Orient holiday rentals

We found 3,079 holiday rentals — enter your dates for availability
Discover a selection of 17 homes and other holiday rentals in Orient that are perfect for your trip. Holiday homes provide the amenities that you need and want for you and your friends, family or even pets, such as Wi-Fi and cable 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

Showing deals for:25 Dec - 1 Jan

Pool
Living area
Exterior
Living area
Exceptional
(12 reviews)

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

Orient

8% off
AU$17,088
for 7 nights, 1 room
AU$2,441 per night
includes taxes & fees
Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach
Exterior
Exterior
Exterior detail
Beach
Wonderful
(59 reviews)

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

Old Lyme

8% off
AU$3,622
for 7 nights, 1 cottage
AU$517 per night
includes taxes & fees
2bdr Beachfront; 11A first floor; Old Colony Beach, Old Lyme CT
Room
Exterior
Living area
Dining
Exceptional
(68 reviews)

Brand New, Villa Je t’aime, Across the Street from the beach, Sleeps 6 adults

Westbrook

8% off
AU$10,014
for 7 nights, 1 home
AU$1,431 per night
includes taxes & fees
Brand New, Villa Je t’aime, Across the Street from the beach, Sleeps 6 adults
2nd floor deck with additional dining and leisure seating.
Dining table and picnic table water view
Main Entrance
Heated pool with gorgeous water and natural wetland view
Exceptional
(38 reviews)

Luxurious Waterfront Retreat in Southampton: Breathtaking Views, Pool, and More!

Southampton

5% off
AU$20,781
for 7 nights, 1 home
AU$2,969 per night
includes taxes & fees
Luxurious Waterfront Retreat in Southampton: Breathtaking Views, Pool, and More!
Main Kitchen/Dining/Living Room
Main Kitchen/Dining/Living Room
Relaxing Pond on property
Main Kitchen/Dining/Living Room
Exceptional
(9 reviews)

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

Niantic

8% off
AU$7,971
for 7 nights, 1 home
AU$1,139 per night
includes taxes & fees
Luxury Beach House in Giants Neck Beach - Perfect for Large Families!
Pool
Pool
Terrace/patio
Outdoor dining
Exceptional
(6 reviews)

Newly Built Hamptons House, Pool, Beach Access + Easy Access off Montauk Highway

Hampton Bays

8% off
AU$14,921
for 7 nights, 1 home
AU$2,132 per night
includes taxes & fees
Newly Built Hamptons House, Pool, Beach Access + Easy Access off Montauk Highway
Dining Room
Private kitchen
Exterior
The Harbor
Exceptional
(103 reviews)

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

Sag Harbor

16% off
AU$12,114
for 7 nights, 1 home
AU$1,731 per night
includes taxes & fees
Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
Interior
Living area
Exterior detail
Dining
Exceptional
(39 reviews)

Cottage near the beach

Niantic

7% off
AU$2,493
for 7 nights, 1 cottage
AU$356 per night
includes taxes & fees
Cottage near the beach
kitchen with large island and breakfast table
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$82,398
for 7 nights, 1 home
AU$11,771 per night
includes taxes & fees
Everything in Hamptons special discount available for weekly and monthly renters
Master bedroom with ensuite bathroom
Pool
Dining Room with seating for Ten
Exterior
Exceptional
(28 reviews)

Spacious New 4 Bedroom Home With Pool on 2 Acre Property

Peconic

8% off
AU$12,122
for 7 nights, 1 home
AU$1,732 per night
includes taxes & fees
Spacious New 4 Bedroom Home With Pool on 2 Acre Property
Exterior
Terrace/patio
Living area
Pool
Excellent
(10 reviews)

Stunning fall sunsets, coveted location on Mecox Bay - recently furnished

Water Mill

8% off
AU$55,460
for 7 nights, 1 home
AU$7,923 per night
includes taxes & fees
Stunning fall sunsets, coveted location on Mecox Bay - recently furnished
Interior
Beach
Living area
Room
Exceptional
(29 reviews)

