Rockport Vacation Rentals

Compare 15 vacation rentals.
USA > Massachusetts > Rockport

Make Rockport your next getaway

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 Hot tub Internet
Oceanfront Cottage - Long Beach
5 Bedroom | 2 Bath | Sleeps 10

Oceanfront Cottage - Long Beach - Rockport, MA

$265 avg / night
Vintage Rockport Escape
3 Bedroom | 2 Bath | Sleeps 6

Vintage Rockport Escape - Rockport, MA

$248 avg / night
Andrews Point Ocean Home
5 Bedroom | 3.5 Bath | Sleeps 10

Andrews Point Ocean Home - Rockport, MA

$535 avg / night
High Street Hideaway
4 Bedroom | 3 Bath | Sleeps 8

High Street Hideaway - Rockport, MA

$266 avg / night
Olde New House
1 Bedroom | 1 Bath | Sleeps 3

Olde New House - Rockport, MA

$165 avg / night

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Recent Rockport vacation rental reviews

House was great. Beds were very comfortable. Very interesting library and little surprises around every corner. Quiet, yet walkable to downtown
David P. | Apr 2024
House was large with comfortable seating. Dining room held all 10 of us comfortably. Sun room was beautiful with incredible views of sunrises. Beds were comfortable, bathrooms were clean. Kitchen was fully stocked with everything to cook with including a blender. 2 There were two refridgerators, one made ice. House is older, needs some attention to spackle and wallpaper. Nice and cozy warm even in March. Large back yard. Rock beach which was pretty cool for the kids to climb around on. Quiet neighborhood. Would revisit at another time.
Anita J. | Apr 2024
This house has a spiritual feeling, beautiful relaxing state of mind when you stay there. The crashing waves onto the backyard rocks are priceless the serenity and the beauty of the sorrounding is a dream come true. I highly reccomand this place for the one who love a unique, quite and romantic vacation.
Cristina V. | Mar 2024
Rockport vacation rental FAQ

Yes, 7 of our Rockport 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).

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Yes. 30 of our Rockport vacation rentals have internet access, so you can stay connected throughout your trip.

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Some of the most popular amenities in our Rockport 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 Rockport 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 Rockport, 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

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.