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Islesboro vacation rentals

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Top-rated vacation rentals in Islesboro

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Cabin in Eastbrook

4.96 out of 5 average rating, 241 reviews

Hemlock Cabin.

Nestled in beautiful Hemlock grove is this cozy cabin. Its equiped with all the necessities of home to make your stay comfortable. Guests will have private access to Scammons Pond, also known as, R. Lyle Frost Managment Area. Its a fun place to kayak and fish. From the cabin its about a 45 minute drive to Acadia National Park or Schoodic Point. Besides Acadia, there is local hiking, nearby shopping, local restaurants, the Sunrise Trail, and other Maine adventure just waiting to be explored.

Cottage in Trenton

4.97 out of 5 average rating, 331 reviews

NEW Whitetail Cottage, Acadia National Park 7m

NEW Whitetail Cottage East only 6.9 mi to Acadia National Park Maine - a hikers paradise! Centrally located for a perfect Acadia Adventure! Book for the convenient location - stay for the style. Tiny home has WIFI & SMART TV. Off the main(e) drag but nestled in a wooded property 1/2 mile from Bar Harbor Rd/Route 3 down the road from Mount Desert Island and a stones throw from multiple authentic Maine lobster pounds. Perfect for 2 . A short drive to MDI, Acadia, Bar Harbor,Southwest Harbor

Guesthouse in Orland

4.99 out of 5 average rating, 137 reviews

Cozy cottage in Orland Village-Penobscot Bay area

Charming cottage in Orland Village, 2 minutes from Bucksport, a short walk away from the Orland River and its estuary on the Penobscot Bay. Nestled on 3.5 acres of wooded land, 300 ft behind an 18th-century colonial house. Completely self-contained with equipped kitchen. Fast 400 Mbs cable internet/WiFi. 45 minutes to Acadia National Park, 30 min. to Belfast, 20 min. to Castine. Perfect base for hiking, kayaking, sailing, or discovering the maritime past of the area. Pet friendly!

Rental unit in Belfast

4.98 out of 5 average rating, 303 reviews

Room with a Brew

Welcome to our new building. "A Room With a Brew" is located above Belfast's newest craft brewery, Frosty Bottom Brewing. A small community supported brewery open 2 days/week for 3-4 hours for beer share members. Guests can request a tour of the brewery and sample some fresh beer. Owners live in downtown Belfast and are available should any issues arise during your stay. The apartment/brewery is located 3 miles from downtown on a quiet road that offers local hiking and biking.

Cottage in Edgecomb

4.97 out of 5 average rating, 232 reviews

Charming Cottage With Spectacular Water View

Find peace and serenity as you gaze at the glistening waters of the Sheepscot River. Our property sitting on Davis Island in Edgecomb, Maine overlooks the quaint town of Wiscasset, providing a calm atmosphere, stunning evening sunsets, and panoramic views. Located within the Sheepscot Harbour Village Resort, you are in a prime location to have access to local shops, antique markets, and restaurants. Take a stroll down to the Pier where you can experience the water up close.

Guest suite in Mount Desert

4.97 out of 5 average rating, 215 reviews

Otter Creek Retreat hosted by Elaine & Richard

Between Bar Harbor and Seal Harbor, 10 minutes by car to both and just 5 minutes by car to the Otter Cliff entrance to Acadia Park Loop Road. Walk to the Causeway via the Grover Path in 15 minutes. 5-minute walk to the Cadillac South Ridge Trail. Large high-ceiling studio with private parking and entrance with beautiful sheltered second-story deck. We are on the Blackwoods/Bar Harbor bus route so you can catch the free Island Explorer LL Bean buses to Bar Harbor and back.

Rental unit in Camden

4.99 out of 5 average rating, 124 reviews

Sunny In-Town Camden Studio, 10% weekly discount

Make this cozy, contemporary studio apartment your home-away-from-home. Located just two blocks from downtown Camden, it's a five minute walk to downtown in one direction, or to one of the many trailheads in Camden Hills State Park in the other. In any season, our central location gives you access to the best of the Midcoast. *COVID19 Update: We are following CDC guidelines to clean and disinfect our space and offer self check-in to minimize person to person contact.

Cottage in Belfast

4.99 out of 5 average rating, 122 reviews

Spectacular Cottage on Penobscot bay in Belfast

Spectacular cottage on Penobscot bay in Belfast. The cottage is focused on the views from the great room and screened porch. You’ll love the spacious, clean, open cottage with a complete kitchen and propane fireplace. Sit on the porch with a book/glass of wine and watch for seals and schooners. Easy access to the shore along a gradual path and short boardwalk. Great amenities and comfort for vacationers both young and old. Perfect for couples and families (with kids).

