Orient Point holiday rentals

We found 2,122 holiday rentals — enter your dates for availability
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:13 Nov - 20 Nov

Pool
Living area
Dining
Living area
Exceptional
(10 reviews)

Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach

Orient

8% off
AU$16,951
for 7 nights, 1 room
AU$2,422 per night
includes taxes & fees
Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach
Exterior detail
Exterior
Beach
Private kitchen
Wonderful
(58 reviews)

2bdr Beachfront; 11A first floor; Old Colony Beach, Old Lyme CT

Old Lyme

8% off
AU$3,593
for 7 nights, 1 cottage
AU$513 per night
includes taxes & fees
2bdr Beachfront; 11A first floor; Old Colony Beach, Old Lyme CT
Main Kitchen/Dining/Living Room
Main Kitchen/Dining/Living Room
Main Kitchen/Dining/Living Room
Relaxing Pond on property
Exceptional
(8 reviews)

Luxury Beach House in Giants Neck Beach - Perfect for Large Families!

Niantic

8% off
AU$8,896
for 7 nights, 1 home
AU$1,271 per night
includes taxes & fees
Luxury Beach House in Giants Neck Beach - Perfect for Large Families!
Kitchen
Front of House
Side of House with outdoor shower to rinse off from the beach.
Living Room
Exceptional
(11 reviews)

4 BED/2 BATH -PRIVATE BEACH: OLD COLONY

Old Lyme

7% off
AU$6,691
for 7 nights, 1 home
AU$956 per night
includes taxes & fees
4 BED/2 BATH -PRIVATE BEACH: OLD COLONY
Private backyard to enjoy grilling, Cornhole or toasting smores over campfire
Exterior
Living room looking into Kitchen
Living room with Queen size pullout Bed
Exceptional
(49 reviews)

Beach Ready 3-bdrm house, Short Walk to Private Beach and Park, Lots of Parking

Niantic

7% off
AU$2,056
for 7 nights, 1 home
AU$294 per night
includes taxes & fees
Beach Ready 3-bdrm house, Short Walk to Private Beach and Park, Lots of Parking
Dining Room
Private kitchen
Exterior
Patio
Exceptional
(97 reviews)

Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town

Sag Harbor

16% off
AU$11,885
for 7 nights, 1 home
AU$1,698 per night
includes taxes & fees
Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
Spacious Main Floor Living room
Exterior
Large Dining/Kitchen Space
Exterior
Exceptional
(11 reviews)

New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!

Southold

8% off
AU$13,788
for 7 nights, 1 home
AU$1,970 per night
includes taxes & fees
New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!
view from living room towards pool, outdoor dining
aerial view
living room
master bedroom with balcony
Exceptional
(7 reviews)

Everything in Hamptons special discount available for weekly and monthly renters

Water Mill

17% off
AU$81,733
for 7 nights, 1 home
AU$11,676 per night
includes taxes & fees
Everything in Hamptons special discount available for weekly and monthly renters
Entry Hall
Inner Hall
Whitefield Rock and rear view of Ludington House (Whitefield Suite is at left)
Outdoor dining
Exceptional
(20 reviews)

Ludington House, Historic CT Shoreline Mansion filled with luxury and antiques

Old Lyme

10% off
AU$21,082
for 7 nights, 1 home
AU$3,012 per night
includes taxes & fees
Ludington House, Historic CT Shoreline Mansion filled with luxury and antiques
Terrace/patio
Pool
Living area
Private kitchen
Exceptional
(16 reviews)

PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

East Hampton

8% off
AU$23,294
for 7 nights, 1 home
AU$3,328 per night
includes taxes & fees
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
Living area
Dining
Room
Private kitchen
Exceptional
(18 reviews)

Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe

Cutchogue

8% off
AU$6,984
for 7 nights, 1 cottage
AU$998 per night
includes taxes & fees
Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe
Den
Pool
Front Porch
Living room w/ screen porch beyond
Exceptional
(46 reviews)

Quiet Family Friendly Hideaway With Pool And Poolhouse

East Hampton

8% off
AU$18,863
for 7 nights, 1 home
AU$2,695 per night
includes taxes & fees
Quiet Family Friendly Hideaway With Pool And Poolhouse
Living area
Living area
Exterior
Dining
Exceptional
(25 reviews)

PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS

Niantic

11% off
AU$4,754
for 7 nights, 1 home
AU$679 per night
includes taxes & fees
PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS
Kitchen from dining room
Master bed onto balcony
Dining room from kitchen
Hall into sitting room
Exceptional
(34 reviews)

Bohemian Old Life Saving Station with Beach & Pool

East Marion

8% off
AU$13,972
for 7 nights, 1 home
AU$1,996 per night
includes taxes & fees
Bohemian Old Life Saving Station with Beach & Pool
8 Hands Farm
Crushpad of Charming Boutique vineyard nearby-  Rosehill
Kitchen Fireplace Eat In Kitchen & in the next photo includes new kitchen table
Living area
Exceptional
(30 reviews)

North Fork Ranch Home in Wine Country with Pool- 2 Beaches 5 Min Walk

Laurel

9% off
AU$3,977
for 7 nights, 1 home
AU$568 per night
includes taxes & fees
North Fork Ranch Home in Wine Country with Pool- 2 Beaches 5 Min Walk
Private kitchen
Living area
Exterior
Living area
Exceptional
(29 reviews)

Incredible Beachfront Home w/ Private Beach!

Mattituck

7% off
AU$5,239
for 7 nights, 1 cottage
AU$748 per night
includes taxes & fees
Incredible Beachfront Home w/ Private Beach!
Exterior
Outdoor dining
Welcome to Vineyard View
More vineyard views
Exceptional
(24 reviews)

Vineyard View, Bike to the Most Beautiful Beach

Mattituck

8% off
AU$9,881
for 7 nights, 1 home
AU$1,412 per night
includes taxes & fees
Vineyard View, Bike to the Most Beautiful Beach
Living area
Private kitchen
Living area
Exterior
Exceptional
(34 reviews)

Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

Cutchogue

8% off
AU$3,783
for 7 nights, 1 cottage
AU$540 per night
includes taxes & fees
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Pool
Living area
Interior
Exceptional
(10 reviews)

Just Posted for Summer 2026! SECLUDED SAG HARBOR COTTAGE w/ HUGE POOL

Sag Harbor

8% off
AU$20,618
for 7 nights, 1 cottage
AU$2,945 per night
includes taxes & fees
Just Posted for Summer 2026! SECLUDED SAG HARBOR COTTAGE w/ HUGE POOL
Exterior detail
Interior
Interior
Exterior detail
Exceptional
(140 reviews)

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Old Saybrook

8% off
AU$4,901
for 7 nights, 1 home
AU$700 per night
includes taxes & fees
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Dining
Private kitchen
Property grounds
Room
Exceptional
(14 reviews)

Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country

Southold

8% off
AU$6,453
for 7 nights, 1 home
AU$922 per night
includes taxes & fees
Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
Fully stocked kitchen - coffee, tea, sugar, creamer, pantry staples
Interior
Entryway
Bedroom 2
Exceptional
(32 reviews)

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Waterford

8% off
AU$2,818
for 7 nights, 1 cottage
AU$403 per night
includes taxes & fees
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
living area with gas fire leads onto the deck
huge swimming pool and deck surrounded by trees
kitchen backs onto the garden
Queen bedroom leading onto deck.  Ensuite bathroom, walk-in closet and tv.
Exceptional
(53 reviews)

Large heated pool, games room, private bay beach access, gardens, kid-friendly

East Hampton

8% off
AU$7,195
for 7 nights, 1 home
AU$1,028 per night
includes taxes & fees
Large heated pool, games room, private bay beach access, gardens, kid-friendly
Interior
Terrace/patio
Living area
Pool
Exceptional
(11 reviews)

Large East Hampton house with heated pool and home gym - fully fenced

East Hampton

12% off
AU$17,789
for 7 nights, 1 home
AU$2,541 per night
includes taxes & fees
Large East Hampton house with heated pool and home gym - fully fenced
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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)
  • Croteaux Vineyards (12.3 mi / 19.8 km)
  • Noyac Golf Club (13.1 mi / 21.1 km)
  • Raphael Winery (13.6 mi / 21.9 km)
  • Pindar Vineyards (13.9 mi / 22.4 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)
  • Sunset Beach (8.1 mi / 13 km)
  • Crescent Beach (8.4 mi / 13.5 km)
  • Attawan Beach (10.8 mi / 17.3 km)
  • Harvey's Beach (11.2 mi / 18.1 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.

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