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

Holiday Homes in Islesboro

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Islesboro holiday homes

Property grounds

Charming Retreat for a Romantic Getaway near Penobscot Bay, Maine

Charming Retreat for a Romantic Getaway near Penobscot Bay, Maine
Lincolnville
The price is AU$446
includes taxes & fees
2 Aug - 3 Aug
Charming Retreat for a Romantic Getaway near Penobscot Bay, Maine
1 bedroom, free WiFi, bed sheets

Simplicity-Just what you need! STR24-20

Simplicity-Just what you need! STR24-20
Rockland
9.6 out of 10, Exceptional, (26 reviews)
"Very clean and allows for easy access around the area! "
United States
Sarah V.
The price is AU$258
includes taxes & fees
28 July - 29 July
Simplicity-Just what you need! STR24-20
Exterior

Romantic Coastal Escape near Harbor

Romantic Coastal Escape near Harbor
Rockport
10.0 out of 10, Exceptional, (3 reviews)
"A wonderful place to stay close walking distance to downtown Rockport"
United States
Joshua H.
The price is AU$462
includes taxes & fees
18 Aug - 19 Aug
Romantic Coastal Escape near Harbor
TV, offices

Fully Updated Airy Historic Home in West Rockport

Fully Updated Airy Historic Home in West Rockport
Rockport
The price is AU$872
includes taxes & fees
28 July - 29 July
Fully Updated Airy Historic Home in West Rockport
Exterior

Drift A-Frame - NEW A-Frame in Blue Hill!

Drift A-Frame - NEW A-Frame in Blue Hill!
Blue Hill
The price is AU$656
includes taxes & fees
28 July - 29 July
Drift A-Frame - NEW A-Frame in Blue Hill!
Interior

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$821
includes taxes & fees
28 July - 29 July
Cheerful Two Bedroom Cabin - 10 minutes to Camden!
Property grounds

Waterfront Getaway Near Acadia w/ Spectacular View

Waterfront Getaway Near Acadia w/ Spectacular View
Deer Isle
10.0 out of 10, Exceptional, (21 reviews)
"Great location with everything we needed."
United States
Thomas P.
The price is AU$823
includes taxes & fees
29 July - 30 July
Waterfront Getaway Near Acadia w/ Spectacular View
Property grounds

Stylish Vacation Rental for Couples Overlooking West Penobscot Bay, Maine

Stylish Vacation Rental for Couples Overlooking West Penobscot Bay, Maine
Lincolnville
The price is AU$460
includes taxes & fees
2 Aug - 3 Aug
Stylish Vacation Rental for Couples Overlooking West Penobscot Bay, Maine
Property grounds

Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston
Thomaston
9.8 out of 10, Exceptional, (6 reviews)
"Host was fast in responding to all questions and concerns. Location was good for being close to all shopping and eating. "
United States
Kim W.
The price is AU$442
includes taxes & fees
3 Aug - 4 Aug
Bright 2-Bedroom Apartment Near Downtown Thomaston
Property grounds

Lovely Retreat with a Private Deck in a Bed and Breakfast near Rockland, Maine

Lovely Retreat with a Private Deck in a Bed and Breakfast near Rockland, Maine
Lincolnville
The price is AU$500
includes taxes & fees
2 Aug - 3 Aug
Lovely Retreat with a Private Deck in a Bed and Breakfast near Rockland, Maine
Property grounds

Fabulous Bed and Breakfast Getaway for Four in Lincolnville, Maine

Fabulous Bed and Breakfast Getaway for Four in Lincolnville, Maine
Lincolnville
The price is AU$500
includes taxes & fees
2 Aug - 3 Aug
Fabulous Bed and Breakfast Getaway for Four in Lincolnville, Maine
Property grounds

