Vacation rentals in Harpswell

Two wooden Adirondack chairs are positioned on a stone patio facing a serene body of water. A small fire pit, surrounded by stones, is visible in the background, framed by lush greenery and tall trees.

4.96 out of 5 average rating, 72 reviews

Private oceanfront cottage, great views, and float

Cozy cottage on Quahog Bay . Open space Livingroom / kitchen area offers beautiful views of the bay . Second floor is one large bedroom with large windows overlooking the bay. Beautiful recently renovated bathroom with large walk in shower . Wake up to gorgeous sunrises and end your day with a moonrise. Watch a large variety of birds soar over head . Laze on the large deck or walk down to the large private float, go for a swim or venture out on a kayak ride . Enjoy the patio and fire pit area .

A serene waterfront view showcases a vibrant sunset reflected on calm waters. Silhouetted trees frame the scene, highlighting the tranquil atmosphere created by the array of warm colors in the sky and the peaceful surrounding landscape.

4.89 out of 5 average rating, 65 reviews

Basin Cove Retreat: Perfect to explore Mid-Coast

Welcome to our peaceful waterfront cottage on Basin Cove, perfect for year-round relaxation. This cozy 2-bedroom, 1-bath retreat offers serene water views and breathtaking sunsets. Just 12 miles from Brunswick, 30 mins from iconic LL Bean in Freeport, and an hour from Portland, you'll enjoy both tranquility and convenience. Ideal for a quiet winter escape or a summer adventure. The cottage is close to Live Well Farm and Bowdoin College, providing the perfect blend of relaxation and exploration.

4.98 out of 5 average rating, 58 reviews

The exterior of a two-story home is showcased, featuring a light gray façade with white trim. A spacious yard is visible, surrounded by trees and a circular driveway. A small balcony is located on the second floor, and large windows invite natural light into the sunroom.

Townhouse in Harpswell

Tower Hill House Harpswell, Orr’s Island, Maine

Gather with family (including canine family members!) and friends at our airbnb in Maine. Explore the coast, shops and restaurants or simply relax! Curl up with a book in the cozy reading nook, play board games or put together a puzzle on the game table. Enjoy a game of croquet or corn hole, dine alfresco, sit by the fire pit on a chilly evening. Source ingredients from local farmers and fishermen and prepare a meal in the fully equipped kitchen or enjoy dining at our local restaurants.

Superhost

An aerial view captures a serene point surrounded by calm water, with lush green trees lining the rocky shore. The rocky outcrop extends into the water, providing direct access to the tidal area. The tranquil setting highlights the natural beauty of the landscape.

4.89 out of 5 average rating, 123 reviews

Rising Tide Times - quintessential Maine cottage

Out of State guests please read the Maine State COVID-19 restrictions currently in affect. Classic Maine cottage on the end of a point, surrounded by water on 3 sides provides stunning views. The perfect backdrop for the quintessential cottage vacation. Features spacious decks, direct tidal access for kayaking, and outdoor firepit. 15 min to downtown Brunswick/45 min to Portland. We even have Kayaks onsite for guests to paddle around Cards Cove. Perfect for couples and families!

Apartment in Orr's Island

The exterior of the multi-unit house is shown, featuring a light gray facade and a red roof. An expansive wooden deck is visible on the second level, overlooking the green lawn. Bright flowers adorn the entrance, adding a touch of color to the outdoor space.

4.95 out of 5 average rating, 101 reviews

Shore House, Leona Unit - Ocean Front Property

This is the ground level of a multi-unit house. It is wheelchair friendly, with cathedral ceilings, a modern kitchen, and wide plank pine floors. The expansive deck will only enhance you experience overlooking a working wharf on Garrison Cove and Casco Bay. Dogs allowed upon approval. Must not be big barkers and owners are responsible for any waste. We want to be courteous with all renters and their pets. Weekly rentals preferred in July and August months (Saturday - Saturday)

A tranquil view of the ocean is visible from a spacious wooden deck, featuring several white Adirondack chairs. The calm water reflects the clear blue sky and surrounding greenery, while distant islands can be seen along the horizon.

4.89 out of 5 average rating, 160 reviews

Classic Maine Cottage - dock, sauna & kayaks

The Perfect Maine Cottage! On the edge of the ocean, carefully preserved with traditional details. Charming, open floor plan, with a wall of windows to the ocean. Sunny large wrap-around deck and screen porch creates beautiful outside spaces to enjoy. Perfect for listening to waves and watch lobstermen pull up their traps. Cathedral ceilings and Scandinavian design gives the cottage an exclusive feeling. Gentle stairs lead to the private deep water dock for all kinds of boating.

Superhost

An aerial view of the Orchid Harbor cottage is captured, showcasing the surrounding landscape and coastal waters of Casco Bay. The image features the expansive lawn, nearby homes, and a serene shoreline, with glimpses of the water's edge and distant landforms.

4.8 out of 5 average rating, 49 reviews

Orchid Harbor, Bailey Island 3BR

Welcome to Orchid Harbor, a classic New England-style cottage home with stunning southerly views of Casco Bay. Perfectly located in the heart of Bailey Island, it's within walking distance of Cook's Lobster & Ale House, Morse's Seafood Grille, the historic Cribstone Bridge, and the Salt Cod Cafe. You'll love the breathtaking sunsets painting the sky. Enjoy easy water access, perfect for launching a kayak to explore the coast of Harpswell or combing the shoreline for treasures.

A charming waterfront cabin is surrounded by lush greenery, with a welcoming red exterior and a pitched roof. A path leads to the entrance, which is framed by large trees. The scenic view of the water can be seen in the background, hinting at a peaceful atmosphere.

