A coastal landscape with a sandy beach, dense forest, and a bay surrounded by hills.

Holiday Homes in Great Island

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Great Island holiday 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 NZ$801
includes taxes & fees
27 Oct - 28 Oct
Orchid Harbor, Bailey Island 3BR
A lakeside property with a deck, picnic table, and barbecue grill.

2. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (71 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is NZ$635
includes taxes & fees
18 Oct - 19 Oct
Camp Forever cottage
A wooden deck with a view of a lake, surrounded by trees and shrubs.

3. Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (73 reviews)
"Incredible home in a beautiful location!"
United States
Catherine G.
The price is NZ$823
includes taxes & fees
11 Oct - 12 Oct
Centerview cottage
A treehouse with a wooden staircase and a small building with a colorful mural.

4. 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 NZ$314
includes taxes & fees
11 Oct - 12 Oct
Perfect stopover, getaway, base to explore the area, or to simply stay in town.
A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

5. 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 NZ$377
includes taxes & fees
5 Nov - 6 Nov
Mid Coast Getaway w/ water views
A wooden staircase with a wooden railing, surrounded by green foliage.

6. 1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!

1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!
Bath
8.2 out of 10, Very good, (21 reviews)
"Cute but aging small space, Near attractions"
United States
michael
The price is NZ$321
includes taxes & fees
12 Oct - 13 Oct
1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!
A compact kitchen with a dishwasher, microwave, and coffee maker on the countertop.

7. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is NZ$649
includes taxes & fees
11 Oct - 12 Oct
Quiet Spot in lovely Freeport neighborhood
A stone fireplace with a TV mounted above it, a wooden mantel, and a hanging light fixture.

8. The Outlet Studio, Rustic Comfort w Fireplace

The Outlet Studio, Rustic Comfort w Fireplace
Freeport
10.0 out of 10, Exceptional, (14 reviews)
"Cottage is just as described. Great place to stay for a few nights to explore the area.Easy walk to Outlets and Restaurants."
United States
Joanne H.
The price is NZ$481
includes taxes & fees
11 Oct - 12 Oct
The Outlet Studio, Rustic Comfort w Fireplace
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.

9. 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 NZ$418
includes taxes & fees
1 Nov - 2 Nov
2 bedroom w/ expansive water views
A covered porch with a view of a lake and trees.

10. 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 NZ$709
includes taxes & fees
13 Oct - 14 Oct
Mere Point Sunrise Views at Eastern Shore!
A deck with white railings overlooking a body of water, boats, and a forested shoreline.

11. Captains Watch: A Coastal Escape

Captains Watch: A Coastal Escape
West Point
The price is NZ$383
includes taxes & fees
8 Nov - 9 Nov
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.

12. Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.6 out of 10, Exceptional, (20 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is NZ$371
includes taxes & fees
28 Oct - 29 Oct
Fantastic Waterfront Views
A two-story white house with a front porch, green shutters, and a covered patio area with chairs.

13. 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 NZ$1,253
includes taxes & fees
19 Oct - 20 Oct
Charming Historic home steps away from downtown
A rocking chair and a small table with a decorative plate, both placed on a wooden deck in front of a red building with a white door.

14. 2BR Apt. Authenticic value, Walk to everything, Large yard, Treehouse. No fees.

2BR Apt. Authenticic value, Walk to everything, Large yard, Treehouse. No fees.
Bath
9.0 out of 10, Wonderful, (28 reviews)
"Clean, walkable to town, nice backyard to sit and talk."
United States
Kathleen
The price is NZ$434
includes taxes & fees
12 Oct - 13 Oct
2BR Apt. Authenticic value, Walk to everything, Large yard, Treehouse. No fees.
A wooden deck with outdoor seating and string lights.

15. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (72 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
The price is NZ$657
includes taxes & fees
14 Oct - 15 Oct
Full sized home
A modern kitchen with dark blue cabinets, a stainless steel stove, and marble backsplash.

16. Award Winning Luxury Carriage House a short stroll from town!

Award Winning Luxury Carriage House a short stroll from town!
Bath
10.0 out of 10, Exceptional, (14 reviews)
"The house matches exactly what was described online. It's clean and cozy in a quite neighborhood. I'd rate it a five star and highly recommend!"
United States
Shisheng
The price is NZ$874
includes taxes & fees
7 Nov - 8 Nov
Award Winning Luxury Carriage House a short stroll from town!
A lush garden with a hammock, a variety of flowers, and a lake in the background.

17. 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 NZ$3,064
includes taxes & fees
9 Nov - 10 Nov
Classic New England Waterfront House Big Lawn Beautiful Sunrise
A garden with hydrangea flowers, a wooden chair, and a "NO PARKING" sign.

18. Boothbay Harbor, 2-Story Cottage, downtown

Boothbay Harbor, 2-Story Cottage, downtown
Boothbay Harbor
9.4 out of 10, Exceptional, (31 reviews)
"Location, location, location! We stayed for 4 days and didn't have to drive ONCE. David was easy to communicate with and very helpful. House was clean and comfortable. Would definitely stay again!"
United States
Justin T.
The price is NZ$635
includes taxes & fees
19 Oct - 20 Oct
Boothbay Harbor, 2-Story Cottage, downtown
A bedroom with a bed, a small table with a yellow mug, and a window with a view of a forest.

19. 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 NZ$726
includes taxes & fees
25 Oct - 26 Oct
Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
A room with a sliding glass door leading to an outdoor deck with Adirondack chairs and a table.

20. Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
Freeport
10.0 out of 10, Exceptional, (12 reviews)
The price is NZ$1,659
includes taxes & fees
8 Nov - 9 Nov
Three bedroom in United States of America, Freeport
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 Great 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

8/10 Good
"Nice size and quiet rooms. Convenient location"
Gary 1-night trip
Posted 6 hours ago
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Find out more about Great Island

Great Island Holiday Homes information

Number of reviews
349
Accommodation
657 Holiday Homes
Lowest Price
NZ$314
Highest Price
NZ$3,064

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