Islesboro Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

Our top choices for Islesboro vacation rentals

1 bedroom, bed sheets

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

Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine
Lincolnville
8.0 out of 10, Very Good, (11 reviews)
"The cabin is exactly as advertised. The dogs were happy there and we enjoyed our stay. "
United States
Becki C.
$142 nightly
The price is $154
May 10 - May 11
Total with taxes and fees
Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine
Property grounds

Cozy Cabin By The Pond, Sleeps 2

Cozy Cabin By The Pond, Sleeps 2
Waldo
10.0 out of 10, Exceptional, (204 reviews)
"Very peaceful and cozy cabin! We had a wonderful weekend getaway and will definitely be back! "
United States
Johanna W.
$211 nightly
The price is $230
May 8 - May 9
Total with taxes and fees
Cozy Cabin By The Pond, Sleeps 2
Outdoor dining

The Lewis R. French- Inn on the Harbor

The Lewis R. French- Inn on the Harbor
Stonington
9.2 out of 10, Wonderful, (10 reviews)
"Made wonderful memories and really enjoyed the beautiful oceanfront town of Stonington."
United States
Elizabeth P.
$123 nightly
The price is $134
May 12 - May 13
Total with taxes and fees
The Lewis R. French- Inn on the Harbor
Cottage (2 Bedrooms) | Interior

Rustic Retreat Across From Lake; Family Friendly!

Rustic Retreat Across From Lake; Family Friendly!
3.0 star property
Union
9.0 out of 10, Wonderful, (2 reviews)
"I liked that it was by the lake quiet and secluded. "
United States
Wilma
$370 nightly
The price is $403
May 20 - May 21
Total with taxes and fees
Rustic Retreat Across From Lake; Family Friendly!
Smart TV

Peaceful, Centrally Located Home with Seasonal River Views

Peaceful, Centrally Located Home with Seasonal River Views
Thomaston
9.4 out of 10, Exceptional, (32 reviews)
"Great stay and host was very responsive with a forgotten item. "
United States
Yvonne T.
$246 nightly
The price is $268
May 8 - May 9
Total with taxes and fees
Peaceful, Centrally Located Home with Seasonal River Views
Property grounds

Waterfront Getaway Near Acadia w/ Spectacular View

Waterfront Getaway Near Acadia w/ Spectacular View
Deer Isle
10.0 out of 10, Exceptional, (20 reviews)
"Great location with everything we needed."
United States
Thomas P.
$369 nightly
The price is $403
May 9 - May 10
Total with taxes and fees
Waterfront Getaway Near Acadia w/ Spectacular View
Lobby sitting area

Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (381 reviews)
"Great location, friendly staff. "
United States
Connor
$109 nightly
The price is $119
May 11 - May 12
Total with taxes and fees
Trade Winds on the Bay
Exterior

Dome 1 - Luxury Dome at Come Spring Farm

Dome 1 - Luxury Dome at Come Spring Farm
Union
9.6 out of 10, Exceptional, (17 reviews)
"We had never stayed in a yurt before and this one had everything you need. We ate breakfast out on the deck and enjoyed the scenery. We had a really nice time!"
United States
Karen I.
$212 nightly
The price is $227
May 10 - May 11
Total with taxes and fees
Dome 1 - Luxury Dome at Come Spring Farm
Terrace/patio

SeaRiver Cabin on the Bagaduce, Kayaks Included. Seals, Wildlife, Birds & Nature

SeaRiver Cabin on the Bagaduce, Kayaks Included. Seals, Wildlife, Birds & Nature
Penobscot
10.0 out of 10, Exceptional, (8 reviews)
"All was fabulous!!!"
United States
Maria M.
$346 nightly
The price is $377
May 11 - May 12
Total with taxes and fees
SeaRiver Cabin on the Bagaduce, Kayaks Included. Seals, Wildlife, Birds & Nature
Terrace/patio

Starry Artsy Garage Loft

Starry Artsy Garage Loft
Sedgwick
9.8 out of 10, Exceptional, (28 reviews)
"Absolutely great stay. Wonderful home, wonderful host! I will be keeping this place in mind for when I come back to Maine! "
United States
Kellee M.
$290 nightly
The price is $316
May 10 - May 11
Total with taxes and fees
Starry Artsy Garage Loft
Interior

2 Bedroom Close to Town Home

2 Bedroom Close to Town Home
Thomaston
9.0 out of 10, Wonderful, (46 reviews)
"We loved our stay here! Check-in was easy and the host was responsive!"
United States
Jessica H.
$240 nightly
The price is $262
May 13 - May 14
Total with taxes and fees
2 Bedroom Close to Town Home
Interior

Cheerful Two Bedroom Cabin - 10 minutes to Camden!

