Vacation rentals in Harpswell

A clear glass desk with a sleek chair is positioned near a large window, offering views of the serene water and surrounding trees. Natural light filters through sheer curtains, creating a bright workspace. A small decorative piece and a dish are placed gracefully on the desk.

4.95 out of 5 average rating, 64 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 charming cottage exterior is displayed, showcasing blue siding and a welcoming front door. Lush green grass surrounds the home, with colorful flower beds and a hammock visible. Scenic water views can be seen in the background, contributing to a serene atmosphere.

4.89 out of 5 average rating, 54 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.

4.96 out of 5 average rating, 23 reviews

Home in Georgetown

Breathtaking Bay Views!

Enjoy glorious sunsets over Sagadahoc Bay on Indian Point at the tip of Georgetown Island! Walls of glass bring the outside in to this 3 bed, 2 bath contemporary home where the only decisions you'll make are whether to spend your days at the beach, on the ocean, or exploring the trails... Later in the day you need to choose whether to grill under the stars, take a short drive to one of the great local spots, or head to Five Islands on the wharf for some of the best lobster Maine has to offer!

A spacious outdoor seating area is presented with a light-colored sofa, inviting relaxation. The glass doors provide access to an interior space with sheer curtains. Surrounding greenery is visible, enhancing the connection to nature.

4.94 out of 5 average rating, 122 reviews

Brand new Scandinavian cottage: dock & kayaks!

Brand new architectural cottage and detached 'boathouse' with sweeping elevated ocean views both east and west, private waterfront lawns and deep water dock with kayaks. This property was built in 2020 so expect a fresh and clean experience on one of Harpswell's most private peninsulas. Watch the sunrise from the cantilevered 2nd floor deck, sit by the campfire on your private lawn oceanside, or walk down to the dock for a paddle in the west facing protected cove. The best of coastal Maine!

Top guest favorite

Guesthouse in Harpswell

4.95 out of 5 average rating, 462 reviews

Harpswell Studio on Waterview Property! Lobster!

Available dates in late June! 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!

Top guest favorite

4.98 out of 5 average rating, 61 reviews

New Modern Cottage with Ocean Views & Wildlife

The Salty Roost, a modern Scandinavian-inspired guest cottage is positioned on one acre adjacent to our main home in a coastal neighborhood. This property offers distance water views of Middle Bay, dock/water access, on-site parking, grill, hammock chairs, kitchen with all the amenities, WIFI, washer and dryer combo unit, hardwood floors. The cottage is minutes from great restaurants, breweries, hiking trails, and shopping. The most amazing sunsets will surely bring joy to your stay.

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.

4.9 out of 5 average rating, 115 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!

4.91 out of 5 average rating, 116 reviews

An airy cabin interior features wood beams and a large sliding glass door, providing access to a deck and surrounding greenery. A small dining area with a table and two chairs is visible alongside a well-equipped kitchen area, complete with modern appliances.

Tiny home in Bowdoinham

Sweet Fern Cabin on Merrymeeting Bay

Nestled in the woods on 2.5 waterfront acres where the Muddy River meets Merrymeeting Bay. The cabin is 350 square feet of simple living with a panoramic view. There is a three season hot water outdoor shower and wood burning stove with plenty of wood included. Kitchen is fully stocked with cooking supplies and has off grid cold water sink. Outbuilding with composting toilet is right out the back door. Kayaks and stand up paddle board are available to rent for an additional fee.

5 out of 5 average rating, 6 reviews

The interior features a high wood-paneled ceiling with exposed beams, lending an open feel. Large windows provide views of the waterfront, while natural light fills the space. Decorative items are placed along shelves and surfaces, contributing to the cabin's character.

Cabin in Harpswell

Waterfront Log cabin on the bay. Pet 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.

Top guest favorite

A bright bedroom features a spacious bed adorned with a colorful coral-patterned quilt. Two bedside tables with lamps are placed on either side of the bed. A window offers a view of the outdoors, and a chest of drawers is positioned against the wall.

4.96 out of 5 average rating, 47 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.

4.91 out of 5 average rating, 23 reviews

A sliding glass door opens to a serene view of the water, framed by trees transitioning into fall colors. A wooden deck extends outward, featuring a patterned chair and leaves scattered across the floor, inviting relaxation in a natural setting.

Cabin in Harpswell

Super-Cozy, Old Town Cabin ~ Relaxing Ocean Views

Take a break and unwind at this rustic, peaceful oasis ! Perfect couples getaway ! Cozy cabin in Harpswell, with picturesque views of the Atlantic. This quaint location is conveniently located as a home base for exploring our Maine coast, or simply just to enjoy our fishing village. Harpswell offers amazing views around every corner, fine shops, restaurants, galleries, hiking trails, as well as preserves, little beaches & the rocky shore !

4.91 out of 5 average rating, 11 reviews

A clear view of the water shows sailboats gently bobbing in the serene bay, framed by lush green grass. Several Adirondack chairs are arranged on the lawn, providing a perfect spot for relaxation, while the horizon showcases a tranquil landscape of the coastal area.

