An aerial view of a river with a series of floating docks and a small island with trees.

Holiday Homes in Orrs Island

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Orrs 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$689
includes taxes & fees
28 Oct - 29 Oct
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 NZ$371
includes taxes & fees
3 Nov - 4 Nov
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, (71 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 NZ$634
includes taxes & fees
1 Nov - 2 Nov
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
9.8 out of 10, Exceptional, (6 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$412
includes taxes & fees
1 Nov - 2 Nov
2 bedroom w/ expansive water views
A wooden deck with outdoor seating and string lights.

5. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (77 reviews)
"Wonderful stay!"
United States
Erika T.
The price is NZ$645
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 NZ$701
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 NZ$328
includes taxes & fees
28 Oct - 29 Oct
Captains Watch: A Coastal Escape
A lush garden with a hammock, a variety of flowers, and a lake in the background.

8. 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$2,907
includes taxes & fees
22 Nov - 23 Nov
Classic New England Waterfront House Big Lawn Beautiful Sunrise
A spacious bedroom with a large bed, a rocking chair, and a view of a balcony with a white railing.

9. Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.6 out of 10, Exceptional, (21 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is NZ$315
includes taxes & fees
3 Nov - 4 Nov
Fantastic Waterfront Views
A backyard with a red Adirondack chair, a barbecue grill, and a wooden treehouse.

10. 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$310
includes taxes & fees
23 Oct - 24 Oct
Perfect stopover, getaway, base to explore the area, or to simply stay in town.
A compact kitchen with a dishwasher, microwave, and coffee maker on the countertop.

11. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is NZ$583
includes taxes & fees
27 Oct - 28 Oct
Quiet Spot in lovely Freeport neighborhood
A room with a sliding glass door leading to an outdoor deck with Adirondack chairs and a table.

12. Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
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 NZ$1,642
includes taxes & fees
8 Nov - 9 Nov
Three bedroom in United States of America, Freeport
A silver convertible car parked in front of a red house with a garden.

13. 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$333
includes taxes & fees
26 Oct - 27 Oct
1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!
A spacious living room with a wooden floor, a white sofa, a coffee table, and a dining area with a white table and chairs.

14. Beautiful 3BR Home with Office in Town of Brunswick with King beds

Beautiful 3BR Home with Office in Town of Brunswick with King beds
Brunswick
9.2 out of 10, Wonderful, (7 reviews)
"Great place for our family to stay while visiting the Maine coast."
United States
Craig C.
The price is NZ$688
includes taxes & fees
3 Nov - 4 Nov
Beautiful 3BR Home with Office in Town of Brunswick with King beds
A cozy room with wooden flooring, wicker furniture, and a white brick wall.

15. 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.
The price is NZ$1,259
includes taxes & fees
22 Nov - 23 Nov
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
A modern kitchen with a large island, dark cabinetry, and a view of a lake.

16. 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 NZ$3,865
includes taxes & fees
28 Oct - 29 Oct
The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury
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.

17. 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$445
includes taxes & fees
23 Oct - 24 Oct
2BR Apt. Authenticic value, Walk to everything, Large yard, Treehouse. No fees.
A living room with a grey sofa, a coffee table, and a dining area with a wooden table and chairs.

18. 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 NZ$914
includes taxes & fees
27 Oct - 28 Oct
Private Home w/ Office Year Round in town Brunswick next to Bowdoin
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$703
includes taxes & fees
4 Nov - 5 Nov
Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
A modern kitchen with dark cabinetry, a stainless steel range, and a window with a view of greenery.

20. 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)
"Another great stay by a great host. The host Jared even provided some activities for our granddaughters to do while we were on vacation. You will not be disappointed with this property. Looking to stay there again in the future. Thank you, Jared!"
United States
Ronald H.
The price is NZ$862
includes taxes & fees
14 Nov - 15 Nov
Award Winning Luxury Carriage House a short stroll from 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 Orrs Island Hotel Reviews

Comfort Inn South Portland Airport

Comfort Inn South Portland Airport

8/10 Good
"The front desk staff and airport shuttle driver were both excellent. The room was clean and comfortable. It is a little outdated and could benefit from updates."
Sara 1-night trip
Posted 2 hours ago
Comfort Inn South Portland Airport

Find out more about Orrs Island

Orrs Island Holiday Homes information

Number of reviews
292
Accommodation
552 Holiday Homes
Lowest Price
NZ$310
Highest Price
NZ$3,865