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

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.

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.

Rustic Chic Private Getaway Cabin @Diagonair
Pet-friendly Maine cabin on 12 private acres of woods and blueberry fields, 1 hour to Acadia National Park. A favorite of couples visiting Maine for the first time. • Fifteen minutes to shopping, hiking, swimming • Open kitchen and sitting room with new appliances and gas fireplace • Screened porch with rocking chairs and chaise • Loft bedroom with full bed and new linens • WiFi, Roku TV, gas grill, stocked bar • EV charger • Seasonal wild blueberries • Dark skies, slow mornings, quiet nights

The Cabins at Currier Landing Cabin 2: Meadow
Tranquil cabin; open plan. Bedroom w/queen bed & privacy doors. Alcove w/bunkbeds. 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 studio cabin. Centrally located on the Blue Hill Peninsula near Deer Isle, the cabins offer access to outdoor activities, cultural events, restaurants & shops.

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.

Bayview House 1br 2ba Stunning Harbor Views
Do you crave balmy summer evenings or frosty winter days that make you feel like you've been transported back to a simpler time? Or long for days spent on the water or experiencing village life with friendly locals in charming pubs tasting local eats? Experience the simple joys of life with rustic yet modern amenities offered at this coastal 2-story home. Whether daily strolls by the water or taking in the sunset on your deck, you'll fall in love with this lovely New England destination.

"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.

Beachfront Guest Cottage - Year-round Hot Tub!
Our cozy guest cottage has easy beachfront/kayak/canoe access, and is located very close (within walking distance at low tide) to the public boat launch for larger boats. Great location to explore Deer Isle, Acadia (approx 1hr), Castine (45m), and the Bangor (1hr) area. Brave children and adults even swim from the beach but comfortable swimming ponds/lakes are 10m in several directions. The hot-tub is open year-round! Additional guests can be considered prior to booking.

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.

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 vacation rentals
Other great vacation rentals in Islesboro

Sunny 2 Bedroom cottage - Walk to the beach!

Private Forest Retreat • Spa Bath • Near the Coast

Unique Octagonal House with Private Beach!

Magical Lakefront Cabin on 5 Acres-25 Mi to Acadia

Megunticook Retreat

New Bar Harbor listing- Evergreen Yurts, #3 Spruce

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 | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$41,003 GYD | G$41,840 GYD | G$41,840 GYD | G$46,024 GYD | G$41,840 GYD | G$55,647 GYD | G$58,157 GYD | G$57,530 GYD | G$51,881 GYD | G$48,325 GYD | G$36,610 GYD | G$41,840 GYD |
| 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 apartment rentals in Islesboro have air conditioning?
Absolutely! We offer over 20 apartment rentals with air conditioning in Islesboro. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in Islesboro have wifi?
Absolutely! We offer over 50 cabin rentals with wifi in Islesboro. Enjoy a tailored experience with all the comforts you desire.
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.
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 vacation rentals in Islesboro

Total vacation rentals
Explore 230 vacation rentals in Islesboro

Nightly prices starting at
Islesboro vacation rentals start at G$14,644 GYD per night before taxes and fees

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

Family-friendly vacation rentals
150 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 100 rentals that welcome pets

Rentals with dedicated workspaces
120 properties have a dedicated workspace

Wi-Fi availability
210 of Islesboro vacation 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
- Rockland Breakwater Light
- University of Maine
- Schoodic Peninsula
- Bass Harbor Head Light Station
- Moose Point State Park
- Maine Lighthouse Museum
- Cellardoor Winery
- Hollywood Slots Hotel & Raceway
- Camden Hills State Park




