
Holiday houses in Islesboro
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Top-rated holiday rentals in Islesboro
Guests agree: these stays are highly rated for location, cleanliness and more.

Loon Lodge
Located on beautiful Damariscotta Lake, "Loon Lodge" is a rustic cabin from another era. Fall asleep to the sound of crickets and frogs and wake every morning to the call of the lake's many loons. The cabin is 30 minutes from Augusta and 15 minutes from Damariscotta. Hiking enthusiasts will enjoy climbing the Camden Hills-a quick 45 minute drive from the lake. You’ll love my place because of the views, the ambiance, the people, and the location. My place is good for couples and solo adventurers.

BREEZE, in a tree The Appleton Retreat
BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE guests may reserve the wood fired cedar hot tub and the sauna, which are close by and private, at an additional charge. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

Cozy Cottage on the Penobscot — Panoramic Luxury!
Escape to your private waterfront retreat where tranquility meets luxury. Our Coastal Maine Cottage style home rests on a granite ledge that disappears twice daily with the tide. Enjoy a sun-filled interior with cherry floors, a gourmet kitchen, and a private deck for sunrise coffee or evening wine. Wake to sweeping Penobscot River views & unwind by the fire pit at river’s edge. Just 10 minutes to downtown Bangor, with easy access to urban amenities, Bar Harbor, and Acadia Park. @cozycottageinme

The Greenhouse Cottage
We feel that the best way to describe our getaway to be “Rustic Elegance”. When you walk through the door you will instantly feel the warmth of a uniquely styled Adirondack cottage. Located nearby to the Acadia Highway (aka Route 1), we are close by to historic Fort Knox, Castine, and Acadia. Enjoy our attached “Greenhouse” which has been made over into a delightful screenhouse/patio, the country setting, blueberry fields, and the beautiful sunrises and sunsets! Fire pit, horseshoes, more!!!

Milk House
nice little cottage in Dark Harbor, near to everything. queen bed, so sleeps up to two in a quiet location for short or medium term stays. most reasonable amenities provided; hiking or social recommendations are available on request. (Wi-Fi speed excellent, though I was not able to use AirB&B's official Wi-Fi measurement option.) *Please be aware, we are on an island, which must be accessed by boat or ferry, so service can be interrupted. there's a gym at the Community Center, $10/day pass.

Moss House: A Modern Waterfront Cabin in the Woods
Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

Eco-friendly studio - ocean views, close to beach
Sunny eco-friendly cottage on Route 1, steps from the beach! A cozy studio with a Murphy bed, a full bath, and kitchenette - stovetop, fridge, toaster, & microwave. Beautiful views of Penobscot Bay – don't worry, the blinds will keep the sunshine at bay when you need a nap! You're within easy walking distance of sandy beaches, restaurants, shops, a coffee roaster, and a market. Explore nearby hiking trails, Mount Battie, and the charming towns of Belfast, Camden, Rockport, and Rockland.

Exquisitely Modern Stargazing Cottage @Diagonair
Romantic and private, this 2,000 sf modern luxury cottage nestled on twelve acres is a favorite of honeymooners and lovers of modern design * One hour to Acadia National Park & Bar Harbor; 15 min to shopping, hiking, swimming * Stargazing deck * 2 full baths, one with steam shower * Fully equipped kitchen with under-counter fridge/freezer * Two gas fireplaces, one indoors, one on a covered deck * Queen bed with luxurious linens and pillows * WIFI, streaming TV, grill, bar * EV charger

Nomad's Rest-Secluded Modern Camp 30 miles to MDI
The modern Maine camping experience. Enjoy an unforgettable stay in a geodesic dome outfitted with detached bathroom and shower. A fantastic jumping-off point for your favorite outdoor sports with hiking and biking trails within 10 minutes of the property and 30 miles from Acadia National Park. Return from a day of exploration to views of Maine lakes, the national park and a roaring fire pit! @nomaddomehome on Insta for more pictures.

