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Vacation Rentals & Apartments in Rockport

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151 apartments

GLORIOUS OCEAN VIEWS FROM LOBLOLLY COVE - DECK - SEASIDE PATH TO BEACH AND TOWN

Rockport apartment

2 bedrooms / 1 bathroom / sleeps 3

Price per night from

$258

The Rockporter: Enjoy beautiful views of Pigeon Cove Harbor.

Rockport house

4 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$857

Back Beach

Rockport house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$492

The Little Red House with Prize Ocean View

Rockport house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$149

Granite Cottage: Charming cottage in Rockport with private deck and views

Rockport cottage

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$415

GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM

Rockport cottage

2 bedrooms / 1 bathroom / sleeps 2

Price per night from

$257

The Sail Loft of Bearskin Neck- Old Harbor Retreat

Rockport apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$235

18th Century Cottage with attached guest suite

Rockport cottage

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$220

Happy Days Cottage: Charming Folly Cove house with waterfront deck

Rockport cottage

4 bedrooms / 1 bathroom / sleeps 7

Price per night from

$492

Granite Pier: Blends traditional craftsmanship with modern amenities. Views!

Rockport house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$836

Captain's Cottage: Traditional setting with a private footbridge to the beach

Rockport house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$417

Quarry Crest House: Includes swimming rights to Little Parker quarry

Rockport house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$603

Quaint Seaside Village Ground floor Studio Steps From Beach WITH PARKING

Rockport b&b

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 55 minutes

Price per night from

$172

The Robert House: 4 bedroom Rockport village house, sleeps 7

Rockport house

4 bedrooms / 1 bathroom / sleeps 7

Price per night from

$545

LOVER'S COVE AT THE SEAWARD WITH OCEAN VIEWS & SEASIDE PATH TO BEACH &TOWN

Rockport apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$256

Sage Hill: Easy access to both Gloucester & Rockport

Rockport house

4 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$640

Straitsmouth Cove: Outstanding ocean views at Gap Head Cove in Rockport.

Rockport house

5 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$1,178

Responds fast! avg. 55 minutes

Price per night from

$144

Periwinkle Cottage #1 - OPEN ALL YEAR, walk to everything, parking, wifi, quiet

Rockport cottage

1 bedroom / 1 bathroom / sleeps 2

“An Oasis By The Sea” August 30, 2012 Dear Rose & Guy- Thank you very, very much for our wonderful stay at Periwinkle Cottage! From the beautifully decorated rooms, the most comfortable beds, soft luxurious towels and linens, convenient kitchen, TV to the lovely outdoor sitting area and garden... Omg...what a gem! It is a true delight! And the cottage is immaculate and very peaceful and tranquil. We will definitely recommend your "oasis by the sea" to our family and friends! Love, Penny and Urs Westport, Connecticut

Travelers’ Choice award

Price per night from

$161

Beach & King Street Inn / Beach House Rental

Rockport house

6 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$1,045

Can't wait to return to Four Winds in Rockport, MA

Rockport condo

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$375

Gap Cove at The Seaward

Rockport apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$338

Mill Brook Cottage: Enjoy New England charm in Rockport. Walk to the beach!

Rockport house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$643

Classic Victorian home with views of the ocean and twin light houses.

Rockport house

7 bedrooms / 2 bathrooms / sleeps 14

Price per night from

$1,379

Beach Bungalow: The perfect getaway to two of Rockport's finest beaches!

Rockport cottage

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$433

OCEAN VIEW COTTAGE AT THE SEAWARD - EASY SEASIDE PATH TO OLD GARDEN BEACH

Rockport cottage

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$282

Sunrise on the Cove: Unobstructed 180 degree views of Pigeon Cove

Rockport house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$1,079

Sea You on Marmion: A gracious Victorian vacation home, steps from the beach.

Rockport house

4 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$827

Ocean Front Cottage on Scenic Long Beach

Rockport cottage

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$516

New! Sea Star: Spacious private oasis, Private Fast WiFi, 2min walk to shops, ea

Rockport house

5 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$511

Beautiful oceanfront home with sweeping water views and private beach.

Rockport house

6 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$2,057

The Lady Bug House

Rockport house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$536

A sunny and charming 2-bedroom beach retreat close to Rockport's Front Beach.

