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

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Bailey Island vacation homes

A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

1. Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR
Harpswell
10.0 out of 10, Exceptional, (13 reviews)
"Lovely property, close to what we needed and wanted, host communicated promptly. Would definitely stay there again."
United States
Jane D.
The price is AED 634
AED 1,561 total
includes taxes & fees
16 Nov - 17 Nov
Orchid Harbor, Bailey Island 3BR
A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

2. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (12 reviews)
"The location and views from the cottage are quintessential coastal Maine. Small community with lobster pound and Maine Oyster Company across the street. John is a welcoming host and eager to make sure you enjoy your stay. The cottage is great for 2 people, equipped with the basics and has a great deck to enjoy the views. Planning to return next year. Great spot!"
United States
Rebecca
The price is AED 347
AED 742 total
includes taxes & fees
27 Oct - 28 Oct
Mid Coast Getaway w/ water views
A spacious room with a wooden floor, a dining area with chairs and a table, a sofa, a TV, and a balcony with a view of the sea.

3. 2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
9.8 out of 10, Exceptional, (7 reviews)
"Place was clean, beautiful and the photos do not do it justice. The perfect get away vacation from the rat race."
United States
Gregory M.
The price is AED 463
AED 884 total
includes taxes & fees
1 Nov - 2 Nov
2 bedroom w/ expansive water views
A dining area with a wooden table and chairs, a red sofa, and a small round table with a decorative plate.

4. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is AED 308
AED 1,223 total
includes taxes & fees
27 Oct - 28 Oct
Quiet Spot in lovely Freeport neighborhood
A wooden deck with outdoor seating and string lights.

5. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (79 reviews)
"Wonderful stay!"
United States
Erika T.
The price is AED 744
AED 1,355 total
includes taxes & fees
27 Oct - 28 Oct
Full sized home
A covered porch with a view of a lake and trees.

6. Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (10 reviews)
"Lovely location "
United States
Michelle S.
The price is AED 533
AED 1,444 total
includes taxes & fees
17 Nov - 18 Nov
Mere Point Sunrise Views at Eastern Shore!
A deck with white railings overlooking a body of water, boats, and a forested shoreline.

7. Captains Watch: A Coastal Escape

Captains Watch: A Coastal Escape
West Point
The price is AED 606
AED 686 total
includes taxes & fees
27 Oct - 28 Oct
Captains Watch: A Coastal Escape
A spacious bedroom with a large bed, a rocking chair, and a view of a balcony with a white railing.

8. Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.4 out of 10, Exceptional, (22 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is AED 579
AED 663 total
includes taxes & fees
1 Nov - 2 Nov
Fantastic Waterfront Views
A lakeside property with a deck, picnic table, and barbecue grill.

9. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (73 reviews)
"We had a really nice day in communication and check-in were very easy. Overall, it was a lovely day and we would definitely consider returning."
United States
Len B.
The price is AED 771
AED 1,345 total
includes taxes & fees
1 Nov - 2 Nov
Camp Forever cottage
A living room with a sofa, armchair, wooden coffee table, and a potted plant.

10. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
10.0 out of 10, Exceptional, (1 review)
"Great property well kept and close to everything we wanted to do"
United States
boodu
Fully Updated Airy Historic Home in South Freeport
A lush garden with a hammock, a variety of flowers, and a lake in the background.

11. Classic New England Waterfront House Big Lawn Beautiful Sunrise

Classic New England Waterfront House Big Lawn Beautiful Sunrise
Harpswell
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful stay! "
United States
Ashma B.
The price is AED 1,286
AED 6,174 total
includes taxes & fees
23 Nov - 24 Nov
Classic New England Waterfront House Big Lawn Beautiful Sunrise
A spacious living room with large windows, a sofa, a chair, and a small table.

12. 1 Mi to Maine Street! MCM-Style Home in Brunswick

1 Mi to Maine Street! MCM-Style Home in Brunswick
Brunswick
9.6 out of 10, Exceptional, (13 reviews)
"Quiet, clean, well appointed house close to Maine St Brunswick and convenient to both Portland and points north. "
United States
Kendra G.
The price is AED 404
AED 1,213 total
includes taxes & fees
1 Nov - 2 Nov
1 Mi to Maine Street! MCM-Style Home in Brunswick
A treehouse with a wooden staircase and a small building with a colorful mural.