Romantic Getaway Accommodation Overlooking West Penobscot Bay in Maine

Romantic Getaway Accommodation Overlooking West Penobscot Bay in Maine
Lincolnville
The price is AU$441
includes taxes & fees
2 Aug - 3 Aug
Romantic Getaway Accommodation Overlooking West Penobscot Bay in Maine
Property grounds

Inviting Bed and Breakfast for a Romantic Getaway near Belfast, Maine

Inviting Bed and Breakfast for a Romantic Getaway near Belfast, Maine
Lincolnville
The price is AU$431
includes taxes & fees
2 Aug - 3 Aug
Inviting Bed and Breakfast for a Romantic Getaway near Belfast, Maine
Property grounds

Cozy Bed and Breakfast with Beautiful Bay Views near Rockland, Maine

Cozy Bed and Breakfast with Beautiful Bay Views near Rockland, Maine
Lincolnville
The price is AU$485
includes taxes & fees
2 Aug - 3 Aug
Cozy Bed and Breakfast with Beautiful Bay Views near Rockland, Maine
Property grounds

The Mount Battie Inn near Penobscot Bay, Maine

The Mount Battie Inn near Penobscot Bay, Maine
Lincolnville
The price is AU$515
includes taxes & fees
4 Aug - 5 Aug
The Mount Battie Inn near Penobscot Bay, Maine
Property grounds

Bed and Breakfast Perfect for a Romantic Getaway near Camden Hills State Park, Maine

Bed and Breakfast Perfect for a Romantic Getaway near Camden Hills State Park, Maine
Lincolnville
The price is AU$524
includes taxes & fees
2 Aug - 3 Aug
Bed and Breakfast Perfect for a Romantic Getaway near Camden Hills State Park, Maine
Property grounds

Oceanview Bungalow Style Home in Owls Head

Oceanview Bungalow Style Home in Owls Head
Owls Head
9.8 out of 10, Exceptional, (64 reviews)
"Perfect home away from home. Very well stocked kitchen, the beds were very comfy and everything was just overall cozy. Such a serene location. We will definitely stay again next time we come to visit our grandkids. "
United States
Tina B.
The price is AU$868
includes taxes & fees
5 Aug - 6 Aug
Oceanview Bungalow Style Home in Owls Head
Dining

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$821
includes taxes & fees
28 July - 29 July
Relaxing Two Bedroom Cabin - 10 minutes to Camden!
Marina

Harbor/🦞 Pound Access & Views from Large Deck

Harbor/🦞 Pound Access & Views from Large Deck
Owls Head
9.6 out of 10, Exceptional, (78 reviews)
"Beautiful house with a beautiful location!"
United States
Angel H.
The price is AU$734
includes taxes & fees
2 Aug - 3 Aug
Harbor/🦞 Pound Access & Views from Large Deck
Exterior

Dome 1 - Luxury Dome at Come Spring Farm

Dome 1 - Luxury Dome at Come Spring Farm
Union
9.6 out of 10, Exceptional, (19 reviews)
"We had never stayed in a yurt before and this one had everything you need. We ate breakfast out on the deck and enjoyed the scenery. We had a really nice time!"
United States
Karen I.
The price is AU$460
includes taxes & fees
28 July - 29 July
Dome 1 - Luxury Dome at Come Spring Farm
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Islesboro Hotel Reviews

Colonial Gables Oceanfront Village

Colonial Gables Oceanfront Village

10/10 Excellent
"This place was a real gem. There are a few dozen cottages all with an ocean view. We walked the beach at low tide to collect shells. The cabins are small, but very well equipped. We went to a nearby grocery and made our dinner at the cabin. We will definitely go back. The price was a fraction of what staying in down town Bar Harbor costs, and its views are much better."
Eric 1-night trip
Posted 1 hour ago
Colonial Gables Oceanfront Village

Find out more about Islesboro

Islesboro Holiday Homes information

Number of reviews
232
Accommodation
567 Holiday Homes
Lowest Price
AU$258
Highest Price
AU$872