
Cottage holiday rentals in Islesboro
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Top-rated cottage rentals in Islesboro
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Quiet cottage on the bay
Settle in at this mid-coast Maine treasure, where you will find more than you hoped for in a getaway. Located in a private neighborhood and setback on a private road on 2.5 acres. You can take a short stroll down a wooded path to the Belfast bay and watch the sunset or simply enjoy the view from living room. The rocky beach gives you access to a wonderful piece of the Maine coastline. Come make some memories at this unique, pet and family-friendly quiet cottage just 1 mile to downtown Belfast.

Private Waterfront Home with Kayaks and Firepit
Retreat to your own coastal oceanfront paradise, where each day begins with breathtaking views. A private boardwalk leads to your secluded beach — perfect for morning strolls, exploring tidal pools, or launching kayaks into sparkling waters. Evenings bring fireside marshmallows under the stars with waves as your soundtrack. Whether you seek adventure with scenic drives to Acadia National Park or quiet mornings with coffee, sea breezes, and seabirds, this is where comfort meets Maine’s coast.

Exquisitely Modern Maine Cottage @Diagonair
Romantic and secluded, this 2,000-sq-ft modern luxury cottage nestled on 12 private acres is a favorite of honeymooners and lovers of modern design * 1 hour to Acadia National Park & Bar Harbor; 15 min to shopping, hiking, swimming * 2 full baths, one with a steam shower * Fully equipped kitchen with Wolf stove and under-counter Sub-Zero fridge * Two gas fireplaces, one indoors, one on a covered deck * Queen bed with luxurious linens and pillows * WIFI, streaming TV, grill, bar * EV charge

Whitetail by the River, Acadia National Park 10m
Whitetail Cottage - 4 MILES TO MDI- nestled between woods edge & rolling meadows w/views distant views of the Jordan River! Tiny home with WIFI is ONLY 10 MILES to Acadia National Park -a hikers paradise! Minutes to Mount Desert Island but secluded enough to disconnect &get back to nature. Enjoy a stroll to the water, privacy, breathtaking sunsets,stargazing & local wildlife! Perfect for 2 & cozy for 4. Short drive to MDI,Acadia, Bar Harbor,Ellsworth,Southwest Harbor,Shops & Lobster Pound

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.

The Cottage at the McCobb House
Freshly renovated inside and out, the cottage is your private Maine camp. Located on an acre and a half of wooded grounds, and surrounded by forest, the cottage feels secluded, but it’s only a mile to the restaurants, shops, and waterfront attractions of bustling Boothbay Harbor. With hiking trails in the Pine Tree Preserve that adjoins the property and the Lobster Cove Meadow Preserve a five minute walk up the road, you can also explore nature and enjoy the solitude of the woods.

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.

Charming Cottage With Spectacular Water View
Find peace and serenity as you gaze at the glistening waters of the Sheepscot River. Our property sitting on Davis Island in Edgecomb, Maine overlooks the quaint town of Wiscasset, providing a calm atmosphere, stunning evening sunsets, and panoramic views. Located within the Sheepscot Harbour Village Resort, you are in a prime location to have access to local shops, antique markets, and restaurants. Take a stroll down to the Pier where you can experience the water up close.

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.

Cottage by Acadia National Park
Located by the Giant Slide Trail and bordering Acadia National Park the nature enthusiast will enjoy the comfort and central location of this cottage on Mt. Desert Island. Making touring in Acadia easy with trails, sites, and Bar Harbor within easy access. Walk right from the cottage to access the carriage roads and the Giant Slide Trail which leads up Sargeant Mountain.
Popular amenities for cottage rentals in Islesboro
Cottage rentals with a hot tub

Maine Cottage - HOT TUB, Dead End, 100+ft shore.

Lakeview Cottage

11 Cute 1Br Acadia Cottage Open Hearth Inn

Canoe House Bungalow and Spa Retreat ,Searsport

Penobscot Bayview Fireplace Hot tub

Beach cottage on Penobscot Bay

Lawn Cottage - Newly Renovated 2024

Nashport on the Penobscot
Pet-friendly cottage rentals

Up Back Cottage

Ferry Keeper’s Cottage: Deer Isle (Waterviews)

Vacation Cottage in Bar Harbor

Chic Farmhouse Cottage, WiFi, Private Beach, A/C

Lakefront Cottage on Tracy Pond

Cozy Cottage on Frenchman Bay

Modern RV on Tracy Pond

Lakefront Stargazing Haven w/Loons, 45 Min Acadia
Private cottage rentals

Charming Maine Cottage Overlooking Penobscot Bay

POST OFFICE COTTAGE Pemaquid Point

Cozy Cottage on u pick blueberry farm.

Cottage near Lighthouse, Trails, Ocean & Seafood

Ocean Front Island Cottage

Meadow Point Cottage

"Eagles Nest" Waterfront Cottage

Cozy Seal Harbor Cottage
Quick stats about cottage rentals in Islesboro
Total rentals
30 properties
Nightly prices starting at
£60 before taxes and fees
Total number of reviews
1.6K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Destinations to explore
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- Acadia National Park
- Pemaquid Beach
- Northeast Harbour Golf Club
- Pemaquid Point Lighthouse
- Samoset Resort
- Coastal Maine Botanical Gardens
- Hermon Mountain Ski Area
- Dragonfly Farm & Winery
- Sandy Point Beach
- Sand Beach
- Bear Island Beach
- Kebo Valley Golf Club
- Eaton Mountain Ski Resort
- Farnsworth Art Museum
- Spragues Beach
- Lighthouse Beach
- Narrow Place Beach
- Three Island Beach
- Driftwood Beach
- Wadsworth Cove Beach
- Islesboro Town Beach
- The Camden Snow Bowl
- North Point Beach
- Hero Beach