Yurt in Appleton

4.95 out of 5 average rating, 241 reviews

SNOW SWEET, A Yurt for All Seasons

Snow Sweet at The Appleton Retreat is very private, check out the Trail Map. This contemporary yurt faces the Field of Dreams and has a nice view of Appleton Ridge. It features a private therapeutic hot tub on the deck, a fire pit, and fast wifi. The Appleton Retreat encompasses 120 acres hosting six unique retreats. To the south is the Pettengill Stream, a resource protected area. To the north is the Nature Conservancy's 1300 acre reserve.

Cottage in Waltham

4.95 out of 5 average rating, 745 reviews

Quiet lakefront cottage on Graham Lake

Waterfront cottage on quiet Graham lake in the middle of our small working farm. Great spot for quiet relaxation, fishing or kayaking. 2 canoes on the property. Good central location for visiting Bangor, Bar Harbor, Acadia National Park and Downeast Sunrise ATV Trail. Private setting. Wifi available at the farmhouse. Because of family allergies, we cannot host pets

Home in Belfast

4.96 out of 5 average rating, 168 reviews

La Mer - Musicians' Home on the Sea

This gorgeous oceanfront house, with breathtaking unobstructed ocean views from the large deck and nearly every room, is owned by classical musicians and is aptly named La Mer (“The Sea”), after a famous orchestral work of the same name. Our sanctuary is private, cozy, spacious, and artistically inspiring. Downtown Belfast is less than 10 minutes away by car.

Cottage in Lincolnville

4.97 out of 5 average rating, 106 reviews

The Cottage - close to Camden and Belfast

Beautiful newly renovated guest cottage minutes to Camden and Belfast and a day trip to Acadia National Park. All modern amenities, private back yard, and back deck, lovely covered porch. The cottage is located within walking distance to Nortons Pond, Lincolnville General Store (opening this summer!), the post office and the Lincolnville Library.

Vacation rentals for every style

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Quaint homes, peaceful surroundings

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Popular amenities for Islesboro vacation rentals

Laptop-friendly workspace

Air conditioning

Stay near Islesboro's top sights

Hannaford Supermarket115 locals recommend

Lincolnville Beach42 locals recommend

The Hoot26 locals recommend

Whale's Tooth Pub & Restaurant - Lobster Rolls - Cocktails - Craft Beer - Waterfront Dining23 locals recommend

Belfast City Park19 locals recommend

Bell the Cat18 locals recommend

Other great vacation rentals in Islesboro

Home in Belfast

5 out of 5 average rating, 36 reviews

Sail Loft

Condo in Northport

5 out of 5 average rating, 9 reviews

Lovely 1 bedroom apartment in Northport

Cottage in Lincolnville

5 out of 5 average rating, 65 reviews

Sunny 2 Bedroom cottage - Walk to the beach!

Cottage in Northport

4.96 out of 5 average rating, 55 reviews

The Gatehouse

Cottage in Lincolnville

4.95 out of 5 average rating, 39 reviews

Seafront Cottage with private beach

Guesthouse in Lincolnville

4.95 out of 5 average rating, 44 reviews

Peaceful cottage in coastal Lincolnville

Tiny home in Islesboro

4.97 out of 5 average rating, 30 reviews

"Bohemian Bungalow" Studio Island Guest Cottage

Cabin in Searsmont

4.98 out of 5 average rating, 66 reviews

Birch Hill Cabin w/Hot Tub

Quick stats about vacation rentals in Islesboro

Total rentals
160 properties
Nightly prices starting at
$70 before taxes and fees
Total number of reviews
6.3K reviews
Family-friendly rentals
100 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with dedicated workspaces
70 properties have a dedicated workspace

Frequently Asked Questions

Do cottage rentals in Islesboro have a bbq area?
Absolutely! We offer over 10 cottage rentals with a bbq area in Islesboro. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Islesboro?
Islesboro has more than 50 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do cabin rentals in Islesboro have air conditioning?
Absolutely! We offer over 10 cabin rentals with air conditioning in Islesboro. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Islesboro have wireless internet?
Absolutely! We offer over 60 house rentals with wireless internet in Islesboro. Enjoy a tailored experience with all the comforts you desire.
Are there house rentals with a dedicated workspace in Islesboro?
Yes! Work meets play with ease at over 30 house rentals in Islesboro featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly house rentals in Islesboro?
Four-legged friends are welcome in Islesboro. Choose from more than 20 house rentals for guests traveling with pets.
How much does it cost to stay in house rentals in Islesboro?
Experience the best of Islesboro with our house rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
What are the most popular amenities for House Rentals in Islesboro?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with air conditioning, over 40 homes with a bbq area, over 60 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.

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