Islesboro Holiday Rentals

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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

Our top choices for Islesboro holiday rentals

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 HK$599
HK$1,208 total
includes taxes & fees
4 May - 5 May
Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine
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, (32 reviews)
"Great stay and host was very responsive with a forgotten item. "
United States
Yvonne T.
The price is HK$987
HK$2,152 total
includes taxes & fees
4 May - 5 May
Peaceful, Centrally Located Home with Seasonal River Views
Property grounds

Cozy Cabin By The Pond, Sleeps 2

Cozy Cabin By The Pond, Sleeps 2
Waldo
10.0 out of 10, Exceptional, (204 reviews)
"Very peaceful and cozy cabin! We had a wonderful weekend getaway and will definitely be back! "
United States
Johanna W.
The price is HK$940
HK$1,563 total
includes taxes & fees
5 May - 6 May
Cozy Cabin By The Pond, Sleeps 2
Outdoor dining

The Lewis R. French- Inn on the Harbor

The Lewis R. French- Inn on the Harbor
Stonington
9.2 out of 10, Wonderful, (10 reviews)
"Made wonderful memories and really enjoyed the beautiful oceanfront town of Stonington."
United States
Elizabeth P.
The price is HK$518
HK$949 total
includes taxes & fees
4 May - 5 May
The Lewis R. French- Inn on the Harbor
Lobby sitting area

Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (379 reviews)
"Great location, friendly staff. "
United States
Connor
The price is HK$770
HK$839 total
includes taxes & fees
7 May - 8 May
Trade Winds on the Bay
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 HK$1,234
HK$2,951 total
includes taxes & fees
4 May - 5 May
SeaRiver Cabin on the Bagaduce, Kayaks Included. Seals, Wildlife, Birds & Nature
Interior

Cheerful Two Bedroom Cabin - 10 minutes to Camden!

Cheerful Two Bedroom Cabin - 10 minutes to Camden!
Lincolnville
10.0 out of 10, Exceptional, (13 reviews)
"This is a great place, nice and quiet, very clean and cozy. Loved it here!!"
United States
Lorna W.
The price is HK$1,377
HK$3,183 total
includes taxes & fees
4 May - 5 May
Cheerful Two Bedroom Cabin - 10 minutes to Camden!
Interior

Rustic Retreat Across From Lake; Family Friendly!

Rustic Retreat Across From Lake; Family Friendly!
3.0 star property
Union
9.0 out of 10, Wonderful, (2 reviews)
"I liked that it was by the lake quiet and secluded. "
United States
Wilma
The price is HK$956
HK$3,157 total
includes taxes & fees
20 May - 21 May
Rustic Retreat Across From Lake; Family Friendly!
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 HK$1,051
HK$2,469 total
includes taxes & fees
4 May - 5 May
Starry Artsy Garage Loft
Interior

2 Bedroom Close to Town Home

2 Bedroom Close to Town Home
Thomaston
9.0 out of 10, Wonderful, (46 reviews)
"We loved our stay here! Check-in was easy and the host was responsive!"
United States
Jessica H.
The price is HK$917
HK$2,058 total
includes taxes & fees
11 May - 12 May
2 Bedroom Close to Town Home
Fridge, microwave, oven, stovetop

In-town, coastal + relaxing in Rockland

In-town, coastal + relaxing in Rockland
Rockland
10.0 out of 10, Exceptional, (44 reviews)
"Super clean… great location… fabulous hosts… total pleasure to stay there…"
United States
James B.
The price is HK$2,057
HK$4,513 total
includes taxes & fees
5 May - 6 May
In-town, coastal + relaxing in Rockland
Property grounds

Waterfront Getaway Near Acadia w/ Spectacular View

Waterfront Getaway Near Acadia w/ Spectacular View
Deer Isle
10.0 out of 10, Exceptional, (20 reviews)
"Great location with everything we needed."
United States
Thomas P.
The price is HK$1,107
HK$3,085 total
includes taxes & fees
7 May - 8 May
Waterfront Getaway Near Acadia w/ Spectacular View
Living area

Ferry Cottage | Eco-Chic Escape, Ocean Views, Steps to Beach

Ferry Cottage | Eco-Chic Escape, Ocean Views, Steps to Beach
Lincolnville
9.4 out of 10, Exceptional, (10 reviews)
"Great view. Very enjoyable stay. "
United States
Jerry C.
The price is HK$1,170
HK$1,881 total
includes taxes & fees
5 May - 6 May
Ferry Cottage | Eco-Chic Escape, Ocean Views, Steps to Beach
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 HK$1,390
HK$1,695 total
includes taxes & fees
26 May - 27 May
Pine Grove Cottages : Cottage 6 - Studio Cottage - Pet Friendly
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 HK$1,377
HK$3,141 total
includes taxes & fees
4 May - 5 May
Relaxing Two Bedroom Cabin - 10 minutes to Camden!
Fridge, microwave, oven, stovetop

Tides' Reach - Private Waterfront King Beds

Tides' Reach - Private Waterfront King Beds
Orland
9.8 out of 10, Exceptional, (24 reviews)
"This place is an absolute treasure! Secluded but close to all the necessities need to make your vacation amazing!"
United States
Joshua G.
The price is HK$900
HK$3,363 total
includes taxes & fees
4 May - 5 May
Tides' Reach - Private Waterfront King Beds
Interior

Inkwell Suite at Spofford Lodge

Inkwell Suite at Spofford Lodge
Bucksport
10.0 out of 10, Exceptional, (15 reviews)
"We had a wonderful stay at Spofford Lodge. The room was beyond our expectations and immaculate. Check in process was easy and great communication by Lisa. Many thanks"
United Kingdom
Richard G.
The price is HK$982
HK$1,651 total
includes taxes & fees
5 May - 6 May
Inkwell Suite at Spofford Lodge
Exterior

Romantic Coastal Escape near Harbor

Romantic Coastal Escape near Harbor
Rockport
10.0 out of 10, Exceptional, (1 review)
The price is HK$932
HK$1,896 total
includes taxes & fees
25 May - 26 May
Romantic Coastal Escape near Harbor
Interior

Bayside vista

Bayside vista
Bucksport
10.0 out of 10, Exceptional, (17 reviews)
"We loved our stay in Bucksport. The apartment was comfortable, clean and had everything we needed - and the view could not be beat! "
United States
Allison M.
The price is HK$1,509
HK$3,097 total
includes taxes & fees
5 May - 6 May
Bayside vista
Property grounds

Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston
Thomaston
10.0 out of 10, Exceptional, (3 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 HK$1,058
HK$2,041 total
includes taxes & fees
4 May - 5 May
Bright 2-Bedroom Apartment Near Downtown Thomaston
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

10/10 Excellent
"Great location, close walking distance to everything! "
Calvin 2-night trip
Posted 19 hours 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 holiday rental in Islesboro?

Yes, there are holiday rentals close to the most popular sights in Islesboro, or you can select a more secluded option if you're looking for a relaxing stay.

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

Island log home in Maine with ocean views: This highly rated holiday home rental in Islesboro offers a fireplace, a patio and a BBQ 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 holiday with amenities such as a garden.

How many holiday rentals are there in Islesboro?

With 8 Expedia holiday rentals, you're guaranteed 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 wider area.

What’s a holiday rental in Islesboro like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Islesboro. Holiday rentals offer extras like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for families.