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.

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.

Downtown-Walk to All Things Rockland

Cute, convenient, and clean recently renovated 1930’s cottage has two bedrooms, sleeps 4, a private backyard, and is within walking distance to downtown, restaurants, nightlife, co-op & supermarket, museums, shops, art galleries, Harbor Park, ferry and the waterfront. Enjoy off-street parking and an ocean view with the sun glistening off the harbor at the end of the street. This is a perfect home-base for a coastal Maine vacation and festivals. Discounts offered for weekly and monthly stays!

Private Bright Forest House by Lake

Enjoy a very private experience at this newly built centrally-located home. located in the lake district of Camden. Moments from hiking trails, set back on the hillside across from Megunticook Lake, and watch the lake sparkle between the trees. Soaking bath, firepit, beautiful walks. This is our private home which we only put up when we are away for work or travel. We move our most personal belongings but please note things like closets still contain our clothes, pantry goods & such remain.

"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

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 privacy and 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.

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!