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

Islesboro Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Islesboro vacation rentals

A coastal town with boats docked at a marina, surrounded by lush greenery and hills.

1. Pine Grove Cottages

Pine Grove Cottages
2.5 star property
Lincolnville
9.8 out of 10, Exceptional, (93 reviews)
"Wonderful quiet place, The Host was a great person."
United States
clinch
The price is P14,363
P16,439 total
includes taxes & fees
Oct 13 - Oct 14
Pine Grove Cottages
Lobby sitting area

2. Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (510 reviews)
"the views were incredible, staff friendly and accommodations comfortable."
United States
Allene
The price is P5,142
P5,605 total
includes taxes & fees
Nov 2 - Nov 3
Trade Winds on the Bay
A dining area with a wooden table and chairs, a chandelier, and large windows.

3. Hidden Gem Cottage' Near Blue Hill Peninsula

Hidden Gem Cottage' Near Blue Hill Peninsula
3.0 star property
Brooklin
The price is P13,180
P20,643 total
includes taxes & fees
Oct 15 - Oct 16
Hidden Gem Cottage' Near Blue Hill Peninsula
A wooden deck with a grill, chairs, and a table, overlooking a forested area.

4. Waterfront Deer Isle Retreat w/ Fire Pit!

Waterfront Deer Isle Retreat w/ Fire Pit!
3.0 star property
Deer Isle
The price is P22,909
P45,892 total
includes taxes & fees
Oct 18 - Oct 19
Waterfront Deer Isle Retreat w/ Fire Pit!
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

Camden Riverhouse Hotel

Camden Riverhouse Hotel

8/10 Good
"Parking and the location to walk to shops was excellent. Some rooms were in better shape than others. The rooms were very spacious (actually more than needed) but the bathroom was split in two and very impractical. The toilet and tub was in a cramped corner to the left of the hotel room door and a single sink was on the other side of the door with open hanging space for clothes. The fire pit outback was a very nice amenity with comfortable chairs."
Lisa 2-night trip
Posted less than an hour ago
Camden Riverhouse Hotel

Find out more about Islesboro

Search for holiday rentals in Islesboro on Expedia! You can easily find your home rentals, villas, holiday apartments in Islesboro using one of the methods below:

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Look no further and take a look at our great range of rental properties in Islesboro!

Frequently asked questions

Can I find a vacation rental in Islesboro?

Yes, you can find vacation rentals close to the most popular points of interest in Islesboro, or you can choose a more remote option if you're looking for a relaxing stay.

How many vacation rentals are there in Islesboro?

With 9 Expedia vacation rentals, you're sure to find just the right place for your Islesboro stay.

What’s there to see and do in Islesboro?

While exploring the area, visit family-friendly sights like Penobscot Marine Museum, or get outside and enjoy nature at Lincolnville Beach. Warren Island State Park and Camden Hills State Park are a couple of places you'll find in the larger area.

What’s a vacation rental in Islesboro like?

Vacation rentals are private properties where you can stay for short or long periods in Islesboro. Vacation rentals offer amenities like WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for family trips.