5 out of 5 average rating, 14 reviews

Waterfront Log cabin on the bay. Dog Friendly!

"BAY VIEW" is a beautiful waterfront cabin just feet from the shore of Casco Bay's Merriconeag Sound, which separates the two sides of Harpswell. Smell the salt air, listen to the sounds of waves lap the shoreline and watch the eagles, sea gulls and local Lobstermen haul their traps. You may even see seals at play in the waters. Whether at sunrise or the end of the day, there is something for your senses to take in as you relax on the deck enjoying the coast of Maine.

The exterior of a cottage with a white facade and green trim is showcased. A wooden staircase leads to a screened porch with a door displaying the number 9. An American flag is visible in the background, complementing the natural surroundings.

4.96 out of 5 average rating, 54 reviews

Old fashion neighborhood near the water.

This cottage was built in 1930 and has been in our family ever since. It has been fully renovated with loving care. We would love to share this property with the right person/family who will appreciate it as we do. The ocean can be seen in two directions and is steps away. There is a half mile of beach access as well as trails, restaurants, and beautiful coastline to discover. This property includes a fully equipped kitchen, linens, blankets, towels and washer/dryer.

The living room features two comfortable sofas arranged around a central coffee table. Large windows provide views of the water, while a TV is mounted on a wall. Soft lighting and natural wood beams enhance the inviting space.

4.97 out of 5 average rating, 29 reviews

Oceanfront Serenity – Stargaze & Unwind-

Enjoy panoramic ocean views from this charming Harpswell cottage on Sebascodegan Island. With a private dock, kayaks, large deck, and cozy interior, it’s the perfect coastal escape. Sleeps 5 adults comfortably. Close to Brunswick, many Harpswell coastal hiking trails, fresh lobster, and beaches. Summer stays require a 7-night minimum (Sun–Sun); shorter spring/fall stays welcome. Relax, explore, and experience the magic of coastal Maine—just steps from the water!

4.95 out of 5 average rating, 469 reviews

The studio's interior displays rustic charm with original rough-hewn beams overhead. A spacious bed is visible in the back area, while a comfortable seating arrangement and TV are situated in the front. Natural light streams through multiple windows, enhancing the welcoming atmosphere.

Guesthouse in Harpswell

Harpswell Studio on Waterview Property! Lobster!

Cottage Style Studio! Clean, spacious, colorful, comfy, bright! Easy access to Harpswell’s 216 miles of coastline via coastal trails, lovely side roads, small beaches and preserves. Too many trails to count in the surrounding area! Fresh lobster and seafood! Popham Beach and Reid State Park with expansive beaches are 35 minutes or less away. Enjoy the trails in the woods with spectacular views or walk on the beach at one of the state parks! So beautiful!

A serene view of the water is framed by lush greenery, showcasing the calm lake surrounded by trees. A cozy cabin is partially visible, nestled among nature, with clear blue skies reflecting off the water's surface.

4.91 out of 5 average rating, 32 reviews

Peaceful, Rustic Old Town Cabin Harpswell Getaway

Peaceful Old Town Cabin in Harpswell with gentle ocean views through the trees. Named for the family behind Old Town Canoe, this cozy, rustic retreat offers a true taste of Maine’s coastal charm. Small kitchen and bathroom, but stocked with all you need. Explore nearby trails, rocky shores, fresh seafood spots, and quiet villages. With a deck, A/C (in the main bedroom) Tesla charger, it’s the perfect couples’ getaway to relax and unwind.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Harpswell vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Harpswell

5 out of 5 average rating, 5 reviews

A cozy studio space is highlighted by a comfortable queen Murphy bed dressed in soft bedding. Natural light enters through a window beside a wooden armchair and small dining table. A mix of wooden furniture and shelves provides functional storage in a tranquil atmosphere.

Guest suite in Harpswell

Long Point Studio

A charming cottage is situated on a grassy lot, surrounded by tall trees. The building features a wraparound porch and is located near Harpswell Sound, with clear blue water visible in the background under a sunny sky.

4.96 out of 5 average rating, 26 reviews

Waterledge Cottage - Orrs Island, Maine

A charming house is set amidst a grassy area, featuring a wraparound porch with wooden railings and steps leading to the entrance. Tall trees provide shade, and the exterior is adorned with light-colored siding and contrasting blue trim.

5 out of 5 average rating, 12 reviews

Cricket Lodge

A charming cottage exterior is showcased, featuring gray siding and a sloped roof. Large windows allow for natural light, while a welcoming porch adds to the home’s appeal. Lush green landscaping surrounds the cottage, contributing to a picturesque setting in a tranquil environment.

4.97 out of 5 average rating, 39 reviews

Cottage with Ocean Views on Pott’s Point

A wooden dock extends over the calm water of Quahog Bay, surrounded by lush greenery. Pink flowers bloom prominently in the foreground, complementing the scenic view of boats in the distance and the dense forested shoreline.

5 out of 5 average rating, 11 reviews

Cedar Cottage on Quahog Bay

A charming cottage is nestled by a calm waterway, surrounded by tall trees displaying autumn colors. A small dock extends into the water, while patches of green grass create a natural setting. Soft shadows cast by the trees enhance the peaceful ambiance of the property.

4.9 out of 5 average rating, 20 reviews

Cozy Waterfront Cottage

A wooden walkway leads to a dock over calm waters, with a railing providing safety. A green table stands nearby, and a decorative fish sign adds a touch of charm. The scene is complemented by natural surroundings, creating a serene atmosphere.

4.72 out of 5 average rating, 25 reviews

Camp forever