
Holiday rentals in Islesboro
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Islesboro
Guests agree: these stays are highly rated for location, cleanliness and more.

The Cabins at Currier Landing Cabin 1: Fern
Stylish Cabin w/Loft - Sleeps 3 - loft w/queen bed; 1st level twin daybed. The Cabins at Currier Landing, featured in Dwell as “Three Magical Tiny Cabins Take Root in a Maine Forest,” are located on the Thos. Currier Saltwater Farm. Glimpses of water & access to 300’ of the Benjamin River Harbor shore. 2 seasonal cabins. 1 year round studio cabin. Centrally located on the Blue Hill Peninsula, near Deer Isle, the cabins offer access to outdoor activities, cultural events, restaurants & shops.

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.

Private Sauna+Near Best Beach+FirePit+Pond+FirePit
Relax at your own private forest retreat! * Private Cedar Glass Sauna * Minutes Reid State Park Beach & 5 Island🦞 * Private Outdoor Shower * Private Fire Pit w/S'mores * 100% Cotton sheets/towels * Rain Shower & Heated Bathroom Floor * AC/Heat * SmartTV & Record Player w/Vinyl * Fast Broadband Wifi *Pine Cabin is one of two cabins on 8 acres right down the road from one of the best beaches in Maine! The cabins are 150ft. apart and separated by a privacy screen and natural landscaping.

Acadia Region New Oceanfront Cottage
Relax and unwind at this unique waterfront retreat where you can enjoy breathtaking views of the ever-changing tides. Keep an eye out for bald eagles, osprey, and the occasional seal as you soak in the natural beauty around you. This renovated former boathouse combines comfort with convenience, offering the perfect base for your coastal adventures. Situated in Mid Coast, Maine, it's ideally located just an hour from Acadia National Park, 15 minutes from Belfast, and 45 minutes from Camden.

Hand built cabin overlooking a pond
Beautiful hand built cabin, overlooking Cotton Pond. Ten minutes from Camden, the sailing mecca of the east coast. Solar lights, (we are off the grid) gravity fed kitchen water, gas-hot water outdoor shower, outhouse overlooking the forest. Hiking trails everywhere! Swimming across the road on Hobbs Pond. If you book in November, there is a possibility that if it gets cold, you will not have a hot outdoor shower and will use water from a 5 gallon ceramic container for drinking and cooking.

"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.

Rocky Top Hideaway with level 2 charging station.
Feel the magic in this quiet secluded hillside retreat. Awaken your senses with the smell of the salt air, pines and an occasional whiff of coffee beans roasting all while watching the ferry go back and forth to Ilesboro. Early risers will enjoy spectacular sunrises. Experience nature without being too far off the beaten path. A private half mile walk down the driveway will end at brick sidewalks leading you to Lincolnville Beach, one of Maine's stretches of sandy shoreline.

Modern Treehouse w/Water Views+Cedar Hot Tub
Stay in our custom designed tree dwelling w/ wood-fired cedar hot tub up among the trees! This unique structure is perched atop a 21-acre wooded hill sloping to water views. Enjoy stunning views from the King size bed through a wall of windows. Located in a classic coastal Maine village w/ Reid State Park's miles of beaches + famed Five Islands Lobster Co. (See 2 other tree dwellings on our 21 acre property listed on AirBnb as "Tree Dwelling w/Water Views." See our 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).

Timeless Tides Cottage
This comfortable 2 bedroom, one bathroom, A-frame pine cottage is set on its own private point with 350 feet of waterfront! Cook out on the grill, lounge on the deck or dock while taking in the wildlife on a beautiful tidal river. Watch nesting Bald Eagles and Great Blue Herons fishing! There is plenty of sight-seeing in this picturesque area. Rockland is just 10-minutes away where you can enjoy shopping, restaurants, museums, galleries, lighthouses and festivals.

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.

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.
Popular amenities for Islesboro holiday rentals
Other great holiday rentals in Islesboro

Cottages at Oakland Seashore (Cottage #8)

Ledgewood Cottage

Double On The Rocks, ocean view family retreat

Four-Season Luxury Lakefront Cabin Close to Camden

Main Cabin at Coveside on Islesboro

Megunticook Retreat

Off-Grid Oasis with Ocean Views, Near Rt. 1

Oceanfront on Somes Sound, Acadia National Park ME
When is the best time to visit Islesboro?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $267 SGD | $286 SGD | $267 SGD | $280 SGD | $255 SGD | $339 SGD | $354 SGD | $350 SGD | $316 SGD | $294 SGD | $223 SGD | $255 SGD |
| 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 vacation rentals in Islesboro?
Islesboro has more than 150 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in cottage rentals in Islesboro?
Experience the best of Islesboro with our cottage rentals, starting at about $130 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 vacation rentals in Islesboro?
Four-legged friends are welcome in Islesboro. Choose from more than 100 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Islesboro?
Yes! Work meets play with ease at over 120 vacation rentals in Islesboro featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Islesboro have air conditioning?
Absolutely! We offer over 40 house 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 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.
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 230 holiday rentals in Islesboro

Nightly prices starting at
Islesboro holiday rentals start at $89 SGD 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 & child-friendly amenities

Pet-friendly holiday rentals
Find 100 rentals that welcome pets

Rentals with dedicated workspaces
120 properties have a dedicated workspace

Wifi availability
210 of Islesboro holiday rentals include wifi 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!
Destinations to explore
- Boston Holiday rentals
- Québec City Holiday rentals
- The Hamptons Holiday rentals
- Island of Montreal Holiday rentals
- Capital District, New York Holiday rentals
- Quebec City Area Holiday rentals
- Halifax Holiday rentals
- Laval Holiday rentals
- Québec Holiday rentals
- Portland Holiday rentals
- Newport Holiday rentals
- Martha's Vineyard Holiday rentals
- Rentals with a patio Islesboro
- Rentals with a washing machine and dryer Islesboro
- House rentals Islesboro
- Fitness-friendly rentals Islesboro
- Rentals with a firepit Islesboro
- Rentals with beach access Islesboro
- Pet-friendly rentals Islesboro
- Beachfront rentals Islesboro
- Waterfront rentals Islesboro
- Cabin rentals Islesboro
- Family-friendly rentals Islesboro
- Cottage rentals Islesboro
- Rentals with breakfast Islesboro
- Rentals with a fireplace Islesboro
- Flat rentals Islesboro
- Rentals with outdoor seating Islesboro
- 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
- Rockland Breakwater Light
- University of Maine
- Schoodic Peninsula
- Bass Harbor Head Light Station
- Moose Point State Park
- Maine Lighthouse Museum
- Hollywood Slots Hotel & Raceway
- Cellardoor Winery
- Camden Hills State Park





