Harpswell Vacation Rentals

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USA > Maine > Harpswell

Make Harpswell your next getaway—choose from 8 great vacation rentals

To explore the northeastern reaches of Casco Bay is to discover a narrow scenic peninsula, a collection of more than 200 tranquil islands, and nearly 216 miles of shoreline that comprise the coastal community of Harpswell. As the American author Harriet Beecher Stowe once wrote, this town of just under 5,000 residents is "of more varied and singular beauty than can ordinarily be found on the shores of any land." It's a place full of history, natural beauty, and open seascapes, and you'll feel its wonder all around you at our Harpswell vacation homes. 

Explore Harpswell house rentals, condo rentals, cabins, and more


House rentals

View 4 House rentals

Condo rentals

View 2 Condo rentals


View 1 Cabins

Harpswell vacation rentals for every getaway

Dog-friendly Internet Ocean view
The Sou'Wester on Orr's Island, Unit 4, Alongside  The Chestnut Tree
1 Bedroom | 1 Bath | Sleeps 2

The Sou'Wester on Orr's Island, Unit 4, Alongside The Chestnut Tree - Harpswell, ME

$161 avg / night
Casco Breeze
2 Bedroom | 2 Bath | Sleeps 6 (4 Adults Max)

Casco Breeze - Harpswell, ME

$292 avg / night
Harpswell Bay House
3 Bedroom | 1 Bath | Sleeps 6

Harpswell Bay House - Harpswell, ME

$245 avg / night
Harpswell Retreat
2 Bedroom | 2 Bath | Sleeps 4

Harpswell Retreat - Harpswell, ME

$308 avg / night
Casa Familia
3 Bedroom | 2 Bath | Sleeps 10 (8 Adults Max)

Casa Familia - Harpswell, ME

$320 avg / night

View 3 more homes

Recent Harpswell vacation rental reviews

This place was cozy and authentic - someone has loved this cottage for a long time. Charmed us.
Christopher M. | Dec 2022
We loved staying at the house - to wake up to the view of the harbor was fabulous! The house is lovely with nice space to gather for breakfast or watch a movie. Loved the ease of turning on the fireplace. The master bathroom is gorgeous!
Karen M. | Oct 2022
Lovely, well appointed with beautiful grounds. Could have stayed all Winter. Definitely off the beaten path. Thank you for sharing your property with us.
Lechell C. | Oct 2022
Harpswell vacation rental FAQ

Yes, 8 of our Harpswell homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 21 of our Harpswell vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >

Some of the most popular amenities in our Harpswell vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Harpswell team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Harpswell, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

Where is Harpswell, ME?

With borders that encompass the peninsula of Harpswell Neck, Sebascodegan Island (known locally as Great Island), Orr's Island, Bailey Island, and 200 smaller islands accessible only by boat, Harpswell sits in Casco Bay just 40 miles east of historic downtown Portland. The peninsula and its three main islands (which are connected by bridges) are only 13 miles south of Bowdoin College in Brunswick, 17 miles south of Bath, and 20 miles southeast of the famous outlets in Freeport. 

Things to Do in Harpswell, ME

For more than a century, Harpswell has welcomed visitors in search of ocean views, working harbors, public trails and marinas, and quiet natural splendor. Set sail on your own craft from one of the town's 11 public landings, marinas, and boat launches, or book a charter excursion with ALERT Windjammer Cruises, H2Outfitters, or Sail Casco to see the gorgeous coastline from the water.

Thanks to the town's cooperation with the Harpswell Heritage Land Trust, our Harpswell vacation rentals enjoy direct access to beautiful walking trails, serene nature preserves, and pristine beaches. Take a walk along the 2.3-mile Cliff Trail to soak in views that overlook Long Reach, or stroll the easy half-mile Giant's Stairs Trail to admire spectacular vistas of eastern Casco Bay. Johnson Field at Mackerel Cove is also a beloved local landmark for its picturesque Bailey Island harbor, its lovely beach, and its ideal setting for picnicking and kayaking.

View the islands through the eyes of local painters at the Sebascodegan Artists Gallery, or catch a summer evening concert with a crowd of locals at Mitchell Field's Bandstand by the Sea.

Day Trips from Harpswell, ME

While Harpswell is known for its peace and quiet, the beauty of this bayfront community is its close proximity to Maine's largest city, one of its most respected colleges, and a bastion of the state's shipbuilding history.

Take a short and scenic drive to reach the old port of Portland, a thriving and artistic city that boasts some of New England's most charming streets and exciting cuisine. Grab morning pastries at Standard Baking Co., savor a lunchtime lobster roll at Fishermen's Grill, and taste the divine local bounty at Eventide Oyster Co.

Guarding the northern reaches of Harpswell Neck is the shopping mecca of Freeport (the flagship location of the iconic outfitter L.L. Bean), while nearby Brunswick has gained fame as the home of Bowdoin College. You'll also be just 18 miles from the Maine Maritime Museum in the historic town of Bath on the Kennebec River. 

The countless wonders of Midcoast Maine await - plan an escape to our Harpswell vacation homes for an experience you'll never forget.