Discover a selection of 334 vacation rentals in Rockport, MA 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 swimming pools and air conditioning. Prices start at $129 per night, and houses and cottages are popular options for a stay in Rockport. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Rockport
Destination guide

Art, wildlife, and beautiful scenery in Rockport

The creative seaside community of Rockport welcomes you for your quiet family-friendly getaway. Protected from harsh sea weather by its bay, and known for its rich artistic history, Rockport has become a destination for water enthusiasts and art lovers alike. A Rockport vacation rental near the water allows you to paddle out to the old lighthouses or get some good shots for your album. Stay active out of the water on various hikes and tours, or shop and dine in style in a setting fit for the movies. It’s Massachusetts, so don’t miss out on getting your fill of fresh lobster.

Things to do

Rockport’s world-class art and cultural experience

Home to the oldest art colony in the country, Rockport’s charm is in its artistic culture. The Shalin Liu Performance Arts Center hosts world-class shows all year, and a multitude of galleries highlight local artists. Meet up at Dock Square for a free family-friendly walking tour of the downtown art district. Learn the history and see notable architecture such as Motif No. 1, an old boating house once used by the fisheries. Known as the most painted building in America, you must get a picture in front of it, or no one will believe you were here.


Pristine waters ideal for diving and sailing in Rockport

A Rockport vacation rental near Loblolly Cove is the perfect place to dock between family-friendly water-bound adventures. Go diving and swim among marine life. Tour the bay on a seal-watching cruise or sign up to learn how lobsters are caught and processed. Then, eat at one of many excellent seaside restaurants. The tranquil water is perfect for sailing and kayaking. Later, take a stroll down Main Street where you will find unique boutiques and art galleries for your shopping pleasures. You can’t leave this picturesque town without an authentic souvenir.


Seasonal weather in Rockport

If you're hoping to enjoy some warm-weather activities on your vacation, July, August, June and September are the hottest months to visit, when temperatures average 65°F.

Natural features

Rockport: guided hikes, breathtaking views, and seals!

An intimate Rockport vacation rental lets you experience this small and quiet seaside town. Get away from the demands of city life by spending a family-friendly day on a guided tour of the natural space. Marvel at breathtaking views as you explore Halibut Point State Park, or join a tour of the quarry during the summer. Guided tours through the Rockport woods lead you to the ghost town Dogtown and by the Babson Word Rocks from the Great Depression. Back at the water, there are birds, seals and other marine life to appreciate.

How to get there

Transportation options to and around Rockport

Fly into Logan International Airport (BOS), the closest airport, located 28.5 mi (45.9 km) from the city center. If you can't find a flight that's convenient for your trip, you might consider flying into Boston, MA (BNH-Boston Harbor Seaplane Base), which is 29.1 mi (46.8 km) away.

If you prefer train travel, the main station serving the city is Rockport Station.

What are the top vacation rentals in or near Rockport?

Whatever you're seeking in a vacation, you'll find a rental in or around Rockport that's a perfect match. Here are some of our faves:

  • Around 30 miles from the center of Rockport, it's hard to beat "Near Boston Historic Two - Bedroom With Modern Amenities". It has 2 bedrooms and handy features including games and an oven.
  • Alternatively, make yourself comfortable at "Historic Home At Freedom Trail". Around 30 miles from the heart of Rockport, it has 1 bedroom and comes with a hair dryer and a separate dining area.

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

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

Clock out on Friday and then forget all about the office. If it's time for some relaxation and fun, these rentals in and near Rockport promise the perfect weekend getaway:

  • Located 0.1 miles to the southwest of the center of Rockport, "Periwinkle Cottage #1 - Open All Year" is a hit with nature fans and adventure lovers. Keep busy by exploring nearby attractions, such as Stoney Point and Short Beach. If you still have time, try some water skiing or basketball.
  • Alternatively, enjoy a short and sweet break at "Goosebump Views On The Beach Giant Decks Seen On Hgtv Xtra Clean Chefs Kitchen". Stay in and relax, or head out and try your hand at some skiing and sailing. When you're ready to explore more of the area, visit Singing Beach and Apple Hill Golf Course. This attractive vacation rental is around 17 miles northwest of Rockport.

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

Studio apartments are a hard act to beat when it comes to character, convenience and location. Take a look at these studio apartments for rent in or near Rockport and get a taste of the vibrant local culture:

  • Wake up, explore and then do it all over again at "Historic Home At Freedom Trail". This vacation rental is a great base for discovering the sights and features amenities including heating and cable/satellite TV services.
  • "Periwinkle Cottage #1 - Open All Year" is another great option. Settle in and enjoy the use of internet services, a garden and more.

There are plenty of sights around Rockport to put on your to-do list. Nourish the culture vulture within and visit House of Blues Boston and The Alchemist.

Can I find short term rentals in or near Rockport?

