Islesboro Vacation Rentals

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Check prices for these dates

In two weeks
Jun 26 - Jun 28
In two months
Aug 7 - Aug 9
In three months
Sep 4 - Sep 6
In four months
Oct 2 - Oct 4

Our top choices for Islesboro vacation rentals

Lobby sitting area

Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (407 reviews)
"Everything was great and the location was amazing. Right in the arts district and surrounded by interesting shops, amazing eats and coffee & right on the harbor."
United States
Gerald
The price is ￥20,046
￥21,850 total
includes taxes & fees
Jun 18 - Jun 19
Trade Winds on the Bay
Property grounds

Cozy Cabin By The Pond, Sleeps 2

Cozy Cabin By The Pond, Sleeps 2
Waldo
10.0 out of 10, Exceptional, (207 reviews)
"Very peaceful and cozy cabin! We had a wonderful weekend getaway and will definitely be back! "
United States
Johanna W.
The price is ￥23,201
￥36,975 total
includes taxes & fees
Jun 21 - Jun 22
Cozy Cabin By The Pond, Sleeps 2
Exterior

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

Drift A-Frame - NEW A-Frame in Blue Hill!
Blue Hill
The price is ￥25,922
￥74,816 total
includes taxes & fees
Jun 14 - Jun 15
Drift A-Frame - NEW A-Frame in Blue Hill!
1 bedroom, bed sheets

Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine

Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine
Lincolnville
8.0 out of 10, Very Good, (11 reviews)
"The cabin is exactly as advertised. The dogs were happy there and we enjoyed our stay. "
United States
Becki C.
The price is ￥12,241
￥24,680 total
includes taxes & fees
Jun 19 - Jun 20
Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine
Terrace/patio

Rustic Retreat Across from Lake; Family Friendly!

Rustic Retreat Across from Lake; Family Friendly!
Union
8.8 out of 10, Excellent, (18 reviews)
"Great location for visiting the coast."
United States
Sallie S.
The price is ￥17,601
￥65,988 total
includes taxes & fees
Jun 26 - Jun 27
Rustic Retreat Across from Lake; Family Friendly!
Property grounds

Glamping at Maine Water Buffalo Farm

Glamping at Maine Water Buffalo Farm
Appleton
10.0 out of 10, Exceptional, (2 reviews)
"Really great place….very thoughtful set up for us to enjoy."
United States
Peter P.
The price is ￥20,641
￥25,987 total
includes taxes & fees
Jun 16 - Jun 17
Glamping at Maine Water Buffalo Farm
Interior

2 Bedroom Close to Town Home

2 Bedroom Close to Town Home
Thomaston
9.0 out of 10, Wonderful, (47 reviews)
"We loved our stay here! Check-in was easy and the host was responsive!"
United States
Jessica H.
The price is ￥30,446
￥56,940 total
includes taxes & fees
Jun 14 - Jun 15
2 Bedroom Close to Town Home
Boating

Pine Grove Cottages

Pine Grove Cottages
2.5 star property
Lincolnville
9.8 out of 10, Exceptional, (90 reviews)
"Wonderful quiet place, The Host was a great person."
United States
clinch
The price is ￥31,143
￥35,643 total
includes taxes & fees
Jun 15 - Jun 16
Pine Grove Cottages
Smart TV

Peaceful, Centrally Located Home with Seasonal River Views

Peaceful, Centrally Located Home with Seasonal River Views
Thomaston
9.4 out of 10, Exceptional, (33 reviews)
"Great place at a great price! We look forward to staying there again. "
United States
Stephen H.
The price is ￥23,075
￥47,683 total
includes taxes & fees
Jun 15 - Jun 16
Peaceful, Centrally Located Home with Seasonal River Views
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, (25 reviews)
"Very comfortable, well stocked and quiet."
United States
Lucy F.
The price is ￥19,469
￥28,732 total
includes taxes & fees
Jun 14 - Jun 15
Simplicity-Just what you need! STR24-20
Terrace/patio

SeaRiver Cabin on the Bagaduce, Kayaks Included. Seals, Wildlife, Birds & Nature

SeaRiver Cabin on the Bagaduce, Kayaks Included. Seals, Wildlife, Birds & Nature
Penobscot
10.0 out of 10, Exceptional, (8 reviews)
"All was fabulous!!!"
United States
Maria M.
The price is ￥29,356
￥61,516 total
includes taxes & fees
Jun 14 - Jun 15
SeaRiver Cabin on the Bagaduce, Kayaks Included. Seals, Wildlife, Birds & Nature
Cottage (1 Bedroom) | Interior

