
Vacation rentals in South Shore
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Top-rated vacation rentals in South Shore
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Paradise Found
This spacious lower level, light -filled apartment has a large living area, private queen bedroom, and a lovely kitchenette.There is a queen sofa bed in the living room.The bathroom has a large rainfall shower.There is also a patio for guests to enjoy. This is a lower level apartment, so it is not handicapped accessible.There are 12 stairs. We also offer chartered fishing trips or harbor sunset cruises at an additional charge to our guests. Please inquire for more details when requesting a stay!

In-Town Cottage - Walk to Shops & Restaurants!
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 shows throughout with the modern beach chic decor. We do not allow pets at our cottage.

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.

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.

Nantucket Farmhouse-Walk to Beach-Near Sunset
The Nantucket Farm House was built in 1840 and was completely renovated and refurnished in 2023. If you are having trouble with ferry reservations and need a car, please let us know. We might be able to help. The home very private and is very close to beaches, bike paths, and the Nantucket public transportation stop. We are experienced Air BnB Superhosts and are committed to excellent service and guest satisfaction. We also have a full-time caretaker on island for your convenience.

“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!

Downtown Condo 3 minute walk from Ferries.
Stay in the best location on Nantucket! This stylish downtown condo has Ocean views and is a 4-min walk from ferries and steps from top restaurants, shops, and nightlife. Perfect for couples, friends, or solo travelers. Enjoy a private entry, self check-in, and a fully equipped space with WiFi and AC. Walk to cafés, museums, and galleries, with easy access to bikes, buses, and taxis for beach trips. No car needed! 2nd floor unit with deck. Fully equipped Kitchen.

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.

Madaket Bright and Airy Guest Cottage
Escape to this charming guest cottage in Madaket, just a short walk from Madaket Beach, known for its stunning sunsets. This peaceful retreat offers a cozy, light-filled space with a well-equipped kitchen and comfortable sleeping arrangements. Enjoy mornings on the private patio, bike scenic paths, or dine at Millie’s. Easily explore Nantucket’s shops, restaurants, and history. End your day with a breathtaking sunset—your perfect island getaway awaits!

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.

Attic apartment with private entrance
2 bedrooms / 1 bath apartment with kitchenette near Nantucket Airport. Private entrance and one parking spot. The apartment is adjacent to the hosts' living area and guests will be expected to observe quiet hours between 11 PM and 7 AM during which timeframe guests should refrain from load or disruptive activities. The apartment is located on an unpaved road in a thickly settled residential neighborhood.

The Mermaid Suite, walk to Beaches, 15 min to town
The Mermaid Suite is an efficiency apartment within walking distance to Nobadeer, Stones and Fisherman's Beaches. Well equipped with queen bed, desk, galley kitchen, full bath, outdoor shower, private entrance, linens, towels, parking, a/c and heating, etc. The Studio is a spacious 400 sq. ft. Secluded, private location. Comfortable, Cozy, and convenient.
Popular amenities for South Shore vacation rentals
Other great vacation rentals in South Shore

Apres Sea

The Cisco Loft

Beachfront Cottage w. Yard + Town Access

Surfside Beach Getaway

Woodys cottage

“Amada” forest hideaway

Nantucket “Pine-a-terre” suite near airport & bus

The Boucher Hideaway
All about 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.
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.
Destinations to explore
- New York Vacation rentals
- Philadelphia Vacation rentals
- Boston Vacation rentals
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- Jersey City Vacation rentals
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- Providence Vacation rentals
- Atlantic City Vacation rentals
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- York County Vacation rentals
- Cambridge Vacation rentals
- Bar Harbor Vacation rentals
- Cape Cod
- Mayflower Beach
- West Dennis Beach
- Craigville Beach
- Onset Beach
- East Sandwich Beach
- Sandy Neck Beach
- New Silver Beach
- Coast Guard Beach
- Nauset Beach
- Falmouth Heights Beach
- Skaket Beach
- Cape Cod Inflatable Park
- Nickerson State Park
- Lighthouse Beach
- Cape Cod Canal
- Popponesset Peninsula
- Cahoon Hollow Beach
- Sea Gull Beach
- Marconi Beach
- Inkwell Beach
- Sandwich Glass Museum
- Bass River Beach
- Town Neck Beach





