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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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Apartment in Searsport

4.82 out of 5 average rating, 292 reviews

Lakefront Vacation Apartment in Searsport ME

All season private top floor apartment. Hammock, loungers, floats. Acadia/State parks close. Canoe, kayaks, hot tub/wood floating dock (seasonal use), fire pit, grill, swim, fish. Modern/Antique furnished: queen bed plus loveseat twin. Massage/lounger. 2nd queen, twin inflatables. Fully equipped kitchen. Families w/kids, business guests welcome. Wifi smart TV. Great hikes, mountain bike rentals close. Snow shoes/sled included, skiing close. Separate entrance/apt above home not full home.

Feb 6 – 13

Home in Camden

5.0 out of 5 average rating, 156 reviews

Quaint 3 Bedroom In Town Camden Home

Our 1900’s New England style home is located in a quiet neighborhood less than a mile from the heart of downtown Camden. Midcoast Maine is home to many great restaurants, shops, and art galleries, as well as events such as the National Toboggan Championships, North Atlantic Blues Festival, Maine Lobster Festival, and more! With Rockland just a quick 15 min. drive and Belfast located approximately half an hour north, you’ll be in a prime location to experience everything this area has to offer.

Jan 23 – 30

Guesthouse in Lincolnville

4.97 out of 5 average rating, 327 reviews

"The Lair" Guesthouse

"The Lair" is a just recently renovated small 200 square foot cabin with vaulted ceilings and plenty of natural sunlight. The building is located close to Green Tree Coffee and Tea, a coffee roaster, so the aroma of coffee will be in the air. We located about 400 yards South of the Islesboro Ferry and Lincolnville Beach and 2.4 milres North of Camden Hills State Park and Mount Battie. Free coffee and tea everyday, all day! We are closed for Winter, will re-open Mid-April. Thank you.

May 16 – 23

Guesthouse in Lincolnville

4.98 out of 5 average rating, 161 reviews

Peaceful Suite - Hiking, Beach, Nature

Welcome to the “East Wing”! The complete apartment is new: salt box style with beautiful views of nature (hummingbirds, fireflies, starry skies). The East Wing is first to greet the sun in the morning. Enjoy your coffee on the private deck, or sip wine at night by the fire pit. Close to Tanglewood Rd (4H camp) , Camden Hills State Park trails, and Lincolnville Beach(1 -2 miles). The area is quiet- yet just a few miles away from shopping and restaurants in Camden, Belfast, & Rockland.

Oct 6 – 13

Guesthouse in Orland

4.99 out of 5 average rating, 103 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!

Jan 17 – 24

Apartment in Belfast

4.99 out of 5 average rating, 262 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.

Dec 8 – 15

Home in Appleton

4.96 out of 5 average rating, 122 reviews

The Barn

I call my place "The Barn" because as I was finishing it it took the shape and feel of a barn. It's not a barn. It's a quiet post and beam open concept building (a Jamaica Cottages kit) set among the fields of Appleton Maine. You'll sleep in the loft or on a futon on the main floor. The bathroom is huge, 10X10, with a heated floor. It's an open concept kitchen and living space. From Appleton you are 20 miles away from the tourist destinations of Camden, Rockland, and Belfast.

May 21 – 28

Apartment in Camden

4.99 out of 5 average rating, 110 reviews

Sunny In-Town Camden Studio, 15% 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.

Sep 22 – 29

Cabin in Freedom

4.9 out of 5 average rating, 288 reviews

Cozy Lakefront Cabin in Freedom, ME

Our secluded, very quiet and private two bedroom cabin with loft features a bug-free screened-in porch on its large deck. The cabin overlooks peaceul Sandy Pond, inhabited by bald eagles, loons, and herons. Watch beautiful sunrises and sunsets, and swim, fish and kayak from our dock. We're close to coastal Belfast, Unity, MOFGA (annual Common Ground Fair), Waterville, Acadia and Camden. Eat at The Lost Kitchen, visit the Amish, hike the Hills to Sea Trail.

Dec 14 – 21

Cottage in Rockport

4.95 out of 5 average rating, 165 reviews

Designer’s Coastal Retreat with Simple Luxuries

A designer’s stunning retreat just a short walk to Rockport harbor. This newly renovated 1920’s one bedroom cottage is tucked into a forested granite hillside with oversized windows to take in the view. Artfully furnished with a minimalist sensibility, the space has been fully winterized in order to be a year round sanctuary. A top of the line steam shower, heated bathroom floor, modern gas fire place, and pigmented plaster walls add touches of luxury.

