Holiday 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

Guest house 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

Flat 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!

4.94 out of 5 average rating, 212 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.

4.9 out of 5 average rating, 90 reviews

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.

Superhost

4.8 out of 5 average rating, 113 reviews

Deb Mar Cottages

On a quiet street one mile from town, this Cape Cod cottage provides 3 bedrooms, 2 full bathrooms upstairs and downstairs, a fully equipped kitchen with dishwasher, washer and dryer, fireplace, cable TV, a patio with furniture, grill and enclosed outdoor shower. There are four tower fans. Please respect the 10am check out time and the 4pm check in time .

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Other great holiday rentals in South Shore

Private room in Nantucket

4.99 out of 5 average rating, 112 reviews

Serendipity by the sea

KimberlyRating, 5 stars2 weeks ago

Loved our stay at Serendipity by the sea! Comfortable room, clean and all that was promised. Delicious coffee cake in the morning! Beautiful neighborhood. Wonderful conversation with host. Easy access to bus service to get all around the island.

4.89 out of 5 average rating, 9 reviews

South of Town Surf Shack. Best Deal on Island.

AlisonRating, 5 stars6 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!

Private room in Nantucket

4.93 out of 5 average rating, 160 reviews

Room# 4 *Two Beds * CoZy & PriVaTe * EnjOy & ReLaX

AnthonyRating, 5 stars2 days ago

Very professionally run by Emo. The room was comfortable and really clean! Great little value on the island.

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:)

4.71 out of 5 average rating, 65 reviews

Cottage in Nantucket

Quaint Nantucket Surfside cottage

AngusRating, 5 stars10 months ago

I stayed with my 11 year twins. Was exactly what we wanted for a week on Nantucket. Close to town, beaches, bus routes and bike paths. The house was clean, pretty and private, we even saw a deer and rabbits when we arrived roaming around the woods near the house. I am coming back next year, and for as many years as Wendy will let us. The beds were comfortable, the kitchen had everything we needed and the front porch was great for sundowners and BBQs. She is a great hostess with a beautiful cottage.

Flat 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.