Shorewood holiday homes

We found 21 holiday rentals — enter your dates for availability

Discover a selection of 7 homes and other holiday rentals in Shorewood that are perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a pool. Whatever you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.
  • Peace of mind

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  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Shorewood

  • Stunning Beaches: Shorewood offers beautiful sandy shores perfect for sunbathing and swimming, ideal for beach lovers.
  • Cultural Experiences: Explore historic buildings and local culture, particularly in the Southwestern part of Shorewood Hills.
  • Family-Friendly Activities: Enjoy the vibrant school district and community events that cater to families.
  • Lush Parks: Relax in the urban parks, providing a peaceful escape amidst nature.
  • Shorewood Country Club: Visit this local gem for a taste of leisure and recreational activities.

Top attractions near Shorewood

Shorewood on Shelter Island is a delightful destination for beach lovers and culture enthusiasts alike. You can explore the sandy shores, visit historic buildings, and enjoy the lush urban parks. Don't miss out on local attractions like the Shorewood Country Club, the public library, and the vibrant school district, perfect for family experiences. Whether you're after relaxation or adventure, Shorewood offers a fantastic mix for all types of travellers.

  • Sag Harbor Marine Park: A charming marina offering outdoor adventures and beach vibes. Perfect for boating, fishing, and soaking up the sun, this spot is ideal for those keen on maritime activities.
  • East Hampton Main Beach: Renowned for its stunning sandy shores and inviting waves, this beach is a quintessential New York coastal experience. Enjoy swimming, sunbathing, and beachside relaxation.
  • Foster Memorial Town Beach: An urban park perfect for families, featuring picnic areas and recreational opportunities. It blends outdoor fun with a city vibe, making it a great spot for a day out.

Things to do recommended for couples

For a romantic getaway in Shorewood, visit Kontokosta Winery for a lovely wine tasting experience, just 8.0km away. Enjoy a fun mini-golf game at Shelter Island Whale's Tail, only 3.2km away, and unwind at Raphael Winery, 11.3km away, for more enchanting moments together.

Things to do recommended for families

Families will love the Greenport Carousel, a delightful outdoor attraction just 6.4km from Shorewood, and Cedar Point County Park, a peaceful recreational area 8.0km away, perfect for wellness and relaxation.

Things to do recommended for groups

Groups visiting Shorewood can enjoy a lively performance at the Bay Street Theatre, hit the greens at Noyac Golf Club, or explore local produce at the Greenport Farmers' Market. Each experience offers a unique taste of the area’s culture and outdoor charm.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Shorewood

If you're heading off on a trip with friends, family, your furry companions, or planning for an extended getaway, it's important to prioritise your filters. Here are some helpful Vrbo booking tips tailored for you.

  • Traveling to Shorewood with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group get-togethers. The good news is that you can easily filter for these options and many more on Vrbo.
  • Traveling to Shorewood with young kids: Travelling with young kids can be quite a task. It’s important to prioritise their comfort and safety, along with suitable facilities like a private swimming pool. Additionally, keeping in mind how close you are to family-friendly activities can make all the difference.
  • Taking your pets with you to Shorewood: For many, a family holiday isn't truly complete without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Shorewood: If you’re seeking holiday rentals with great offers for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on long-term rentals. Don’t forget to include amenities like a car park, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Shorewood

Shorewood, a charming neighbourhood on Shelter Island, offers a delightful beach getaway filled with family-friendly excursions and stunning scenery. Explore the welcoming community and unwind along the Southern Shore, where you can soak up the sun and relish the relaxed atmosphere. Venture into the Southwestern part of Shorewood Hills for a taste of local culture and budget-friendly activities that will make your holiday truly memorable.

  • Hamptons: Situated 11.3km from Shorewood, the Hamptons is renowned for its stunning beaches and a quintessential outdoor lifestyle. It's a popular spot for those seeking a romantic getaway, offering activities like golfing, music concerts, and luxurious resort stays. The local attractions include picturesque family beaches and serene lakes, making it an ideal destination for relaxation and adventure alike. Whether you're lounging on the sandy shores or enjoying a round of golf, the Hamptons promises a delightful experience amidst breathtaking coastal scenery.
  • Greenport: Located a mere 6.4km from Shorewood, Greenport is a charming city that attracts visitors with its outdoor and beach experiences. This delightful locale is perfect for couples looking to escape into nature, with access to golf courses, music events, and upscale resorts. The nearby beaches, including family-friendly spots, provide ample opportunities for sunbathing and swimming. Additionally, Greenport hosts an event conference venue, making it an excellent choice for both leisure and business travelers seeking a scenic backdrop.
  • Sag Harbor: Also just 6.4km away from Shorewood, Sag Harbor is a quaint city that offers an outdoor haven for beach lovers and romantics alike. Visitors can indulge in activities such as golfing and even skiing at nearby fields. The area's attractions include beautiful beaches, family-friendly spots, and relaxing parks, perfect for picnics or leisurely strolls. With its charming streets and vibrant community, Sag Harbor is a delightful stop on your holiday, combining relaxation with engaging outdoor pursuits.

