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Check prices for these dates

In two weeks
Oct 17 - Oct 19
In one month
Oct 31 - Nov 2
In two months
Nov 28 - Nov 30
In three months
Dec 26 - Dec 28

Vacation Homes in Bailey Island

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, (229)
"Beautiful views, very clean and enjoyed the oceanside vibe both inside and out! Easy walk to general store and walkable to Giant Stairs trail and Cedar Beach."
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Camp Forever cottage
Outdoor dining

Camp Forever cottage

9.6 out of 10, Exceptional, (55)
"Connie and Mike are great hosts. The camp was clean and air conditioned! The view from camp was beautiful. The dock was amazing. "
The price is ￥17,573
￥37,212 total
includes taxes & fees
Oct 14 - Oct 15
Camp Forever cottage
Full sized home
Terrace/patio

Full sized home

9.8 out of 10, Exceptional, (43)
"The house was lovely. Very comfortable place. Within 15- 20 mins to a store or restaurants."
Full sized home
5 Star Back Cove Hide-Away 1 bedroom Back Cove apartment with water views!
Fridge, microwave, oven, stovetop

5 Star Back Cove Hide-Away 1 bedroom Back Cove apartment with water views!

10.0 out of 10, Exceptional, (149)
"This was our second stay at Beth’s home, and it certainly won’t be the last (as long as she’s willing to have us!) Everything is absolutely perfect. Beth is a thoughtful host, the location is perfect and the home is beautiful - you can’t go wrong!"
5 Star Back Cove Hide-Away 1 bedroom Back Cove apartment with water views!
Executive Falmouth Waterfront Home on the Presumpscot River
Terrace/patio

Executive Falmouth Waterfront Home on the Presumpscot River

10.0 out of 10, Exceptional, (55)
"I visited Maine with several family members. We stayed in this lovely home and used it as a homebase. It is very well located and quite nicely equipped. "
Executive Falmouth Waterfront Home on the Presumpscot River
Captain's Quarters 2BR Apartment. Walk to Everything!
Property grounds

Captain's Quarters 2BR Apartment. Walk to Everything!

8.6 out of 10, Excellent, (7)
"Nice, clean, cosy, conveniently located and easy enough to find. Great communication with host, comfortable beds and plenty of hot water. very responsive and would definitely consider using again. "
The price is ￥23,667
￥36,438 total
includes taxes & fees
Oct 8 - Oct 9
Captain's Quarters 2BR Apartment. Walk to Everything!
Beautiful Oceanfront House- Stunning Water Views
4 bedrooms, iron/ironing board, WiFi, bed sheets

Beautiful Oceanfront House- Stunning Water Views

9.6 out of 10, Exceptional, (16)
"The Host and his wife were so pleasant and accommodating. We enjoyed watching seals, fish and birds during our visit. Highly recommend."
Beautiful Oceanfront House- Stunning Water Views
Sunny Modern Oasis in Portland’s Trendy East End
Exterior detail

Sunny Modern Oasis in Portland’s Trendy East End

10.0 out of 10, Exceptional, (57)
"Wonderful all around"
Sunny Modern Oasis in Portland’s Trendy East End
Beautiful house on the Harpswell Peninsula over looking Casco Bay
Terrace/patio

Beautiful house on the Harpswell Peninsula over looking Casco Bay

9.6 out of 10, Exceptional, (73)
"Great view, nice property, cool area in Harpswell. Great to stay at if you are in town for Live Well Farm. Lots of rooms, beds, and privacy. "
Beautiful house on the Harpswell Peninsula over looking Casco Bay
Oceanfront Retreat with Dock, Boothbay Harbor
Terrace/patio

Oceanfront Retreat with Dock, Boothbay Harbor

2.0 star property
10.0 out of 10, Exceptional, (2)
"Convenient location to downtown. Views are superb of the harbor. Quiet neighborhood.The kitchen is not very well equipped, but we survived. Need additional silverware, plates, etc.."
Oceanfront Retreat with Dock, Boothbay Harbor
Spacious Historic Home | 7BR West End for Groups
Marina

Spacious Historic Home | 7BR West End for Groups

10.0 out of 10, Exceptional, (6)
"Perfect accommodation for extended family to get together for a long weekend. House was comfortable and well-appointed with plenty of space, beds, towels etc. Air conditioning worked perfectly when needed."
The price is ￥103,840
￥237,286 total
includes taxes & fees
Oct 8 - Oct 9
Spacious Historic Home | 7BR West End for Groups
Large, light filled 4 bedroom house - walk to ocean and ferry
Terrace/patio

Large, light filled 4 bedroom house - walk to ocean and ferry

9.8 out of 10, Exceptional, (35)
"I stayed here for a weekend with a group of friends and it was a dream! So lovely!"
Large, light filled 4 bedroom house - walk to ocean and ferry
Elegant and efficient Island home 4 miles from downtown Portland
Outdoor dining

Elegant and efficient Island home 4 miles from downtown Portland

9.0 out of 10, Wonderful, (2)
"An ideal home away from home at our most favorite place in Maine. Plenty of extra touches to make guests feel welcome and comfortable. Owner is quick to respond to any questions, and went well above-and-beyond to help us out when we experienced an unforeseen situation. I am so very grateful! I hope we can book this wonderful home again next summer. Thank you!"
Elegant and efficient Island home 4 miles from downtown Portland
Tranquil Seaside Cottage with Spectacular Views, Wifi & Washer/Dryer
Fridge, microwave, oven, stovetop

Tranquil Seaside Cottage with Spectacular Views, Wifi & Washer/Dryer

2.0 star property
10.0 out of 10, Exceptional, (29)
"The cottage is just lovely, very “Maine”, newly redone and extremely comfortable. Communication with the host was easy. We thoroughly enjoyed our stay."
Tranquil Seaside Cottage with Spectacular Views, Wifi & Washer/Dryer
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
Fridge, microwave, oven, stovetop

Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

9.2 out of 10, Wonderful, (93)
"Fantastic coastal cottage feel! Beautiful view of the the bay. Updated bathrooms and kitchen. Perfect location to walk to center of Boothbay harbor shops and restaurants. My only suggestion...replace any bad window shades with working ones..andCheck all ac unit filters.maybe consider updating the upstairs ac units.We had an amazing time."
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
Newly Renovated Haven w/ Deck, Walk to Shops, Dining & Marina, Pet friendly
Fridge, microwave, oven, stovetop

Newly Renovated Haven w/ Deck, Walk to Shops, Dining & Marina, Pet friendly

9.2 out of 10, Wonderful, (60)
"The house was the perfect size for my family of 7 adults. We enjoyed the short walk to downtown Boothbay too."
Newly Renovated Haven w/ Deck, Walk to Shops, Dining & Marina, Pet friendly
Nicest Waterfront in Maine w/ Private Beach!
Fridge, microwave, oven, stovetop

Nicest Waterfront in Maine w/ Private Beach!

9.6 out of 10, Exceptional, (43)
"Beautiful property with plenty of room for our family of 6."
Nicest Waterfront in Maine w/ Private Beach!
Charming 2-bedroom house in small-town neighborhood
Microwave, oven, stovetop, dishwasher

Charming 2-bedroom house in small-town neighborhood

9.2 out of 10, Wonderful, (7)
"Cute neighborhood. Very quiet. I do have a couple things that wasn’t very pleasant…there was a loofa with hair left in the shower. Nothing felt clean. The rug was dirty in the back sitting room. It was very very hot . There was nowhere to put the trash because the trash was full outside. A lock should be on cellar door. Owner was very easy yo deal with. "
Charming 2-bedroom house in small-town neighborhood
On Sebasco Estates, 4 Bedroom House, Ocean Views, Close to Beaches and Golfing.
Beach nearby

On Sebasco Estates, 4 Bedroom House, Ocean Views, Close to Beaches and Golfing.

10.0 out of 10, Exceptional, (67)
"We thoroughly enjoyed our stay. The owner is wonderful and accomodating. The property location is ideal for access to many attractions. "
On Sebasco Estates, 4 Bedroom House, Ocean Views, Close to Beaches and Golfing.
Quaint Coastal Cottage w/ Deck & High-Speed WiFi - Walk to Town
Dining

Quaint Coastal Cottage w/ Deck & High-Speed WiFi - Walk to Town

8.0 out of 10, Very Good, (24)
"Wonderful stay!"
Quaint Coastal Cottage w/ Deck & High-Speed WiFi - Walk to Town
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

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

10/10 Excellent
"Whole hotel was immaculate. Frontt desk lady very helpful. Breakfast very good and ample. "
Lynn 1-night trip
Posted 4 hours ago
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Find out more about Bailey Island

Find out more about Bailey Island

Bailey Island Vacation Homes information

Number of reviews
923
Accommodation
524 Vacation Homes
Lowest Price
￥36,761
Highest Price
￥237,286

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