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

Holiday Homes in Islesboro

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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 Islesboro holiday homes

1. Romantic Coastal Escape near Harbor

Romantic Coastal Escape near Harbor
Rockport
10.0 out of 10, Exceptional, (5 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 NZ$437
includes taxes & fees
21 Oct - 22 Oct
Romantic Coastal Escape near Harbor
A covered porch with a grill, a potted plant, and a small table.

2. 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 NZ$987
includes taxes & fees
28 Sept - 29 Sept
Cheerful Two Bedroom Cabin - 10 minutes to Camden!
A large, light-colored house with a garage, surrounded by lush greenery and a lake.

3. 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 compact bedroom with a bed, a small table, a bench, a TV, and a kitchenette.

4. 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 NZ$268
includes taxes & fees
8 Oct - 9 Oct
Simplicity-Just what you need! STR24-20
A wooden dock leading to a beach with a picnic table and chairs, surrounded by greenery.

5. 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 NZ$1,014
includes taxes & fees
12 Oct - 13 Oct
Waterfront Getaway Near Acadia w/ Spectacular View
An aerial view of a marina with numerous boats docked and a small island with houses and greenery.

6. 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 NZ$823
includes taxes & fees
27 Sept - 28 Sept
Harbor/🦞 Pound Access & Views from Large Deck
A marina with boats docked, a building labeled 'LYMAN-MORSE', and a residential area in the background.

7. Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town

Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town
Camden
9.2 out of 10, Wonderful, (87 reviews)
"Very convenient and great beds!"
United States
Teresa O.
Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town
A wooden cabin-style kitchen with a central dining table, wooden cabinets, and a hanging light fixture.

8. 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 NZ$999
includes taxes & fees
26 Sept - 27 Sept
Relaxing Two Bedroom Cabin - 10 minutes to Camden!
A two-story house with a dark exterior, a balcony, and a well-maintained garden with rocks and plants.

9. 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 NZ$1,036
includes taxes & fees
27 Sept - 28 Sept
Oceanview Bungalow Style Home in Owls Head
A living room with a brown leather sofa, a wooden coffee table, and a window with curtains.

10. 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 NZ$504
includes taxes & fees
21 Oct - 22 Oct
2 Bedroom Close to Town Home
A wooden deck with Adirondack chairs and a grill.

11. 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 NZ$449
includes taxes & fees
26 Oct - 27 Oct
Bright 2-Bedroom Apartment Near Downtown Thomaston
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 NZ$854
includes taxes & fees
1 Oct - 2 Oct
Tides' Reach - Private Waterfront King Beds
A spacious living room with a black leather sofa, a glass coffee table, and large windows offering a view of greenery.

13. 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 NZ$526
includes taxes & fees
20 Oct - 21 Oct
Peaceful, Centrally Located Home with Seasonal River Views
A covered patio with wicker furniture, a stone wall, and a view of a lake.

14. Waterfront Home - Mid Coast Maine near Camden and Belfast

Waterfront Home - Mid Coast Maine near Camden and Belfast
Belmont
10.0 out of 10, Exceptional, (25 reviews)
"Beautiful, peaceful home with lots of activities for families. Between the kayaking, hiking, and convenience of the house to Acadia and surrounding towns, we could not have asked for a better home to house my entire family for the week. "
United States
Michael L.
The price is NZ$2,077
includes taxes & fees
26 Sept - 27 Sept
Waterfront Home - Mid Coast Maine near Camden and Belfast
A room with a large window offering a view of a snowy landscape and a body of water.

15. 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 NZ$683
includes taxes & fees
26 Oct - 27 Oct
Comfortable, Close to Town Home, with Oceanview.
A modern kitchen with a stainless steel refrigerator, a coffee maker, and a sink.

16. 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 NZ$1,053
includes taxes & fees
5 Oct - 6 Oct
In-town, coastal + relaxing in Rockland
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 NZ$494
includes taxes & fees
27 Sept - 28 Sept
Dome 3 at Come Spring Farm Glamping - Alpaca Farm
A cozy room with a large arched window, a potted plant on a wooden side table, and two white armchairs.

18. 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 NZ$441
includes taxes & fees
26 Oct - 27 Oct
Inkwell Suite at Spofford Lodge
A deck with wicker furniture and a glass table, overlooking a marina with boats and a lighthouse.

19. 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 NZ$1,139
includes taxes & fees
27 Sept - 28 Sept
A+ on Harbor w/ 8 Kayaks, Deck, Patio, Beach, Walk To Town, Best Views
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 NZ$764
includes taxes & fees
26 Oct - 27 Oct
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

Harborline Hotel

Harborline Hotel

10/10 Excellent
"Staff was very friendly and helpful. The bed was comfortable and the room was clean."
Debra 1-night trip
Posted 3 hours ago
Harborline Hotel

Find out more about Islesboro

Islesboro Holiday Homes information

Number of reviews
611
Accommodation
510 Holiday Homes
Lowest Price
NZ$268
Highest Price
NZ$2,077