Orient Point holiday rentals

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Discover a selection of 10 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:5 Feb - 12 Feb

Image gallery for Everything in Hamptons special discount available for weekly and monthly renters

aerial view
10 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)

Everything in Hamptons special discount available for weekly and monthly renters

Water Mill

17% off
Price is AU$81,104
for 7 nights, 1 home
AU$11,586 per night
includes taxes & fees
Everything in Hamptons special discount available for weekly and monthly renters

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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:

  • 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)
  • Wolffer Estates Vineyard (14.4 mi / 23.2 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:

  • Orient Point County Park (0.8 mi / 1.2 km)
  • 67 Steps Beach (6.5 mi / 10.5 km)
  • Mashomack Preserve (7.1 mi / 11.5 km)
  • Sunset Beach (8.1 mi / 13 km)
  • Harvey's Beach (11.2 mi / 18.1 km)
  • McCook Point Beach (11.7 mi / 18.9 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 best area to stay in Orient Point when booking a holiday rental?
When considering a holiday rental in Orient Point, New York, the area around the waterfront is particularly appealing. This picturesque neighbourhood offers stunning views of the Long Island Sound and is a short distance from some delightful attractions. One of the highlights is the Orient Beach State Park, where visitors can enjoy sandy shores and scenic walking trails. Additionally, the historic Orient Point Lighthouse, which dates back to the 19th century, is a must-see for those interested in maritime history.

There are a variety of properties available in this charming area, ranging from cosy cottages to more spacious homes, suiting different group sizes and preferences. Staying in this part of Orient Point allows for easy access to local restaurants and shops, enhancing the overall holiday experience.
When is the best time to visit Orient Point for a holiday rental?
The best time to book a holiday rental in Orient Point is during the peak summer season, which spans from June to August. July, in particular, stands out as the most popular month, attracting families and beachgoers eager to soak up the sun along the picturesque shores of Long Island Sound. This vibrant period is superb for those who enjoy outdoor activities such as swimming, fishing, and exploring the stunning coastal scenery.

With temperatures typically ranging from 18 to 30 degrees Celsius, the summer climate is warm and inviting, ideal for enjoying scenic walks and beach picnics. The area comes alive with a variety of local events, making it a lively time to visit. Whether you're wandering through charming local markets or indulging in fresh seafood at waterfront restaurants, there's always something happening.

For those looking for a more budget-friendly option, consider visiting in December. While this month is quieter, it offers a unique charm with festive decorations and fewer crowds. Exploring the area during the off-peak season can provide a more relaxed atmosphere, superb for enjoying the natural beauty without the hustle and bustle.
What are the top attractions in Orient Point?
In Orient Point, visitors can enjoy a range of attractions that highlight the area's natural beauty and maritime charm. One of the main draws is the Orient Beach State Park, where guests can relax on sandy shores, enjoy picnicking, and take in stunning views of the Long Island Sound. The park also offers opportunities for hiking and birdwatching, making it a great spot for nature enthusiasts.

Another highlight is the historic Orient Point Lighthouse, which stands as a picturesque landmark and offers insight into the region's maritime history. The nearby ferry terminal provides access to Shelter Island and further exploration of the surrounding waters, ideal for those looking to enjoy boating or fishing.

For a taste of local culture, the nearby vineyards and wineries in the North Fork region offer wine tastings and tours, allowing visitors to experience the local viticulture.
Are all fees included in the Orient Point holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Orient Point holiday homes with parking?
Stayz offers a wide selection of holiday homes in Orient Point with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Orient Point holiday homes?
You can find great discounts on holiday homes in Orient Point on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Orient Point holiday home booking on Stayz?
To find Orient Point holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Orient Point?
A long-stay holiday home in Orient Point is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Orient Point holiday home?
Book your Orient Point holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Orient Point?
Prices for holiday homes in Orient Point vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Orient Point to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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