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
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 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, (12 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
2 Oct - 3 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, (65 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is NZ$612
includes taxes & fees
16 Sept - 17 Sept
Camp Forever cottage
A wooden deck with outdoor seating and string lights.

3. 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 NZ$676
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.

4. 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 NZ$473
includes taxes & fees
13 Sept - 14 Sept
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.

5. 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$492
includes taxes & fees
7 Sept - 8 Sept
2 bedroom w/ expansive water views
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, (70 reviews)
"Incredible home in a beautiful location!"
United States
Catherine G.
The price is NZ$814
includes taxes & fees
7 Sept - 8 Sept
Centerview cottage
A treehouse with a wooden staircase and a small building with a colorful mural.

7. Perfect stopover, getaway & great base to explore Maine or simply stay in town.

Perfect stopover, getaway & great base to explore Maine or simply stay in town.
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 NZ$269
includes taxes & fees
6 Sept - 7 Sept
Perfect stopover, getaway & great base to explore Maine or simply stay in town.
A living room with a sofa, armchair, wooden coffee table, and a potted plant.

8. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
The price is NZ$830
includes taxes & fees
7 Sept - 8 Sept
Fully Updated Airy Historic Home in South Freeport
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 NZ$276
includes taxes & fees
7 Sept - 8 Sept
Captain's 1BR Suite. Authenticity. Value. Walk to everything. Large yard.
A deck with white railings overlooking a body of water, boats, and a forested shoreline.

10. Captains Watch: A Coastal Escape

Captains Watch: A Coastal Escape
West Point
The price is NZ$701
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.

11. 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 NZ$731
includes taxes & fees
9 Sept - 10 Sept
Fantastic Waterfront Views
A compact kitchen with a microwave, coffee maker, and a sink. There are cabinets, a dishwasher, and a dining table with chairs.

12. Quiet Spot in lovely Freeport desert pines neighborhood

Quiet Spot in lovely Freeport desert pines neighborhood
Freeport
The price is NZ$690
includes taxes & fees
14 Sept - 15 Sept
Quiet Spot in lovely Freeport desert pines neighborhood
A lush garden with a hammock, a variety of flowers, and a lake in the background.

13. 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$3,217
includes taxes & fees
5 Oct - 6 Oct
Classic New England Waterfront House Big Lawn Beautiful Sunrise
A wooden deck with a railing overlooking a calm body of water, boats, and a distant shoreline.

14. Tide Haven Cottage on Bay Point

Tide Haven Cottage on Bay Point
Georgetown
The price is NZ$842
includes taxes & fees
20 Sept - 21 Sept
Tide Haven Cottage on Bay Point
A room with a sliding glass door leading to an outdoor deck with Adirondack chairs and a table.

15. Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
Freeport
10.0 out of 10, Exceptional, (8 reviews)
The price is NZ$1,765
includes taxes & fees
9 Sept - 10 Sept
Three bedroom in United States of America, Freeport
A cozy room with wooden flooring, wicker furniture, and a white brick wall.

16. 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 NZ$1,229
includes taxes & fees
14 Sept - 15 Sept
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
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.

17. 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 NZ$1,030
includes taxes & fees
6 Sept - 7 Sept
Lush Coastal Downtown Home - Beaches & Shopping
A bedroom with a bed, a small table with a yellow mug, and a window with a view of a forest.

18. 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$706
includes taxes & fees
30 Sept - 1 Oct
Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
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 NZ$860
includes taxes & fees
5 Oct - 6 Oct
Private Home w/ Office Year Round in town Brunswick next to Bowdoin
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.

20. Captain's 2BR. Authenticity. Value, Near everything. Yard. Treehouse. No fees.

Captain's 2BR. Authenticity. Value, Near everything. Yard. Treehouse. No fees.
Bath
8.8 out of 10, Excellent, (23 reviews)
"Clean, walkable to town, nice backyard to sit and talk."
United States
Kathleen
The price is NZ$403
includes taxes & fees
14 Sept - 15 Sept
Captain's 2BR. Authenticity. Value, Near everything. Yard. Treehouse. No fees.
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 room was clean, staff were friendly."
Teresa 2-night trip
Posted 1 hour ago
Comfort Inn South Portland Airport

Find out more about Orrs Island

Orrs Island Holiday Homes information

Number of reviews
202
Accommodation
653 Holiday Homes
Lowest Price
NZ$269
Highest Price
NZ$3,217