, Exceptional, (6)
"It was absolutely amazing. Gorgeous grounds and surroundings. The host Jane is wonderful. Her cooking is most delicious. Most tranquil vacation!"
"SABINO" 1 Bdrm Suite
The Chadwick Bed & Breakfast
View from room
The Chadwick Bed & Breakfast
3.5 star property
9.8 out of 10, Exceptional, (39)
"Great getaway within Portland. The breakfast is first rate!"
The price is AED 1,098
AED 1,197 total
includes taxes & fees
26 Jun - 27 Jun
The Chadwick Bed & Breakfast
Brewster House Bed & Breakfast
Exterior
Brewster House Bed & Breakfast
4.0 star property
9.8 out of 10, Exceptional, (105)
"The breakfasts are to die for. Freeport is a lovely place and easy to walk into from Brewster’s. Kelleigh and Dave are so welcoming. Would love to go back."
The price is AED 1,095
AED 1,193 total
includes taxes & fees
23 Jun - 24 Jun
Brewster House Bed & Breakfast
Guest room with private bath and gourmet breakfast served daily
Exterior
Guest room with private bath and gourmet breakfast served daily
10.0 out of 10, Exceptional, (4)
"Book with the property (online or call) to avoid extra charges! John and Loretta are amazing people and inn keepers. The breakfast is delicious and the house itself is styled as it would have been almost 100 years ago. 10/10, we will be back! Thank you!"
Guest room with private bath and gourmet breakfast served daily
Charming rm w/king bed, w/sm ensuite w/shw. Sitting area, writing desk+chair.
Room
Charming rm w/king bed, w/sm ensuite w/shw. Sitting area, writing desk+chair.
6.0 out of 10, (2)
"The house is very beautiful and lovingly maintained. It is set on a peninsula with views of the water looking both ways. The owner/manger was wonderful. Breakfast was great and we sat and talked over breakfast with her and her husband for almost four hours one day. We have never done that before. Great people. Great place. By far the best stay we have ever had at a B and B."
Charming rm w/king bed, w/sm ensuite w/shw. Sitting area, writing desk+chair.
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
Kendall Tavern Inn
Exterior
Kendall Tavern Inn
3.5 star property
9.8 out of 10, Exceptional, (121)
"What a fantastic stay!"
Kendall Tavern Inn
Don't see what you're looking for?
See all available properties in Bailey Island
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.

Other property types in Bailey Island

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
THE GILLS GROUP has two additional cottages available for larger groups
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
10.0 out of 10, Exceptional, (94)
"We celebrated our Mom’s 70th birthday in this beautiful space. It exceeded our expectations and the property manager David is the best!"
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
8.6 out of 10, Excellent, (35)
"Great views. House pretty clean & supplies were fine except only 3 coffee cups for 6 adults. VACasa said they would get more cups. They failed, never received. Some lights didn't work & lots of dead bugs in light fixtures."
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
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'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 Cobwork Bridge 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.

Recent reviews of Bailey Island hotels
Expedia verified reviews

Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

5/5 Excellent
Comfortable and Inviting
"From the moment we arrived the entire staff was very friendly, welcoming and accommodating. Joe had us checked in quickly. Our room was beautiful , the living room area looked out onto Casco Bay, the bed was extremely comfortable ( it has the extra pillows I requested ) Once unpacked we decided to go to the on-site restaurant, Alto. My husband had a local IPA and thanks to Avry I had fresh brewed iced tea. We inquired about room service for breakfast, unfortunately Alto doesn’t offer it. However Avry told us he was working in the morning and would be happy to bring our order to our room. My husband said he would go down and get it on his way back from his morning walk. The following morning I called the restaurant and put in our order, everything was perfect. Since we were only staying 3 nights we didn’t require housekeeping we called Guest Services and they said someone would be coming with the items requested. On our last evening, after returning from dinner, we stopped at Alto for a nightcap. Avry and Mel were working. As always we we greeted with friendly faces and fabulous service. We ended up sitting outside by the fire and my husband played guitar for a while. Eventually we went back inside and had a great conversation with Avry. Overall our stay was absolutely wonderful. There is valet parking with $40/ night fee. The garage isn’t run by the hotel. The attendants were prompt. Only suggestion: offer charging stations for EV vehicles!"
A verified traveler stayed at Cambria Hotel Portland Downtown-Old Port
Posted 23 hours ago
Cambria Hotel Portland Downtown-Old Port