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

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Check prices for these dates

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

Our top choices for Islesboro vacation homes

Exterior

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 AED 448
AED 901 total
includes taxes & fees
21 Oct - 22 Oct
Romantic Coastal Escape near Harbor
A wooden dock leading to a beach with a picnic table and chairs, surrounded by greenery.

2. Waterfront Getaway Near Acadia w/ Spectacular View

Waterfront Getaway Near Acadia w/ Spectacular View
Deer Isle
9.8 out of 10, Exceptional, (27 reviews)
"Great location with everything we needed."
United States
Thomas P.
The price is AED 595
AED 1,533 total
includes taxes & fees
28 Oct - 29 Oct
Waterfront Getaway Near Acadia w/ Spectacular View
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, (37 reviews)
"Very nice tiny house in a quiet neighborhood. Easy walk to downtown"
United States
sarah
The price is AED 357
AED 557 total
includes taxes & fees
18 Oct - 19 Oct
Simplicity-Just what you need! STR24-20
An aerial view of a marina with numerous boats docked and a small island with houses and greenery.

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

Harbor/🦞 Pound Access & Views from Large Deck
Owls Head
9.6 out of 10, Exceptional, (83 reviews)
"Great place for a girls' weekend!! Had a wonderful stay!"
United States
Jeanette Q.
The price is AED 579
AED 1,591 total
includes taxes & fees
1 Nov - 2 Nov
Harbor/🦞 Pound Access & Views from Large Deck
A living room with a brown leather sofa, a wooden coffee table, and a window with curtains.

5. 2 Bedroom Close to Town Home

2 Bedroom Close to Town Home
Thomaston
9.0 out of 10, Wonderful, (57 reviews)
"It was in a perfect location for our planned trip. Thank you"
United States
Nita S.
The price is AED 422
AED 961 total
includes taxes & fees
27 Oct - 28 Oct
2 Bedroom Close to Town Home
A large, light-colored house with a garage, surrounded by lush greenery and a lake.

6. 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, (3 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 room with a large window offering a view of a snowy landscape and a body of water.

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

Comfortable, Close to Town Home, with Oceanview.
Owls Head
9.6 out of 10, Exceptional, (102 reviews)
"Great location close to town"
United States
Rich W.
The price is AED 643
AED 1,297 total
includes taxes & fees
15 Nov - 16 Nov
Comfortable, Close to Town Home, with Oceanview.
A modern kitchen with a central island, white cabinetry, and a stainless steel range hood.

8. Tides' Reach - Private Waterfront King Beds

Tides' Reach - Private Waterfront King Beds
Orland
9.8 out of 10, Exceptional, (28 reviews)
"We were greeted by deers in the property. It’s very peaceful and closest to nature."
United States
Anup B.
The price is AED 716
AED 1,838 total
includes taxes & fees
18 Oct - 19 Oct
Tides' Reach - Private Waterfront King Beds
A wooden deck with Adirondack chairs and a grill.

9. Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston
Thomaston
9.2 out of 10, Wonderful, (15 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 AED 463
AED 921 total
includes taxes & fees
9 Nov - 10 Nov
Bright 2-Bedroom Apartment Near Downtown Thomaston
A cozy room with a large arched window, a potted plant on a wooden side table, and two white armchairs.

10. Inkwell Suite at Spofford Lodge

Inkwell Suite at Spofford Lodge
Bucksport
10.0 out of 10, Exceptional, (21 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 AED 517
AED 847 total
includes taxes & fees
9 Nov - 10 Nov
Inkwell Suite at Spofford Lodge
A dining area with a round table, chairs, and a wooden counter with a toaster.

11. Ladyslipper – Cozy Cottage with Loft in Blue Hill town center

Ladyslipper – Cozy Cottage with Loft in Blue Hill town center
Blue Hill
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful cottage in a cute location! We loved the character of the loft and the loft window was great for sunrise and set! Would 100% stay here again. "
United States
Kaylyn T.
The price is AED 735
AED 1,593 total
includes taxes & fees
1 Nov - 2 Nov
Ladyslipper – Cozy Cottage with Loft in Blue Hill town center
A covered porch with a grill, a potted plant, and a small table.

