
Cottage holiday rentals in Islesboro
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Top-rated cottage rentals in Islesboro
Guests agree: these cottages are highly rated for location, cleanliness and more.

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.

Southwest Harbor Cottage
Enjoy unparalleled views of bustling Southwest Harbor and the beauty of Acadia National Park from the comfort of Eagle's Nest. Perched on a granite cliff, this thoughtfully designed little home provides for your every need. For anything else, take the ten minute stroll into the village, where you'll find plenty of local shops and restaurants. You can access the water via a set of stairs leading from the property to the shoreline. End your days on the deck and keep your eyes peeled for seals!

Lakefront Cottage on Tracy Pond
Lakefront cottage on 47 acre Tracy pond. The pond has no public access so it is quiet with only my home and another Air BnB on site. You share the backyard with my home. Loons, eagle, deer, otter and beaver are around. It has a fully equipped kitchen, deck and gas grill along with a stone firepit. Minutes to Bangor airport and downtown and one hour to Acadia National Park. You can swim and boat on the pond with kayaks and a canoe provided. Pets welcome but keep on leash and clean up after.

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.

Cottage by the sea private oceanfront shoreline
Breathtaking oceanfront private cottage. Spiral staircase to second floor bedroom. Sliding glass doors open to wrap-around deck and lawn that slopes to Ocean. 300 + feet of deep water frontage. Separated from lawn by broad rock ledge. Perfect spot for sunbathing or having a campfire in the evening. Enjoy your morning coffee watching lobster and sailboats in the Mussel Ridge Channel. Unbelievable and peaceful views out to ocean and north to the Camden Hills. Unparalleled views everywhere.

Lamoine Modern Guest House
Relax, recharge, & escape here. A unique & peaceful guest house in the woods of Lamoine, Maine with large windows looking out to the woods. Close enough to Bar Harbor / Acadia National Park (45 minutes) but removed from the hustle & bustle. A 10-minute walk down a gravel road to a beach in Lamoine with distant views of Acadia National Park. Enjoy all weather with our new wood stove fireplace surrounded by large windows. We have a comprehensive guidebook for our guests upon check-in.

Brand new cottage close to downtown Blue Hill
The cottage is brand new on 27 acres of land 3 min to Blue Hill Mountain and 5 min to Blue Hill downtown which is right on the water of Blue Hill Bay. This is an edge wood retreat perfect for two to hear birds, squirrels and porcupines. Remember to pick some blueberries when it is in season before the black baby bears down the road eat them all. 3D nature is unfolding right in front of your eyes and Acadia National Park is a 50 min drive from here. Oh man, you are free!

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.

Gateway Cottage Acadia National Park Bar Harbor
Keep life simple at this cozy, peaceful and private little "cottage in the woods". Centrally-located to many attractions such as Acadia National Park, Bar Harbor, Whale Watching, Lobster Fishing tours. Less than 5 minutes from local Ellsworth restaurants, unique shops, gas stations and supermarkets. The enclosed sunroom is perfect for morning coffee, winding down at the end of the day with a glass of wine or curling up with a good book on the boat bed.
Popular amenities for cottage rentals in Islesboro
Cottage rentals with a hot tub

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

Lakeview Cottage

Canoe House Bungalow and Spa Retreat ,Searsport

Penobscot Bayview Fireplace Hot tub

Beach cottage on Penobscot Bay

Nashport on the Penobscot

Tree House, Where Seaside & Serenity come together

Megunticook Retreat
Pet-friendly cottage rentals

Ferry Keeper’s Cottage: Deer Isle (Waterviews)

Stonington Harbor Cottage

Driftwood Cottage

Lake Great Pond| Dog Friendly | Boat Launch

Modern RV on Tracy Pond

Our charming,oceanfront, Bradford point cottage

Cozy cottage close to Acadia National Park!

Katy's Seaside Cottage
Private cottage rentals

Sunny 2 Bedroom cottage - Walk to the beach!

Charming Private camp on China Lake

Little Loon Cottage · Ski, Swim & Hike in Camden

The Gatehouse

Cozy Cottage on u pick blueberry farm.

Classic, adorable cottage by the seaside.

Ledgewood Grove Cottage in Bar Harbor

Waterfront Cottage
Quick stats about cottage rentals in Islesboro

Total holiday rentals
Explore 30 holiday rentals in Islesboro

Nightly prices starting at
Islesboro holiday rentals start at £97 per night before taxes and fees

Verified guest reviews
Over 1,630 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
30 of Islesboro holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Islesboro rentals

4.9 Average rating
Islesboro stays are highly rated by guests – averaging 4.9 out of 5!
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- Cottage rentals Waldo County
- Cottage rentals Maine
- Cottage rentals United States
- 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
- Schoodic Peninsula
- Bass Harbor Head Light Station
- Moose Point State Park
- Maine Lighthouse Museum
- Hollywood Slots Hotel & Raceway
- Cellardoor Winery
- Camden Hills State Park




