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. 

Explore Rockport house rentals, cottages, apartments, and more


House rentals

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Rockport vacation rentals for every getaway

Dog-friendly Hot tub Internet
Olde New House 3D Tour
1 Bedroom | 1 Bath | Sleeps 3

Olde New House - Rockport, MA

From $75
Starfish Cottage 3D Tour
2 Bedroom | 1.5 Bath | Sleeps 4

Starfish Cottage - Rockport, MA

From $153
Vintage Rockport Escape 3D Tour
3 Bedroom | 2 Bath | Sleeps 6

Vintage Rockport Escape - Rockport, MA

From $153
Rustic Rockport Cottage 3D Tour
2 Bedroom | 1 Bath | Sleeps 3

Rustic Rockport Cottage - Rockport, MA

From $118
High Street Hideaway 3D Tour
4 Bedroom | 3 Bath | Sleeps 8

High Street Hideaway - Rockport, MA

From $244

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Recent Rockport vacation rental reviews

This is my second time staying here. The first time was last year with a group of friends and I fell in love with the area. This past weekend I came up again but this time with my family. It fit us all perfectly. The home is beautifully done and clean. We visited Gloucester and Rockport and went to Hammond Castle. We never had a bad meal. Would definitely come back.
Lisa V. | May 2022
Judith K. | May 2022
A lovely cottage tucked at the corner of a quiet street. Beautifully decorated, calling to mind the expatriot days of Paris. Well stocked, and entertainment options abound. Tha only reason it isn't a 5 star rating is the untended landscaping! Beautiful perennial plantings are overgrown, and bits of discarded odds and ends along the sides and rear of the home need to be addressed. As a master gardener, this truly special place is a bit of a diamond in the rough. With a minimal effort it could be a treasure. Otherwise, Check-in was easy, and the interior was lovely.
Karen G. | Apr 2022

Book confidently. Stay comfortably.

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