Holiday houses 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.

4.93 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

4.77 out of 5 average rating, 177 reviews

Apartment in Nantucket

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.

4.95 out of 5 average rating, 61 reviews

Townhouse in Nantucket

You've Got Whale | Charming Island Home + Fire Pit

Welcome to "You've Got Whale" — your bright, beachy Nantucket escape. Relax around the patio fire pit, load up the beach gear, and explore Nobadeer or Surfside Beaches, just minutes away. Located at the end of a cul-de-sac in a picturesque enclave of 13 homes, this home with 4 levels of livings space can sleep up to 7 and is centrally located, near pristine beaches, hiking, parks, great restaurants and historic downtown Nantucket.

4.83 out of 5 average rating, 35 reviews

Beautiful Cottage | Historic Home

This quaint cottage house is located Mid-Island (about 1 mile from Downtown), making it the perfect Nantucket home-base for your group. This 2 bedroom, 1 bathroom cottage can comfortably accommodate 4 guests. Amenities include a hot tub plus a patio with an outdoor dining area. Inside, the professionally designed space offers coastal-inspired decor with blue and white accents

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.

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

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 stars1 week 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:)

4.85 out of 5 average rating, 48 reviews

Dreamy Nantucket Home w/ HVAC + In-Law Suite

AlexandraRating, 5 stars4 days ago

Beautiful stay in Nantucket! Loved how peaceful it was. Easily accessible with car and Uber. Very close to main town center. House was spotless when we arrived! We were comfortable and felt right at home. Taylor was incredibly responsive throughout our stay. I recommend this place to anyone staying in the area!

Guesthouse in Nantucket

5 out of 5 average rating, 8 reviews

Beach Chic Guest Cottage, Town

ClaireRating, 5 stars10 months ago

We had a wonderful stay at Deborah’s gorgeous cottage. It is charming and on a beautiful street a close walk to town. Deborah was communicative and helpful throughout our trip. We hope to stay again!

4.98 out of 5 average rating, 48 reviews

Cottage in Nantucket

New Free Standing/Studio/with optional car rental.

KrissyRating, 5 stars4 days ago

My husband and I had a fantastic stay at Laurel’s place! It was extremely cozy, clean, and well-decorated. The location was fantastic, and everything we wanted to do was a bike ride or quick uber away. The studio felt larger than the photos depicted and had everything we needed for the perfect long weekend in Nantucket. :)