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South Shore vacation rentals

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Top-rated vacation rentals in South Shore

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

  1. Entire cottage
  2. Nantucket
Oceanfront Vintage Cottage

Waterfront vintage guest cottage directly on the ocean. Perfect for a relaxing, romantic getaway. Enjoy the sunsets, surf, and stars. Listen to the sound of the waves as you fall asleep. Instagram @55Nobadeer

$336 per night
SUPERHOST
  1. Entire rental unit
  2. Nantucket
“Somer Sweet” is Moments Away to the Beach!

So close to the beach! 2nd floor apt with private entrance decorated with vacation in mind offering an open living, dining and kitchenette area with cathedral ceilings. Beautiful bedroom with a queen bed, bureau and closet. A hall bathroom with a new tiled shower and vanity with marble top. In the hallway is a laundry area with full size washer/dryer. 2nd floor private entrance is located over our two bay garage which is attached to our home. Super location just .2m to beach road!

$225 per night
SUPERHOST
  1. Entire home
  2. Nantucket
"Upon a Rock" Peace & Quiet - Mid island retreat!

Our guest suite is a separate wing on the main house. It is separated by a locked door. You have your own separate private entrance. You must come into the backyard of the main house. Look for the arbor with BAIRD written on top. These is an extra charge for any guests after the first 2 guests. $100 per guest per night. If you were bringing a car please let us know in advance so we can make parking arrangements

$326 per night

Vacation rentals for every style

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South Shore beach vacation rentals

  1. Entire guest suite
  2. Nantucket
ACK Getaway
$294 per night
SUPERHOST
  1. Private room
  2. Nantucket
Beautiful cottage with a private queen size room
$225 per night
  1. Private room
  2. Nantucket
Comfortable Room in our Family Home on Nantucket
$150 per night
SUPERHOST
  1. Private room
  2. Nantucket
In-Town Bedroom w/ Private Entrance
$307 per night
  1. Private room
  2. Nantucket
Get away to Nantucket! Close to Surfside beach!
$250 per night
  1. Private room
  2. Nantucket
'Tucked Away
$204 per night
SUPERHOST
  1. Entire cottage
  2. Nantucket
Charming 3BR Nantucket Cottage by Town/Beach
$550 per night
  1. Private room
  2. Nantucket
In town studio with private entrance
$300 per night
  1. Entire guest suite
  2. Nantucket
Cozy Island Retreat
$360 per night
  1. Entire home
  2. Nantucket
1930s Nantucket Cottage
$500 per night
SUPERHOST
  1. Entire home
  2. Nantucket
40 CLIFF ROAD GUEST COTTAGE
$357 per night
  1. Hotel room
  2. Nantucket
Cliffside Queen in Boutique Nantucket Motel
$588 per night

Your guide to South Shore

Welcome to South Shore

For a coastal New England vacation with a side of history, there’s no place like Massachusetts’ South Shore, where quaint towns dating back to before the Revolutionary War and beach-lined suburbs fill the space between Boston and Cape Cod. Settled by the Pilgrims more than 400 years ago, the area surrounding Route 3 brims with Colonial architecture, migrating whales (and the boats that watch for them), cranberry bogs, and picture-perfect stretches of rocky coastline where you can relax, breathe in the salty air, and gaze out over the water. Most of the South Shore towns boast convenient connections to Boston, invitingly cool Atlantic waters for escaping summer heat, and wind-wisped sand for shoreline strolls, but each has its own charms. The legendary and emblematic Plymouth Rock can be found in a state park in the town of Plymouth, Hull brings people in for its famous Nantasket Beach, and birders flock to Marshfield’s wildlife sanctuaries, Daniel Webster and North River.


When is the best time to stay in a vacation rental in South Shore?

Summer is peak season along the South Shore, when the coastal winds bring relief to the often stifling heat and humidity, and you can jump into the refreshing Atlantic for additional reprieve. But as summer fades, the mild temperatures of autumn and picturesque fall colors also make for a nice time to visit before the winters bring freezing temperatures and snow.

Summer also coincides with the South Shore’s festival season. With the region’s prominent place in America’s Colonial and Revolutionary history, there’s no shortage of big celebrations, especially around Independence Day, where it can seem like every town throws a party. There’s also Flag Day (June 14) in Quincy and Marshfield’s annual August fair, while later in the year, Plymouth honors its own role in history with Thanksgiving celebrations.


What are the top things to do in South Shore?

Cranberry Bogs

Watch as harvesters wade through layers of bright red baubles as they rake cranberries from flooded fields. Farms around the region are open to visitors looking to catch a glimpse of the unique and colorful way that the holiday staple makes its way to tables around the country. Pick up fresh berries in season ― mid-October through the end of the year ― or pop by for frozen or canned products anytime.

Whale Watching

Book a tour on a whale-watching boat from Plymouth during whale season, from late spring to early fall, and relish the chance to spot majestic humpback whales as they frolic just off the coast.

Nantasket Beach

Considered by many to be the South Shore’s best beach, this sandy stretch of shoreline in the town of Hull clocks in at just over a mile long. On hot weekends, it can seem like the entire Commonwealth of Boston is here. Families in particular love it for its historic carousel, playground, and evening concerts. When the tide is out, the beach turns into a hotspot for tidepooling.

  1. Airbnb
  2. United States
  3. Massachusetts
  4. Nantucket
  5. South Shore