South Shore vacation rentals

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Popular amenities for South Shore vacation rentals

Other great vacation rentals in South Shore

Guest favorite

Apartment in Nantucket

4.94 out of 5 average rating, 48 reviews

Trotacre Kin - A Relaxing Cisco Sanctuary

May 29 – Jun 5

G$123,709 GYD per night
Guest favorite

Home in Nantucket

5.0 out of 5 average rating, 25 reviews

Humble beach home in Madequecham 🐋🐚

Dec 6 – 13

G$190,931 GYD per night
Guest favorite

Home in Nantucket

5.0 out of 5 average rating, 39 reviews

Updated In-Town Cottage. Walk to Town and Harbor!

Feb 14 – 21

G$119,456 GYD per night
Guest favorite

Guesthouse in Nantucket

4.99 out of 5 average rating, 82 reviews

Quality stay

Jun 3 – 10

G$157,797 GYD per night
Guest favorite

Cottage in Nantucket

5.0 out of 5 average rating, 14 reviews

Expansive views of Madaket Harbor

Nov 30 – Dec 7

G$129,813 GYD per night
Guest favorite

Guesthouse in Nantucket

4.94 out of 5 average rating, 53 reviews

Bright and Airy 2 Bedroom Guest Cottage

Jan 5 – 12

G$118,182 GYD per night
Guest favorite

Home in Nantucket

5.0 out of 5 average rating, 10 reviews

The Nantucket Farmhouse

Sep 28 – Oct 5

G$118,813 GYD per night
Guest favorite

Guesthouse in Nantucket

4.97 out of 5 average rating, 63 reviews

Entire rental unit• Adorable second floor 2BD, 2BT

Aug 7 – 14

G$184,721 GYD per night

Other great vacation rentals in South Shore

Guest favorite

Home in Nantucket

5.0 out of 5 average rating, 16 reviews

In-Town, Historic District, Nantucket Home + Yard

Oct 9 – 16

G$191,559 GYD per night
Guest favorite

Apartment in Nantucket

5.0 out of 5 average rating, 24 reviews

Newly renovated home in Nantucket (sleep 3)

Oct 22 – 29

G$94,364 GYD per night
Guest favorite

Cottage in Nantucket

5.0 out of 5 average rating, 21 reviews

Brand new upscale cottage-great location

Feb 22 – Mar 1

G$172,341 GYD per night
Guest favorite

Vacation home in Nantucket

5.0 out of 5 average rating, 33 reviews

3 Queen, 1 King, 3 baths apartment in Nantucket

Oct 14 – 21

G$191,240 GYD per night
Guest favorite

Home in Nantucket

5.0 out of 5 average rating, 39 reviews

Charter House Luxury Home 2 Blocks from Town

Dec 10 – 17

G$191,373 GYD per night
Guest favorite

Home in Nantucket

5.0 out of 5 average rating, 74 reviews

Private Beach Cottage in Historic Sconset!

Jun 4 – 11

G$190,756 GYD per night
Guest favorite

Apartment in Nantucket

4.92 out of 5 average rating, 37 reviews

Perfect Couple's Getaway!

Sep 2 – 9

G$70,665 GYD per night
Guest favorite

Home in Nantucket

5.0 out of 5 average rating, 11 reviews

*Parker House*/Nantucket/Newly Updated

Jan 31 – Feb 7

G$181,562 GYD 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.


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.


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.

Destinations to explore