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
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Islesboro holiday homes

Exterior

1. Romantic Coastal Escape near Harbor

Romantic Coastal Escape near Harbor
Rockport
10.0 out of 10, Exceptional, (4 reviews)
"The home is clean and very well stocked with anything you might need. Ty reached out to me to make sure everything was good and offered to bring anything I might need while staying there. Property is very well kept. I love the neighbors too. Bed was comfortable. We will be back next year."
United States
Sheila D.
The price is AU$380
includes taxes & fees
5 Oct - 6 Oct
Romantic Coastal Escape near Harbor
Property grounds

2. Waterfront Getaway Near Acadia w/ Spectacular View

Waterfront Getaway Near Acadia w/ Spectacular View
Deer Isle
10.0 out of 10, Exceptional, (26 reviews)
"Great location with everything we needed."
United States
Thomas P.
The price is AU$705
includes taxes & fees
16 Sept - 17 Sept
Waterfront Getaway Near Acadia w/ Spectacular View
Outdoor dining

3. Privately owned water view cottage with fabulous views of Penobscot Bay!

Privately owned water view cottage with fabulous views of Penobscot Bay!
Belfast
10.0 out of 10, Exceptional, (79 reviews)
"Great location and loved the cottage! Would stay again."
United States
Karie L.
The price is AU$591
includes taxes & fees
12 Sept - 13 Sept
Privately owned water view cottage with fabulous views of Penobscot Bay!
Living area

4. 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
Exterior

5. Magical Home & Setting on Reversing Falls. Kayaks, Recreation, Beauty & FUN!

Magical Home & Setting on Reversing Falls. Kayaks, Recreation, Beauty & FUN!
Penobscot
Magical Home & Setting on Reversing Falls. Kayaks, Recreation, Beauty & FUN!
Room

6. Simplicity-Just what you need! STR24-20

Simplicity-Just what you need! STR24-20
Rockland
9.8 out of 10, Exceptional, (33 reviews)
"Very nice tiny house in a quiet neighborhood. Easy walk to downtown"
United States
sarah
Simplicity-Just what you need! STR24-20
Interior

7. Cheerful Two Bedroom Cabin - 10 minutes to Camden!

Cheerful Two Bedroom Cabin - 10 minutes to Camden!
Lincolnville
10.0 out of 10, Exceptional, (15 reviews)
"This is a great place, nice and quiet, very clean and cozy. Loved it here!!"
United States
Lorna W.
The price is AU$793
includes taxes & fees
13 Sept - 14 Sept
Cheerful Two Bedroom Cabin - 10 minutes to Camden!
Property grounds

8. Oceanview Bungalow Style Home in Owls Head

Oceanview Bungalow Style Home in Owls Head
Owls Head
9.8 out of 10, Exceptional, (73 reviews)
"We really enjoyed staying at this house! It was in a good location and was cute and cozy!"
United States
Victoria S.
The price is AU$825
includes taxes & fees
16 Sept - 17 Sept
Oceanview Bungalow Style Home in Owls Head
Interior

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

Comfortable, Close to Town Home, with Oceanview.
Owls Head
9.6 out of 10, Exceptional, (97 reviews)
"Great location close to town"
United States
Rich W.
The price is AU$604
includes taxes & fees
16 Sept - 17 Sept
Comfortable, Close to Town Home, with Oceanview.
Dining

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

Relaxing Two Bedroom Cabin - 10 minutes to Camden!
Lincolnville
8.0 out of 10, Very good, (5 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$793
includes taxes & fees
13 Sept - 14 Sept
Relaxing Two Bedroom Cabin - 10 minutes to Camden!
Marina

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

Harbor/🦞 Pound Access & Views from Large Deck
Owls Head
9.6 out of 10, Exceptional, (80 reviews)
"Beautiful house with a beautiful location!"
United States
Angel H.
The price is AU$640
includes taxes & fees
23 Sept - 24 Sept
Harbor/🦞 Pound Access & Views from Large Deck
Property grounds

12. Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston
Thomaston
8.8 out of 10, Excellent, (10 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$402
includes taxes & fees
15 Sept - 16 Sept
Bright 2-Bedroom Apartment Near Downtown Thomaston
Living area

13. 2 Bedroom Close to Town Home

2 Bedroom Close to Town Home
Thomaston
9.0 out of 10, Wonderful, (53 reviews)
"Perfect location to everything. Spacious house and clean. The directions for check in and check out where very clear and helpful!"
United States
Brianna M.
The price is AU$440
includes taxes & fees
15 Sept - 16 Sept
2 Bedroom Close to Town Home
Private kitchen

14. In-town, coastal + relaxing in Rockland

In-town, coastal + relaxing in Rockland
Rockland
10.0 out of 10, Exceptional, (49 reviews)
"Great location, great house! It was a perfect getaway for us, highly recommend."
United States
Rob J.
The price is AU$837
includes taxes & fees
5 Oct - 6 Oct
In-town, coastal + relaxing in Rockland
Interior

15. Inkwell Suite at Spofford Lodge

Inkwell Suite at Spofford Lodge
Bucksport
10.0 out of 10, Exceptional, (18 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$408
includes taxes & fees
22 Sept - 23 Sept
Inkwell Suite at Spofford Lodge
Living area

16. Peaceful, Centrally Located Home with Seasonal River Views

Peaceful, Centrally Located Home with Seasonal River Views
Thomaston
9.6 out of 10, Exceptional, (40 reviews)
"Great Stay!"
United States
Pastor Heidi G.
The price is AU$449
includes taxes & fees
15 Sept - 16 Sept
Peaceful, Centrally Located Home with Seasonal River Views
Room

17. Dome 3 at Come Spring Farm Glamping - Alpaca Farm

Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Union
8.6 out of 10, Excellent, (14 reviews)
"Beautiful location and a unique stay."
United States
Sabrina D.
The price is AU$390
includes taxes & fees
13 Sept - 14 Sept
Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Exterior

18. Dome 1 - Luxury Dome at Come Spring Farm

Dome 1 - Luxury Dome at Come Spring Farm
Union
9.6 out of 10, Exceptional, (20 reviews)
"Scenery was amazing, it was a bit chilly at night but a great place for peace and quiet!"
United States
Maurice E.
The price is AU$445
includes taxes & fees
13 Sept - 14 Sept
Dome 1 - Luxury Dome at Come Spring Farm
Private kitchen

19. Tides' Reach - Private Waterfront King Beds

Tides' Reach - Private Waterfront King Beds
Orland
9.8 out of 10, Exceptional, (26 reviews)
"Everything was great but at this price the expectation is better and clearer coffee pot and softer toilet tissue. Three large king beds were excellent, better than expected. Bath towels also were excellent size and quality. We knew and we're able to manage with only one and half bath but if you have more people staying at the property, then only one shower may delay in every body getting ready."
United States
Anil
The price is AU$820
includes taxes & fees
12 Sept - 13 Sept
Tides' Reach - Private Waterfront King Beds
Outdoor dining

20. 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, (51 reviews)
"This is a gorgeous cottage in a perfect location to enjoy Stonington!"
United States
Kate S.
The price is AU$973
includes taxes & fees
6 Oct - 7 Oct
A+ on Harbor w/ 8 Kayaks, Deck, Patio, Beach, Walk To Town, Best Views
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

Whitehall

Whitehall

10/10 Excellent
"The staff was friendly, the property was lovely, the bed was incredibly comfortable. We appreciated the extra touches like ice for the water bottles and our cooler. We also enjoyed walking the neighborhood and sitting on the porch with coffee. Lovely stay."
Lacey 1-night trip
Posted 5 hours ago
Whitehall

Find out more about Islesboro

Islesboro Holiday Homes information

Number of reviews
584
Accommodation
567 Holiday Homes
Lowest Price
AU$380
Highest Price
AU$973