Coastal Charm Awaits at This Orr’s Island Retreat ! | Cottage in Harpswell

Welcome to Island Breeze Retreat, a charming 4-bedroom, 1.5-bath getaway nestled on peaceful Orr’s Island. The getaway is peacefully situated just off the main road in this part of the picturesque Harpswell peninsula. Harpswell, known for its rugged coastline, hidden coves, and serene beauty, is a true Maine gem. Whether you’re hiking along scenic trails, exploring the little area beaches, enjoying the stunning views, or simply breathing in the fresh ocean air, this special place is all about relaxation and rejuvenation.
The cozy, well-maintained home is ideal for families or small groups with its three queen-size beds and one double, comfortably sleeping up to six guests.
Inside, as you enter, you will be greeted by the fully equipped kitchen featuring all of the cookware and tools you need. Whether you're cooking in or just heating up leftovers from a local lobster shack, this kitchen makes mealtime a breeze. The bright, inviting dining area is just around the corner where you will have a view of the back deck and yard area. The living room offers a warm, relaxed space to gather, kick back and relax after a day by the coast, or simply the perfect spot to curl up with a book! The main floor also features the washer and dryer, as well as a half bath. On the second floor, you'll find four thoughtfully arranged bedrooms and a full bath, offering a peaceful retreat at the end of the day. Each room is simply furnished and comfortably appointed—three with queen-size beds and one with a double—making it easy for everyone to settle in and feel at home. Open the windows at night and let the gentle salt air drift in—one of the small joys of island living. The full bathroom has been recently refreshed, featuring double sinks for added convenience—ideal for groups or families getting ready for the day.
Step outside to enjoy a nicely furnished deck that makes the most of its cozy footprint—just the right size for relaxing with a morning coffee, afternoon cocktails, or sharing a casual meal fresh off the gas grill. It’s a sweet little spot to soak up the island air and take in the quiet surroundings!
Just beyond the deck, a charming firepit area offers a great place to unwind in the evening. Whether you're roasting marshmallows, swapping stories, or simply enjoying the salty breeze under the stars, this outdoor space invites you to slow down and savor the moment.
Orr’s Island and neighboring Bailey Island are part of the stunning seaside community of Harpswell, known for its winding shoreline, working lobster boats, and postcard-worthy views around every corner. With rocky coves, saltwater inlets, and peaceful coastal roads, this part of Maine feels like a well-kept secret. Be sure to stop at one of the many local lobster shacks and waterfront eateries—you haven’t truly visited Harpswell until you’ve had a fresh lobster roll with a view. From the iconic Cribstone Bridge to scenic spots like Land’s End, Harpswell offers endless opportunities to explore, unwind, and experience authentic coastal life—without the crowds.
While Harpswell offers peaceful beauty and classic coastal charm, a short drive brings you to the vibrant town of Brunswick—home to Bowdoin College and a hub for arts and culture. In the summer, the Maine State Music Theatre puts on top-notch performances, and the town’s culinary scene is full of surprises, from fresh seafood to global flavors. It’s the perfect place to spend an afternoon exploring after a quiet morning by the sea. You’ll find plenty of day trip options nearby. Freeport is just up the road, known for its charming village vibe, outlet shopping, and the iconic L.L. Bean flagship store. Head a bit farther to Portland, a small city with big character—packed with art galleries, historic waterfront charm, and a nationally recognized food scene. For a more classic Maine coastal town, visit Bath, with its rich shipbuilding history, the Maine Maritime Museum, and a quaint downtown that’s perfect for strolling.
There are many destinations within reach for unforgettable day trips.
Whether you’re here for springtime walks along quiet trails, sun-soaked summer days filled with lobster rolls and beach adventures, or the crisp magic of a coastal Maine fall, Island Air Retreat is your perfect home base. It’s laid-back, comfy, and full of the little things that make a getaway great—like salty breezes, cozy evenings by the firepit, and that unmistakable island charm. Come relax, explore, and breathe in that island air—we can't wait to welcome you! Managed by Maine Coastal Connections, Harpswell, ME.

Coastal Charm Awaits at This Orr’s Island Retreat ! is located in Orrs Island. Coastal Charm Awaits at This Orr’s Island Retreat ! provides accommodation, featuring Parking, View, Ocean View, among other amenities. This Cottage features Parking, View, Ocean View, to make your stay a comfortable one.

Coastal Charm Awaits at This Orr’s Island Retreat ! has 4 Bedrooms , 1 Bathroom, and max occupancy of 6 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated Cottage because of the excellent services rendered by the owner or manager of this Cottage, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. Cottage has a friendly neighborhood, and the Orrs Island has interesting places to visit. If you want to learn more about the Cottage in Orrs Island, such as places to visit and things to do nearby, you can check below to learn more.