Orient Point holiday rentals

We found 2,123 holiday rentals — enter your dates for availability

Discover a selection of 8 homes and other holiday rentals in Orient Point that are perfect for your trip. Whether you're travelling with a group or just with your pet, holiday rentals have the best amenities for spending time at your holiday home, including parking and a TV. No matter what you're looking for, you'll be able to choose a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Orient Point

Showing deals for:25 Sept - 2 Oct

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Why visit Orient Point

  • Scenic coastline: Orient Point boasts stunning views of the Long Island Sound and picturesque sandy beaches, perfect for a coastal retreat.
  • Outdoor adventures: Enjoy water activities and scenic trails in local parks, ideal for families and outdoor enthusiasts alike.
  • Relaxed ambience: The village offers a charming, laid-back atmosphere with budget-friendly excursions for a memorable escape.
  • Cultural charm: Discover the local ambience with a blend of beach experiences and cultural attractions, perfect for a romantic getaway.
  • Convenient getaways: A variety of holiday stay options, including private homes and cottages, ensure a comfortable retreat in this coastal community.

Popular types of accommodation in Orient Point

Planning a getaway to Orient Point, New York? You'll find a charming selection of holiday rentals, including private holiday homes, cottages, and apartments. Nestled at the tip of the North Fork, Orient Point offers stunning views of the Long Island Sound, picturesque beaches, and unique local attractions. Enjoy a relaxed atmosphere as you explore the beautiful surroundings and indulge in memorable experiences. Choose your ideal accommodation and make the most of your stay in this delightful coastal community.

  • Private Holiday Homes: The top pick for visitors in Orient Point, offering exclusive and relaxed settings for a memorable escape.
  • Cottages: A favourite for those seeking a quaint, cosy retreat with traditional charm.
  • Apartments: Ideal for travellers desiring a modern, self-catered stay in a convenient location.
  • Condos: A stylish option providing comfortable and well-appointed spaces for a pleasant holiday.
  • Villas: Perfect for those looking for a spacious, luxurious getaway with ample room for families or groups.**

Top attractions near Orient Point

Orient Point, New York, is a charming destination perfect for outdoor enthusiasts and families alike. Visitors can enjoy the stunning vistas at Orient Beach State Park, explore the scenic trails of local parks, and partake in various water activities. The area offers a delightful mix of beach experiences and cultural attractions, making it an ideal spot for a romantic getaway or family holiday. Discover the beauty of the natural surroundings and create lasting memories in this picturesque locale.

  • Hole-in-the-Wall Beach: A hidden gem with stunning coastal views, this beach offers a serene escape for sunbathing and picnicking amidst natural beauty, perfect for relaxation.
  • Island's End Golf and Country Club: A family-friendly venue that provides a delightful golfing experience, featuring scenic landscapes and opportunities for excursions in a welcoming atmosphere.
  • Sylvester Manor: A historic estate brimming with cultural significance, offering insights into local history and heritage through its beautifully preserved architecture and gardens.

Things to do recommended for couples

Discover quaint Orient Point, New York, with its captivating coastal charm. Enjoy a serene harbour walk, savour intimate seaside dining, and explore hidden local gems, perfect for a romantic escape.

Things to do recommended for families

Families visiting Orient Point can enjoy a delightful day at the nearby Montauk Point Lighthouse, exploring its history and stunning views. They can also take a scenic ferry ride to Shelter Island, where kids can engage in nature walks and beach fun, making for a memorable family adventure.

Things to do recommended for groups

Groups visiting Orient Point can enjoy an adrenaline-filled outing at Waterford Speedbowl, a motor racing facility located 27km away, offering a blend of sports and adventure for an authentic local experience.

*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 in Orient Point

Whether you're journeying with a group, travelling as a family, accompanied by your pets, or seeking extended stays, ensure you filter by the appropriate criteria. Here are some Stayz booking pointers for you.

