Rockport Vacation Rentals

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USA > Massachusetts > Rockport

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

For a classic New England destination, it doesn't get any better than the small town of Rockport, MA. Located just 40 miles northeast of the metropolis of Boston, this small seafaring town looks out to the Atlantic Ocean from the Cape Ann peninsula. 

When you stay at one of our vacation rentals in Rockport, you'll have the comfort of home with the beauty of this seaside town all at your fingertips. Gloucester is only 4 miles away, and the popular summertime destination, Plum Island, is about 30 miles away. From local art galleries and museums to nearby historic sights, there's plenty to do and see in and around Rockport. 

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House rentals

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Rockport vacation rentals for every getaway

Dog-friendly Internet Ocean view
Starfish Cottage 3D Tour
2 Bedroom | 1.5 Bath | Sleeps 4

Starfish Cottage - Rockport, MA

From $110
Olde New House 3D Tour
1 Bedroom | 1 Bath | Sleeps 3

Olde New House - Rockport, MA

From $72
Andrews Point Ocean Home 3D Tour
5 Bedroom | 3.5 Bath | Sleeps 10

Andrews Point Ocean Home - Rockport, MA

From $165
High Street Hideaway 3D Tour
4 Bedroom | 3 Bath | Sleeps 8

High Street Hideaway - Rockport, MA

From $227
Sunset Cottage 3D Tour
4 Bedroom | 2 Bath | Sleeps 8

Sunset Cottage - Rockport, MA

From $154

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Recent Rockport vacation rental reviews

Our family had a great weekend in Rockport at this funky cottage that was easy walking distance to town. We are a family that can appreciate antiques and charm, so we really liked the style and quirks. But could see how someone wanting more updated decor wouldn’t enjoy it as much. A little dusty in corners, but overall a positive experience!
Alexandra K. | Nov 2021
We enjoyed the stay with our kids (6 and 3). We were a few minute drive to the shops and beaches. We spend some time in Salem, MA as well as it was only 30 minutes away. It was October so we did not walk around to the beaches too much, but they are accessible by walking on a sidewalk to the location, roughly 5 min walk. We look forward to staying again!
Justin B. | Oct 2021
We found this place 2 days before a wedding weekend and we were incredibly pleased with the location, the cleanliness of the place and the amenities! Cute little house!
Justine D. | Oct 2021

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
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Professional cleaning

Culture in Rockport, MA

The quaint coastal village of Rockport was originally settled in 1623. It was once used as the primary source of timber for shipbuilding, and the area around Cape Ann was known for being one of the best fishing grounds in New England. Today, Rockport is also well-known among art history students and painting aficionados; a former fishing shack located on Bradley Wharf, called Motif Number 1, is known as the most frequently painted building in America. 

With more than four miles of lovely beaches, scenic paths through the woods and glades, and beautiful coastal light that has inspired many famous painters, it's no surprise Rockport has become a popular destination. 

Things to do in Rockport, MA

Today, Rockport is a small seaside town with an active fishing scene, scenic New England homes, and quaint shops and restaurants. From clothing to delicious local fudge, there's plenty to explore and discover.

For a fun stroll through town, check out the Bearskin Neck area, which offers an array of local shops, restaurants, and amenities on the bay. Nearby Halibut Point State Park features great hiking trails along the glades and coastline, plus Front Beach is the perfect place to walk along the coast. The Twin Lights on Thatcher's Island is also a fun spot - you can view the lighthouses from across the water, or take a small boat out to the island for a closer look. 

Day trips near Rockport, MA

No matter where you are in Rockport, you're never more than a few minutes drive to Gloucester, which is just four miles away. This larger seaside town features more classic Massachusetts attractions, like the working fish pier and harbor. With a mix of quaint beach cottages, colonial-inspired town buildings, and oceanfront estates, there's plenty of classic architecture to admire. 

Head up north to the town of Salem, MA and learn more about colonial American history, including the infamous Salem Witch Trails. For great antiquing, venture inland a bit to Essex, MA. Whether you're looking for big city conveniences in downtown Boston or scenic hiking in New Hampshire, our Rockport vacation rentals put you in the heart of New England. 

Book your stay today at one of our charming vacation rentals in Rockport, MA, and experience all this historic seaside town has to offer.