House holiday rentals in Islesboro

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.

"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

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.

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!

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.

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!

Cozy home near the coastal town of Camden, Maine!

This home is in a country setting on Hatchet Mountain in Hope near the beautiful Maine coast and about 8 miles from Camden. About a mile from our home, is Hobbs Pond (2 miles long!) with public access for swimming, boating and kayaking. Hiking trails surround us, too! Beaver Lodge, a favorite spot for weddings and other family events, is also nearby. This listing has an exemption for all animals. For safety reasons, it may not be suitable for young children.

Intown Camden, 2 bedroom, 2nd floor, own entrance

Restaurants, shopping, and the harbor are a five-minute walk from one of the oldest capes in Camden village. House was built in 1800 on a quiet one-way street. The second-floor apartment has a private entrance and includes one bedroom with a queen-size bed, and a sitting room with a single bed, a seating area, t.v, . Wifi access. Private outside garden with own entrance. Minimum 3 night stay - 10% off for full week stays.

Modern Lakefront Estate | Hot Tub • Gym

Wander Northport Harbor is a luxurious mountaintop retreat with stunning views of Penobscot Bay. The home features floor-to-ceiling windows, a cozy fireplace, a private gym, and a spa-like bathroom with a sauna, bathtub, and its own fireplace. Surrounded by nature trails and blueberry fields, this property offers the perfect mix of outdoor adventure and upscale comfort for a relaxing, unforgettable stay.