Photo by Carolyn Baker Reck

Harpswell vacation rentals

We found 486 vacation rentals — enter your dates for availability

your current months are May, 2024 and June, 2024.
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June 2024
Select from 83 homes, 45 cottages, and other vacation rentals in Harpswell to find one that's perfect for your trip. Vacation homes provide the best amenities for you and your friends, family, or even pets, such as parking and air conditioning. At the end of the day, you'll find a rental for everyone's needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

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.

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.

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.

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 to get to and around Harpswell

The nearest airport is in Portland Intl. Jetport Airport (PWM), located 20 mi (32.1 km) from the city center. If you can't find a flight that's convenient for your trip, you can also fly into Wiscasset, ME (ISS), which is 17.4 mi (28 km) away.

Frequently asked questions

What is the best area to stay in Harpswell when booking a vacation rental?

One of the more popular neighborhoods to get a Harpswell vacation home is Cundys Harbor. When you book your Vrbo vacation property, you will have the entire place to yourself. That means you don't have to share it with anyone except for your favorite people.

What is the most popular type of vacation rental accommodation in Harpswell?

The most desirable types of vacation rentals in Harpswell are houses. Ready for more choices? Vrbo has numerous options to match our guests' unique requirements, so you'll see vacation properties in lots of shapes and sizes. The ideal home away from home is waiting for you — get hold of yours today.

How much does it cost to rent a vacation rental in Harpswell?

The average price for a vacation home in Harpswell depends on a number of factors, such as property type, length of stay and time of year. Whether you're thinking about a sprawling villa with lots of bedrooms or a quaint cabin perfect for just you and the kids, just enter your dates of travel to discover stays with unbeatable value.

How much does it cost to rent a beach house in Harpswell?

The average price for a vacation rental close to the beach in Harpswell depends on when you're traveling and the type and size of property you're looking for. You can easily find prices on Vrbo by entering your destination and travel dates. Then use our handy filter tool to choose the number of bedrooms and amenities that you need, like WiFi, air conditioning and a pool.

Are there pet-friendly vacation rentals in Harpswell?

With 200 properties that host four-legged guests, your little buddy can also come along on your Harpswell vacation. Use the filter tool to search our pet-friendly vacation rentals and find a vacation home that'll set tails wagging on Vrbo.

Can I rent a house with a pool in Harpswell?

Add a whole new level of fun to your adventure by booking your crew into one of the eight houses with a private pool in Harpswell. Use our search filter to find the kind of property you want on Vrbo, and then spend your days splashing about in a swimming pool that's only for you.

What are popular rental amenities in Harpswell?

Some of the most popular rental amenities guests are looking for in Harpswell are a garden, an ocean view and nearby museums. Whether you're on the road with family, friends or even pets, Vrbo vacation properties feature the best amenities for starting a new adventure with your loved ones.

Are there large group vacation rentals in Harpswell?

With 37 properties that can sleep 10 people or more in Harpswell, you won't have to leave anyone off your guest list. From family get-togethers to events like birthday parties and weddings, Vrbo can help you find a large group rental to match the occasion.

Are there vacation rentals in Harpswell that welcome kids?

With 199 family-friendly vacation homes available in Harpswell, now is the perfect time to introduce the kiddos to the pleasures of travel. Simply click on our "Properties good for families" filter box to search for stays packed with amenities perfect for families on the move, such as dining rooms, patios, hot tubs and bunk beds.

What are the top attractions for families in Harpswell?

Keep the kids busy at these awesome family-friendly attractions in Harpswell:

  • Thomas Point Beach
  • Wolfes Neck Farm
  • Brunswick Naval Aviation Museum

Are there one-bedroom vacation rentals in Harpswell?

Yes, there are 36 one-bedroom properties in Harpswell to choose from. A one-bedroom vacation rental is an excellent choice if it's only the two of you or if you're flying solo. Throw in more privacy, convenience and space compared to a hotel, and you've got yourself an unforgettable break.

Can I find two-bedroom vacation rentals in Harpswell?

Take off with your loved ones and enjoy peace, privacy and comfort in one of the 43 two-bedroom vacation properties Harpswell has to offer.

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