  • Traveling to Orient Point with a group: Consider how many bedrooms you require, along with facilities like a fully-equipped kitchen or an outdoor area for group gatherings. Fortunately, you can refine your search on Stayz to accommodate all these needs and beyond.
  • Traveling to Orient Point with young kids: Traveling with young children can present challenges. It is important to guarantee their comfort and safety, while also providing suitable amenities for their age, such as a private swimming pool. Additionally, it is wise to take into account your closeness to attractions that are friendly for families.
  • Taking your pets with you to Orient Point: For many, a family holiday isn't truly fulfilling without their four-legged companion by their side. If this resonates with you, take a look at Stayz properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Orient Point: If you’re seeking holiday rentals with offers for stays of a month or more, you’ve come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include options like a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay near Orient Point

Orient Point offers a delightful escape, perfect for outdoor, family, or romantic holidays. Explore the charm of Orient Bay, enjoy a beach getaway on its sandy shores, and indulge in the local ambience with budget-friendly excursions. The village’s friendly atmosphere and scenic views, accessible via convenient transportation options, make it an ideal destination for memorable beach holidays and relaxing adventures.

  • Greenport: Greenport is a charming city located 11km from Orient Point, renowned for its inviting outdoor and romantic ambience. Visitors can enjoy the refreshing beach appeal, with family-friendly sands and scenic parks dotting the landscape. A visit here offers a delightful blend of leisure and activity, including a well-regarded golf course and vibrant local music concerts. The recreational area provides ample space for family outings and energetic pursuits, making Greenport a perfect destination for those seeking both relaxation and adventure.
  • Old Saybrook: Old Saybrook is a picturesque city situated 19km from Orient Point, celebrated for its serene outdoor settings and captivating scenery. This destination is ideal for couples seeking a romantic retreat, with its blend of natural beauty and recreational charm. Highlights include expansive recreational areas, a distinguished golf course, and a selection of resorts that cater to the discerning traveller. The proximity to a national state park further enriches the experience, while the local beach and family beach provide ample opportunities to bask in the coastal splendour.
  • Sag Harbor: Sag Harbor, located 18km from Orient Point, is a delightful city that exudes a relaxed, outdoor vibe with a particular emphasis on beach and romantic experiences. Here, visitors can indulge in a range of activities, from playing golf at esteemed courses to enjoying winter sports. The city's nearby family beach and picturesque lake offer a serene backdrop for leisurely walks and reflective moments, making Sag Harbor a compelling destination for those who appreciate the blend of nature and recreational pursuits.

Best time to go to Orient Point

If you're planning a trip to Orient Point, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from June to August, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January35.6°F (2.0°C)Light RainMostly SunnyLowModerately Low
February35.8°F (2.1°C)Light RainMostly CloudyAverageModerately Low
March39.7°F (4.3°C)Light RainMostly SunnyAverageModerately Low
April47.3°F (8.5°C)Light RainMostly SunnyAverageAverage
May55.6°F (13.1°C)Light RainMostly SunnyAverageAverage
June64.8°F (18.2°C)Light RainMostly SunnyHighModerately High
July72.7°F (22.6°C)Light RainMostly SunnyHighModerately High
August73.2°F (22.9°C)Light RainMostly SunnyHighModerately High
September68.0°F (20.0°C)Light RainMostly SunnyAverageAverage
October59.7°F (15.4°C)Light RainMostly SunnyAverageAverage
November49.8°F (9.9°C)Light RainMostly SunnyLowAverage
December42.3°F (5.7°C)Light RainMostly CloudyLowAverage

Booking with Stayz is a breeze

Looking to cut down on travel expenses for your upcoming journey? It might be worth considering some flexibility with your travel dates, as prices can vary. Additionally, booking a longer stay can often lead to substantial savings. Use our filters to sort by price, location, and type of holiday rental to find the ideal Stayz property that suits your budget.

Stayz Trips: Planning as easy as it gets

Stayz’s Trip Board provides a convenient space for you to plan new journeys, manage your existing arrangements, or review and organise your bookings. The properties you’ve saved or reserved are now categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

Delight in the waterfront landscape of Orient Point

The parks and surrounding scenery provide a peaceful ambience to your holiday home in Orient Point. This city has something for everyone. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around Orient Point

Do you want to find things to do in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Orient Point a one-of-a-kind holiday spot. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Gardiner's Bay Country Club (5.7 mi / 9.2 km)
  • Kontokosta Winery (6.4 mi / 10.4 km)
  • LongHouse Reserve (12 mi / 19.4 km)
  • Raphael Winery (13.6 mi / 21.9 km)
  • Pindar Vineyards (13.9 mi / 22.4 km)
  • Bedell Cellars (14.2 mi / 22.8 km)