Cheerful Two Bedroom Cabin - 10 minutes to Camden!
Lincolnville
10.0 out of 10, Exceptional, (13 reviews)
"This is a great place, nice and quiet, very clean and cozy. Loved it here!!"
United States
Lorna W.
$373 nightly
The price is $406
May 9 - May 10
Total with taxes and fees
Cheerful Two Bedroom Cabin - 10 minutes to Camden!
Interior

Inkwell Suite at Spofford Lodge

Inkwell Suite at Spofford Lodge
Bucksport
10.0 out of 10, Exceptional, (15 reviews)
"We had a wonderful stay at Spofford Lodge. The room was beyond our expectations and immaculate. Check in process was easy and great communication by Lisa. Many thanks"
United Kingdom
Richard G.
$194 nightly
The price is $207
May 11 - May 12
Total with taxes and fees
Inkwell Suite at Spofford Lodge
Exterior

Pine Grove Cottages : Cottage 6 - Studio Cottage - Pet Friendly

Pine Grove Cottages : Cottage 6 - Studio Cottage - Pet Friendly
Lincolnville
10.0 out of 10, Exceptional, (10 reviews)
"Great owner and quick night stay. "
United States
Jeanean W.
$198 nightly
The price is $216
May 26 - May 27
Total with taxes and fees
Pine Grove Cottages : Cottage 6 - Studio Cottage - Pet Friendly
Exterior

Romantic Coastal Escape near Harbor

Romantic Coastal Escape near Harbor
Rockport
10.0 out of 10, Exceptional, (1 review)
$229 nightly
The price is $250
May 25 - May 26
Total with taxes and fees
Romantic Coastal Escape near Harbor
WiFi

Dome 3 at Come Spring Farm Glamping - Alpaca Farm

Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Union
9.0 out of 10, Wonderful, (8 reviews)
"Beautiful location and a unique stay."
United States
Sabrina D.
$263 nightly
The price is $284
May 10 - May 11
Total with taxes and fees
Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Interior

Bayside vista

Bayside vista
Bucksport
10.0 out of 10, Exceptional, (17 reviews)
"We loved our stay in Bucksport. The apartment was comfortable, clean and had everything we needed - and the view could not be beat! "
United States
Allison M.
$341 nightly
The price is $371
May 11 - May 12
Total with taxes and fees
Bayside vista
Exterior

Blue Hill in the Woods

Blue Hill in the Woods
Blue Hill
8.0 out of 10, Very Good, (1 review)
"Nice new apartment upstairs of the garage. It’s a spacious single room (except the bathroom of course), nicely laid out with pleasant lighting through windows looking out towards the trees. The “kitchen” is minimal: a dorm-sized fridge, microwave, toaster oven, water kettle and coffee maker. Sufficient for our needs but not enough for an extended stay. Given that the rental is a one-room studio with laminate flooring, the pet fee seemed a bit steep, but the apartment itself was a good bargain...
United States
Eric S.
$207 nightly
The price is $225
May 14 - May 15
Total with taxes and fees
Blue Hill in the Woods
Fridge, microwave, oven, stovetop

In-town, coastal + relaxing in Rockland

In-town, coastal + relaxing in Rockland
Rockland
10.0 out of 10, Exceptional, (44 reviews)
"Super clean… great location… fabulous hosts… total pleasure to stay there…"
United States
James B.
$546 nightly
The price is $595
May 8 - May 9
Total with taxes and fees
In-town, coastal + relaxing in Rockland
Terrace/patio

Cozy Little Carriage House with Spectacular Sunsets at The Rockbound House

Cozy Little Carriage House with Spectacular Sunsets at The Rockbound House
Brooklin
10.0 out of 10, Exceptional, (1 review)
"The space was perfect for us. It was lovely and super convenient both for classes at WoodenBoat School and hikes at Acadia."
United States
Strephon T.
$306 nightly
The price is $334
May 15 - May 16
Total with taxes and fees
Cozy Little Carriage House with Spectacular Sunsets at The Rockbound House
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Islesboro Hotel Reviews

Belfast Harbor Inn

Belfast Harbor Inn

8/10 Good
"it was a good hotel room on a fast moving business trip. all was good. no issues. would use again, if in the area."
Philip 1-night trip
Posted 6 hours ago
Belfast Harbor Inn

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 $119 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

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?

Island log home in Maine with ocean views: This highly rated vacation home rental in Islesboro offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a garden.

How many vacation rentals are there in Islesboro?

With 8 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 Penobscot Marine Museum, 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.