Best time to go to Shorewood

If you're planning a trip to Shorewood, it's a good idea to check both the weather and property rates. The warmest month is August.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.6°F (2.0°C)Light RainMostly Sunny
February35.8°F (2.1°C)Light RainMostly Cloudy
March39.7°F (4.3°C)Light RainMostly Sunny
April47.5°F (8.6°C)Light RainMostly Sunny
May55.8°F (13.2°C)Light RainMostly Sunny
June64.9°F (18.3°C)Light RainMostly Sunny
July73.0°F (22.8°C)Light RainMostly Sunny
August73.4°F (23.0°C)Light RainMostly Sunny
September68.2°F (20.1°C)Light RainMostly Sunny
October59.7°F (15.4°C)Light RainMostly Sunny
November49.6°F (9.8°C)Light RainMostly Sunny
December42.1°F (5.6°C)Light RainMostly Cloudy

Booking with Vrbo is a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can change quite a bit. Plus, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a handy platform for you to plan new adventures, continue from where you paused, or review and manage your travel arrangements. You'll discover your saved or booked properties neatly sorted into Potential, Upcoming, or Current Trips. To get started with Trip Boards, head over to: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday home accommodation in Shorewood?
The most popular types of holiday homes in Shorewood are houses. Hoping for something different? Bookabach has a variety of options to match the unique needs of our guests, so you'll see properties in all shapes and sizes, and for all budgets. The perfect fit is waiting for you — book yours today.
How much does it cost to rent a holiday home in Shorewood?
The average price for a holiday home in Shorewood is based on several factors, including property type, length of stay and season. Whether you're dreaming about a sprawling villa with lots of space or a cosy cabin for just you and your sweetheart, just enter your travel dates to see stays that offer great value.
How much does it cost to rent a beach house in Shorewood?
The average price for a holiday home close to the beach in Shorewood depends on when you'll be there and the size and type of property you want. You can easily and quickly find prices on Bookabach by entering the dates you'll be travelling. Then use the handy filter tool to pick the number of bedrooms and amenities important to you, such as WiFi, air conditioning and a hot tub.
Are there pet-friendly holiday homes in Shorewood?
There are, yes. Pick from four stays that allow pets in Shorewood on Bookabach. Our cuddly best friends also need a break, so simply use our search function for pet-friendly holiday homes to find a pad where your pooch can lap up the good times.
What are popular home amenities in Shorewood?
When it comes to home amenities that people are on the lookout for in Shorewood, a nearby waterfront, an ocean view and a fireplace are the most popular. With Bookabach holiday homes, there are options to suit your taste and style, whether you're travelling with your partner, your friends or even pets.
Are there large group holiday homes in Shorewood?
With two holiday homes that can sleep 10 or more people in Shorewood, you won't have to cross anyone off the invite list. From family get-togethers to special events like Christmas and birthday parties, Bookabach will help you find a large group home to suit the occasion.
Are there holiday homes in Shorewood that welcome kids?
Bring the whole family together for an unforgettable adventure in Shorewood at one of our four family-friendly properties. These stays feature amenities that are great for getaways with children, such as kitchens, multiple bedrooms and outdoor spaces. Just check the "Properties good for families" filter and choose your favourite.
What are the top attractions for families in Shorewood?
Keep the kids happy at these popular family-friendly attractions in Shorewood:

  • Shell Beach
  • Menhadden Lane Beach
  • Wades Beach

How can I find holiday homes with air conditioning in Shorewood?
Select your dates and then use our filters to view holiday homes with air conditioning in Shorewood on Bookabach. With three air-conditioned properties available, you can look forward to a cool and comfortable trip.
How old do you have to be to rent a holiday home in Shorewood?
The minimum age is generally 16, 18 or 21. It can differ between properties on Bookabach, so look at the rules of your chosen Shorewood holiday home before booking your trip.
How long can I rent a holiday home in Shorewood for?
The amount of time you can book a Shorewood holiday home for depends on each property. Simply tap in your dates of travel to view available options offering longer term stays. They include all the things you need to make your extended trip more comfortable and enjoyable, like laundries and air conditioning. Some Bookabach holiday homes may also offer weekly or monthly discounts, so you can have a longer stay for less.

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