House vacation rentals in Islesboro

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Top-rated house rentals in Islesboro

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Top guest favorite

A charming modern cottage with a red exterior and a pitched roof stands amidst lush greenery. The covered porch is furnished with comfortable seating, inviting relaxation. Large windows allow natural light to enter, enhancing the welcoming atmosphere of the property.

Home in Northport

4.97 out of 5 average rating, 186 reviews

Cute Midcoast Cottage w Hot Tub

Kick back and relax in this ideally located modern cottage. Enjoy a soak in the hot tub or the peace of the covered porch. Situated in the heart of midcoast Maine, this cottage has it all. An elegant kitchen that awaits your culinary delights, a spacious living area, a primary bedroom with a TV, a kingsize bed and a luxurious bath with a soaking tub and a walk-in rainfall shower, plus twin bunk beds for the kiddos. A small store and a farm to table restaurant are conveniently across the street.

Top guest favorite

An aerial view captures the coastal cottage set on a granite ledge beside the Penobscot River. Surrounding trees in autumn hues frame the property, and the tranquil water reflects the colorful foliage, creating a serene natural setting.

Home in Hampden

5 out of 5 average rating, 113 reviews

Cozy Cottage on the Penobscot — Panoramic Luxury!

Escape to your private sanctuary where tranquility meets luxury. Our Coastal Maine Cottage home is perched on a granite ledge that disappears twice daily with the rising tide. Enjoy the pristine interior bathed in natural light, cherry floors, and gourmet kitchen. Wake to panoramic views of the Penobscot River from the owner's suite. Conveniently located 12 minutes to downtown Bangor, our retreat offers easy access to urban amenities, an international airport, and Acadia! IG @cozycottageinmaine.

Top guest favorite

The modern house is positioned on a gentle slope, featuring large windows and a wraparound deck. A red umbrella is partially extended over the outdoor seating area, enhancing the inviting exterior. Surrounding wild grass sways gently in the breeze, providing a natural backdrop.

Home in Hope

5 out of 5 average rating, 101 reviews

Treetop Vista: stunning views, modern farmhouse

Relax in this beautiful, architect-designed new house. Enjoy expansive 180-degree views to the south and west, including spectacular sunsets and incredible foliage. Immerse yourself in the scenery, go hiking out the door, go swimming in nearby Hobbs pond, or take a 10-minute drive into Camden to enjoy food, art, shopping, and the ocean. This area is a mecca for outdoor and cultural activities. The house has 3 bedrooms, 2.5 bathrooms, a great room with kitchen, dining, living areas, and a deck.

Top guest favorite

A calm cove surrounded by dense green trees reflects serene water. A sailboat gently floats on the bay, complemented by soft rock formations emerging from the water's surface. Sunlight brightens the landscape, casting a tranquil atmosphere over the scene.

Home in Deer Isle-Stonington

4.95 out of 5 average rating, 164 reviews

Blue Arches: waterfront vacation home on 18+ acres

A lovely custom-designed home nestled in a pristine oceanfront cove, Blue Arches offers 18 acres of privacy and relaxation on beautiful Deer Isle, Maine. Charming Stonington Village is just five minutes away & features harbor-front restaurants, shops, kayaking adventures, galleries and the acclaimed Opera House Arts center. Day trips to nearby Bar Harbor, Mt. Desert Island and Acadia National Park expand your possibilities and let you create a truly memorable vacation for your friends & family.

Guest favorite

A charming porch entrance features a light green wall adorned with a decorative sign reading 'The Gables.' A basket of flowers hangs beside a comfortable wicker chair with a striped pink cushion, inviting guests to relax and enjoy the pleasant surroundings.

Home in Islesboro

4.9 out of 5 average rating, 79 reviews

"The Gables" on Penobscot Bay, Mid-Coast Maine

The Gables is a historic cottage built in the mid-late 1800's and has always been family owned. The 2+ acre property is located on a quiet road surrounded by cottages built by our great great grandfather. The Gables comes with its own private beaches, a lawn for yard games, a hammock for naps and a porch overlooking the bay. We can put you in touch with a local fishermen for fresh lobster or mussels. Check the ferry schedule-see photos. www.townofislesboro.com/special-pages/getting-here

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Home in Belfast

4.91 out of 5 average rating, 109 reviews

Historic Stephenson Farm on 35 acre Mason Pond

This water front historic Stephenson Farmhouse is a cozy 3 bedroom farmhouse that sits on 5 acres with frontage on Lower Mason Pond. A bird lovers paradise along with sightings of beaver & river otters. Trail from house leads to waterfront, canoes, paddles & PFD’s and a picnic table. We’ve maintained the antiquity of the house along with many antique pieces of furniture. Enjoy amazing sunsets, expand your birding life list, pick apples and blueberries in season. . . on a nature preserve.