Hidden Gem Cottage' Near Blue Hill Peninsula

Hidden Gem Cottage' Near Blue Hill Peninsula
3.0 star property
Brooklin
The price is ￥29,164
￥52,622 total
includes taxes & fees
Jun 27 - Jun 28
Hidden Gem Cottage' Near Blue Hill Peninsula
WiFi

Dome 3 at Come Spring Farm Glamping - Alpaca Farm

Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Union
8.4 out of 10, Very Good, (9 reviews)
"Beautiful location and a unique stay."
United States
Sabrina D.
The price is ￥32,002
￥45,264 total
includes taxes & fees
Jun 14 - Jun 15
Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Exterior

Pine Grove Cottages : Cottage 6 - Studio Cottage - Pet Friendly

Pine Grove Cottages : Cottage 6 - Studio Cottage - Pet Friendly
Lincolnville
10.0 out of 10, Exceptional, (10 reviews)
"Great owner and quick night stay. "
United States
Jeanean W.
The price is ￥36,794
￥44,292 total
includes taxes & fees
Jun 21 - Jun 22
Pine Grove Cottages : Cottage 6 - Studio Cottage - Pet Friendly
Exterior

Cozy cottage -Close to Downtown Camden!

Cozy cottage -Close to Downtown Camden!
Camden
9.8 out of 10, Exceptional, (22 reviews)
"Charming property with many nice touches. Excellent location between the lake and town.We truly enjoyed staying there!"
United States
Susan B.
The price is ￥32,729
￥70,781 total
includes taxes & fees
Jun 15 - Jun 16
Cozy cottage -Close to Downtown Camden!
Property grounds

Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston
Thomaston
9.6 out of 10, Exceptional, (4 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 ￥23,201
￥43,951 total
includes taxes & fees
Jun 15 - Jun 16
Bright 2-Bedroom Apartment Near Downtown Thomaston
Dining

Hidden Gem Cottage' Near Blue Hill Peninsula

Hidden Gem Cottage' Near Blue Hill Peninsula
Brooklin
10.0 out of 10, Exceptional, (42 reviews)
"We enjoyed our stay very much."
Germany
Richard O.
The price is ￥26,082
￥53,184 total
includes taxes & fees
Jul 12 - Jul 13
Hidden Gem Cottage' Near Blue Hill Peninsula
Outdoor dining

Country Charm: Cozy getaway in delightful Searsport

Country Charm: Cozy getaway in delightful Searsport
Searsport
9.6 out of 10, Exceptional, (17 reviews)
"Lovely spot, thoughtfully equipped — we had a wonderful, restful stay. Highly recommended!"
United States
Jerry K.
The price is ￥20,161
￥30,173 total
includes taxes & fees
Jun 14 - Jun 15
Country Charm: Cozy getaway in delightful Searsport
Exterior

Cozy Waterfront Guesthouse Getaway in Camden with Mountain Views

Cozy Waterfront Guesthouse Getaway in Camden with Mountain Views
Camden
The price is ￥32,402
￥53,981 total
includes taxes & fees
Jun 17 - Jun 18
Cozy Waterfront Guesthouse Getaway in Camden with Mountain Views
Terrace/patio

Starry Artsy Garage Loft

Starry Artsy Garage Loft
Sedgwick
9.8 out of 10, Exceptional, (28 reviews)
"Absolutely great stay. Wonderful home, wonderful host! I will be keeping this place in mind for when I come back to Maine! "
United States
Kellee M.
The price is ￥24,805
￥54,983 total
includes taxes & fees
Jun 25 - Jun 26
Starry Artsy Garage Loft
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

Lord Camden Inn

Lord Camden Inn

8/10 Good
"Everything was great, good location, friendly staff, good breakfast. TV was small, not the newer generation!"
Tiruvilvamalai 3-night trip
Posted 12 hours ago
Lord Camden Inn

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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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.

What are some of the best vacation rentals that Islesboro has to offer?

Island log home in Maine with ocean views: This highly rated vacation home rental in Islesboro offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a garden.

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 Perry's Nut House, 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.