Photo by Colleen Johnson

Holiday Homes in Islesboro

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Check prices for these dates

Our top choices for Islesboro holiday homes

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 NZ$244
includes taxes & fees
14 Nov - 15 Nov
Simplicity-Just what you need! STR24-20

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 NZ$673
includes taxes & fees
10 Nov - 11 Nov
Waterfront Getaway Near Acadia w/ Spectacular View

3. Fully Updated Airy Historic Home in West Rockport

Fully Updated Airy Historic Home in West Rockport
Rockport
The price is NZ$989
includes taxes & fees
10 Nov - 11 Nov
Fully Updated Airy Historic Home in West Rockport

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 NZ$714
includes taxes & fees
10 Nov - 11 Nov
Harbor/🦞 Pound Access & Views from Large Deck

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 NZ$742
includes taxes & fees
10 Nov - 11 Nov
Tides' Reach - Private Waterfront King Beds

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 NZ$437
includes taxes & fees
18 Nov - 19 Nov
2 Bedroom Close to Town Home

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 NZ$578
includes taxes & fees
22 Nov - 23 Nov
Comfortable, Close to Town Home, with Oceanview.

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 NZ$969
includes taxes & fees
10 Nov - 11 Nov
Cheerful Two Bedroom Cabin - 10 minutes to Camden!

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 NZ$969
includes taxes & fees
10 Nov - 11 Nov
Relaxing Two Bedroom Cabin - 10 minutes to Camden!

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 NZ$382
includes taxes & fees
7 Dec - 8 Dec
Inkwell Suite at Spofford Lodge

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 NZ$399
includes taxes & fees
1 Dec - 2 Dec
Bright 2-Bedroom Apartment Near Downtown Thomaston

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 NZ$448
includes taxes & fees
1 Dec - 2 Dec
Peaceful, Centrally Located Home with Seasonal River Views

13. Meadow Place Modern 3BR Belfast Getaway with Deck

Meadow Place Modern 3BR Belfast Getaway with Deck
Belfast
The price is NZ$1,127
includes taxes & fees
10 Nov - 11 Nov
Meadow Place Modern 3BR Belfast Getaway with Deck

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 NZ$1,365
includes taxes & fees
7 Dec - 8 Dec
Spacious, bright, oceanfront house on the Blue Hill Peninsula.

15. Silver Oak Retreat Private Forest Getaway

Silver Oak Retreat Private Forest Getaway
Belfast
The price is NZ$1,040
includes taxes & fees
19 Nov - 20 Nov
Silver Oak Retreat Private Forest Getaway

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 NZ$967
includes taxes & fees
13 Nov - 14 Nov
In-town, coastal + relaxing in Rockland

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

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 NZ$1,951
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.

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.

A calm lake with a dock, boats, and a forested shoreline.
Photo by Colleen Johnson
Open Photo by Colleen Johnson

Top reviews in Islesboro