Apartment in Harpswell

Sunset Hideaway on Bailey Island

Welcome to Sunset Hideaway, a comfortable one bedroom apartment sleeping 4 guests. Perfectly located in the heart of Bailey Island within walking distance of local food options. The large lawn just across the street lends to easy water access, perfect for launching a kayak to explore the coast of Harpswell or combing the shoreline for treasures. You'll love the stunning sunsets painting the sky with beautiful purple, rose, and orange hues.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

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A space thats all yours, with room for everyone

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

Apartment in Orr's Island

A glass table with blue chairs is positioned on a spacious deck, providing a clear view of the water and nearby lawn. Lush greenery surrounds the area, while a hint of the working wharf and recreational chairs by the shore can be seen in the distance.

4.95 out of 5 average rating, 99 reviews

Shore House, Leona Unit - Ocean Front Property

JoAnneRating, 5 stars2 weeks ago

Beautiful spot right on the water. In walking distance to the one of a kind Cribstone bridge. The kitchen was equipped with plenty of cookware to eat in and the home was cozy. We loved our stay and can’t wait to return!

A sun-drenched deck is surrounded by lush greenery, offering serene views of the ocean. A dining table with chairs is set in the center, while potted plants add a touch of nature. The space invites relaxation in a peaceful outdoor setting.

4.87 out of 5 average rating, 157 reviews

Quaint & Peaceful Designer's Oceanfront Cottage

GeorgiaRating, 5 stars3 weeks ago

My partner and I had a lovely stay at this home! It was beautifully decorated and the view was gorgeous, even in the fog. We especially enjoyed the cozy gas fireplace.

An open concept living area features a modern kitchen with wooden cabinetry and countertops. A cozy seating area is arranged around a low table, with a sliding glass door leading to the outside. Stairs ascend to the upper level, while warm wooden ceilings enhance the space.

4.9 out of 5 average rating, 21 reviews

Overlooking the working waterfront.

NancyRating, 5 stars11 months ago

We really enjoyed our stay at the cottage. The inside looked exactly as pictured. We were immediately struck by the beautiful view we could see of the harbor through the sliding doors and from the back deck. A new dock was being built at an neighboring property and watching the craftsmanship of the builders was fascinating. The bedroom upstairs was lovely with a comfortable king-sized bed and nice bedding. It was lovely waking up to views of the harbor. We would recommend this cottage to others looking for a clean, cozy, and well-appointed place to stay in Harpswell. The cottage was a great jumping off place for our adventures to other parts of Harpswell.

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.

LilyRating, 5 stars2 weeks ago

Cricket Lodge

What a beautiful house and location! We feel so lucky that we found the Cricket Lodge. Nikoline was a lovely and responsive host, and the home was even more charming in person. My friends and I are already talking about trying to plan a trip back. Thank you so much!

A spacious deck offers multiple seating areas with views of Harpswell Sound. A dining table is positioned nearby, surrounded by lush greenery and colorful landscaping. The expansive lawn leads to the water, inviting relaxation and enjoyment of the serene coastal environment.

5 out of 5 average rating, 7 reviews

Coastal Home away from Home

TerriRating, 5 stars2 weeks ago

This is an absolutely beautiful home! It was very comfortable and had an amazing view from the back porch. The home was very clean and had all of the amenities that we needed. Kathryn was extremely responsive to all of our questions and needs. We would most definitely stay here again if we travel back to the area.

A serene outdoor area features a circular stone fire pit surrounded by wooden seating. Several adirondack chairs in gentle pastel colors are positioned on sandy terrain, providing a clear view of the calm waters and lush greenery in the background.

Apartment in Harpswell

4.83 out of 5 average rating, 265 reviews

Sunny Apartment on the Ocean.

CarissaRating, 5 stars2 weeks ago

Jane’s place was lovely and peaceful. Check in was smooth and the entire stay was relaxing

A cozy seating area features a light-colored armchair beside a large window overlooking the serene waters of Quahog Bay. Natural light enters the space, highlighting the soft gray carpet and the nearby dining area with white chairs.

5 out of 5 average rating, 5 reviews

Cedar Cottage on Quahog Bay

MikeRating, 5 stars8 months ago

Absolutely beautiful setting over looking a bay full of lobster boats and sailboats. You can enjoy your morning coffee on the deck right outside your den, in some large Adirondack chairs under some trees, or out at the end of a long floating pier. Miles and miles of hiking trails are minutes away. We saw large flocks of turkeys every day within a couple of hundred yards of the cabin. We saw deer and seals on hikes. When you find something like this, there’s no reason to keep looking for something better. You’re not going to find it.

The exterior of a brick building is shown, featuring large glass windows that allow a view inside. The sign above the entrance displays the name 'Portland Pie Co.' in elegant lettering. Decorative lights hang inside, providing a welcoming impression.