Orient Point vacation rentals

We found 2,154 vacation rentals — enter your dates for availability

Discover a selection of 9 homes and other vacation rentals in Orient Point that are perfect for your trip. Whether you're traveling with a group or just with your pet, vacation rentals have the amenities you need and want for your stay, which might include parking and a garden. No matter what you're looking for, you'll be able to choose a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Orient Point

Showing deals for:Jul 3 - Jul 10

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

9% off
Price is $8,289
$58,023 for 7 nights
All fees included
Everything in Hamptons special discount available for weekly and monthly renters

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Find out more about Orient Point

Why visit Orient Point

  • Stunning Beaches: Enjoy beautiful beaches with easy access and breathtaking ocean views, perfect for relaxation and water activities.
  • Outdoor Adventures: Explore nearby state and national parks that offer various recreational opportunities for nature lovers.
  • Family-Friendly Activities: Engage in numerous attractions that cater to families, ensuring a fun-filled experience for all ages.
  • Charming Vacation Rentals: Choose from cozy homes, quaint cottages, or spacious apartments for a comfortable stay.
  • Friendly Locals: Experience the warmth of the community with budget-friendly excursions and local culture.

Popular types of accommodation in Orient Point

Discover the charm of Orient Point with a variety of vacation rentals that cater to every traveler's needs. Whether you're looking for cozy houses, quaint cottages, or spacious apartments, our platform has you covered. With options for holiday rentals and hotels, you can enjoy comfort and convenience during your stay. Explore Orient Point and find the perfect home rental for your getaway.

  • Houses: The top choice for travelers in Orient Point, offering spacious and comfortable settings perfect for families or groups.
  • Cottages: A charming option, ideal for those seeking a cozy and quaint atmosphere while enjoying the coastal views.
  • Apartments: A convenient selection for solo travelers or couples, providing essential amenities and easy access to local attractions.
  • Condos: A popular choice that combines comfort with modern conveniences, often featuring great community amenities.
  • Villas: An upscale option for those wanting luxury and privacy, perfect for a memorable getaway.**

Top attractions near Orient Point

Orient Point, New York, is perfect for outdoor enthusiasts and families seeking a romantic getaway. Visitors can enjoy beautiful beaches, explore urban parks, and discover national and state parks. The area offers a variety of attractions that highlight local culture and provide memorable family experiences, ensuring there's something for everyone to enjoy while soaking in the scenic beauty of this charming destination.

  • Orient Beach State Park: Enjoy the serene beach vibes just 2 miles from Orient Point. Here, you can relax on sandy shores, swim in the calm waters, or explore scenic walking trails along the coastline.
  • Rocky Neck State Park: Located 11 miles away, this national state park boasts stunning scenery and outdoor adventures. Hike through lush landscapes, picnic by the water, or discover the diverse wildlife that calls this park home.
  • Eastern Long Island Hospital: Situated 6 miles from Orient Point, this medical center provides essential healthcare services with a welcoming, family-oriented atmosphere, making it a vital part of the community.

Things to do recommended for couples

Seeking a romantic getaway in Orient Point? Enjoy a scenic ferry ride to Shelter Island, explore the charming vineyards, or take a sunset stroll along the beach. Finish your day with a candlelit dinner at a local seafood restaurant, savoring the fresh catch together.

Things to do recommended for families

Families will love exploring the scenic beaches at Orient Beach State Park, where kids can build sandcastles and enjoy picnics. Take a ferry ride to Shelter Island for a day of nature trails and wildlife spotting, or visit the local farm stands for fresh produce and family-friendly activities.

Things to do recommended for groups

Groups visiting Orient Point can enjoy a scenic ferry ride to Shelter Island, explore the picturesque beaches, and savor fresh seafood at local eateries. Don’t miss the chance to visit the historic Orient Point Lighthouse and take part in a group fishing charter for a memorable 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

When you’re planning a trip—whether it’s with a group, your family, or your pets, or if you’re interested in extended stays—be sure to prioritize your preferences when filtering options. Here are some helpful tips for booking on Vrbo.

  • Traveling to Orient Point with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily refine your search for all of these options and more on Vrbo.
  • Traveling to Orient Point with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, considering how close you are to family-friendly attractions can make a big difference in your experience.
  • Taking your pets with you to Orient Point: For many families, a vacation isn’t truly fulfilling without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Orient Point: If you're searching for vacation rentals with discounts 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 monthly rentals. Don't forget to include features like parking, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Orient Point

Orient Point, New York, offers a charming blend of outdoor adventures and family-friendly activities. With stunning ocean views and easy beach access, it's the perfect spot for a romantic getaway or a fun family vacation. Explore nearby neighborhoods and cities that boast friendly locals and budget-friendly excursions. Whether you're seeking relaxation or adventure, Orient Point is a kind holiday destination that promises memorable experiences for all visitors.

