Holiday rentals in South Shore

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Top-rated holiday rentals in South Shore

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Guest favourite

Flat in Nantucket

4.96 out of 5 average rating, 222 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.

29 Dec – 5 Jan

$473 SGD per night

Guest favourite

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.

24–31 Jul

$851 SGD per night

Guest favourite

Cottage in Nantucket

4.98 out of 5 average rating, 127 reviews

Spouter Cottage

A unique upside down two bedroom cottage with a deck and a view of the Harbor. A curated space with antique beams, handcrafted doors, flooring and cabinetry, antiques and fine art. It all lends a vintage feel to an up to date with all the amenities home. There is a private small side yard and garden with outdoor grill and seating. This is not a party house, it’s a sensitive house, my husband and I live right on the property, adjacent to the cottage, you have full privacy but no shenanigans.

21–28 Nov

$775 SGD per night

Guest favourite

Guest house in Nantucket

4.97 out of 5 average rating, 63 reviews

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

Freshly renovated, well designed, and adorable 2BD, 2BT space located in the mid island area of Nantucket. Great for family or a small group of friends. Up to 4 people could sleep there. One queen bed with a TV and its own bathroom. Closet that includes a baby crib. Another BD with two twin beds and a closet. Kitchen includes a couch, dining table, 2 fridges, and a sink. Also includes a coffee maker, toaster, oven, and utensils. Beach towels, chairs, and an umbrella are provided as well.

8–15 Apr

$670 SGD per night

Guest favourite

Flat in Falmouth

4.98 out of 5 average rating, 119 reviews

Modern Luxury Apt. | 7 min from Commons

This luxury 1Br + 1bth apartment is the perfect getaway. - 650 square feet, newly renovated - 15 Minutes from Old Silver Beach, South Cape Beach, and Falmouth Heights beaches - Steps from 1,700 acres of walking trails (Crane Wildlife) - 7 minutes to Mashpee Commons (shops and restaurants) - 15 minutes to Main Street Falmouth - 13 minutes to Ferry for Marthas Vineyard - 85” smart TV - 5 minutes to Shining Sea Bike Trail - Coffee/Espresso Machine - 2 minutes from Paul Harney Golf Course

14–19 Oct

$102 SGD per night

Guest favourite

Home in Nantucket

4.98 out of 5 average rating, 130 reviews

"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. Our guest suite is not suitable for children. We do not allow pets. If you were bringing a car please let us know in advance so we can make parking arrangements

20–27 May

$542 SGD per night

Guest favourite

Flat in Nantucket

5.0 out of 5 average rating, 63 reviews

“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!

2–9 Oct

$425 SGD per night

Guest favourite

Home in Nantucket

5.0 out of 5 average rating, 39 reviews

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

Moongate Cottage, with quintessential Nantucket charm, is walkable to downtown. Enter through the arched wooden gate in the mature hedges, to your private oasis with a quaint yard and brick patio. The cottage furnishes everything you need. From June to September, we have a 7-night minimum stay from Saturday to Saturday. Enjoy the large living room, spacious bedroom, updated kitchen, and bathroom. The ambiance of Nantucket shows throughout with the modern beach chic decor.

12–19 Feb

$773 SGD per night

Guest favourite

Flat in Nantucket

5.0 out of 5 average rating, 14 reviews

Ahoy ACK

Kick back and relax in this calm, stylish space. Unit has private outdoor stairs and deck with small yard and outdoor shower, leading up to the sunlit Nantucket oasis in Miacomet/Cisco area. See Cisco Brewery and Barlett Farm outside the windows. Close proximity to some of the best beaches on the island, this 1Bed/1Bath with pullout couch will not disappoint. Laundry in unit with kitchen and flatscreen TVs. Unit was completely redone and finished in June 2023.

27 Sep – 4 Oct

$732 SGD per night

Guest favourite

Home in Nantucket

5.0 out of 5 average rating, 25 reviews

Humble beach home in Madequecham 🐋🐚

Wake up to the sounds of chirping birds and the crashing surf of the South shore! Take in the fresh salty air! Just steps from one of the best beaches on the island, and removed enough from the hustle and bustle of town, you will feel right at home in our peaceful abode. Though simple, the house is equipped with everything you need for a comfortable stay: Complete kitchen, gas grill, outdoor shower, lounge chairs, beach chairs, very good wifi, and more.

26 Nov – 3 Dec

$1,236 SGD per night

Guest favourite

Home in Nantucket

4.93 out of 5 average rating, 166 reviews

Mid Island Crash Pad

A conveniently located mid-island Crash Pad for the all movers and shakers that visit Nantucket! This gorgeous, newly built one bedroom studio with its own exterior entrance is just a few steps from the bike path and shuttle that takes you right into town. This location and space offer everything you need to be comfortable in between beach jaunts or shopping trips to town. Like a hotel room, we offer a simple and affordable place to stay on ACK.

18–25 Oct

$393 SGD per night

Guest favourite

Cottage in Nantucket

5.0 out of 5 average rating, 34 reviews

Brand New Free Standing/Studio

This studio has everything you need for an enjoyable Nantucket vacation. Fully equipped kitchen/full bath with tub/patio space for dinning / grilling and outdoor shower . Convenient to bus stop/ town /brewery and Miacomet Beach. Patio photos to come soon. Please ask about our discount for Off season rates and Month long or longer stays .

29 Mar – 5 Apr

$579 SGD per night