A calm lake with a dock, boats, and a forested shoreline.

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Check prices for these dates

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

Our top choices for Islesboro vacation homes

1. Romantic Coastal Escape near Harbor

Romantic Coastal Escape near Harbor
Rockport
10.0 out of 10, Exceptional, (6 reviews)
"My family of four greatly enjoyed our stay at this property. Location was very convenient to explore the mid coast towns of Rockport, Rockland, and Camden and all of their beautiful harbors. Having two bedrooms worked well for us along with the living room and a large open kitchen and full bathroom. The private entrance that leads up to the open top floor was easy to manage and appreciated. The quiet street was frequented by wild turkeys that roamed the yard and crossed the street on two...
United States
Christopher H.
The price is ￥21,862
￥40,116 total
includes taxes & fees
Oct 21 - Oct 22
Romantic Coastal Escape near Harbor
A living room with a sofa, a coffee table, a TV, a fireplace, and a window with curtains.

2. Fully Updated Airy Historic Home in West Rockport

Fully Updated Airy Historic Home in West Rockport
Rockport
The price is ￥26,895
￥91,718 total
includes taxes & fees
Sep 30 - Oct 1
Fully Updated Airy Historic Home in West Rockport
A compact bedroom with a bed, a small table, a bench, a TV, and a kitchenette.

3. Simplicity-Just what you need! STR24-20

Simplicity-Just what you need! STR24-20
Rockland
9.8 out of 10, Exceptional, (35 reviews)
"Very nice tiny house in a quiet neighborhood. Easy walk to downtown"
United States
sarah
The price is ￥15,288
￥23,864 total
includes taxes & fees
Oct 8 - Oct 9
Simplicity-Just what you need! STR24-20
A covered porch with a grill, a potted plant, and a small table.

4. Cheerful Two Bedroom Cabin - 10 minutes to Camden!

Cheerful Two Bedroom Cabin - 10 minutes to Camden!
Lincolnville
9.8 out of 10, Exceptional, (16 reviews)
"This is a great place, nice and quiet, very clean and cozy. Loved it here!!"
United States
Lorna W.
The price is ￥49,014
￥90,110 total
includes taxes & fees
Sep 28 - Sep 29
Cheerful Two Bedroom Cabin - 10 minutes to Camden!
An aerial view of a marina with numerous boats docked and a small island with houses and greenery.

5. Harbor/🦞 Pound Access & Views from Large Deck

Harbor/🦞 Pound Access & Views from Large Deck
Owls Head
9.6 out of 10, Exceptional, (82 reviews)
"Great place for a girls' weekend!! Had a wonderful stay!"
United States
Jeanette Q.
The price is ￥30,004
￥75,084 total
includes taxes & fees
Sep 28 - Sep 29
Harbor/🦞 Pound Access & Views from Large Deck
A two-story house with a dark exterior, a balcony, and a well-maintained garden with rocks and plants.

6. Oceanview Bungalow Style Home in Owls Head

Oceanview Bungalow Style Home in Owls Head
Owls Head
9.8 out of 10, Exceptional, (77 reviews)
"We really enjoyed staying at this house! It was in a good location and was cute and cozy!"
United States
Victoria S.
The price is ￥31,849
￥87,690 total
includes taxes & fees
Sep 27 - Sep 28
Oceanview Bungalow Style Home in Owls Head
A four-poster bed with a ceiling fan, white bedding, and a nightstand with drawers.

7. Silver Oak Retreat Private Forest Getaway

Silver Oak Retreat Private Forest Getaway
Belfast
The price is ￥61,811
￥107,147 total
includes taxes & fees
Sep 27 - Sep 28
Silver Oak Retreat Private Forest Getaway
A wooden deck with Adirondack chairs and a grill.

8. Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston
Thomaston
9.2 out of 10, Wonderful, (13 reviews)
"This place was nice and clean. The only thing was the service was spotty and WiFi was slow. Overall, great place and great location."
United States
Alexis H.
The price is ￥20,604
￥38,745 total
includes taxes & fees
Oct 27 - Oct 28
Bright 2-Bedroom Apartment Near Downtown Thomaston
A wooden dock leading to a beach with a picnic table and chairs, surrounded by greenery.

9. Waterfront Getaway Near Acadia w/ Spectacular View

Waterfront Getaway Near Acadia w/ Spectacular View
Deer Isle
10.0 out of 10, Exceptional, (26 reviews)
"Great location with everything we needed."
United States
Thomas P.
The price is ￥46,712
￥86,403 total
includes taxes & fees
Oct 19 - Oct 20
Waterfront Getaway Near Acadia w/ Spectacular View
A wooden cabin-style kitchen with a central dining table, wooden cabinets, and a hanging light fixture.

10. Relaxing Two Bedroom Cabin - 10 minutes to Camden!

Relaxing Two Bedroom Cabin - 10 minutes to Camden!
Lincolnville
8.0 out of 10, Very good, (5 reviews)
"We booked this place for Memorial Weekend, and drove into Camden to explore the town. Host was so friendly and responsive, the cabin was so clean and quaint/cute, loved the location that we go that cabin feel but could drive a short distance to get into town/harbor, and overall had a great time! "
United States
Kimberly
The price is ￥48,560
￥83,789 total
includes taxes & fees
Sep 27 - Sep 28
Relaxing Two Bedroom Cabin - 10 minutes to Camden!
A large, light-colored house with a garage, surrounded by lush greenery and a lake.

