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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

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.
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, (68 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is AU$518
includes taxes & fees
3 Oct - 4 Oct
Camp Forever cottage
A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

3. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (10 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 AU$288
includes taxes & fees
29 Sept - 30 Sept
Mid Coast Getaway w/ water views
A wooden deck with outdoor seating and string lights.

4. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (69 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
The price is AU$515
includes taxes & fees
5 Oct - 6 Oct
Full sized home
A treehouse with a wooden staircase and a small building with a colorful mural.

5. 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, (30 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 AU$254
includes taxes & fees
26 Sept - 27 Sept
Perfect stopover, getaway, base to explore the area, or to simply stay in town.
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.

6. 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 AU$362
includes taxes & fees
29 Sept - 30 Sept
2 bedroom w/ expansive water views
A wooden deck with a view of a lake, surrounded by trees and shrubs.

7. 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 AU$663
includes taxes & fees
27 Sept - 28 Sept
Centerview cottage
A covered porch with a view of a lake and trees.

8. 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 AU$607
includes taxes & fees
14 Oct - 15 Oct
Mere Point Sunrise Views at Eastern Shore!
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, (20 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is AU$306
includes taxes & fees
28 Sept - 29 Sept
Fantastic Waterfront Views
A wooden staircase with a wooden railing, surrounded by green foliage.

10. 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 AU$263
includes taxes & fees
28 Sept - 29 Sept
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.

11. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is AU$562
includes taxes & fees
26 Sept - 27 Sept
Quiet Spot in lovely Freeport neighborhood
A deck with white railings overlooking a body of water, boats, and a forested shoreline.

12. Captains Watch: A Coastal Escape

Captains Watch: A Coastal Escape
West Point
The price is AU$309
includes taxes & fees
28 Sept - 29 Sept
Captains Watch: A Coastal Escape
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 AU$2,526
includes taxes & fees
19 Oct - 20 Oct
Classic New England Waterfront House Big Lawn Beautiful Sunrise
A room with a sliding glass door leading to an outdoor deck with Adirondack chairs and a table.

14. Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
Freeport
10.0 out of 10, Exceptional, (11 reviews)
The price is AU$1,474
includes taxes & fees
28 Sept - 29 Sept
Three bedroom in United States of America, Freeport
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"
United States
Ashley W.
The price is AU$1,050
includes taxes & fees
28 Sept - 29 Sept
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
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.

16. 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, (27 reviews)
"Clean, walkable to town, nice backyard to sit and talk."
United States
Kathleen
The price is AU$341
includes taxes & fees
28 Sept - 29 Sept
2BR Apt. Authenticic value, Walk to everything, Large yard, Treehouse. No fees.
A bedroom with a bed, a small table with a yellow mug, and a window with a view of a forest.

17. 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 AU$553
includes taxes & fees
25 Oct - 26 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.

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 AU$738
includes taxes & fees
5 Oct - 6 Oct
Private Home w/ Office Year Round in town Brunswick next to Bowdoin
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.

19. Lush Coastal Downtown Home - Beaches & Shopping

Lush Coastal Downtown Home - Beaches & Shopping
Freeport
10.0 out of 10, Exceptional, (6 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 AU$875
includes taxes & fees
28 Sept - 29 Sept
Lush Coastal Downtown Home - Beaches & Shopping
A two-story white house with a front porch, green shutters, and a covered patio area with chairs.

20. Charming Historic home steps away from downtown

Charming Historic home steps away from downtown
Bath
9.0 out of 10, Wonderful, (2 reviews)
"The communication was excellent. The location was excellent."
United States
Holly Y.
The price is AU$1,052
includes taxes & fees
6 Oct - 7 Oct
Charming Historic home steps away from downtown
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

Inn at St John Portland In-Town

Inn at St John Portland In-Town

10/10 Excellent
"Perfect place for a couple to spend a night in the city affordably within walking distance to the important landmarks/restaurants/bars. Added bonus to be in such a quaint old building with a lot of history yet functional updates. Bed/linens extra comfy too. Would stay again if we get the chance to return!"
Jill 1-night trip
Posted 2 hours ago
Inn at St John Portland In-Town

Find out more about Orrs Island

Orrs Island Holiday Homes information

Number of reviews
391
Accommodation
653 Holiday Homes
Lowest Price
AU$254
Highest Price
AU$2,526