Mar 24 – 31

Chalet in Lincolnville

4.98 out of 5 average rating, 132 reviews

Charming home near ocean & close to Camden/Belfast

Cozy coastal home within walking distance of Ducktrap Beach in Lincolnville. Enjoy a relaxing stay at our house situated on 5 private acres of wooded trails, 1/3 mile from a public beach. Private location with spacious deck and open yard, bordered by a meandering stream, beautiful Maine pine trees, wild flowers and ferns. 15 minutes to Camden or Belfast & 1.5 hours to Acadia National Park.

Jan 5 – 12

Apartment in Searsmont

4.97 out of 5 average rating, 109 reviews

Searsmont Studio

Welcome to Searsmont! Entire studio efficiency apartment w/ private entrance above our garage. Fully furnished, including washer and dryer. Country setting on quiet road. WiFi/Satellite TV. Gardens, lawns and picnic table. Close to Camden, Rockport and Belfast, but in the country.

Jun 9 – 16

Vacation rentals for every style

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Stylish accommodations and amenities

Popular amenities for Islesboro vacation rentals

Laptop-friendly workspace

Air conditioning

Stay near Islesboro's top sights

Lincolnville Beach42 locals recommend

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

Lobster Pound Restaurant16 locals recommend

McLaughlin's Lobster Shack11 locals recommend

The Hoot26 locals recommend

Dots18 locals recommend

Other great vacation rentals in Islesboro

Apartment in Lincolnville

4.98 out of 5 average rating, 125 reviews

The Treehouse at Sewall Orchard

Jun 23 – 30

Guest suite in Rockland

4.96 out of 5 average rating, 157 reviews

Salty Dog Hilltop Guest Suite (permit #SDR22-18)

Feb 3 – 10

Guest suite in Rockland

4.98 out of 5 average rating, 347 reviews

5 Laurel Studio private entrance STR20-69

Oct 3 – 10

Cabin in Deer Isle

4.89 out of 5 average rating, 129 reviews

Long Cove Artist Cottage

May 12 – 19

Apartment in Rockport

4.96 out of 5 average rating, 352 reviews

ONE BIG ROOM Studio in Rockport

Mar 4 – 11

Apartment in Rockport

4.96 out of 5 average rating, 231 reviews

The perfect getaway - Camden/Rockport/Rockland

Dec 31 – Jan 7

Yurt in Appleton

4.96 out of 5 average rating, 225 reviews

SUMMER ROSE a Yurt for ALL Seasons

Nov 24 – Dec 1

Guesthouse in Sedgwick

4.96 out of 5 average rating, 235 reviews

Tiny house with AC!!

Feb 28 – Mar 7

Other great vacation rentals in Islesboro

Apartment in Belfast

4.99 out of 5 average rating, 107 reviews

Harborview Escape Downtown Belfast

Nov 20 – 27

Apartment in Belfast

4.89 out of 5 average rating, 212 reviews

Comfy, Convenient Studio Apartment Near Downtown

Sep 3 – 10

Guesthouse in Penobscot

4.99 out of 5 average rating, 167 reviews

Sea Pearl

Aug 16 – 23

Guest suite in Brooksville

4.84 out of 5 average rating, 147 reviews

Western Skies Guesthouse

Jul 6 – 13

Cottage in Blue Hill

4.88 out of 5 average rating, 190 reviews

Brand new cottage close to downtown Blue Hill

Jan 11 – 18

Tiny home in Islesboro

4.95 out of 5 average rating, 19 reviews

"Bohemian Bungalow" Studio Island Guest Cottage

Aug 7 – 14

Cottage in Islesboro

4.83 out of 5 average rating, 42 reviews

Ocean Front Island Cottage

Oct 8 – 15

Guesthouse in Islesboro

4.97 out of 5 average rating, 30 reviews

Main Cabin at Coveside on Islesboro

Dec 25 – Jan 1

Quick stats about vacation rentals in Islesboro

Total rentals
150 properties
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Pet-friendly rentals
50 properties allow pets
Family-friendly rentals
90 properties are a good fit for families
Total number of reviews
5.6K reviews
Nightly prices starting at
$50 before taxes and fees

Frequently Asked Questions

Do house rentals in Islesboro have a bbq area?
Absolutely! We offer over 40 house rentals with a bbq area in Islesboro. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly cottage rentals in Islesboro?
Islesboro has more than 20 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do cottage rentals in Islesboro have air conditioning?
Absolutely! We offer over 10 cottage rentals with air conditioning in Islesboro. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Islesboro have wireless internet?
Absolutely! We offer over 30 cottage 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 20 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 cabin rentals in Islesboro?
Experience the best of Islesboro with our cabin rentals, starting at about $140 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 50 homes with wireless internet, over 20 homes with air conditioning, over 40 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore