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.

Guest favorite

Guest suite in Oak Bluffs

4.94 out of 5 average rating, 301 reviews

Lovely 2 BR Oak Bluffs Apartment

This 100% private apartment is on the first floor of a shared house where owners and their son live upstairs. There are no shared spaces. You have a private entrance and parking. The living room, bedrooms, bathroom, and kitchenette are bright and clean. It is exactly 1 mile from Oak Bluffs Center, a half mile from The Cottages and Farm Neck Golf Course, and a block from Tradewinds walking trails. Across the street is the bike path, & the bus stop is on the corner for easy island transportation!

Nov 16 – 23

$101 per night
Guest favorite

Apartment in Nantucket

4.96 out of 5 average rating, 215 reviews

SUNNY second floor 2BD, 2BT

Newly renovated, bright and well designed 2BD, 2BT in convenient mid island area that is great for family with kids or a small group of friends. Could sleep up to 4 people. Private entrance.1Spacious BD with king bed, a couch, BT/shower, a desk. Another room with queen bed, couch, TV, dining table&chairs, 2nd BT/bathtub, W/D, fully equipped kitchenette( fridge/freeze, conv. oven, microwave, coffeemaker, toaster, hot plates burner), A/C.Bath & beach towels, chairs,umbrella and linens provided.

Jan 14 – 21

$304 per night
Guest favorite

Home in Nantucket

4.93 out of 5 average rating, 160 reviews

Cuddle In Cottage near Surfside Beach

This charming Nantucket chic decorated cottage is your ideal vacation spot. Perfect for 2 and a max of 4 people. The cottage is less than a mile from Surfside Beach, voted the islands favorite, and across the street from a bike path offering biking to the beach or town a safe and easy option. The cottage boasts privacy with fully stocked kitchen, in and out door shower, radiant heat, AC unit in the bedroom, 2 flat screen TV's, top drawer linens, towels, beach chairs and an out door grill.

Jun 30 – Jul 7

$693 per night

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

Aug 3 – 10

$520 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!

Jan 27 – Feb 3

$500 per night
Guest favorite

Cottage in Nantucket

5.0 out of 5 average rating, 14 reviews

Expansive views of Madaket Harbor

Oct 1 – 8

$570 per night
Guest favorite

Guesthouse in Nantucket

4.96 out of 5 average rating, 50 reviews

Bright and Airy 2 Bedroom Guest Cottage

Mar 10 – 17

$495 per night
Guest favorite

Guesthouse in Nantucket

4.99 out of 5 average rating, 82 reviews

Quality stay

Oct 25 – Nov 1

$663 per night
Guest favorite

Home in Nantucket

5.0 out of 5 average rating, 25 reviews

Humble beach home in Madequecham 🐋🐚

Nov 3 – 10

$800 per night
Guest favorite

Apartment in Nantucket

5.0 out of 5 average rating, 14 reviews

Ahoy ACK

Feb 25 – Mar 4

$581 per night
Guest favorite

Home in Nantucket

5.0 out of 5 average rating, 10 reviews

The Nantucket Farmhouse

Oct 19 – 26

$495 per night
Guest favorite

Cottage in Nantucket

4.99 out of 5 average rating, 84 reviews

Attractive 3 Bedroom/2 Bath in Town

Dec 14 – 21

$800 per night
Guest favorite

Home in Nantucket

5.0 out of 5 average rating, 36 reviews

Charter House Luxury Home 2 Blocks from Town

Dec 13 – 20

$800 per night
Guest favorite

Cottage in Nantucket

5.0 out of 5 average rating, 20 reviews

Brand new upscale cottage-great location

Jan 2 – 9

$720 per night
Guest favorite

Apartment in Nantucket

5.0 out of 5 average rating, 22 reviews

Newly renovated home in Nantucket (sleep 3)

Sep 29 – Oct 6

$394 per night

Other great vacation rentals in South Shore

Guest favorite

Condo in Nantucket

5.0 out of 5 average rating, 23 reviews

Spectacular Waterfront Townhouse

May 5 – 12

$881 per night
Guest favorite

Home in Nantucket

5.0 out of 5 average rating, 9 reviews

*Parker House*/Nantucket/Newly Updated

Jan 14 – 21

$760 per night
Guest favorite

Home in Nantucket

5.0 out of 5 average rating, 20 reviews

Perfect Charming Midtown Cottage!

Aug 25 – Sep 1

$750 per night
Guest favorite

Apartment in Nantucket

4.89 out of 5 average rating, 92 reviews

Great Condo In Town!

Oct 30 – Nov 6

$431 per night
Guest favorite

Apartment in Nantucket

4.92 out of 5 average rating, 37 reviews

Perfect Couple's Getaway!

Sep 1 – 8

$295 per night
Guest favorite

Home in Nantucket

5.0 out of 5 average rating, 17 reviews

rel-ACK-s Here, Bike Everywhere!

Apr 8 – 15

$407 per night
Guest favorite

Home in Nantucket

4.88 out of 5 average rating, 32 reviews

Samtucket cottage in town.

Nov 12 – 19

$283 per night
Guest favorite

Condo in Nantucket

4.95 out of 5 average rating, 56 reviews

Newly renovated one-bedroom condo in Town

Sep 1 – 8

$684 per night
Superhost

Apartment in Nantucket

4.94 out of 5 average rating, 78 reviews

Brand New modern 2 bedroom 2nd floor apartment

Sep 15 – 22

$684 per night
Guest favorite

Home in Nantucket

4.98 out of 5 average rating, 51 reviews

3 Bedroom with fenced in yard in Surfside Area

Feb 14 – 21

$904 per night
Guest favorite

Vacation home in Nantucket

5.0 out of 5 average rating, 31 reviews

3 Queen, 1 King, 3 baths apartment in Nantucket

Jul 11 – 18

$799 per night
Guest favorite

Home in Nantucket

5.0 out of 5 average rating, 71 reviews

Private Beach Cottage in Historic Sconset!

Aug 12 – 19

$899 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