Cottage holiday rentals in Islesboro

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Top-rated cottage rentals in Islesboro

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Guest favourite
A spacious screened-in porch is visible, furnished with a white table and chairs. Decorative cushions in green and blue provide comfort. A view of Penobscot Bay is framed by large windows, allowing natural light to fill the space.
Cottage in Belfast
4.93 out of 5 average rating, 117 reviews

Moon Bay Cottage - Absolutely Amazing Bay Views!

Moon Bay Cottage is the quintessential Maine seaside retreat, tucked away in a small cottage community, with beautiful views, and only a few steps away to the private community beach on Penobscot Bay. We named Moon Bay Cottage for our favorite time to visit, when the moon is full, and the moonlight shimmers on the waters of Penobscot Bay. We invite you to come and fall in love with this wonderful spot where you drift to sleep listening to the lapping waters of the Bay, and calls of the Loons.

Top guest favourite
The image captures a serene view of the water at sunset, with the sun reflecting on the surface. Framed by lush green foliage, a small rustic bench is positioned on the shore, inviting quiet moments of contemplation.
Cottage in Belfast
4.97 out of 5 average rating, 196 reviews

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.

Guest favourite
A fire pit area is surrounded by four Adirondack-style chairs, set on a grassy patch. Views of the harbor and surrounding trees provide a tranquil backdrop, with the cottage’s red exterior visible in the corner of the image. The scene captures a peaceful outdoor gathering space.
Cottage in Southwest Harbor
4.97 out of 5 average rating, 156 reviews

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!

Guest favourite
The cottage is surrounded by a large, lush green yard, with a serene landscape featuring trees and shrubs. A generous blue sky provides natural light, emphasizing the relaxed atmosphere. The unique architecture of the cottage is highlighted by large windows and a spacious deck.
Cottage in Lincolnville
4.92 out of 5 average rating, 417 reviews

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.

Top guest favourite
A serene ocean view showcases a sailboat gliding across calm waters, framed by lush greenery and a rocky coastline. The expansive sky is filled with soft clouds, creating a tranquil atmosphere that invites relaxation and reflection.
Cottage in South Thomaston
4.93 out of 5 average rating, 137 reviews

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.

Top guest favourite
A newly constructed cottage is nestled among trees, featuring a screened porch with wooden rocking chairs. The entrance is defined by a bright red door, inviting guests to enjoy the surrounding natural beauty. Gravel pathways lead to the entry, with a lawn area visible.
Cottage in Lincolnville
5 out of 5 average rating, 129 reviews

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.

Top guest favourite
A hot tub is situated outdoors amidst a serene wooded setting, surrounded by trees with the faint hint of steam rising. The structure features a partially enclosed wooden fence for privacy, with a few nearby seating options visible, set against a softly lit twilight sky.
Cottage in Deer Isle
4.94 out of 5 average rating, 414 reviews

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.

Top guest favourite
A screened porch offers a view of Penobscot Bay, featuring two green wicker chairs adorned with floral cushions. The scenery includes a lush lawn and Adirondack chairs positioned for relaxation, with water visible in the background and distant hills framing the horizon.
Cottage in Belfast
4.99 out of 5 average rating, 157 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).

Top guest favourite
An open-concept great room features high wooden ceilings with exposed beams. Large windows provide ample natural light and views of the surroundings. A comfortable seating area includes a sofa and coffee table, while a dining space with chairs is positioned near the kitchen.
Cottage in South Thomaston
4.96 out of 5 average rating, 202 reviews

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.

Guest favourite
A charming cottage exterior is framed by lush green grass and shrubs. A stone pathway leads to the entrance, while the sky above features soft clouds, suggesting a warm day. The cottage is adorned with wood shingles and large windows, providing a welcoming appeal.
Cottage in Deer Isle
4.89 out of 5 average rating, 158 reviews

Ferry Keeper’s Cottage: Deer Isle (Waterviews)

The Ferrykeeper’s Cottage is a light filled oasis, surrounded by water, meadows & views of the famous Eggemoggin Reach. Our cottage offers handcrafted counters, stone sinks, & oceanic tile to create a unique setting. 3 houses to the beach. Borrow a kayak & explore our shore. Property borders Scott’s Landing - a treasure trove of birds, sand dollars, porpoises, seals & a family of foxes. *Queen bed + flip down sofa (latter suitable for 1 adult OR 2 small kids)

Top guest favourite
The cottage is surrounded by tall pine trees, offering a serene setting. A grassy area is visible in front of the porch, while a rocky shoreline is seen in the foreground. The warm glow of the sunset highlights the natural landscape and adds a peaceful ambiance.
Cottage in Lamoine
4.97 out of 5 average rating, 123 reviews

Meadow Point Cottage

Meadow Point cottage is located on a very quiet five acre property with panoramic views of Frenchman's Bay and Mount Desert Island. It takes about thirty minutes to drive over to MDI and Acadia National Park. The property has a private beach for kayaking and woods with a picnic area and fire pit. It is a wonderful spot for walking and viewing wildlife; ducks, eagles, shore birds, seals and deer.

Top guest favourite
A clear blue sky stretches over a view of the ocean, framed by lush greenery and tall trees. The tranquil waters are visible in the distance, enhancing the natural beauty of the surrounding landscape.
Cottage in Camden
4.97 out of 5 average rating, 135 reviews

Owls Head Oceanview Cottage Cedar Hot Tub/Sauna

This ocean view cottage on the side of Mt Battie has a master suite with a private bathroom and a wood burning fireplace, a living room with a queen sofa bed and another wood burning fireplace, sauna, a large 6 ft wide Maine Cedar hot tub off the back deck. Hiking trails to Mt Battie summit and the rest of Camden Hills State park are accessible from our parking lot.

Popular amenities for cottage rentals in Islesboro

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 £96 per night before taxes and fees

  • Verified guest reviews

    Over 1,630 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 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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