Holiday Rentals in Islesboro

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Islesboro holiday rentals

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 €135
includes taxes & fees
12 May - 13 May
Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine

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 €197
includes taxes & fees
12 May - 13 May
Cozy Cabin By The Pond, Sleeps 2

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 €320
includes taxes & fees
12 May - 13 May
SeaRiver Cabin on the Bagaduce, Kayaks Included. Seals, Wildlife, Birds & Nature

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.
2 Bedroom Close to Town Home

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 €109
includes taxes & fees
12 May - 13 May
The Lewis R. French- Inn on the Harbor

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 €269
includes taxes & fees
13 May - 14 May
Starry Artsy Garage Loft

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.
Cheerful Two Bedroom Cabin - 10 minutes to Camden!

Dome 1 - Luxury Dome at Come Spring Farm

Dome 1 - Luxury Dome at Come Spring Farm
Union
9.6 out of 10, Exceptional, (17 reviews)
The price is €194
includes taxes & fees
12 May - 13 May
Dome 1 - Luxury Dome at Come Spring Farm

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 €342
includes taxes & fees
5 Jun - 6 Jun
Rustic Retreat Across From Lake; Family Friendly!

Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (383 reviews)
"Great location, friendly staff. "
United States
Connor
The price is €94
includes taxes & fees
17 May - 18 May
Trade Winds on the Bay

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 €236
includes taxes & fees
21 May - 22 May
Peaceful, Centrally Located Home with Seasonal River Views

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 €315
includes taxes & fees
12 May - 13 May
Bayside vista

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 €349
includes taxes & fees
15 May - 16 May
Waterfront Getaway Near Acadia w/ Spectacular View

Fire Pit & Grill, Movie Room, Workspace, A/C, Pets

Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
Thomaston
10.0 out of 10, Exceptional, (29 reviews)
"Very cute house that was fully equipped for our stay. Great location for touring around Maine to see the sights. Communication was excellent with the host and we would definitely stay here again!"
United States
Elisabeth C.
Fire Pit & Grill, Movie Room, Workspace, A/C, Pets

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 €189
includes taxes & fees
26 May - 27 May
Pine Grove Cottages : Cottage 6 - Studio Cottage - Pet Friendly

Romantic Coastal Escape near Harbor

Romantic Coastal Escape near Harbor
Rockport
10.0 out of 10, Exceptional, (1 review)
Romantic Coastal Escape near Harbor

Dome 3 at Come Spring Farm Glamping - Alpaca Farm

Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Union
9.0 out of 10, Wonderful, (8 reviews)
"Beautiful location and a unique stay."
United States
Sabrina D.
The price is €241
includes taxes & fees
13 May - 14 May
Dome 3 at Come Spring Farm Glamping - Alpaca Farm

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
Relaxing Two Bedroom Cabin - 10 minutes to Camden!

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 €371
includes taxes & fees
12 May - 13 May
Tides' Reach - Private Waterfront King Beds

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 €195
includes taxes & fees
14 May - 15 May
Blue Hill in the Woods
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.
Save an average of 15% on thousands of hotels when you're signed in

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, apart-hotels, 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 €94 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 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.