Islesboro Holiday Rentals

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Our top choices for Islesboro holiday rentals

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

Drift A-Frame - NEW A-Frame in Blue Hill!
Blue Hill
The price is NZ$708
includes taxes & fees
6 June - 7 June
Drift A-Frame - NEW A-Frame in Blue Hill!

Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (400 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 NZ$167
includes taxes & fees
10 June - 11 June
Trade Winds on the Bay

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 NZ$483
includes taxes & fees
8 June - 9 June
2 Bedroom Close to Town Home

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 NZ$263
includes taxes & fees
7 June - 8 June
Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine

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 NZ$679
includes taxes & fees
6 June - 7 June
Rustic Retreat Across from Lake; Family Friendly!

Cozy Cabin By The Pond, Sleeps 2

Cozy Cabin By The Pond, Sleeps 2
Waldo
10.0 out of 10, Exceptional, (205 reviews)
"Very peaceful and cozy cabin! We had a wonderful weekend getaway and will definitely be back! "
United States
Johanna W.
The price is NZ$379
includes taxes & fees
15 June - 16 June
Cozy Cabin By The Pond, Sleeps 2

Blueprint Suite at Spofford Lodge

Blueprint Suite at Spofford Lodge
Bucksport
10.0 out of 10, Exceptional, (10 reviews)
"Had a wonderful stay. The property is beautiful and each room is professionally decorated with a high end touch."
United States
Gay M.
The price is NZ$522
includes taxes & fees
8 June - 9 June
Blueprint Suite at Spofford Lodge

Come Spring Farm Airstream , Lake & farm animals

Come Spring Farm Airstream , Lake & farm animals
Union
10.0 out of 10, Exceptional, (2 reviews)
"Pet Friendly, Great surroundings, close to popular tourist towns in Maine"
United States
Thomas W.
The price is NZ$451
includes taxes & fees
10 June - 11 June
Come Spring Farm Airstream , Lake & farm animals

Inkwell Suite at Spofford Lodge

Inkwell Suite at Spofford Lodge
Bucksport
10.0 out of 10, Exceptional, (15 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 NZ$484
includes taxes & fees
8 June - 9 June
Inkwell Suite at Spofford Lodge

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 NZ$370
includes taxes & fees
7 June - 8 June
Pine Grove Cottages : Cottage 6 - Studio Cottage - Pet Friendly

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 NZ$641
includes taxes & fees
7 June - 8 June
SeaRiver Cabin on the Bagaduce, Kayaks Included. Seals, Wildlife, Birds & Nature

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 NZ$379
includes taxes & fees
7 June - 8 June
Pine Grove Cottages

The Nathaniel Bowditch - Inn on the Harbor

The Nathaniel Bowditch - Inn on the Harbor
Stonington
10.0 out of 10, Exceptional, (12 reviews)
"We enjoyed our stay. Great location . "
United States
Barbara A.
The price is NZ$305
includes taxes & fees
9 June - 10 June
The Nathaniel Bowditch - Inn on the Harbor

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 stay and host was very responsive with a forgotten item. "
United States
Yvonne T.
The price is NZ$503
includes taxes & fees
8 June - 9 June
Peaceful, Centrally Located Home with Seasonal River Views

Peaceful 2-bedroom cottage in charming Lincolnville, near lake, winery & Camden

Peaceful 2-bedroom cottage in charming Lincolnville, near lake, winery & Camden
Lincolnville
9.0 out of 10, Wonderful, (2 reviews)
"This cabin had everything we needed for a one-night pit stop up to Bar Harbor. We especially liked the rural location, the tea kettle, and stove for heat. We were able to sign into our Netflix and watch a thriller on a dark, rainy night, gathered in the living room area. We did not like that there were several large flies inside of the cabin. We killed a few that were bothering us, but even after that my nephew made a cup of tea at night and one of the flies flew into his tea cup!"
United States
Leona
The price is NZ$384
includes taxes & fees
8 June - 9 June
Peaceful 2-bedroom cottage in charming Lincolnville, near lake, winery & Camden

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 NZ$300
includes taxes & fees
8 June - 9 June
Simplicity-Just what you need! STR24-20

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 NZ$274
includes taxes & fees
22 June - 23 June
Glamping at Maine Water Buffalo Farm

Blue Hill in the Woods

Blue Hill in the Woods
Blue Hill
8.0 out of 10, Very good, (1 review)
"Nice new apartment upstairs of the garage. It’s a spacious single room (except the bathroom of course), nicely laid out with pleasant lighting through windows looking out towards the trees. The “kitchen” is minimal: a dorm-sized fridge, microwave, toaster oven, water kettle and coffee maker. Sufficient for our needs but not enough for an extended stay. Given that the rental is a one-room studio with laminate flooring, the pet fee seemed a bit steep, but the apartment itself was a good bargain...
United States
Eric S.
The price is NZ$375
includes taxes & fees
15 June - 16 June
Blue Hill in the Woods

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 NZ$456
includes taxes & fees
15 June - 16 June
Bright 2-Bedroom Apartment Near Downtown Thomaston

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 NZ$316
includes taxes & fees
7 June - 8 June
Country Charm: Cozy getaway in delightful Searsport
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

Find out more about Islesboro

Everything you need to know about Islesboro holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Islesboro holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Islesboro holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Islesboro holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Islesboro. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Islesboro holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Islesboro holiday rentals we have selected for you start as low as NZ$167 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Islesboro rentals

At Expedia, we put the best Islesboro holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Islesboro rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Islesboro holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Islesboro. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 9 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 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 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.