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

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 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)
"A wonderful place to stay close walking distance to downtown Rockport"
United States
Joshua H.
The price is AED 452
AED 909 total
includes taxes & fees
25 Oct - 26 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 545
AED 1,471 total
includes taxes & fees
4 Nov - 5 Nov
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)
"This was such a super cute place. Great little get away. Very clean! I would definitely recommend this place if you are in the area!"
United States
Beth
The price is AED 357
AED 557 total
includes taxes & fees
26 Oct - 27 Oct
Simplicity-Just what you need! STR24-20
A living room with a sofa, a coffee table, a TV, a fireplace, and a window with curtains.

4. Fully Updated Airy Historic Home in West Rockport

Fully Updated Airy Historic Home in West Rockport
Rockport
The price is AED 540
AED 2,162 total
includes taxes & fees
26 Oct - 27 Oct
Fully Updated Airy Historic Home in West Rockport
A wooden table and two chairs in a garden with a gravel path, surrounded by lush greenery and trees.

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

Harbor/🦞 Pound Access & Views from Large Deck
Owls Head
9.6 out of 10, Exceptional, (84 reviews)
"Great place for a girls' weekend!! Had a wonderful stay!"
United States
Jeanette Q.
The price is AED 521
AED 1,518 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.

6. 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 929 total
includes taxes & fees
28 Oct - 29 Oct
2 Bedroom Close to Town Home
A large, light-colored house with a garage, surrounded by lush greenery and a lake.

7. 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.
The price is AED 863
AED 1,866 total
includes taxes & fees
29 Oct - 30 Oct
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.

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 535
AED 1,648 total
includes taxes & fees
25 Oct - 26 Oct
Tides' Reach - Private Waterfront King Beds
A room with a large window offering a view of a snowy landscape and a body of water.

9. 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 632
AED 1,293 total
includes taxes & fees
10 Nov - 11 Nov
Comfortable, Close to Town Home, with Oceanview.
A dining area with a round table, chairs, and a wooden counter with a toaster.

10. 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 661
AED 1,505 total
includes taxes & fees
2 Nov - 3 Nov
Ladyslipper – Cozy Cottage with Loft in Blue Hill town center
A covered porch with a grill, a potted plant, and a small table.

11. 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 2,073 total
includes taxes & fees
23 Oct - 24 Oct
Cheerful Two Bedroom Cabin - 10 minutes to Camden!
A wooden deck with Adirondack chairs and a grill.

12. Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston
Thomaston
9.2 out of 10, Wonderful, (16 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 444
AED 897 total
includes taxes & fees
17 Nov - 18 Nov
Bright 2-Bedroom Apartment Near Downtown Thomaston
A modern bathroom with a skylight, a mirror, and a towel rack.

13. 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
4 Nov - 5 Nov
Inkwell Suite at Spofford Lodge
A wooden cabin-style kitchen with a central dining table, wooden cabinets, and a hanging light fixture.

14. 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
23 Oct - 24 Oct
Relaxing Two Bedroom Cabin - 10 minutes to Camden!
A modern living room with a wooden coffee table, grey sofas, and a large plant.

15. 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
23 Oct - 24 Oct
Meadow Place Modern 3BR Belfast Getaway with Deck
A spacious tent with a large skylight, a bed, a sofa, a lamp, and a fireplace.

16. 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 606
AED 883 total
includes taxes & fees
26 Oct - 27 Oct
Dome 3 at Come Spring Farm Glamping - Alpaca Farm
A spacious living room with a black leather sofa, a glass coffee table, and large windows offering a view of greenery.

17. 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 489
AED 1,045 total
includes taxes & fees
16 Nov - 17 Nov
Peaceful, Centrally Located Home with Seasonal River Views
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
25 Oct - 26 Oct
A+ on Harbor w/ 8 Kayaks, Deck, Patio, Beach, Walk To Town, Best Views
A bedroom with a bed, a ceiling fan, a window with curtains, a mirror, and a bedside table.

19. 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
A modern kitchen with a stainless steel refrigerator, a coffee maker, and a sink.

20. In-town, coastal + relaxing in Rockland

In-town, coastal + relaxing in Rockland
Rockland
10.0 out of 10, Exceptional, (57 reviews)
"Great location, great house! It was a perfect getaway for us, highly recommend."
United States
Rob J.
The price is AED 911
AED 2,050 total
includes taxes & fees
28 Oct - 29 Oct
In-town, coastal + relaxing in Rockland
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

Ledges by the Bay

Ledges by the Bay

10/10 Excellent
"Top"
Celso Tiago 1-night trip
Posted 10 hours ago
Ledges by the Bay