The Loft. A Midcoast Maine Home Base.
A perfect place to use as your base for exploring Midcoast Maine. We are 8 miles from Camden or Rockland. 34 miles from Boothbay Harbor and 90 miles from Bar Harbor. This is your home away from home. A fully stocked kitchen, ready for meals after a long day of exploring. We have 1.5 baths, a washer and dryer and three Smart Tv’s. This 1700 sq foot warehouse loft has central air conditioning, two bedrooms and a large living space.

Cozy Cottage With River View
Beautifully recently renovated cottage with a wonderful river view. The home is an easy 10-15 minute walk to the center of town and a 5-10 minute walk to Camden's thriving seasonal farmer's market. There is a small fenced in yard. This is the perfect home to relax in while being in easy distance of everything Camden & mid coast Maine has to offer. Our Town of Camden Short Term Rental license number is STR-00036.

Pretty Marsh Cottage
This beautiful, light-filled cottage on waterfront property on the western side of Mount Desert Island has picturesque views of the Mount Desert Narrows and access to a private pebble beach. The house is on very secluded wooded property for a nice private getaway. All you will hear are the sounds of birds and waves lapping up on the beach. Just a short drive to all that Acadia National Park has to offer!
Popular amenities for Islesboro holiday rentals
Other great holiday rentals in Islesboro

Surrounded by Water

The Gatehouse

Ocean Front Island Cottage

Hidden Gem - Cozy and quiet lakefront cottage

Main Cabin at Coveside on Islesboro

Waterfront Deer Isle Retreat w/ Fire Pit!

New Bar Harbor listing- Evergreen Yurts, #3 Spruce

Wildwood Acadia Salt House: 55 minutes from Acadia
When is the best time to visit Islesboro?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $280 AUD | $285 AUD | $285 AUD | $314 AUD | $285 AUD | $380 AUD | $397 AUD | $392 AUD | $354 AUD | $330 AUD | $250 AUD | $285 AUD |
| Avg. temp | -7°C | -6°C | -1°C | 6°C | 13°C | 18°C | 21°C | 20°C | 16°C | 9°C | 3°C | -3°C |
Frequently Asked Questions
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.
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.
Are there pet-friendly house rentals in Islesboro?
Four-legged friends are welcome in Islesboro. Choose from more than 30 house rentals for guests traveling with pets.
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.
Do cabin rentals in Islesboro have air conditioning?
Absolutely! We offer over 40 cabin rentals with air conditioning in Islesboro. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Islesboro have wifi?
Absolutely! We offer over 20 apartment rentals with wifi in Islesboro. Enjoy a tailored experience with all the comforts you desire.
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.
Do cabin rentals in Islesboro have a gym?
Absolutely! We offer over 30 cabin rentals with a gym in Islesboro. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Islesboro

Total holiday rentals
Explore 220 holiday rentals in Islesboro

Nightly prices starting at
Islesboro holiday rentals start at $86 AUD per night before taxes and fees

Verified guest reviews
Over 7,380 verified reviews to help you choose

Family-friendly holiday rentals
150 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 100 rentals that welcome pets

Rentals with dedicated workspaces
120 properties have a dedicated workspace

Wi-Fi availability
210 of Islesboro holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Islesboro rentals

4.8 Average rating
Islesboro stays are highly rated by guests—averaging 4.8 out of 5!
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- Acadia National Park
- Acadia National Park Pond
- Pemaquid Beach
- Pemaquid Point Lighthouse
- Coastal Maine Botanical Gardens
- The Camden Snow Bowl
- Sand Beach
- Farnsworth Art Museum
- University of Maine
- Rockland Breakwater Light
- Maine Discovery Museum
- Bass Harbor Head Light Station
- Schoodic Peninsula
- Moose Point State Park
- Hollywood Slots Hotel & Raceway
- Cellardoor Winery
- Maine Lighthouse Museum
- Camden Hills State Park




