Vacation rentals in South Shore

5 out of 5 average rating, 38 reviews

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 with sheets and baby chair. 1 pet allowed fee $200 per stay. Security camera on driveway no other cameras on property

4.85 out of 5 average rating, 105 reviews

Beach "Loft"

Enjoy The Beach Loft Apartment's convenient proximity to beaches, town and S’conset. Located 4 miles from the ctr. of the Historic District and 1 mile to Nobadeer beach our lofty spacious 900 sq. ft., 10 foot ceiling height apartment is the lower level (basement) of our home. Yet you will have complete privacy with separate parking as well as separate entrance and your own outdoor deck. The neighborhood is 3 acre zoning. It is secluded and quiet with many pine trees, oak and sassafras trees.

4.95 out of 5 average rating, 94 reviews

Captain's House 1750 In town

Our 1750 house is just over a block from the cobblestones of Main St. and only one block from the harbor. You can walk from the Hy-Line Ferry. At night, just walk home from dinner at any restaurant in town. There are 3 bedrooms (1 has a bunk bed) and two and a half baths. In the morning, walk next door for great coffee and cinnamon muffin. Have a cookout and eat in our small backyard area. Come for a visit! (Restaurants, Buses and Cars can cause some noise FYI) Drip coffee maker/filters too!

4.93 out of 5 average rating, 60 reviews

Guest suite in Nantucket

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

Convenient, quiet, mid island location, one street over from public NRTA “Wave” bus stop, Airport (ACK) and Old South bike path. Close to several restaurants. Our comfy lower-level guest suite offers private entrance, A/C, Queen size bed with closet system, full bathroom with W/D, galley kitchen area with microwave, apartment fridge, and stocked Keurig. Bonuses include free parking, a treadmill, electric fireplace, outdoor seating, and two televisions with Roku. No children or pets please.

4.94 out of 5 average rating, 185 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.

4.89 out of 5 average rating, 147 reviews

Guesthouse in Nantucket

LOVELY 1BD, 1BT Studio with backyard & BBQ

SUNRISE-Recently renovated 1BD, 1BT Studio with backyard and BBQ. It's a separate dwelling behind the main house( that has been rented too).Sleeps up to 4 people. With kitchenette, window units A/C, Wifi, parking on the driveway for 1 car. 1min away from bike path.Walking distance to coffee shop, bike rental shop, play ground. Easy access to town and beaches.Guests can get around by bus(The WAVE stop is right on the corner),bike, uber/taxi. Beach chairs and towels,umbrella&linens provided

4.97 out of 5 average rating, 151 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.,$150 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

Superhost

Apartment in Nantucket

4.77 out of 5 average rating, 177 reviews

Cozy studio-apartment

It is charming well appointed studio apartment conveniently located between down town and Surfside beach. It is walk-able to major Nantucket attractions -bars, restaurants, beaches, supermarket. In addition there is a bicycle rentals shop next door at your convenience. The studio is equipped with crisp linens, free Wi-Fi, kitchenette and bath essentials —everything you need for an exceptional stay. If you don't find something you wish you had before or during your stay, please ask!

5 out of 5 average rating, 84 reviews

Apartment in Nantucket

“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!

4.96 out of 5 average rating, 89 reviews

Guesthouse in Nantucket

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!

4.94 out of 5 average rating, 211 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.

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Other great vacation rentals in South Shore

5 out of 5 average rating, 63 reviews

Loft in Nantucket

Cottage Suite

MaxineRating, 5 stars6 months ago

David was an amazing host!! He let us check in early since we had an early ferry ride. He communicated very well anytime we had a question. The location was perfect - a 20 minute walk or 5 minute drive to the town. We will definitely be back!!

4.89 out of 5 average rating, 9 reviews

South of Town Surf Shack. Best Deal on Island.

AlisonRating, 5 stars5 days ago

Our stay on Nantucket was fantastic! An easy walk into town and the house had everything we needed, including items for our child. Gaelen was very responsive and her recommendations and instructions were great. We can’t wait to come back!

5 out of 5 average rating, 25 reviews

Cottage in Nantucket

Cisco Surf Shack

LisaRating, 5 stars8 months ago

We visited Nantucket for our annual girl's trip. We all thought the home was very cozy and comfortable. We cooked dinner in one night and found the kitchen to be well-equipped for making a meal. The bottle of wine and snacks upon arrival were appreciated. The beds were all comfortable. We enjoyed walking to the beach each morning and we rented bikes to ride on the paths all over the island.

4.73 out of 5 average rating, 11 reviews

Updated house .3 miles to beach peaceful

AllieRating, 5 stars3 weeks ago

Absolutely amazing day! It is the perfect location and size house for our group. It was beautiful, very clean and very updated. Would highly recommend staying here again and probably will in the future!! Beautiful house and Edith was great to work with:)

Apartment in Nantucket

4.86 out of 5 average rating, 72 reviews

Easy Nantucket Downtown Apartment

PamelaRating, 5 stars3 weeks ago

The cottage was exactly as described. It’s an easy mile walk to town, which we did several times a day. When we had any questions Nick was quick to respond and at one time came over when I had a question about the heat. They also gave us great restaurant recommendations. I felt confident that if we ever needed them they’d be there to lend a hand.

5 out of 5 average rating, 32 reviews

Humble beach home in Madequecham 🐋🐚

DonaldRating, 5 stars1 week ago

Absolutely incredible and relaxing stay. Waking up to hearing and seeing the water from our bedroom was a highlight of the trip. The house is very charming with everything you'd hope from a beach side property. Renting a car to get into town was a must, but this is well worth it for having a private beach house with a scenic walkable road. I'd absolutely recommend anyone who's looking for a relaxing stay to consider this property.

5 out of 5 average rating, 18 reviews

Quiet Cul-de-Sac near Sconset

TammiRating, 5 stars1 week ago

The house is beautiful and it felt very comfortable, giving the essence of Nantucket. Great communication and instructions. Overall excellent experience and would highly recommend and will definitely be back!