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Islesboro Holiday Rentals

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Holiday Rentals in Islesboro

Trade Winds on the Bay

3.5 star property
8.4 out of 10, Very good, (263)
"The Tradewinds on bay,quiet local rest and relax...."
Trade Winds on the Bay

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

2.0 star property
8.8 out of 10, Excellent, (11)
"Very peaceful !"
Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm

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

9.0 out of 10, Wonderful, (2)
"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 AU$159
includes taxes & fees
14 Sept - 15 Sept
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, (89)
"Wonderful quiet place, The Host was a great person."
The price is AU$397
includes taxes & fees
17 Sept - 18 Sept
Pine Grove Cottages

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

WATERFRONT Maine Historical Cottage with Separate Guest Cottage

8.6 out of 10, Excellent, (8)
"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

Point Lookout

3.0 star property
9.6 out of 10, Exceptional, (7)
"Great location. Away from the down town bustle, but close enough to enjoy the best of both worlds. Clean cabin, great amenities. "
Point Lookout

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

9.8 out of 10, Exceptional, (83)
"This VRBO was fantastic. The kitchen was better stocked than any other rental i have stayed. Everything was clean and tidy. The views are beautif. It is a quick drive to grocery, gas, walking trails, and the down town Camden area. Lisa gave us great recommendations for hikig trails, site seeing, and food! We really enjoyed our stay and woukd book again if we make our way back to Maine. "
Morning sun, coffee in hand, a good book and so much more...

Unique Coastal Maine Flower Farm Stay

9.4 out of 10, Exceptional, (13)
"Very spacious unique space. Beautiful cathedral ceilings and the use of natural wood gave it the feel of a large cabin. Quick ride into Camden very nice."
The price is AU$642
includes taxes & fees
21 Sept - 22 Sept
Unique Coastal Maine Flower Farm Stay

Cozy 2 BR by River- Crooked Steeple Hall

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

Comfortable, Close to Town Home, with Oceanview.

9.6 out of 10, Exceptional, (76)
"We had a great stay while in town for a family event. We were ecstatic to be able to take our family dog with us on the trip. The view from the back deck was incredible and close to many local parks for hiking."
The price is AU$581
includes taxes & fees
12 Sept - 13 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, (132)
"Property was perfect for a stay of two. Morning coffee was enjoyed with a beautiful view of the water and comfy patio chairs. Second story bedroom loft had a wall of windows to showcase the ocean view. It was noted that the property owners put thought into every amenity. "
Unobstructed Ocean Views Private Onsite Access to the water & small sandy beach.

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

9.6 out of 10, Exceptional, (87)
"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

Waterfront cottage with deep water dock, ocean front.

9.8 out of 10, Exceptional, (100)
"Beautiful swing and convenient to town. Live the stay even though the weather was less than cooperative."
Waterfront cottage with deep water dock, ocean front.

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

9.8 out of 10, Exceptional, (67)
"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

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

10.0 out of 10, Exceptional, (123)
"Awesome place to stay .Close to so many great things to see and do. Highly recommended. "
Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach

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

10.0 out of 10, Exceptional, (123)
"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

Tranquil Lakefront Cottage Near Acadia Nat’l Park.

9.6 out of 10, Exceptional, (107)
"What a wonderful view, loved our stay!"
Tranquil Lakefront Cottage Near Acadia Nat’l Park.

Peaceful Getaway: Tiny Home Studio in Sedgwick, Maine

10.0 out of 10, Exceptional, (14)
"I had a great stay at the Peaceful Getaway in Sedgwick. Listing was just as described. Very cute and clean tiny home with everything an individual or couple might need. Beautiful spot to relax, and close to Blue Hill and other wonderful areas. (I recommend a walk through the Harriman Point Preserve in nearby Brooklin.) Check-in process was great, and although the main house is nearby it felt very private. I highly recommend this spot. "
The price is AU$243
includes taxes & fees
4 Oct - 5 Oct
Peaceful Getaway: Tiny Home Studio in Sedgwick, Maine
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

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 favourite 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 depend 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 AU$159 per night. Entering your travel dates in the search wizard might find you 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?

1812 Pierce House: This holiday home rental outside of 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.

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.