Just because you only have a few days off work doesn't mean you have to spend it in a lifeless hotel room. Take off on vacation but still have the comforts of home at one of these short-term rentals in or around Rockport:

  • Close to the heart of Rockport, "Best Patio On Commercial" Steps To Everything Exclusive Tropical Gated Gardens" is a terrific base for a short and sweet break. While you're about, check out leading attractions like Walden Pond and Louisa May Alcott's Orchard House.
  • Eat, sleep and discover your surroundings from "4 Bedroom Lux House/with Pool Next Door", another enticing option. Old Manse and Concord Visitors Center should be on your itinerary when you're ready to sightsee.

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

Forget roses and chocolates. Sometimes all you need is to take off for a weekend, just you and your sweetheart. At Vrbo, we've got romantic getaways in and around Rockport that would make Cupid envious. Here are some to tempt you:

  • Put on some soft tunes and slow dance the nights away at "Near Boston Historic Two - Bedroom With Modern Amenities". Around 30 miles from Rockport, this property has all you need for a romantic weekend away, including a balcony and air conditioning.
  • "Historic Home At Freedom Trail" is another top option that's bound to impress. It's around 30 miles from Rockport and comes with beauty services and a restaurant dining guide.

Are there mansions for rent in or near Rockport?

If you're searching for somewhere to reconnect with the family this vacation, you're going to need somewhere spacious. These mansions for rent in or around Rockport will fit your entire crew while doing it in style:

  • Character, charm and style — "Historic Oceanfront Mansion" has it all. Around 17 miles northwest of Rockport and offering golf and a fireplace, this lovely place is hard to beat.
  • With a fireplace, golf and a host of other top-notch amenities, "Historic Brick Federal Period Mansion On Fabled Chestnut Street" will get your guests' tick of approval. This sleek retreat is roughly 17 miles to the southwest of Rockport.

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

Big groups mean big fun. They also mean finding a place that'll comfortably fit your entire gang. Check out our large group vacation rentals in or around Rockport and get your loved ones together under the one roof:

  • Providing space, comfort and privacy, you'll get your guests' stamp of approval at "Walk To Downtown Rockport, Front Beach And Old Garden Beach". Up to 12 people can be accommodated at this escape which has 5 bedrooms, a fireplace and a kitchen. This top pick is around 1 mile to the southeast of Rockport.
  • Invite up to 12 of your best friends to "Spectacular, Luxury Waterfront Property Directly Overlooking Sandy Bay" and fill the place with love and laughter. This popular option has 5 bedrooms and is around 1 mile to the east of central Rockport. It's packed with features to keep a large group occupied, including a fireplace and a garden.

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

Nothing says fun like a pool. Dig out your unicorn floatie and check out these rental houses in or near Rockport that feature this added bonus:

  • Say hello to "4 Bedroom Lux House/with Pool Next Door", where your main priority will be chilling by the pool. Amenities such as a swimming pool and coffee and tea making facilities help make this escape a guest favorite.
  • "Good Harbor Beach House" is the sort of place you go to escape from it all and enjoy your surroundings, starting with its inviting pool. Cable/satellite TV services and nearby birdwatching activities are also on hand to make your stay a memorable one.

Unsure how to pack your bags for your Rockport getaway? This leading destination has a humid continental climate. In the summer months, expect average temperatures ranging from 65 ºF to 70 ºF. Check out our selection of Rockport vacation rentals by using the search bar at the top of the page. Simply adjust the filters to get more ideas about where to stay.

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

No matter if your idea of the perfect escape is up in the hills or near the beach, you'll enjoy it even more if you share it with family and friends. Check out these large family vacation rentals in or near Rockport and bring the entire crew along:

  • Sleeping as many as 8 guests in 3 bedrooms, "Goosebump Views On The Beach Giant Decks Seen On Hgtv Xtra Clean Chefs Kitchen" is the ideal place to spend time together. This retreat is 17 miles to the northwest of Rockport and has creature comforts that include free toiletries and a stereo.
  • "Good Harbor Beach House" is also a top pick for families. It's about 2 miles to the south of Rockport, has 4 bedrooms and accommodates up to 8 people. Handy amenities here include a fridge and a separate dining area.

If you're chasing family-friendly attractions in the area, you're spoiled for choice. New England Aquarium, Newbury Street and CoCo Key Water Resort - Boston promise lots of fun for all the crew.

What are the best large houses to rent with indoor pools in or near Rockport?

Take a dip anytime you like at one of our large rental houses with an indoor pool. Grab your swimsuit and consider these homes in or near Rockport that feature this brag-worthy perk:

  • Settle into "Beach, Pool, Housekeeping And More Inquire First For Best Rate" and spend your days kicking back poolside. This sprawling pad has 4 bedrooms sleeping up to 14 guests and a host of other excellent amenities. A water view and a swimming pool are among them.
  • Besides its impressive indoor pool, "Beach, Pool, Housekeeping And More Inquire First For Best Rate" comes with an ocean view and a swimming pool. It has 4 bedrooms that can cater for up to 14 guests, so you can bring your entire crew along.

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