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
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Islesboro holiday homes

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

1. 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 AU$219
includes taxes & fees
6 Nov - 7 Nov
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.

2. Fully Updated Airy Historic Home in West Rockport

Fully Updated Airy Historic Home in West Rockport
Rockport
The price is AU$805
includes taxes & fees
30 Oct - 31 Oct
Fully Updated Airy Historic Home in West Rockport
A wooden dock leading to a beach with a picnic table and chairs, surrounded by greenery.

3. 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 AU$554
includes taxes & fees
8 Nov - 9 Nov
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.

4. 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 AU$569
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
8.8 out of 10, Excellent, (58 reviews)
"It was in a perfect location for our planned trip. Thank you"
United States
Nita S.
The price is AU$364
includes taxes & fees
28 Oct - 29 Oct
2 Bedroom Close to Town Home
A modern kitchen with a central island, built-in appliances, and a dining area with a high chair.

6. 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, (45 reviews)
"I always enjoy staying at this place!"
United States
Stephen H.
The price is AU$523
includes taxes & fees
31 Oct - 1 Nov
Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
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 AU$707
includes taxes & fees
28 Oct - 29 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, (29 reviews)
"We were greeted by deers in the property. It’s very peaceful and closest to nature."
United States
Anup B.
The price is AU$614
includes taxes & fees
2 Nov - 3 Nov
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, (103 reviews)
"We weren’t even there for 24 hours. It was a great stop on the coast. Close to Rockland and a nice view of the ocean."
United States
Ted H.
The price is AU$481
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 AU$565
includes taxes & fees
3 Nov - 4 Nov
Ladyslipper – Cozy Cottage with Loft in Blue Hill town center
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, (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 AU$347
includes taxes & fees
2 Nov - 3 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.

12. 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 AU$326
includes taxes & fees
16 Nov - 17 Nov
Inkwell Suite at Spofford Lodge
A covered porch with a grill, a potted plant, and a small table.

13. 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 AU$789
includes taxes & fees
28 Oct - 29 Oct
Cheerful Two Bedroom Cabin - 10 minutes to Camden!
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 AU$386
includes taxes & fees
2 Nov - 3 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 AU$789
includes taxes & fees
28 Oct - 29 Oct
Relaxing Two Bedroom Cabin - 10 minutes to Camden!
A modern kitchen with a wooden ceiling, a dining area with a wooden table and chairs, and a view of the outdoors through large windows.

16. Meadow Place Modern 3BR Belfast Getaway with Deck

Meadow Place Modern 3BR Belfast Getaway with Deck
Belfast
The price is AU$932
includes taxes & fees
28 Oct - 29 Oct
Meadow Place Modern 3BR Belfast Getaway with Deck
A modern kitchen with a central island, stainless steel appliances, and wooden cabinetry.

17. Silver Oak Retreat Private Forest Getaway

Silver Oak Retreat Private Forest Getaway
Belfast
The price is AU$866
includes taxes & fees
25 Nov - 26 Nov
Silver Oak Retreat Private Forest Getaway
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.
A+ on Harbor w/ 8 Kayaks, Deck, Patio, Beach, Walk To Town, Best Views
A cozy interior of a geodesic dome tent with a bed, a sofa, a small table with a bottle, a fireplace, and a view of the outdoors.

19. Come Spring Farm Glamping Dome 2

Come Spring Farm Glamping Dome 2
Union
5.6 out of 10, (4 reviews)
"My friends and I had a great time at Come Spring Farm! We got hit with a lot of rain as soon as we arrived and it was really cool to watch the storm through the windows in the dome. We were impressed with the bathroom/shower facilities and the Coop hang out space, and I was thrilled to help feed the animals in the morning. We hope to return soon!"
United States
Healy C.
The price is AU$307
includes taxes & fees
1 Nov - 2 Nov
Come Spring Farm Glamping Dome 2
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

Trade Winds on the Bay

Trade Winds on the Bay

8/10 Good
"Nice place. It was fine. The Host was very helpful."
Rose 1-night trip
Posted 12 hours ago
Trade Winds on the Bay

Find out more about Islesboro

Islesboro Holiday Homes information

Number of reviews
553
Accommodation
513 Holiday Homes
Lowest Price
AU$219
Highest Price
AU$932