Rockport house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$483

Landmark Lookout: Lovely views of Sandy Bay and the Atlantic Ocean

Rockport house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$643

Bearskin Nest: Contemporary living in the heart of coastal charm.

Rockport apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$368

Steps to Long Beach

Rockport house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$524

Pleasant House: Old-world charm w/ modern updates in the heart of the village

Rockport house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$755

Mill Lane: Enjoy all of Rockport's charms, right outside your door.

Rockport apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$503

Viewing 38 of 151
rentals in Rockport

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About Rockport

Head to Rockport this year to discover a quirky beach-town located in Massachusetts. Surrounded by naturally beautiful scenery and plenty of activity to keep you entertained, you'll never want to leave this charming resort. Book your Rockport rental with FlipKey today for a great vacation.

About Rockport

Located an hour from Boston, Rockport is characterized by several beaches which include Long Beach, Cape Hedge Beach, Pebble Beach, and Front and Back Beach. Heading into the downtown area, you'll find a variety of art galleries, shops and restaurants.

Bearskin Neck is a popular resort in Rockport, with some houses here over 300 years old. The area is completely unspoiled and hasn't been altered in any way by major re-developments. You'll find a culture centered around art with a real eccentric vibe. You may even find local fisherman hoping for their daily catch as well as artists painting their surroundings.

The red fishing shack within downtown Rockport is considered to be the “most painted building” in the world. This would be a great way to relax if you consider yourself crafty and wish to try your hand at painting.

What to do

Some of the most popular outdoor activities within Rockport include kayaking, diving or hiking. For a more chilled-out option, you may decide to take a cruise and watch the sun go down, or go out on a boat for a whale watching experience. The range of beaches mean you can take a slow-paced walk and enjoy the scenery.

Main Street is Rockport's shopping district and has a wide range of unique shops which sell the likes of clothing, gifts, crafts and household items.

Rockport is home to over 30 art galleries as well as the Rockport Art Association. Here you can learn about the history of the area as well as pieces from the modern day and the past. There are also festivals held throughout the months of May-December each year.

If you’re a movie fan, you may wish to take a trip to Bearskin Neck where some scenes of Sandra Bullock and Ryan Reynolds’ 'The Proposal' were filmed.

Top travel tips

You can catch public transport easily within Rockport to get to local attractions. Buses are provided by Cape Ann Transportation Authority which is a mere $1 per person each way. There are also 13 daily commuter trains which depart from Rockport to Boston from the Newbury/Rockport line.

Despite this, the main tourist attracts are all within walking distance of each other and are located over a small area, however you may even decide to hire a car to reach the more rural and coastal areas. Public transport is more accessible in the downtown area which is something to keep in mind if you plan on exploring further.

If you're looking for more than your everyday beach resort, Rockport will certainly impress. With its spectacular coastal views and arty culture, you'll certainly wish to re-visit again and again. Book your property rental with FlipKey today to discover our wide range of options via our website.

Top Destination reviews

Ocean Front Cottage on Scenic Long Beach
Don't want to share this beautiful place.

Last house on the boardwalk before pebble beach. ....get to chat with all the walkers! Besides an awesome location, the house itself is very well appointed....hairdryer, plenty of lobster pots and pans, washer & dryer, easy to clean tiled floors downstairs and beautiful wood upstairs, mesmerizing views from all directions, sun deck, shade deck. No need for the big TV because you'll probably be spending your time watching the ever-changing tidal river. Beautiful!see more
Periwinkle Cottage #1 - OPEN ALL YEAR, walk to everything, parking, wifi, quiet
It was very peaceful and welcoming.

Forgot your toothbrush? Don't worry, there's one there. Forgot your shaving cream? Again, not to worry. Rosemarie provided all that was needed and more. We prefer to cook our own breakfast and found that all the necessary gadgets were available. The cottage is located off the main road in a very quiet and safe neighborhood. The decor is tasteful, and the bed was very comfortable. We would not recommend this cottage to those with young children, as the steps to upstairs are narrow and winding - close to what we would call a "Jersey Winder." The cottage was perfect for the two of us and although it is advertised as sleeping up to four, it would most likely feel somewhat crowded. This, however, would not stop us from renting again and bringing along another couple! This was a lovely and relaxing place to stay.see more

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