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
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Bailey Island holiday homes

A wooden deck with outdoor seating and string lights.

1. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (68 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
The price is HK$1,764
HK$3,119 total
includes taxes & fees
22 Sept - 23 Sept
Full sized home
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
9.6 out of 10, Exceptional, (8 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 HK$1,235
HK$2,207 total
includes taxes & fees
14 Sept - 15 Sept
Mid Coast Getaway w/ water views
A lakeside property with a deck, picnic table, and barbecue grill.

3. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (65 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is HK$1,646
HK$2,846 total
includes taxes & fees
16 Sept - 17 Sept
Camp Forever cottage
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.

4. 2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
10.0 out of 10, Exceptional, (5 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 HK$1,276
HK$2,261 total
includes taxes & fees
8 Sept - 9 Sept
2 bedroom w/ expansive water views
A lush garden with a hammock, a variety of flowers, and a lake in the background.

5. 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 HK$4,312
HK$15,134 total
includes taxes & fees
5 Oct - 6 Oct
Classic New England Waterfront House Big Lawn Beautiful Sunrise
A wooden deck with a view of a lake, surrounded by trees and shrubs.

6. Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (69 reviews)
"Incredible home in a beautiful location!"
United States
Catherine G.
The price is HK$2,313
HK$3,546 total
includes taxes & fees
7 Sept - 8 Sept
Centerview cottage
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 HK$1,940
HK$3,224 total
includes taxes & fees
8 Sept - 9 Sept
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
9.8 out of 10, Exceptional, (18 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is HK$2,140
HK$3,360 total
includes taxes & fees
9 Sept - 10 Sept
Fantastic Waterfront Views
A wooden staircase with a wooden railing, surrounded by green foliage.

9. Captain's 1BR Suite. Authenticity. Value. Walk to everything. Large yard.

Captain's 1BR Suite. Authenticity. Value. Walk to everything. Large yard.
Bath
8.0 out of 10, Very good, (19 reviews)
"Cute but aging small space, Near attractions"
United States
michael
The price is HK$776
HK$1,274 total
includes taxes & fees
6 Sept - 7 Sept
Captain's 1BR Suite. Authenticity. Value. Walk to everything. Large yard.
A compact kitchen with a microwave, coffee maker, and a sink. There are cabinets, a dishwasher, and a dining table with chairs.

10. Quiet Spot in Lovely Freeport Neighborhood

Quiet Spot in Lovely Freeport Neighborhood
Freeport
The price is HK$1,333
HK$3,466 total
includes taxes & fees
14 Sept - 15 Sept
Quiet Spot in Lovely Freeport Neighborhood
A treehouse with a wooden staircase and a small building with a colorful mural.

11. Guest room + bath in Bath!. Authenticity. Value. Large yard. Walk to everything.

Guest room + bath in Bath!. Authenticity. Value. Large yard. Walk to everything.
Bath
8.2 out of 10, Very good, (29 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 HK$745
HK$1,239 total
includes taxes & fees
9 Sept - 10 Sept
Guest room + bath in Bath!. Authenticity. Value. Large yard. Walk to everything.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a granite countertop.

12. Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport

Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
Freeport
10.0 out of 10, Exceptional, (11 reviews)
"Our whole family was impressed by this house!"
United States
Gary B.
The price is HK$1,683
HK$5,322 total
includes taxes & fees
7 Sept - 8 Sept
Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
A modern kitchen with a large island, dark cabinetry, and a view of a lake.

13. 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 HK$5,096
HK$18,543 total
includes taxes & fees
5 Oct - 6 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.

14. 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, (4 reviews)
"Great location and super clean house"
United States
Gary R.
The price is HK$1,960
HK$5,862 total
includes taxes & fees
14 Sept - 15 Sept
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
A bedroom with a bed, a small table with a yellow mug, and a window with a view of a forest.

15. Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC

Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
Georgetown
10.0 out of 10, Exceptional, (2 reviews)
"Really lovely cabin with all the amenities within a stone’s throw to amazing trails and beaches. Would love to come back!"
United States
Palmer M.
The price is HK$1,736
HK$3,210 total
includes taxes & fees
29 Sept - 30 Sept
Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
A hallway with a large, rustic mirror leaning against the wall, a potted plant in the foreground, and a glimpse of a bed with a yellow blanket in the background.

16. Lush Coastal Downtown Home - Beaches & Shopping

Lush Coastal Downtown Home - Beaches & Shopping
Freeport
10.0 out of 10, Exceptional, (5 reviews)
"Our stay was very comfortable and easy to navigate. The host was very communicative. We had everything we needed and more. It was nice to be in walking distance from downtown Freeport. Although the price was higher than we wanted, our family of four (2 teens) enjoyed having a clean, comfortable and seamless stay."
United States
Alana K.
The price is HK$2,681
HK$4,743 total
includes taxes & fees
6 Sept - 7 Sept
Lush Coastal Downtown Home - Beaches & Shopping
A spacious living room with a sofa, ottoman, and coffee table, a dining area with chairs, and a kitchen with cabinets and appliances.

17. 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, (2 reviews)
"What a beautiful home! Everything about our stay was perfect. The home has everything you could possibly need and more. My family stayed for a long weekend and everyone was so happy with the accommodations. Hoping to go back!"
United States
Lisa L.
The price is HK$2,886
HK$7,505 total
includes taxes & fees
8 Sept - 9 Sept
Luxe 5 Bed/ 3 Bath with Game Room & AC
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

18. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very good, (61 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is HK$963
HK$3,127 total
includes taxes & fees
20 Sept - 21 Sept
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A living room with a grey sofa, a coffee table, and a dining area with a wooden table and chairs.

19. 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 HK$1,921
HK$4,093 total
includes taxes & fees
5 Oct - 6 Oct
Private Home w/ Office Year Round in town Brunswick next to Bowdoin
A two-story house with a balcony, a covered patio, and a fenced yard.

20. The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries
Munjoy Hill
10.0 out of 10, Exceptional, (105 reviews)
"Everything was as advertised; great accommodations!"
United States
Richard D.
The price is HK$2,509
HK$4,461 total
includes taxes & fees
15 Sept - 16 Sept
The Globe House on Munjoy Hill - Walk to Breweries
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

Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine

10/10 Excellent
"We always stay here when we are in Portland visiting family. A friendly welcoming and fun place. Great bar, the bartender remembered me from 6 months ago. Great breakfast. Don’t miss the chef made omelettes, wow delicious. The lobby is comfortable and a great place to hang out."
Leah 5-night trip
Posted 8 hours ago
Embassy Suites by Hilton Portland Maine

Find out more about Bailey Island

Bailey Island Vacation Homes information

Number of reviews
7,337
Accommodation
612 Vacation Homes
Lowest Price
HK$690
Highest Price
HK$2,008

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