Discover a selection of 322 vacation rentals in Harpswell that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including WiFi and air conditioning. Prices start at $115 per night, and cottages and houses are popular options for a stay in Harpswell. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Harpswell
Destination guide

Cool, coastal, collected—rugged and refined in Maine

Nestled amid a cluster of 5 peninsulas on Casco Bay, the quaint and quiet town of Harpswell offers everything you'd expect from a charming New England town. From Orr's Island's rugged, made-for-exploring coastline to a town center whose classic Americana vibe would put Norman Rockwell to shame, you'll be sure to fall in love with this laid-back island town. Consider Harpswell vacation rentals with a view of the bay or seashore access, and get ready to experience a seaside community unlike any other on the New England coast.

Things to do

Harpswell's art and history—a match made in heaven

Art lover? Then be sure to visit the Sebascodegan Artists Gallery, where you can explore work by a number of regional artists. Other highlights in town include The Elijah Kellogg Church and the nearby Harpswell Town Meeting House, both built in 1757. Afterwards, head to the Historical Society Museum to read all about their role in shaping the town. On nearby Eagle Island, you'd be well advised to take a tour of the summer home of Arctic explorer Admiral Robert E. Peary. From here, you can easily walk the four-mile trail around the island before heading back to Harpswell.


Soak in the unique beauty, both in and out of town

True to coastal Maine, Harpswell and rugged beauty go hand in hand. Rent a kayak or windjammer and make your way along the jagged coastline. Spend time on the local hiking trails, or plan a night under the stars and go camping near the beach. Consider Harpswell vacation rentals in summer, and don't miss the parade and fireworks during the annual Harpswell Festival. But if your trip doesn't fall around the festival, you can still spend your days soaking in the town scenery and enjoying the unique shopping, charming cafes, and farm-to-table dining.


Summers are sure to sparkle in maritime Maine

January through March is the coldest time on Orr's Island, with little to do except relax by the fire. If this sounds like your cup of tea—and trust us, you'll probably need a few—then consider wintertime Harpswell vacation rentals, when crowds are minimal and deals more plentiful. Alternatively, summers see a surge of visitors to the region, making June through August the busier, more expensive season. You'll be rewarded with the best weather of the year, however, and ideal conditions for exploring the great outdoors. Fall can be chilly and wet, but the region's world-famous leaf peeping is always worth the trip.

Natural features

Go forth! Find your inner explorer in Harpswell

Harpswell and Orr's Island offer a quiet coastal escape from the buzz in nearby Portland. With expansive views of forested islands and a famously jagged, craggy coastline, you'd be forgiven for spending time just basking in the region's scenery. Seagulls can be spotted everywhere, while seafood shanties offer up the local catch of the day—including Maine's not-to-be-missed lobster dishes (or "lobstah," as the locals say). Enjoy the tranquil harbor, hike along the tree lined trails, or hop on a boat and sail out to explore the other islands nearby.

How many vacation rentals are available around Harpswell?

Our 2021 property listings offer a large selection of 322 vacation rentals around Harpswell. From 112 cottage rentals to 298 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.