Photo by Colleen Johnson

Holiday Homes in Islesboro

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Find holiday rentals that suit your style

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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

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, (41 reviews)
"The perfect spot for quiet and privacy yet a short trip to town."
United States
jennifer
The price is €124
includes taxes & fees
14 Nov - 15 Nov
Simplicity-Just what you need! STR24-20
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 €331
includes taxes & fees
10 Nov - 11 Nov
Waterfront Getaway Near Acadia w/ Spectacular View
A living room with a sofa, a coffee table, a TV, a fireplace, and a window with curtains.

3. Fully Updated Airy Historic Home in West Rockport

Fully Updated Airy Historic Home in West Rockport
Rockport
Fully Updated Airy Historic Home in West Rockport
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 €372
includes taxes & fees
10 Nov - 11 Nov
Harbor/🦞 Pound Access & Views from Large Deck
A modern kitchen with a central island, white cabinetry, and a stainless steel range hood.

5. 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 €375
includes taxes & fees
10 Nov - 11 Nov
Tides' Reach - Private Waterfront King Beds
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
8.8 out of 10, Excellent, (59 reviews)
"It was in a perfect location for our planned trip. Thank you"
United States
Nita S.
The price is €226
includes taxes & fees
10 Nov - 11 Nov
2 Bedroom Close to Town Home
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, (104 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 €284
includes taxes & fees
22 Nov - 23 Nov
Comfortable, Close to Town Home, with Oceanview.
A covered porch with a grill, a potted plant, and a small table.

8. 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 €485
includes taxes & fees
10 Nov - 11 Nov
Cheerful Two Bedroom Cabin - 10 minutes to Camden!
A wooden cabin-style kitchen with a central dining table, wooden cabinets, and a hanging light fixture.

9. 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 €504
includes taxes & fees
15 Nov - 16 Nov
Relaxing Two Bedroom Cabin - 10 minutes to Camden!
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, (22 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 €196
includes taxes & fees
7 Dec - 8 Dec
Inkwell Suite at Spofford Lodge
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, (17 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 €212
includes taxes & fees
1 Dec - 2 Dec
Bright 2-Bedroom Apartment Near Downtown Thomaston
A spacious living room with a black leather sofa, a glass coffee table, and large windows offering a view of greenery.

12. 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 €225
includes taxes & fees
1 Dec - 2 Dec
Peaceful, Centrally Located Home with Seasonal River Views
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.

13. Meadow Place Modern 3BR Belfast Getaway with Deck

Meadow Place Modern 3BR Belfast Getaway with Deck
Belfast
The price is €581
includes taxes & fees
10 Nov - 11 Nov
Meadow Place Modern 3BR Belfast Getaway with Deck
A wooden deck with a view of a landscaped garden and a body of water.

14. Spacious, bright, oceanfront house on the Blue Hill Peninsula.

Spacious, bright, oceanfront house on the Blue Hill Peninsula.
Penobscot
10.0 out of 10, Exceptional, (8 reviews)
"Great view and ambience!"
United States
Cameron C.
The price is €672
includes taxes & fees
1 Dec - 2 Dec
Spacious, bright, oceanfront house on the Blue Hill Peninsula.
A modern kitchen with a central island, stainless steel appliances, and wooden cabinetry.

15. Silver Oak Retreat Private Forest Getaway

Silver Oak Retreat Private Forest Getaway
Belfast
The price is €537
includes taxes & fees
10 Nov - 11 Nov
Silver Oak Retreat Private Forest Getaway
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, (58 reviews)
"Great location, great house! It was a perfect getaway for us, highly recommend."
United States
Rob J.
The price is €482
includes taxes & fees
13 Nov - 14 Nov
In-town, coastal + relaxing in Rockland
A deck with wicker furniture and a glass table, overlooking a marina with boats and a lighthouse.

17. 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 marina with boats docked, a building labeled 'LYMAN-MORSE', and a residential area in the background.

18. 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, (90 reviews)
"Very convenient and great beds!"
United States
Teresa O.
The price is €997
includes taxes & fees
12 Nov - 13 Nov
Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town
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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Learn more about Islesboro

This tranquil island offers scenic bike rides along coastal roads and peaceful beaches perfect for swimming at Pendleton Point. Catch the ferry to explore historic lighthouses or rent kayaks to paddle around the island's protected harbours.

See all hotels in Islesboro
A calm lake with a dock, boats, and a forested shoreline.
Photo by Colleen Johnson
Open Photo by Colleen Johnson

Top reviews in Islesboro

A white building with a blue awning, a deck with hanging flower baskets, and a sign indicating a coffee shop.
Glen Cove Inn & Suites

Glen Cove Inn & Suites

Glen Cove Inn & Suites
Rockport

10/10 Excellent

This was a very nice stay. Very clean , beds comfortable, good towels. Parking onsite. Nice breakfast and great service.
Ireland
Kathy
Reviewed June 10, 2022
Glen Cove Inn & Suites