11. Magical Home & Setting on Reversing Falls. Kayaks, Recreation, Beauty & FUN!

Magical Home & Setting on Reversing Falls. Kayaks, Recreation, Beauty & FUN!
Penobscot
10.0 out of 10, Exceptional, (2 reviews)
"If you are looking for a true relaxing coastal Maine vacation this is the place for you. The property is so peaceful and Barb, Les and Miss Pepper are the most accomodating hosts. This property is as advertised and then some. We had a wonderful stay!!"
United States
Taasha A.
Magical Home & Setting on Reversing Falls. Kayaks, Recreation, Beauty & FUN!
A modern kitchen with a central island, white cabinetry, and a stainless steel range hood.

12. Tides' Reach - Private Waterfront King Beds

Tides' Reach - Private Waterfront King Beds
Orland
9.8 out of 10, Exceptional, (27 reviews)
"Everything was great but at this price the expectation is better and clearer coffee pot and softer toilet tissue. Three large king beds were excellent, better than expected. Bath towels also were excellent size and quality. We knew and we're able to manage with only one and half bath but if you have more people staying at the property, then only one shower may delay in every body getting ready."
United States
Anil
The price is ￥23,732
￥70,338 total
includes taxes & fees
Sep 30 - Oct 1
Tides' Reach - Private Waterfront King Beds
A living room with a brown leather sofa, a wooden coffee table, and a window with curtains.

13. 2 Bedroom Close to Town Home

2 Bedroom Close to Town Home
Thomaston
9.0 out of 10, Wonderful, (54 reviews)
"Perfect location to everything. Spacious house and clean. The directions for check in and check out where very clear and helpful!"
United States
Brianna M.
The price is ￥20,289
￥41,830 total
includes taxes & fees
Oct 27 - Oct 28
2 Bedroom Close to Town Home
A deck with wicker furniture and a glass table, overlooking a marina with boats and a lighthouse.

14. A+ on Harbor w/ 8 Kayaks, Deck, Patio, Beach, Walk To Town, Best Views

A+ on Harbor w/ 8 Kayaks, Deck, Patio, Beach, Walk To Town, Best Views
Stonington
9.8 out of 10, Exceptional, (51 reviews)
"This is a gorgeous cottage in a perfect location to enjoy Stonington!"
United States
Kate S.
The price is ￥38,337
￥98,190 total
includes taxes & fees
Sep 27 - Sep 28
A+ on Harbor w/ 8 Kayaks, Deck, Patio, Beach, Walk To Town, Best Views
A spacious living room with a black leather sofa, a glass coffee table, and large windows offering a view of greenery.

15. Peaceful, Centrally Located Home with Seasonal River Views

Peaceful, Centrally Located Home with Seasonal River Views
Thomaston
9.6 out of 10, Exceptional, (40 reviews)
"Great Stay!"
United States
Pastor Heidi G.
The price is ￥23,435
￥45,431 total
includes taxes & fees
Oct 20 - Oct 21
Peaceful, Centrally Located Home with Seasonal River Views
A room with a large window offering a view of a snowy landscape and a body of water.

16. Comfortable, Close to Town Home, with Oceanview.

Comfortable, Close to Town Home, with Oceanview.
Owls Head
9.6 out of 10, Exceptional, (98 reviews)
"Great location close to town"
United States
Rich W.
The price is ￥31,456
￥57,431 total
includes taxes & fees
Oct 27 - Oct 28
Comfortable, Close to Town Home, with Oceanview.
A spacious tent with a large skylight, a bed, a sofa, a lamp, and a fireplace.

17. Dome 3 at Come Spring Farm Glamping - Alpaca Farm

Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Union
8.8 out of 10, Excellent, (16 reviews)
"Beautiful location and a unique stay."
United States
Sabrina D.
The price is ￥31,456
￥42,434 total
includes taxes & fees
Oct 3 - Oct 4
Dome 3 at Come Spring Farm Glamping - Alpaca Farm
A modern kitchen with a stainless steel refrigerator, a coffee maker, and a sink.

18. In-town, coastal + relaxing in Rockland

In-town, coastal + relaxing in Rockland
Rockland
10.0 out of 10, Exceptional, (50 reviews)
"Great location, great house! It was a perfect getaway for us, highly recommend."
United States
Rob J.
The price is ￥44,038
￥88,803 total
includes taxes & fees
Oct 5 - Oct 6
In-town, coastal + relaxing in Rockland
A cozy room with a large arched window, a potted plant on a wooden side table, and two white armchairs.

19. Inkwell Suite at Spofford Lodge

Inkwell Suite at Spofford Lodge
Bucksport
10.0 out of 10, Exceptional, (19 reviews)
"Property was very nice, clean and Lisa our host was very nice and helpful. Great place, highly recommend!"
United States
brian g.
The price is ￥24,913
￥38,449 total
includes taxes & fees
Oct 26 - Oct 27
Inkwell Suite at Spofford Lodge
A modern kitchen with a central island, built-in appliances, and a dining area with a high chair.

20. Fire Pit & Grill, Movie Room, Workspace, A/C, Pets

Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
Thomaston
10.0 out of 10, Exceptional, (42 reviews)
"Wonderful place at a great price!"
United States
Stephen H.
The price is ￥31,456
￥64,803 total
includes taxes & fees
Oct 26 - Oct 27
Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
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 Islesboro Hotel Reviews

High Tide Inn

High Tide Inn

10/10 Excellent
"Holly, the Innkeeper, Was wonderful! She went above and beyond to accommodate us. The room was very clean with lovely ocean views."
Lori 2-night trip
Posted 6 hours ago
High Tide Inn

Find out more about Islesboro

Islesboro Vacation Homes information

Number of reviews
505
Accommodation
560 Vacation Homes
Lowest Price
￥23,864
Highest Price
￥98,190