12. 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)
"Looking for a quick get-away - this is the place! The cabins are so cute and comfortable. Plenty of room for a couple or a family. It was our second time there and will definitely return!"
United States
Patricia T.
The price is AED 1,134
AED 2,085 total
includes taxes & fees
16 Oct - 17 Oct
Cheerful 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.

13. Oceanview Bungalow Style Home in Owls Head

Oceanview Bungalow Style Home in Owls Head
Owls Head
9.8 out of 10, Exceptional, (85 reviews)
"The property was wonderful! Our group of 5 adults were very comfortable and satisfied with our stay of 3 nights. We were in town for a family reunion, and enjoyed the great amenities of the property as we spent cherished time with our extended family. Comfortable beds, relaxing common areas and great location."
United States
christoohey1
The price is AED 744
AED 2,184 total
includes taxes & fees
16 Oct - 17 Oct
Oceanview Bungalow Style Home in Owls Head
A spacious living room with a black leather sofa, a glass coffee table, and large windows offering a view of greenery.

14. Peaceful, Centrally Located Home with Seasonal River Views

Peaceful, Centrally Located Home with Seasonal River Views
Thomaston
9.6 out of 10, Exceptional, (41 reviews)
"Great Stay!"
United States
Pastor Heidi G.
The price is AED 525
AED 1,089 total
includes taxes & fees
9 Nov - 10 Nov
Peaceful, Centrally Located Home with Seasonal River Views
A wooden cabin-style kitchen with a central dining table, wooden cabinets, and a hanging light fixture.

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

Relaxing Two Bedroom Cabin - 10 minutes to Camden!
Lincolnville
8.4 out of 10, Very good, (6 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 AED 1,134
AED 2,073 total
includes taxes & fees
18 Oct - 19 Oct
Relaxing Two Bedroom Cabin - 10 minutes to Camden!
A modern kitchen with a central island, built-in appliances, and a dining area with a high chair.

16. 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, (44 reviews)
"I always enjoy staying at this place!"
United States
Stephen H.
The price is AED 661
AED 1,509 total
includes taxes & fees
20 Oct - 21 Oct
Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
A modern living room with a wooden coffee table, grey sofas, and a large plant.

17. Meadow Place Modern 3BR Belfast Getaway with Deck

Meadow Place Modern 3BR Belfast Getaway with Deck
Belfast
The price is AED 1,273
AED 2,400 total
includes taxes & fees
18 Oct - 19 Oct
Meadow Place Modern 3BR Belfast Getaway with Deck
A deck with wicker furniture and a glass table, overlooking a marina with boats and a lighthouse.

18. 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, (54 reviews)
"This is a gorgeous cottage in a perfect location to enjoy Stonington!"
United States
Kate S.
The price is AED 813
AED 2,315 total
includes taxes & fees
19 Oct - 20 Oct
A+ on Harbor w/ 8 Kayaks, Deck, Patio, Beach, Walk To Town, Best Views
A spacious tent with a large skylight, a bed, a sofa, a lamp, and a fireplace.

19. 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 AED 735
AED 1,043 total
includes taxes & fees
20 Oct - 21 Oct
Dome 3 at Come Spring Farm Glamping - Alpaca Farm
A modern kitchen with a central island, stainless steel appliances, and wooden cabinetry.

20. Silver Oak Retreat Private Forest Getaway

Silver Oak Retreat Private Forest Getaway
Belfast
The price is AED 1,175
AED 2,334 total
includes taxes & fees
28 Oct - 29 Oct
Silver Oak Retreat Private Forest Getaway
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

Rockland Harbor Hotel

Rockland Harbor Hotel

8/10 Good
"Accommodations were fantastic. Very nice staff and close to everything."
Daryl 1-night trip
Posted less than an hour ago
Rockland Harbor Hotel