  • Greenport: Located 7 miles from Orient Point, Greenport is a charming seaside village known for its vibrant outdoor and romantic atmosphere. Visitors can enjoy various activities, such as golfing at local courses or attending music concerts in scenic areas. The picturesque beaches and family-friendly parks provide perfect spots for relaxation and fun. Stroll through the quaint streets lined with boutiques and restaurants, and don't miss the chance to savor fresh seafood while taking in stunning waterfront views.
  • Old Saybrook: Situated 12 miles from Orient Point, Old Saybrook offers a delightful blend of outdoor activities and scenic beauty. This historic town is perfect for travelers seeking a romantic getaway, with its beautiful beaches and lush landscapes. Explore the local recreational areas or enjoy a round of golf at one of the well-maintained courses. The nearby national state park presents opportunities for hiking and nature walks, making it an ideal destination for adventure enthusiasts and families alike.
  • Orient: Nestled within Orient Point, the quaint town of Orient is a hidden gem for those seeking a serene outdoor experience. With its stunning scenery, visitors can engage in recreational activities such as golf or catch a show at the local theater. The beautiful beaches and tranquil lakes provide ample opportunities for relaxation and family outings. Enjoy the charm of this peaceful destination while soaking in the breathtaking views of the surrounding landscapes, making it a perfect spot for a romantic retreat or a family vacation.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 Vrbo is simple

Are you eager to save on your upcoming journey? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, consider booking a longer stay to unlock even greater savings. To discover a Vrbo property that aligns with your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a convenient space to plan new trips, pick up right where you left off, and manage your travel arrangements. You can easily find the properties you've saved or booked under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Delight in the waterfront landscape of Orient Point

The parks and surrounding scenery provide a peaceful ambiance to your vacation home in Orient Point. There's no shortage of things to see and do in the area.A vacation 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

Are you searching for top things to see and do while you're in the area? Venture out of your vacation home and check out everything that makes Orient Point a fun place to get away. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • 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 spend some time taking in the scenery, Orient Point is a great place to get out in nature. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Havens Beach (10.6 mi / 17.1 km)
  • Harvey's Beach (11.2 mi / 18.1 km)
  • Foster Memorial Town Beach (11.4 mi / 18.3 km)

Traveling to and around Orient Point

The nearest airport is in East Hampton, NY (HTO), located 13.2 mi (21.3 km) from the city center. If you can't find a flight that's convenient for your trip, you could book a flight to 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, New York, United States of America when booking a vacation rental?
When looking for the best area to stay in Orient Point, New York, consider the charming neighborhood surrounding the waterfront. This area offers a serene atmosphere and beautiful views of the Long Island Sound. You'll find a variety of vacation rentals that cater to different preferences, from cozy cottages to spacious homes.

One of the top attractions nearby is the Orient Beach State Park, where visitors can enjoy swimming, sunbathing, and hiking along scenic trails. Additionally, the historic Orient Point Lighthouse is a must-see, providing a picturesque backdrop and a glimpse into the area's maritime history. The proximity to these attractions makes this waterfront neighborhood an excellent choice for a relaxing getaway.
How much does it cost to rent a vacation home in Orient Point?
Prices for vacation rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Orient Point to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Orient Point vacation house rentals?
You can find great discounts on house rentals in Orient Point on Vrbo, 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 find long-stay vacation rentals in Orient Point?
A long-stay vacation rental in Orient Point is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any Orient Point vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Orient Point with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo 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.
When is the best time to visit Orient Point for a vacation rental?
The best time to visit Orient Point for a vacation rental is during the peak travel season from June to August. This vibrant period attracts sun-seekers and beach enthusiasts eager to enjoy the beautiful shores of Long Island Sound. July stands out as the most popular month, offering warm temperatures in the mid-70s to low 80s Fahrenheit, superb for outdoor activities such as swimming, fishing, and exploring the local parks.

During this summer season, visitors can immerse themselves in the lively option, attend local events, or simply relax by the beach while savoring fresh seafood from nearby eateries. The abundance of sunshine and longer days make it an ideal time for sightseeing and enjoying the scenic beauty of the area.

For those seeking a more budget-friendly experience, consider planning your visit in December. While this is the low season, it offers a unique charm with fewer crowds and the beauty of winter landscapes. Enjoy peaceful walks along the coast or cozy evenings in a rental, without the hustle and bustle of peak tourist activity.
How early should I book a Orient Point vacation rental?
Book your Orient Point vacation rental 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 Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Orient Point, New York, United States of America?
In Orient Point, visitors can enjoy a range of attractions that highlight its natural beauty and maritime charm. One of the main draws is the Orient Point Lighthouse, which provides picturesque views and a glimpse into the area's nautical history. The nearby Orient Beach State Park offers sandy shores and scenic walking trails, superb for outdoor enthusiasts and families looking to relax by the water.

The local vineyards, such as those in the North Fork region, are also popular for wine tasting and tours, providing a great experience for visitors interested in local wines. Additionally, the quaint atmosphere of Orient Point is complemented by its proximity to the ferry terminal, which connects to Shelter Island and the Hamptons, allowing for easy day trips.

For those interested in fishing or boating, the waters surrounding Orient Point are ideal, with various charter services available.
Can I change or cancel my Orient Point home rental booking on Vrbo?
To find Orient Point vacation rentals with free cancellation, just use Vrbo'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". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Orient Point vacation rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing 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 favorites, and build the perfect itinerary together.

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