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Islesboro Vacation Rentals

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    Upfront pricing

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Check prices for these dates

In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23

Vacation Rentals in Islesboro

Trade Winds on the Bay
Water view

Trade Winds on the Bay

3.5 star property
8.4 out of 10, Very Good, (254)
"Location is amazing."
$226 nightly
The price is $247
Sep 1 - Sep 2
Total with taxes and fees
Trade Winds on the Bay
Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm
Fridge, microwave, oven, stovetop

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
Property grounds

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! "
$95 nightly
The price is $103
Sep 3 - Sep 4
Total with taxes and fees
Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine
Pine Grove Cottages
Exterior

Pine Grove Cottages

2.5 star property
9.8 out of 10, Exceptional, (89)
"Wonderful quiet place, The Host was a great person."
$240 nightly
The price is $262
Sep 2 - Sep 3
Total with taxes and fees
Pine Grove Cottages
House At The Point - Rustic Cottage on Ocean's Edge
Dining

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
Interior

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
Exterior

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
Cozy 2 BR by River- Crooked Steeple Hall
Signature House, 2 Bedrooms, Patio, River View | Private kitchen | Fridge, microwave, oven, stovetop

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
Interior

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
Front of property

1812 Pierce House

3.5 star property
1812 Pierce House
Morning sun, coffee in hand, a good book and so much more...
Property grounds

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!
House (1 Bedroom) | Interior

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.
Interior

Comfortable, Close to Town Home, with Oceanview.

9.6 out of 10, Exceptional, (76)
"Clean"
$348 nightly
The price is $379
Sep 1 - Sep 2
Total with taxes and fees
Comfortable, Close to Town Home, with Oceanview.
Unobstructed Ocean Views Private Onsite Access to the water & small sandy beach.
Property grounds

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

10.0 out of 10, Exceptional, (131)
"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.
Unique Coastal Maine Flower Farm Stay
Living area

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."
$384 nightly
The price is $419
Sep 1 - Sep 2
Total with taxes and fees
Unique Coastal Maine Flower Farm Stay
Oceanfront Private Ocean Access to a small sandy beach Unobstructed Water Views
On the beach, sun loungers

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

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

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
Exterior detail

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

9.6 out of 10, Exceptional, (85)
"We enjoyed our stay in every way. The house is very clean and comfortable….the gorgeous views were a lucky strike extra. This is a special place!"
Quiet Ocean Front Cottage With Stunning Views & Private Beach Close To Rockland
Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach
On the beach, sun loungers

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
Beach Vacation - Private Balcony - Views
Interior

Beach Vacation - Private Balcony - Views

9.8 out of 10, Exceptional, (76)
"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
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Islesboro vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Islesboro vacation 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 low season months. For more hustle and bustle, you may prefer to visit Islesboro in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $103 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Islesboro rentals

At Expedia, we put the best Islesboro vacation 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 vacation.

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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Islesboro?

Yes, you can find vacation rentals close to the most popular points of interest in Islesboro, or you can choose a more remote option if you're looking for a relaxing stay.

What are some of the best vacation rentals that Islesboro has to offer?

1812 Pierce House: This vacation home rental outside of Islesboro is equipped with a barbecue grill, 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 vacation rentals are there in Islesboro?

With 9 Expedia vacation rentals, you're sure 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 larger area.

What’s a vacation rental in Islesboro like?

Vacation rentals are private properties where you can stay for short or long periods in Islesboro. Vacation rentals offer amenities like WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for family trips.