Discover a selection of 400 vacation rentals in Harpswell, ME 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 $145 per night, and houses and cottages 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.


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 to get there

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.

What are the top vacation rentals in or near Harpswell?

The heart wants what it wants, and right now it wants to take a vacation. It's time to pack your bags and head for one of these top vacation rentals in or near Harpswell:

  • "Henry” Penthouse Suite: Amazing Views" is a hit with guests. Around 18 miles from Harpswell, it has 2 bedrooms and lots of handy amenities, including a TV and a nearby laundromat.
  • "Chic One Bedroom Apartment In Portland's Arts District" is another top-notch choice, offering 1 bedroom, towels, off-street parking options and more. It's around 19 miles from Harpswell.

For even more great options, use the search bar at the top of the page to find the perfect Harpswell vacation rental for you.

Can I find log cabins to rent in or near Harpswell?

Whether you want to spend your getaway chasing adventure outdoors or relaxing with your nearest and dearest, Vrbo has gorgeous log cabins where you can do both. Pack your suitcase and check out these retreats in and around Harpswell:

  • "Cozy Log Cabin - Walking Distance To Morse Mountain And 3 Miles From Popham Beach": This is an ideal base to enjoy the fantastic outdoor activities in and around the region, including surfing and boogie boarding and mountain biking.
  • "Year Round Log Cabin Built In 1989 On Long Lake - 2": Spend your vacation enjoying all the creature comforts at this escape. When it's time for some fresh air, kayaking and fishing are waiting for you.

What are the top-rated vacation rentals for weekend getaways in or near Harpswell?

We all deserve an escape from daily life every now and again. If you're longing for a couple of mornings lingering in your PJs hugging a coffee, there's no shortage of amazing weekend getaways in and around Harpswell. Check out two of our favorites:

  • "Maine Oceanfront Home" is around 3 miles south of Harpswell and the perfect place to recharge your batteries. You'll appreciate the convenient amenities here, including coffee and tea making facilities and a washing machine.
  • Alternatively, live it up with loved ones at "Percival” Penthouse Suite: Breathtaking Views", which is around 18 miles to the southwest of Harpswell. You'll have use of golf, nearby museums and more here.

Can I find studio apartments for rent in and around Harpswell?

You sure can. If you want a simple but stylish stay, you can't beat a studio apartment. These compact properties exude charm and are often conveniently placed in the heart of town. We suggest the following options in or near Harpswell:

  • After a big day of outdoor exploration, enjoy total comfort and privacy at "Chic One Bedroom Apartment In Portland's Arts District". Towels and a microwave oven are among the amenities on offer here.
  • "Historic Condo With Casco Bay Views" is another terrific choice, offering all you could want for a heavenly Harpswell getaway. Handy amenities here include a stovetop and heating.

Can I find short term rentals in or near Harpswell?

Whether you're after a compact apartment or a house with room enough for the whole family, you'll find the ideal place on Vrbo. Sneak in a mini break at one of these retreats in or near Harpswell:

  • Close to the center of Harpswell, "Percival” Penthouse Suite: Breathtaking Views" rolls out the welcome mat for short-term guests. When you're not chilling out in your comfortable digs, get out and explore the area's best sights.
  • Alternatively, spend a couple of relaxing nights at "Margaret” Penthouse Suite: Amazing Views Of Casco Bay". This centrally located property makes it easy to explore the area's sights.

What are the best romantic weekend getaways in or near Harpswell?

Whether spent in a log cabin or a beach house, a romantic weekend getaway is one of the best ways to say "I love you." Whisk your partner off for a few days at one of these appealing escapes in or near Harpswell:

  • Sneak off on Friday for a couple of nights of passion at "Henry” Penthouse Suite: Amazing Views". Located around 18 miles from Harpswell, this place comes with lots of nice touches, including winery tours and a nearby bay.
  • Another option where you can spend a few idyllic days together is "Chic One Bedroom Apartment In Portland's Arts District". Around 19 miles from Harpswell, a nearby bay and winery tours add to the ambiance here.

What are the best large group vacation rentals in or near Harpswell?

Big groups mean a whole lot of fun. They also mean finding someplace that'll comfortably fit your whole gang. Browse our large group vacation rentals in or around Harpswell and get your loved ones together under one roof:

  • A wide array of amenities including a garden and a fireplace make "New Well Built Elegant Home On The Water 2 Miles To Freeport" a favorite. This sizable retreat has 6 bedrooms and accommodates up to 12 people. From the center of Harpswell, it's around 8 miles away to the west.
  • Invite up to 16 of your dearest friends to "700' Oceanfront Retreat, 8 Kayaks" and fill its spaces with laughter and love. This popular option has 6 bedrooms and is around 2 miles to the southeast of central Harpswell. It's packed with features to keep a large group comfortable, such as a kitchen and a firepit.

What are the best houses for rent with a pool in or near Harpswell?

A pool is often a must-have feature of any good vacation. Enjoy hours of entertainment frolicking around or simply unwinding by the water at one of these refreshing escapes in or near Harpswell:

  • Pack your swimsuit and enjoy a fun stay at "Combo Unit, New House And Updated Cottage On Same Property". Other amenities here include a barbecue grill and a toaster.
  • "Beautiful House On The Harpswell Peninsula Over Looking Casco Bay" is another top-rated option. After you've enjoyed a relaxing dip with the fam, make use of cable/satellite TV services and coffee and tea making facilities.

What are the best large family vacation rentals in or near Harpswell?

Every family get-together should be one to remember. Whether you're organizing an action-packed escape with the kids or a long-overdue family reunion, our large family vacation rentals in or near Harpswell offer a home away from home with plenty of space for everyone:

  • Sleeping as many as 11 guests in 4 bedrooms, "Maine Oceanfront Home" is the perfect place to hang out with the family. This escape is 3 miles to the south of Harpswell and has amenities such as towels and nearby whale-watching activities.
  • "New Well Built Elegant Home On The Water 2 Miles To Freeport" is also a top pick for families. It's about 8 miles to the west of Harpswell, has 6 bedrooms and accommodates up to 12 people. Useful amenities here include a kitchen and a smart TV.

If you're looking for family-friendly attractions around the area, you won't have to look far. Children's Museum of Maine, Portland Observatory and Fort Williams Park promise lots of fun for both kids and grown-ups.

Can I find family cabin rentals in or near Harpswell?

Take a break with the kids in a family cabin rental in or near Harpswell and get set to make some wonderful new memories together. Here are a couple we think you'll love:

  • "Secluded Casco Bay Waterfront Cabin" - Enjoy good times with your nearest and dearest at this retreat, which is around 4 miles southwest of the center of Harpswell. Pet-friendly facilities and cable/satellite TV services are some of its family-friendly amenities.
  • "Renovated, Family Friendly Home With Ocean And Golf Views" - Another terrific choice, this cabin comes with books, a toaster and more. You'll find it around 5 miles to the southeast of Harpswell.

For more options, use the search bar at the top of the page and adjust the filters to find the Harpswell vacation rental that's perfect for your needs.