Holiday houses in South Shore

An aerial view captures the surrounding landscape of a Nantucket cottage-style home. Lush greenery and vibrant trees envelop the property, which is bordered by neighboring homes. A glimpse of the coastline and water can be seen in the distance, highlighting the location's proximity to scenic views.

4.91 out of 5 average rating, 34 reviews

Bright South of Town Surf Shack Cottage-Gym Access

Classic Nantucket meets modern surf luxury. Behind cedar shingles and hydrangeas lies a designer retreat with Restoration Hardware decor, Casper beds, and Dan Lemaitre art. Bordering conservation land for wildlife viewing and privacy, yet <1 mile to Town. Complimentary EZIA Athletic Club gym access included! Message me for car ferry assistance by 1/18. Note: Professional staff reside in a separate basement unit to ensure a pristine stay. Quiet enjoyment is a priority; no parties or events.

4.95 out of 5 average rating, 220 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.

5.0 out of 5 average rating, 19 reviews

Apres Sea

Beautifully renovated 2-bed, 2-bath cottage, blends modern comfort with Nantucket charm. Nestled in a quiet neighborhood, it features an open-concept living area, high-end kitchen, and tasteful finishes. The spacious primary suite includes a private bath as does the second bedroom. Enjoy a private screened-in porch for outdoor dining, walk to Surfside Beach and enjoy easy access to town and mid-island amenities via the “Wave”, the islands free shuttle service. A perfect island getaway!

5.0 out of 5 average rating, 38 reviews

A private back yard is displayed, featuring two hammocks gently suspended between trees. Lush green grass surrounds the area, with a stone path leading to outdoor seating, visible through open doors of the cottage. Sunlight bathes the scene, creating a serene ambiance.

Cottage in Nantucket

Cisco Surf Shack

This recently renovated guest cottage is a cozy place to pause between your days on the beach. The house has fresh, laid-back interiors with all the modern amenities you would want for living by the water. The private and sunny back yard is complete with hammocks and a chiminea and is perfect for relaxing. A fabulous home right on the bike path close to Cisco beach (3/4 mile) , Bartlett Farm (1 mile) , Cisco Brewery(3/4 mile) , Miacomet Golf ( 2 miles) , and only 2.5 miles to town!

A cozy living area features a white sofa adorned with patterned throw pillows and a soft blanket. Intricately woven silver side tables sit on a textured area rug. Natural light enters from a nearby window, illuminating the wood-paneled walls and highlighting the adjacent kitchenette.

5.0 out of 5 average rating, 95 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!

4.97 out of 5 average rating, 199 reviews

The living area features high, sloped ceilings supported by wooden beams. Large windows allow natural light to brighten the space, and a working fireplace is positioned on one wall. A comfortable seating arrangement includes light-colored sofas, and a small TV sits on a side table.

Cottage in Nantucket

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, I live right on the property, adjacent to the cottage, you have full privacy but no shenanigans.

5.0 out of 5 average rating, 32 reviews

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.

A light-filled living area features a large gray sectional sofa and a round, textured coffee table. Shelving displays decorative items and a welcoming atmosphere is created by a modern chandelier overhead. Natural light streams through multiple windows, enhancing the bright ambiance.

4.97 out of 5 average rating, 73 reviews

Your family will be close to everything when you stay at this centrally-located Nantucket gem. Walk from the ferry with your belongings and then walk to town for ice cream and dinner. Or walk 100 yards down the road to Francis St beach! This recently renovated four bedroom, two and one half bath home features a new kitchen, large marble baths, gas fireplace, air-conditioning, porch, outdoor shower, large yard and sought after in-Town off street parking .

5.0 out of 5 average rating, 58 reviews

A private outdoor patio is equipped with a wooden dining table and chairs, shaded by a large umbrella. A grill is positioned nearby, and planters with greenery are placed at the base of the fence, enhancing the secluded atmosphere.

Cottage in Nantucket

Brand new upscale cottage-great location

Enjoy a stylish stay at this centrally-located 2 bedroom cottage. Patio dining table, grill, fire pit, outdoor shower. Private driveway. Rain shower, double sink, soaking tub. Master bedroom with king bed his and hers closet tv. Guest bedroom 2 twins. Living room fireplace WIFI. Fully equipped kitchen. Washer and dryer. Toiletries. Beach chairs, umbrella, cooler. Pack and play and baby chair. Security camera on driveway no other cameras on property

4.94 out of 5 average rating, 290 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.

A modern kitchen features soft green cabinetry and a white countertop, complemented by natural wood beams overhead. Pendant lights illuminate the space, and a vase with fresh flowers rests on the kitchen island, adding a touch of color to the functional design.

4.91 out of 5 average rating, 177 reviews

Great Condo In Town!

Great two bedroom condo in town renovated in winter 2025 - new kitchen and updated bathroom. If arriving by ferry, you're just a ten minute walk from dropping off your bags and being on vacation. Convenient to restaurants, bars, shopping and everything town offers. Queen bed in master and single in second bedroom. Couch in living room is a pullout as well as option for blow up mattress. The condo is on the second floor.

A sunlit living area features a light-colored sofa adorned with decorative pillows, complemented by a glass coffee table. Natural light streams through two windows, illuminating the space. A dining area with a wooden table and chairs is visible in the background, along with a fully equipped kitchen.