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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, (80)
"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, (251)
"Location is amazing."
Trade Winds on the Bay

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

2.0 star property
9.2 out of 10, Wonderful, (10)
"Very peaceful !"
Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm

Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine

10.0 out of 10, Exceptional, (1)
"We had the best nights' sleep of our lives in this rustic cabin! Super quiet and peaceful. Excellent star watching. Masha was so nice and extremely hospitable! "
The price is NZ$176
includes taxes & fees
27 Aug - 28 Aug
Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine

Pine Grove Cottages

2.5 star property
9.8 out of 10, Exceptional, (88)
"Wonderful quiet place, The Host was a great person."
The price is NZ$447
includes taxes & fees
25 Aug - 26 Aug
Pine Grove Cottages

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

Cozy Cabin on Blue Hill Farm

9.8 out of 10, Exceptional, (24)
"Great place! My partner and I had so much fun staying here. The location is the best and in a convenient spot. Sean was absolutely amazing! "
Cozy Cabin on Blue Hill Farm

Point Lookout

3.0 star property
9.4 out of 10, Exceptional, (6)
"Great location. Away from the down town bustle, but close enough to enjoy the best of both worlds. Clean cabin, great amenities. "
Point Lookout

Cozy 2 BR by River- Crooked Steeple Hall

4.0 star property
Cozy 2 BR by River- Crooked Steeple Hall

WATERFRONT Maine Historical Cottage with Separate Guest Cottage

8.0 out of 10, Very good, (6)
"loved staying here, such a charming spot. "
WATERFRONT Maine Historical Cottage with Separate Guest Cottage

1812 Pierce House

3.5 star property
1812 Pierce House

Morning sun, coffee in hand, a good book and so much more...

9.8 out of 10, Exceptional, (82)
"Really enjoyed being on the lake and so close to town."
Morning sun, coffee in hand, a good book and so much more...

35 Mi to Acadia: Rustic Retreat in Orland!

2.0 star property
10.0 out of 10, Exceptional, (1)
"Exactly what you think of a cabin in the Maine woods. Close to Bucksport. No wifi. Only got one channel on the rabbit ears for the TV, but many movies available to use on the dvd player. Dark outside at night. Quick response from property manager. Would stay there again. "
35 Mi to Acadia: Rustic Retreat in Orland!

Comfortable, Close to Town Home, with Oceanview.

9.6 out of 10, Exceptional, (74)
"Clean"
The price is NZ$646
includes taxes & fees
1 Sept - 2 Sept
Comfortable, Close to Town Home, with Oceanview.

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

10.0 out of 10, Exceptional, (130)
"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

9.4 out of 10, Exceptional, (12)
"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 NZ$714
includes taxes & fees
25 Aug - 26 Aug
Unique Coastal Maine Flower Farm Stay

Oceanfront Private Ocean Access to a small sandy beach Unobstructed Water Views

9.8 out of 10, Exceptional, (120)
"We had a lovely time staying at your wonderfully cozy and charming property - thank you for a great experience!"
Oceanfront Private Ocean Access to a small sandy beach Unobstructed Water Views

Jaw-Dropping Coastal Mountain & Ocean View Post & Beam Log Getaway

9.8 out of 10, Exceptional, (66)
"Beautiful and very cozy stay close to everything you’d want to do, hike, explore, enjoy. Whirlpool jets in the tub was great after a long hike and we loved stargazing on the terrace. "
Jaw-Dropping Coastal Mountain & Ocean View Post & Beam Log Getaway

Quiet Ocean Front Cottage With Stunning Views & Private Beach Close To Rockland

9.6 out of 10, Exceptional, (85)
"My husband and I just retired and enjoyed this place immensely! Especially the fireplace and the quiet space."
Quiet Ocean Front Cottage With Stunning Views & Private Beach Close To Rockland

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

10.0 out of 10, Exceptional, (122)
"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
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 10 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.