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Holiday Rentals in Islesboro

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Holiday Rentals in Islesboro

Island log home in Maine with ocean views

10.0 out of 10, Exceptional, (72)
"We had a very cozy and comfortable stay here over the christmas holiday! We had everything we needed to hunker down for a few days. Would absolutely stay here again. "
Island log home in Maine with ocean views

Trade Winds on the Bay

3.5 star property
8.4 out of 10, Very good, (229)
"Great place to stay...everything was great"
Trade Winds on the Bay

Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm

2.0 star property
9.6 out of 10, Exceptional, (7)
"Beautiful location, peaceful and great views"
Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm

1812 Pierce House

3.5 star property
1812 Pierce House

Point Lookout

3.0 star property
9.4 out of 10, Exceptional, (3)
"Great location. Away from the down town bustle, but close enough to enjoy the best of both worlds. Clean cabin, great amenities. "
Point Lookout

Peaceful Getaway: Tiny Home Studio in Sedgwick, Maine

10.0 out of 10, Exceptional, (4)
"This efficient little space has everything a traveler needs in a quiet, beautiful setting. It's remote, but not far from Blue Hill and well within reach of Acadian National Park. It would make a great venue for an artist's retreat. "
Peaceful Getaway: Tiny Home Studio in Sedgwick, Maine

Beach Vacation - Private Balcony - Views

9.8 out of 10, Exceptional, (72)
"We enjoyed this place. It had everything we needed and was located between some places we planned to visit. Good restaurant options nearby."
Beach Vacation - Private Balcony - Views

Cozy Cabin By The Pond, Sleeps 2

10.0 out of 10, Exceptional, (172)
"Extremely cozy, easy to find, great hosts, close to some very cute towns."
The price is €176
includes taxes & fees
13 Jul - 14 Jul
Cozy Cabin By The Pond, Sleeps 2

Unobstructed Ocean Views Private Onsite Access to the water & small sandy beach.

10.0 out of 10, Exceptional, (124)
"This was by far one of the best places we have ever stayed , it was so well decorated and stocked with anything you would need. Spotlessly clean and really felt like home. If I ever get back to Maine it will be my go to place to stay"
Unobstructed Ocean Views Private Onsite Access to the water & small sandy beach.

Waterfront cottage with deep water dock, ocean front.

9.8 out of 10, Exceptional, (96)
"The host made the check in process very easy. The cottage was clean and prepared for us when we got there. It was a perfect getaway weekend! "
Waterfront cottage with deep water dock, ocean front.

Pine Grove Cottages

2.5 star property
9.8 out of 10, Exceptional, (86)
"Wonderful quiet place, The Host was a great person."
The price is €224
includes taxes & fees
13 Jul - 14 Jul
Pine Grove Cottages

Lovely home with harbor views, gas grill, streaming, W/D, & gourmet range

9.0 out of 10, Wonderful, (18)
"Great place for a romantic get a way. Great lobster just down the road."
Lovely home with harbor views, gas grill, streaming, W/D, & gourmet range

Sweet Grass Cove Cottage

7.6 out of 10, Good, (17)
"Great place, amazing people to work with. Would stay again!"
Sweet Grass Cove Cottage

Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach

10.0 out of 10, Exceptional, (115)
"Superbly clean, great location!"
Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach

Country Charm: Cozy getaway in delightful Searsport

2.0 star property
10.0 out of 10, Exceptional, (3)
"I had a wonderful stay at this charming property in Searsport! Patty was an excellent host—very responsive and attentive, which made everything smooth and stress-free. The place itself was spotless, cozy, and had everything I needed for a comfortable stay. From the thoughtful touches to the peaceful setting, it truly felt like a home away from home. Highly recommend for anyone looking for a relaxing and well-kept retreat!"
The price is €180
includes taxes & fees
15 Jul - 16 Jul
Country Charm: Cozy getaway in delightful Searsport

Comfortable & Charming 2-bedroom barn in peaceful Brooksville with Waterfront

10.0 out of 10, Exceptional, (4)
"Inside and outside of property was outstanding. I enjoyed my morning coffee on a beautiful sunny deck watching my son and his dog walking across the very large field and down to the water. The beds were really comfortable. The bathrooms, one on each level, were all one could want. Our hosts were very pleasant and helpful. We were absolutely pleased with this private accommodation "
Comfortable & Charming 2-bedroom barn in peaceful Brooksville with Waterfront

Great location! Charming and private 1-bedroom apartment in Camden.

10.0 out of 10, Exceptional, (1)
"I really enjoyed my stay. A comfortable tiny house. Lots of attention to detail. From a pour over coffee set up to a deck that backs up to the woods—I saw deer on a couple mornings, including one time when I watched a young deer follow a neighborhood cat along the grassy edge. Plus it’s tucked into a spot that is still less than a five minute walk to town. The hosts were super friendly. "
Great location! Charming and private 1-bedroom apartment in Camden.

House At The Point - Rustic Cottage on Ocean's Edge

9.8 out of 10, Exceptional, (17)
"We had the most amazing time at this little cabin. Great trips are made by their location and this cabin has the most incredible location. We will definitely stay here again! "
House At The Point - Rustic Cottage on Ocean's Edge

Beautiful hand-built house on organic farm near the beach in East Blue Hill

Beautiful hand-built house on organic farm near the beach in East Blue Hill

Elegant Historic Home with Refined Interiors and Private Outdoor Spaces

10.0 out of 10, Exceptional, (1)
"We had a wonderful family gathering here with 5 adults and 2 kids. The house had a lot of living space for hanging out, playing games, and watching movies. The backyard was very private with lovely gardens. And the location was the best - an easy walk to town. We hope to come back next summer."
Elegant Historic Home with Refined Interiors and Private Outdoor Spaces
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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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?

1812 Pierce House: This holiday home rental outside Islesboro is equipped with a BBQ, air conditioning and free WiFi to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge and a stovetop. Another good choice for your trip to Islesboro is Island log home in Maine with ocean views.

How many holiday rentals are there in Islesboro?

With 12 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 Lincolnville Ferry Terminal 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.