Top guest favorite

A serene waterfront view captures calm waters reflecting the sky and surrounding landscape. Lush greenery is visible along the shore, while scattered clouds drift across the blue sky. The tranquil scene invites relaxation and appreciation of nature.

Home in Newcastle

4.99 out of 5 average rating, 169 reviews

Peaceful Oasis by the Great Salt Bay - 3BR/2Ba

Waterfront Retreat with Gorgeous Views Stunning 3-bedroom, 2-bath home perfect for multi-generational gatherings. Features an open-concept layout, chef’s kitchen, 1st-floor bedroom and bath, 2nd floor with 2 bedrooms and 1 bath. Kayak from your backyard, hike nearby trails, or swim in Damariscotta Lake just a 5-minute walk away. Stay connected with high-speed fiber optic WiFi. Close to charming Newcastle and Damariscotta shops and restaurants. A true oasis for nature and relaxation lovers!

Top guest favorite

A charming cottage is framed by lush green trees and sits along the Penobscot River. The gravel path leads to the entrance, with water visible in the background under a clear blue sky, creating a serene setting for visitors.

Home in Orland

4.98 out of 5 average rating, 134 reviews

Lavender by the Sea

The Cottage rests over the end of Penobscot River as it opens into the Bay. The Cottage will comfortably accommodate two. The Cottage has a spacious bedroom, full kitchen, dining area, den and an all season porch with rockers. From Cottage there are views of the water and the lavender gardens. The gardens are terraced with a path down to the sea. The Carriage House Suite is available for an additional fee. it has has two bedrooms, a full bath and a sitting area. It can easily sleep four.

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Home in Northport

5 out of 5 average rating, 9 reviews

SunnySide - Cottage w/ Pen Bay Views in Bayside

Welcome to Sunny Side Cottage, in the heart of Merithew Square in historic Bayside! This Victorian Cottage has been lovingly restored, combining coastal charm with modern amenities for a memorable and comfortable stay. Boasting a large, wrap around porch and a second floor balcony, you will always find the perfect spot to sit and enjoy a cup of coffee or watch the working bay hum along. Located 4 minutes from the Northport Yacht Club, don't miss your chance to enjoy the summer in Maine!

Guest favorite

A view from a shaded patio showcases a round table surrounded by wicker chairs. The lush green lawn extends to the water's edge, where trees provide a natural frame for the serene expanse of the bay, dotted with clouds reflecting in the distance.

Home in Belfast

4.91 out of 5 average rating, 157 reviews

Belfast Ocean Breeze

Welcome to an exquisite retreat nestled on a tranquil dead-end lane in the thriving coastal town of Belfast. With private access to Belfast City Park and Ocean, this charming space offers unparalleled serenity, and boasting breathtaking views of Penobscot Bay and beyond. The exceptional grounds offer an ideal setting for relaxation with the added allure of explorations along the shoreline or tennis/ pickleball at park/ year round hot tub. Near downtown and Rt. 1. No parties.

Guest favorite

A red, two-story building is set among vibrant autumn trees, with hues of orange, yellow, and green. The structure features multiple windows and a covered porch, surrounded by a grassy field showcasing its peaceful rural setting.

Home in Appleton

4.96 out of 5 average rating, 203 reviews

The Barn

I call my place "The Barn" because as I was finishing it it took the shape and feel of a barn. It's not a barn. It's a quiet post and beam open concept building (a Jamaica Cottages kit) set among the fields of Appleton, Maine. You'll sleep in the loft or on a futon on the main floor. The bathroom is huge, 10X10, with a heated floor. It's an open concept kitchen and living space. From Appleton you are 20 miles away from the tourist destinations of Camden, Rockland, and Belfast.

Guest favorite

The Victorian cottage, painted in a soft yellow hue, is surrounded by lush greenery. A meandering pathway leads to the welcoming front porch, flanked by flowering shrubs. A white picket fence frames the yard, offering a charming entrance to the well-maintained garden.

Home in Islesboro

5 out of 5 average rating, 20 reviews

MASSIVE Oceanfront Dark Harbor Home on ISLESBORO

This elegant 5+ bedroom Victorian Cottage has been carefully restored and renovated to highlight the natural charm and character of the home while integrating sophisticated elements throughout. Prime location within walking distance to local coffee shop, ice cream parlor and charming gift shop. All points of island are within a 10 minute drive of the home. Massive, private bedrooms perfect for multiple couples or families. Reach out with any questions or concerns you may have!