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Islesboro Holiday Rentals

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Holiday Rentals in Islesboro

Island log home in Maine with ocean views

10.0 out of 10, Exceptional, (74)
"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, (241)
"Location is amazing."
Trade Winds on the Bay

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

2.0 star property
9.4 out of 10, Exceptional, (9)
"Beautiful location, peaceful and great views"
Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm

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

1812 Pierce House

3.5 star property
1812 Pierce House

Cozy Cabin on Blue Hill Farm

9.8 out of 10, Exceptional, (24)
"The cottage is very well designed and comfortable. The location is not as desirable as it is situated near the road and pigs which makes sitting outside less appealing: there is a sour smell coming from the vegetable matter in the pig’s pen. That said once inside the cabin it is very charming. Even on very hot days the cabin cooled down at night. (No overhead fan in loft but small battery operated fans can be used). The kitchen area could be cleaner and the water from the hose had bits of...
Cozy Cabin on Blue Hill Farm

Point Lookout

3.0 star property
9.6 out of 10, Exceptional, (4)
"Great location. Away from the down town bustle, but close enough to enjoy the best of both worlds. Clean cabin, great amenities. "
Point Lookout

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

10.0 out of 10, Exceptional, (125)
"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.

Unique Coastal Maine Flower Farm Stay

9.6 out of 10, Exceptional, (10)
"The rental is a spacious 2-bedroom apartment overlooking the grounds, greenhouses, and fields of the unique Leafsong farm, out in the quiet and leafy countryside southwest of Belfast. You may meet the peacocks, sheep, mule, and horse who also call this place home. Many treasures to be found at the flower shop on the premises."
The price is AU$645
includes taxes & fees
29 July - 30 July
Unique Coastal Maine Flower Farm Stay

35 Mi to Acadia: Rustic Retreat in Orland!

2.0 star property
35 Mi to Acadia: Rustic Retreat in Orland!

Peaceful Getaway: Tiny Home Studio in Sedgwick, Maine

10.0 out of 10, Exceptional, (7)
The price is AU$244
includes taxes & fees
25 Aug - 26 Aug
Peaceful Getaway: Tiny Home Studio in Sedgwick, Maine

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.

Pet-friendly Prospect Apartment: 7 Mi to Beach!

3.0 star property
7.0 out of 10, Good, (2)
"Like: Very private, close to nature, extra blankets available, very clean kitchen and bathroom, towels and cafe k-cups available Didn't like: Mattress, odor in the bathroom, yellow pillow under pillowcase"
Pet-friendly Prospect Apartment: 7 Mi to Beach!

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

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

10.0 out of 10, Exceptional, (117)
"This property was more than we could have asked for. The view was spectacular the hosts were great and we had more amenities than we could have asked for."
Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach

Cozy Cabin By The Pond, Sleeps 2

10.0 out of 10, Exceptional, (178)
"Extremely cozy, easy to find, great hosts, close to some very cute towns."
The price is AU$267
includes taxes & fees
28 July - 29 July
Cozy Cabin By The Pond, Sleeps 2

Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town

9.2 out of 10, Wonderful, (70)
"My adult children and grandchildren loved staying here. Our first trip to Maine. No harbor view but a short walk to town. Ana was great at responding to air condiyioner issues."
The price is AU$2,201
includes taxes & fees
23 Aug - 24 Aug
Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town

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 AU$399
includes taxes & fees
28 July - 29 July
Pine Grove Cottages

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

Country Charm: Cozy getaway in delightful Searsport

2.0 star property
9.8 out of 10, Exceptional, (6)
"The set up was different. But it was nice and cozy. I would stay there again."
The price is AU$314
includes taxes & fees
3 Aug - 4 Aug
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

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 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.