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

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Orrs Island vacation 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 ￥28,132
￥68,602 total
includes taxes & fees
Oct 27 - Oct 28
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 ￥16,626
￥33,967 total
includes taxes & fees
Nov 1 - Nov 2
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)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is ￥33,251
￥57,817 total
includes taxes & fees
Oct 16 - Oct 17
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 ￥19,951
￥38,109 total
includes taxes & fees
Nov 1 - Nov 2
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, (75 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
The price is ￥32,064
￥58,423 total
includes taxes & fees
Oct 20 - Oct 21
Full sized home
A deck with white railings overlooking a body of water, boats, and a forested shoreline.

6. Captains Watch: A Coastal Escape

Captains Watch: A Coastal Escape
West Point
The price is ￥30,480
￥33,932 total
includes taxes & fees
Oct 19 - Oct 20
Captains Watch: A Coastal Escape
A covered porch with a view of a lake and trees.

7. 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 ￥33,655
￥74,988 total
includes taxes & fees
Oct 25 - Oct 26
Mere Point Sunrise Views at Eastern Shore!
A treehouse with a wooden staircase and a small building with a colorful mural.

8. 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 ￥17,671
￥28,063 total
includes taxes & fees
Oct 16 - Oct 17
Perfect stopover, getaway, base to explore the area, or to simply stay in town.
A lush garden with a hammock, a variety of flowers, and a lake in the background.

9. 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 ￥69,670
￥283,912 total
includes taxes & fees
Nov 3 - Nov 4
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.

10. 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 ￥29,095
￥33,237 total
includes taxes & fees
Oct 28 - Oct 29
Fantastic Waterfront Views
A spacious living room with large windows, a sofa, a chair, and a small table.

11. 1 Mi to Maine Street! MCM-Style Home in Brunswick

1 Mi to Maine Street! MCM-Style Home in Brunswick
Brunswick
9.6 out of 10, Exceptional, (12 reviews)
"Quiet, clean, well appointed house close to Maine St Brunswick and convenient to both Portland and points north. "
United States
Kendra G.
The price is ￥17,417
￥52,295 total
includes taxes & fees
Oct 20 - Oct 21
1 Mi to Maine Street! MCM-Style Home in Brunswick
A wooden staircase with a wooden railing, surrounded by green foliage.

12. 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 ￥18,051
￥28,305 total
includes taxes & fees
Oct 15 - Oct 16
1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!
A wooden deck with a view of a lake, surrounded by trees and shrubs.

13. Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (74 reviews)
"Incredible home in a beautiful location!"
United States
Catherine G.
The price is ￥46,710
￥75,422 total
includes taxes & fees
Oct 15 - Oct 16
Centerview cottage
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, (13 reviews)
"All we could say was wow! Words cannot express the view from this house! It looked like a picture! Beautiful view, fully loaded kitchen, spacious, comfortable beds, everything was perfect. I have the worst cell service and I couldn’t get the app to work but David answered my call right away and helped us get in. I’d highly recommend this property and we can’t wait to come back!"
United States
Michael L.
The price is ￥58,142
￥141,386 total
includes taxes & fees
Nov 4 - Nov 5
Three bedroom in United States of America, Freeport
A compact kitchen with a dishwasher, microwave, and coffee maker on the countertop.

15. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is ￥16,914
￥57,194 total
includes taxes & fees
Oct 15 - Oct 16
Quiet Spot in lovely Freeport neighborhood
A living room with a sofa, armchair, wooden coffee table, and a potted plant.

16. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
10.0 out of 10, Exceptional, (1 review)
"Great property well kept and close to everything we wanted to do"
United States
boodu
The price is ￥24,543
￥79,392 total
includes taxes & fees
Oct 19 - Oct 20
Fully Updated Airy Historic Home in South Freeport
A two-story white house with a front porch, green shutters, and a covered patio area with chairs.

17. 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 ￥24,736
￥108,598 total
includes taxes & fees
Oct 18 - Oct 19
Charming Historic home steps away from downtown
A modern kitchen with a large island, dark cabinetry, and a view of a lake.

18. 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 ￥92,629
￥361,750 total
includes taxes & fees
Oct 20 - Oct 21
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.

19. 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 ￥38,793
￥117,361 total
includes taxes & fees
Nov 8 - Nov 9
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.

20. 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 ￥31,351
￥38,833 total
includes taxes & fees
Oct 15 - Oct 16
2BR Apt. Authenticic value, Walk to everything, Large 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

Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent
"The room was beautiful, clean and comfortable. The most comfortable hotel beds we have slept in this trip. Front desk staff was extremely helpful and kind. Loved that they have a shuttle to take you to the hotspots so you don’t have to move your car and pay for parking."
James 1-night trip
Posted 5 hours ago
Holiday Inn Portland-By the Bay by IHG

Find out more about Orrs Island

Orrs Island Vacation Homes information

Number of reviews
328
Accommodation
653 Vacation Homes
Lowest Price
￥28,063
Highest Price
￥361,750