Exploring the natural landscape of Orient Point

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Orient Point. These are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • The Hamptons Beaches (15.9 mi / 25.6 km)
  • Orient Point County Park (0.8 mi / 1.2 km)
  • 67 Steps Beach (6.5 mi / 10.5 km)
  • Sunset Beach (8.1 mi / 13 km)
  • Crescent Beach (8.4 mi / 13.5 km)
  • Rocky Neck State Beach (10.2 mi / 16.5 km)

Travelling to and around Orient Point

The nearest airport is in East Hampton, NY (HTO), located 13.2 mi (21.3 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Fishers Island, NY (FID-Elizabeth Field), which is 13.5 mi (21.7 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Orient Point?
According to our research, houses are the most sought-after type of property in Orient Point. But as you might expect, everyone's idea of an awesome stay can differ. Stayz has holiday homes of all sizes and shapes, and we'll help you to find your ideal match.
How much does it cost to rent a holiday home in Orient Point?
The average price for a holiday home in Orient Point is determined by a number of factors, such as season, property type and length of stay. Whether you're dreaming about a sprawling house with room for friends and family or a cosy cottage just enough for two, just add your travel dates to find stays that offer great value.
How much does it cost to rent a beach house in Orient Point?
The average price for a holiday home near the beach in Orient Point depends on when you're visiting the area and the style and size of property you're looking for. You can easily and quickly find prices on Stayz by entering your preferred travel dates. Then use the filter tool to select the number of bedrooms and amenities that you require, like WiFi, air conditioning and a pool.
Are there pet-friendly holiday homes in Orient Point?
Good news. There are. You'll find 12 stays that allow pets in Orient Point on Stayz. Our furry best friends also deserve a getaway, so simply use our search function for pet-friendly holiday homes to find a pad where Spot can be near his favourite humans.
Can I rent a house with a pool in Orient Point?
Add a new level of fun to your trip by booking your family into one of the seven houses with a private pool in Orient Point. Use our search filter to find properties with pools on Stayz, then spend your days playing and splashing in a swimming pool that's just for you.
What are popular home amenities in Orient Point?
When it comes to home amenities that guests are on the lookout for in Orient Point, a firepit, a fireplace and an ocean view are the most popular. With Stayz holiday homes, you'll enjoy choices to fit your taste and style, whether you're taking a trip with your partner, your friends or even pets.
Are there large group holiday homes in Orient Point?
You'll find 10 properties in Orient Point that can accommodate a group of five or more people. From family trips to events like a friend's birthday, these stays have ample space to spend time with the people you love.
Are there holiday homes in Orient Point that welcome kids?
Orient Point has 12 family-friendly holiday homes. And booking a stay that welcomes little ones is a breeze with Stayz's "Properties good for families" filter. In addition to having the whole place to yourselves, you'll also get access to perks and conveniences like multiple bedrooms, full kitchens and yards.
What are the top attractions for families in Orient Point?
Keep your kids occupied at these top family-friendly attractions in Orient Point:

  • Orient Beach State Park
  • Oysterponds Historical Society
  • Orient Point County Park

Are there holiday homes with WiFi in Orient Point?
You can pick from six holiday homes with WiFi in Orient Point. If you want to disconnect from the world during your trip, but still want to be connected to the internet, these getaways are for you. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Orient Point?
There are 12 Stayz holiday homes with air conditioning in Orient Point providing that cooling breeze and extra level of comfort. Enter your dates of travel and then use our handy filter tool to search for stays with air conditioning.
How old do you have to be to rent a holiday home in Orient Point?
The minimum age allowed can vary across properties on Stayz, so look at the rules of the holiday home in Orient Point you want to book. But normally, it's 16, 18 or 21.
How long can I rent a holiday home in Orient Point for?
The length of time you can book a holiday home in Orient Point varies according to the property. Simply enter your selected travel dates to see a list of options offering extended stays. With lots of amenities such as laundries and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to find a perfect place to call your home away from home in Orient Point.