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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, 293 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.

Oct 30 – Nov 6

Cottage in Lincolnville

4.91 out of 5 average rating, 334 reviews

Eco-friendly studio - ocean views, close to beach

Ecofriendly guest cottage in the heart of Lincolnville Beach, on Rt 1 (a busy road that runs from Maine to Florida), is a sunny studio (with blinds) with a murphy bed, full bathroom, breakfast nook (sink/fridge/microwave - no oven, no stovetop) and amazing views of Penobscot Bay. It's a quick walk to one of Maine's sandy beaches, restaurants, shops, coffee roaster, and a neighborhood market. Drive a few miles to hiking trails, Mount Battie, and the towns of Belfast, Camden, Rockport + Rockland.

Dec 8 – 15

Home in Camden

5.0 out of 5 average rating, 157 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.

Mar 7 – 14

Guesthouse in Lincolnville

4.97 out of 5 average rating, 330 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.

Dec 9 – 16

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.

Apr 26 – May 3

Guesthouse in Orland

4.99 out of 5 average rating, 106 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!

Mar 16 – 23

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.

Jan 18 – 25

Home in Appleton

4.96 out of 5 average rating, 123 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.

Oct 30 – Nov 6

Apartment in Lincolnville

4.98 out of 5 average rating, 125 reviews

The Treehouse at Sewall Orchard

Two larger apartments on site, see "The Space" for details. Please visit our mountainside organic orchard! From the tiny, post & beam barn apartment enjoy views of the Camden Hills, or, if you hike our blueberry hill, all the way to Acadia w/ lake & ocean views. Short drive to Lincolnville Beach, Megunticook Lake, hiking trails, towns of Belfast & Camden. 1 br, pull-out sngl couch, tiny br w/ shower, "galley" kitchen, AC. Back deck for breakfast or stargazing.

Mar 29 – Apr 5

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 10 – 17

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.

Dec 10 – 17

Guest suite in Rockland

4.96 out of 5 average rating, 157 reviews

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

This guest suite is located in the lower level of our NetZero post & beam home which sits on a mountain overlooking the Penobscot Bay. The over 600 sq. ft. large open floor plan is spacious & clean with a large private patio. The location is quiet and peaceful while only 5 minutes from the action in downtown Rockland and only 15 minutes from Camden. This is a great home base to explore all that the Midcoast area has to offer.

Mar 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 Rockport

4.96 out of 5 average rating, 231 reviews

The perfect getaway - Camden/Rockport/Rockland

Apr 15 – 22

Guest suite in Rockland

4.98 out of 5 average rating, 350 reviews

5 Laurel Studio private entrance STR20-69

Oct 23 – 30

Apartment in Camden

4.99 out of 5 average rating, 110 reviews

Sunny In-Town Camden Studio, 15% weekly discount

Oct 14 – 21

Apartment in Belfast

4.89 out of 5 average rating, 215 reviews

Comfy, Convenient Studio Apartment Near Downtown

Sep 8 – 15

Guesthouse in Unity

5.0 out of 5 average rating, 194 reviews

Modern Home on Working Farm

Jan 22 – 29

Guesthouse in Lincolnville

4.94 out of 5 average rating, 120 reviews

Ocean View Beach Loft Carriage House Lincolnville

Oct 26 – Nov 2

Guesthouse in Appleton

4.95 out of 5 average rating, 351 reviews

BRAEBURN at The Appleton Retreat

Jan 10 – 17

Apartment in Belfast

4.88 out of 5 average rating, 173 reviews

Sunny apartment overlooks Main St.

Apr 27 – May 4

Other great vacation rentals in Islesboro

Chalet in Lincolnville

4.98 out of 5 average rating, 132 reviews

Charming home near ocean & close to Camden/Belfast

Jan 3 – 10

Apartment in Rockport

4.96 out of 5 average rating, 353 reviews

ONE BIG ROOM Studio in Rockport

Dec 6 – 13

Cottage in Owls Head

4.99 out of 5 average rating, 139 reviews

Coastal Maine contemporary cottage

Mar 27 – Apr 3

Guesthouse in Penobscot

4.99 out of 5 average rating, 167 reviews

Sea Pearl

Oct 16 – 23

Cottage in Sedgwick

4.99 out of 5 average rating, 189 reviews

Exquisitely Modern Maine Cottage @Diagonair

Oct 29 – Nov 5

Tiny home in Islesboro

4.95 out of 5 average rating, 19 reviews

"Bohemian Bungalow" Studio Island Guest Cottage

Sep 24 – Oct 1

Cottage in Islesboro

4.83 out of 5 average rating, 42 reviews

Ocean Front Island Cottage

Oct 17 – 24

Guesthouse in Islesboro

4.97 out of 5 average rating, 30 reviews

Main Cabin at Coveside on Islesboro

May 8 – 15

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 cabin rentals in Islesboro have a bbq area?
Absolutely! We offer over 10 cabin 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 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 cabin rentals in Islesboro have wireless internet?
Absolutely! We offer over 10 cabin rentals with wireless internet in Islesboro. Enjoy a tailored experience with all the comforts you desire.
Are there cottage rentals with a dedicated workspace in Islesboro?
Yes! Work meets play with ease at over 10 cottage rentals in Islesboro featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly cottage rentals in Islesboro?
Four-legged friends are welcome in Islesboro. Choose from more than 10 cottage 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 Cottage Rentals in Islesboro?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 10 homes with a bbq area, over 10 homes with air conditioning, over 30 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore