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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Guest favorite

Cottage in Lincolnville

4.91 out of 5 average rating, 332 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.

Oct 27 – Nov 3

R2,505 ZAR per night

Guest favorite

Guesthouse in Lincolnville

4.97 out of 5 average rating, 328 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.

Oct 17 – 24

R2,591 ZAR per night

Guest favorite

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.

Mar 21 – 28

R3,020 ZAR per night

Guest favorite

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!

Dec 7 – 14

R1,962 ZAR per night

Guest favorite

Apartment in Belfast

4.99 out of 5 average rating, 108 reviews

Harborview Escape Downtown Belfast

Enjoy a bright, sun-filled, stylish experience at this centrally-located 2nd floor apartment. This open concept, king bed studio apartment is perfect for a couple or a solo experience. (The bedroom space is defined but does not have a door.) Spacious and cozy with a well-appointed kitchen and washer/dryer. Lots of restaurants & shops nearby with a superb coffee bar downstairs. Belfast waterfront, Saturday morning United Farmers Market, and the fabulous Harborwalk just 2 blocks away.

Jan 30 – Feb 6

R3,059 ZAR per night

Guest favorite

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 14 – 21

R2,484 ZAR per night

Guest favorite

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.

May 4 – 11

R2,709 ZAR per night

Guest favorite

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.

Jun 29 – Jul 6

R2,360 ZAR per night

Guest favorite

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 3 – 10

R2,760 ZAR per night

Guest favorite

Guest suite in Rockland

4.98 out of 5 average rating, 347 reviews

5 Laurel Studio private entrance STR20-69

Open concept small studio, private patio and entrance, full kitchen. 2 minute walk to the ocean , Lobster and Blues Festivals. A small swimming beach is a 5 minute walK, 5-10 minutes gets you to the Farnsworth and CMCA museums, Strand Theater, restaurants, antiques shops & galleries. ALSO NOTE we do not have television. We have wifi but you must bring your own device . EXEMPT FROM ACCEPTING SERVICE DOGS

Oct 14 – 21

R1,871 ZAR per night

Guest favorite

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.

Dec 24 – 31

R3,741 ZAR per night

Guest favorite

Apartment in Searsmont

4.97 out of 5 average rating, 110 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. Starlink High Speed WiFi/Satellite TV. Gardens, lawns and picnic table. Close to Camden, Rockport and Belfast, but in the country.

Jun 23 – 30

R2,234 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Islesboro vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

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

Guest favorite

Home in Camden

5.0 out of 5 average rating, 157 reviews

Quaint 3 Bedroom In Town Camden Home

Jan 29 – Feb 5

R2,664 ZAR per night

Guest favorite

Guest suite in Rockland

4.96 out of 5 average rating, 157 reviews

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

Nov 1 – 8

R2,873 ZAR per night

Guest favorite

Guesthouse in Camden

4.99 out of 5 average rating, 151 reviews

In-town Private Suite.

May 3 – 10

R2,850 ZAR per night

Guest favorite

Apartment in Camden

4.99 out of 5 average rating, 110 reviews

Sunny In-Town Camden Studio, 15% weekly discount

Sep 24 – Oct 1

R2,869 ZAR per night

Guest favorite

Apartment in Belfast

4.89 out of 5 average rating, 213 reviews

Comfy, Convenient Studio Apartment Near Downtown

Aug 26 – Sep 2

R2,843 ZAR per night

Guest favorite

Guesthouse in Sedgwick

4.96 out of 5 average rating, 235 reviews

Tiny house with AC!!

Apr 1 – 8

R2,655 ZAR per night

Guest favorite

Apartment in Rockport

4.96 out of 5 average rating, 231 reviews

The perfect getaway - Camden/Rockport/Rockland

Apr 2 – 9

R2,715 ZAR per night

Guest favorite

Cabin in Freedom

4.9 out of 5 average rating, 288 reviews

Cozy Lakefront Cabin in Freedom, ME

Dec 14 – 21

R1,563 ZAR per night

Show all

Other great vacation rentals in Islesboro

Guest favorite

Guesthouse in Unity

5.0 out of 5 average rating, 193 reviews

Modern Home on Working Farm

Jan 16 – 23

R1,869 ZAR per night

Guest favorite

Apartment in Rockport

4.94 out of 5 average rating, 193 reviews

Centrally Located Apartment! Rockport, Maine

Apr 17 – 24

R2,525 ZAR per night

Guest favorite

Tiny home in Blue Hill

4.94 out of 5 average rating, 155 reviews

New enchanting retreat near Acadia National

Jan 24 – 31

R2,522 ZAR per night

Guest favorite

Guesthouse in Camden

4.91 out of 5 average rating, 230 reviews

Superb Location! 5 min walk to Downtown & Ocean

Mar 3 – 10

R2,789 ZAR per night

Guest favorite

Home in Rockport

4.95 out of 5 average rating, 261 reviews

Sweet home away (pet friendly)

Sep 22 – 29

R3,254 ZAR per night

Guest favorite

Place to stay in Owls Head

4.98 out of 5 average rating, 162 reviews

A comforting sweet off grid cabin near the beach!

Apr 15 – 22

R2,740 ZAR per night

Guest favorite

Home in Brooks

4.9 out of 5 average rating, 201 reviews

Cedar Swamp Farm

Jan 28 – Feb 4

R2,167 ZAR per night

Guest favorite

Guesthouse in Rockland

4.88 out of 5 average rating, 315 reviews

Sweet Willow Suite, Rockland, private 1st floor

May 15 – 22

R2,087 ZAR per night

Show all

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
R952 ZAR 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 house rentals in Islesboro?
Islesboro has more than 40 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 apartment rentals in Islesboro have wireless internet?
Absolutely! We offer over 10 apartment 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 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.

Islesboro vacation rentals

Top-rated vacation rentals in Islesboro

Vacation rentals for every style

Houses

Cottages

Hotels

Popular amenities for Islesboro vacation rentals

Stay near Islesboro's top sights

Other great vacation rentals in Islesboro

Home in Camden

Guest suite in Rockland

Guesthouse in Camden

Apartment in Camden

Apartment in Belfast

Guesthouse in Sedgwick

Apartment in Rockport

Cabin in Freedom

Other great vacation rentals in Islesboro

Guesthouse in Unity

Apartment in Rockport

Tiny home in Blue Hill

Guesthouse in Camden

Home in Rockport

Place to stay in Owls Head

Home in Brooks

Guesthouse in Rockland

Quick stats about vacation rentals in Islesboro

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do cabin rentals in Islesboro have a bbq area?

Are there family-friendly house rentals in Islesboro?

Do cabin rentals in Islesboro have air conditioning?

Do apartment rentals in Islesboro have wireless internet?

Are there house rentals with a dedicated workspace in Islesboro?

Are there pet-friendly cottage rentals in Islesboro?

How much does it cost to stay in cabin rentals in Islesboro?

What are the most popular amenities for Cottage Rentals in Islesboro?

Destinations to explore