House holiday rentals in South Shore

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Top-rated house rentals in South Shore

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Guest favourite
A clear view of Vineyard Sound is visible through the surrounding trees, showcasing the serene blue waters extending to the horizon. The gentle outlines of land can be seen in the distance, framed by lush greenery and a tranquil atmosphere.
Home in West Tisbury
4.96 out of 5 average rating, 113 reviews

Lambert's Cove, Water view, Beach pass, Ferry Tix

Enjoy stunning views of Vineyard Sound from this cozy three bedroom two bath home in a quiet neighborhood just minutes from Lambert's Cove Beach. This upside down house has one bedroom on the main level along with a full bath and open kitchen, dining, and family room. The downstairs has another living space, two bedrooms, laundry room, and full bath. Enjoy family time in the open upstairs with water views, or retreat to the lower level living room for some separation, quiet time, or work space.

Guest favourite
A living area features a comfortable sofa adorned with decorative pillows and a glass-top coffee table. Two bar stools are positioned at a nearby counter, and a chair is set to the side. Natural light streams through large windows showcasing plants in the outdoor space.
Home in Nantucket
4.85 out of 5 average rating, 117 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.

Top guest favourite
Home in Nantucket
4.95 out of 5 average rating, 203 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.

Top guest favourite
The exterior of a newly constructed guest house is shown, featuring a spacious deck with seating arrangements. Surrounding plant beds with fresh landscaping complement the wooden structure, while a gravel pathway leads towards the entrance, creating an inviting outdoor space.
Home in Edgartown
4.97 out of 5 average rating, 258 reviews

Brand new gorgeous 2 bedroom guest house.

This is a gorgeous brand new 2 bedroom guest house on the bike path that leads to downtown Edgartown and both State Beach and South Beach, as well as 1/4 of a mile from the famous Morning Glory Farm Stand. There are cathedral ceilings in the living room, which provide a open, spacious feel. There is a large deck on the front of the house with a grill, table and chairs. Part of it is covered in shade. Separate parking for guests with privacy, as it sits 200+ feet from the main house.

Top guest favourite
A bright and airy guest suite features a spacious bed with decorative pillows, set against light-colored walls. Sheer curtains allow soft natural light to fill the room. Wooden flooring complements the light decor, while a dresser and small cabinet provide additional storage space.
Home in Nantucket
4.98 out of 5 average rating, 169 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

Top guest favourite
An open living area features a light-colored sofa adorned with blue and white cushions. A flat-screen TV is mounted above a white brick fireplace. Large windows provide natural light, and a dining area with a table and chairs is visible in the background.
Home in Oak Bluffs
4.96 out of 5 average rating, 110 reviews

**Vineyard Vacation Retreat** -3 BR

Just a stone's throw from Oak Bluffs and it's beaches, this chic 3 bedroom home provides comfort and privacy. The large bedrooms and open concept kitchen/dining/living area accommodate up to 6 people comfortably. A place for you to put your feet up, kick away your worries, and enjoy some rest and relaxation. There is so much to do and explore. The adventure is just starting so make sure to pack up your swimmers, suntan lotion and get out the door. Kick back and relax, you're home.

Top guest favourite
A charming two-story home is framed by vibrant greenery and colorful shrubs, with a paved pathway leading to the entrance. Solar panels adorn the roof, reflecting a commitment to sustainability. Lush grass and well-maintained landscaping create an inviting atmosphere.
Home in Falmouth
5 out of 5 average rating, 160 reviews

Private Pond-side Cape Cod Home

Charming 2 bedroom home located on Flax Pond. Enjoy a private sandy beach and dock. Swim, kayak, fish, boat (trolling motors only) and just relax. Enjoy the home’s spacious deck with comfortable seating for the whole family complete with chiminea for late night fires. 2 levels of lodging with central air. 2 full bathrooms, kitchen, dining room and great room. Minutes away from town beaches, bike path, golf, and shopping. Parking for approximately 4 cars.

Top guest favourite
Home in Oak Bluffs
4.92 out of 5 average rating, 289 reviews

The Luxury Vineyard Yurt

Discover this exceptional Luxury Yurt firsthand! Upon entering, you will be welcomed by a distinctive experience, featuring textured concrete radiant floors and a four-foot circular central skylight. Every aspect has been meticulously designed, allowing you to relax in a generous private yard. Enjoy your evenings under the stars, utilize the complimentary paddling, practice yoga in the spacious loft, and indulge in the beauty of your private island Yurt!

Guest favourite
The exterior of a charming two-story house is shown, featuring a wrap-around porch with multiple seating options. The porch is adorned with wooden chairs, and the front yard is grassy, providing ample space for outdoor relaxation. Large windows reflect natural light, contributing to the inviting ambiance.
Home in Oak Bluffs
4.81 out of 5 average rating, 123 reviews

Beautiful 3 bedroom in Oak Bluffs, walk to beach

Located in Martha's Vineyard, close to beach, bike path, oak bluffs center, art and culture, parks,and the airport. You’ll love my place because of the outdoors space with a wrap around farmers porch, the proximity to the ferry, walking distance to neighborhood beach, less than 2 miles from ferry, screened in porch, central a/c, hardwood floors and an open floor plan. Real Cape Cod feel with modern amenities. Most of my guest come back year after year!

Top guest favourite
A cozy sleeping area features a spacious bed with blue and white striped bedding. Natural light enters through two large windows, illuminating the light-colored walls and ceramic tile floor. A wooden bench at the foot of the bed complements a stylish lamp and decorative wall art.
Home in Nantucket
4.94 out of 5 average rating, 254 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.

Top guest favourite
The charming beach cottage features blue shingle siding and a distinctive red door. Flower boxes beneath the windows are filled with colorful blooms. A brick chimney rises from the center, surrounded by well-maintained landscaping including small shrubs and flags.
Home in Nantucket
4.99 out of 5 average rating, 112 reviews

Private Beach Cottage in Historic Sconset!

Charming one bedroom beach cottage in Codfish Park, Siasconset Local Realtor says "You have climbing roses and hydrangeas in the summer, you can walk up the shell path up to the Sconset Market — it's Norman Rockwell at its finest, a really magical Sconset spot," he said. "Wake up in the morning, walk up to the store for your coffee and the paper, then take a little stroll down to the beach, which you can see from the property!”

Top guest favourite
A welcoming entrance is framed by a neat sidewalk leading to a white front door, flanked by two windows. The exterior showcases classic shingle siding, with vibrant flowering shrubs and a well-maintained lawn adding charm to the inviting facade.
Home in Edgartown
4.97 out of 5 average rating, 196 reviews

20-minute walk to Edgartown Village!

This 1550 square foot Ranch-style Condo with loft was built in 2018 and is set on a large nicely landscaped lot with plenty of room inside and out. It has It has 3 bedrooms and sleeps 8. It’s a 20-minute walk to the Edgartown village center, a 10-minute walk to Morning Glory Farm, and just a 10-minute drive to South Beach! All updated furnishings, beds, linens, appliances. Read our reviews! Immaculate!

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