13. Perfect stopover, getaway, base to explore the area, or to simply stay in town.

Perfect stopover, getaway, base to explore the area, or to simply stay in town.
Bath
8.0 out of 10, Very good, (31 reviews)
"A charming, quiet, and clean room with separate bathroom close to everything downtown. Felt a bit like staying at my grandparent’s house in a good way - it’s very homey. Dmitri is very nice and communication was thorough and easy!"
United States
Esther
The price is AED 410
AED 651 total
includes taxes & fees
27 Oct - 28 Oct
Perfect stopover, getaway, base to explore the area, or to simply stay in town.
A spacious living room with a large window overlooking a lake, a flat-screen TV mounted on the wall, and a round wooden coffee table.

14. Casco Bay Oceanfront Retreat by Everrow

Casco Bay Oceanfront Retreat by Everrow
Freeport
10.0 out of 10, Exceptional, (13 reviews)
"What can I say about my stay; peaceful, beautiful views, and relaxing! Home was clean with modern finishes but super comfortable for my four guests. The downstairs area is very private from the main floor. The yard was a great space where we had our outdoor fire looking up at the stars at night. The deck was perfect for our family lunch and dinners. We took chairs down to the beach area to sit closer to the water which was perfect. It's super close to town, Wolfe's Neck and other amenities....
United States
Lisa E.
The price is AED 1,546
AED 3,527 total
includes taxes & fees
9 Nov - 10 Nov
Casco Bay Oceanfront Retreat by Everrow
A wooden staircase with a wooden railing, surrounded by green foliage.

15. 1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Heat set to 70F

1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Heat set to 70F
Bath
8.2 out of 10, Very good, (21 reviews)
"Cute but aging small space, Near attractions"
United States
michael
The price is AED 454
AED 699 total
includes taxes & fees
27 Oct - 28 Oct
1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Heat set to 70F
A living room with a grey sofa, a coffee table, and a dining area with a wooden table and chairs.

16. Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Private Home w/ Office Year Round in town Brunswick next to Bowdoin
Brunswick
8.8 out of 10, Excellent, (28 reviews)
"Perfect spot for us to spend a weekend up at Bowdoin where "
United States
Michaela M.
The price is AED 624
AED 1,529 total
includes taxes & fees
1 Nov - 2 Nov
Private Home w/ Office Year Round in town Brunswick next to Bowdoin
A modern kitchen with a large island, dark cabinetry, and a view of a lake.

17. The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury

The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury
Harpswell
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful property, well equipped, lots of amenities, plenty of space for our large group."
United States
Edwin M.
The price is AED 2,149
AED 8,391 total
includes taxes & fees
27 Oct - 28 Oct
The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury
A cozy room with wooden flooring, wicker furniture, and a white brick wall.

18. Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard

Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
Brunswick
10.0 out of 10, Exceptional, (5 reviews)
"Great location and super clean house"
United States
Gary R.
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
A two-story white house with a front porch, green shutters, and a covered patio area with chairs.

19. Charming Historic home steps away from downtown

Charming Historic home steps away from downtown
Bath
9.4 out of 10, Exceptional, (3 reviews)
"The communication was excellent. The location was excellent."
United States
Holly Y.
The price is AED 613
AED 2,586 total
includes taxes & fees
28 Oct - 29 Oct
Charming Historic home steps away from downtown
A spacious living room with a sofa, ottoman, and coffee table, a dining area with chairs, and a kitchen with cabinets and appliances.

20. Luxe 5 Bed/ 3 Bath with Game Room & AC

Luxe 5 Bed/ 3 Bath with Game Room & AC
Yarmouth
10.0 out of 10, Exceptional, (4 reviews)
"What a great place to stay! The home is very clean and very quiet. Our host was very responsive to any questions we had. We would book this one over and over again."
United States
Michelle T.
Luxe 5 Bed/ 3 Bath with Game Room & AC
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

Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

10/10 Excellent
"Very efficient staff. Hotel easy for parking. Decent breakfast included. Quiet room and comfortable bed. Slept well."
Suzanne 2-night trip
Posted 3 hours ago
Tru by Hilton Portland Airport Area