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

Niantic

12% off
AU$6,593
for 7 nights, 1 home
AU$942 per night
includes taxes & fees
PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS
More vineyard views
Outdoor dining
Exterior
Living area
Exceptional
(26 reviews)

Vineyard View, Bike to the Most Beautiful Beach

Mattituck

8% off
AU$9,961
for 7 nights, 1 home
AU$1,423 per night
includes taxes & fees
Vineyard View, Bike to the Most Beautiful Beach
Living area
Living area
Property grounds
Exterior
Exceptional
(29 reviews)

Incredible Beachfront Home w/ Private Beach!

Mattituck

7% off
AU$5,281
for 7 nights, 1 cottage
AU$754 per night
includes taxes & fees
Incredible Beachfront Home w/ Private Beach!
An elegant dining room (to 10 ppl, joins kitchen +8 and outdoor dining +10,)
Living area
Front entrance, park-like grounds
park-like grounds
Exceptional
(26 reviews)

Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool

Southampton

30% off
AU$14,462
for 7 nights, 1 home
AU$2,066 per night
includes taxes & fees
Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool
Pool
Living area
Living area
Interior
Exceptional
(15 reviews)

PERFECT GETAWAY East Hampton / Sag Harbor

East Hampton

8% off
AU$10,834
for 7 nights, 1 home
AU$1,548 per night
includes taxes & fees
PERFECT GETAWAY East Hampton / Sag Harbor
Pool
Living area
Interior
Exterior detail
Exceptional
(11 reviews)

Secluded Sag Harbor Cottage - HUGE pool and separate bungalow/pool house

Sag Harbor

8% off
AU$14,777
for 7 nights, 1 cottage
AU$2,111 per night
includes taxes & fees
Secluded Sag Harbor Cottage - HUGE pool and separate bungalow/pool house
Living/dining space
Facade
Front yard closeup
From the bedroom
Exceptional
(23 reviews)

Private Hamptons cottage in ideal Amagansett location

Amagansett

8% off
AU$7,768
for 7 nights, 1 cottage
AU$1,110 per night
includes taxes & fees
Private Hamptons cottage in ideal Amagansett location
Exterior
Dining
Dining
Living area
Exceptional
(47 reviews)

Sea Salt Air Changes Everything - ⭐️Stroll to Private Association Beach⭐️

Westbrook

8% off
AU$4,559
for 7 nights, 1 home
AU$651 per night
includes taxes & fees
Sea Salt Air Changes Everything - ⭐️Stroll to Private Association Beach⭐️
Kitchen walks out to covered porch across length of entire back
Featured as one of most beautiful poolsides
Couches on covered porch and outdoor dining table for 8
Living area on 1st floor with wood burning fireplace
Exceptional
(7 reviews)

IN THE ViILLAGE OF SOUTHAMPTON POOL,TENNIS,PICKLEBALL COURTS BEACH CHAIRS&BIKES

Southampton

8% off
AU$26,273
for 7 nights, 1 home
AU$3,753 per night
includes taxes & fees
IN THE ViILLAGE OF SOUTHAMPTON POOL,TENNIS,PICKLEBALL COURTS BEACH CHAIRS&BIKES
Pool
Dining
outdoor shower
kitchen
Exceptional
(60 reviews)

Southampton Village Renovated Sun-filled Charming Home, Heated Salt water Pool

Southampton

8% off
AU$20,014
for 7 nights, 1 home
AU$2,859 per night
includes taxes & fees
Southampton Village Renovated Sun-filled Charming Home, Heated Salt water Pool
Private kitchen
Terrace/patio
Interior
Interior
Exceptional
(20 reviews)

Entire, new, roomy, village beach house close to beach, park, and town center

Greenport

8% off
AU$6,728
for 7 nights, 1 home
AU$961 per night
includes taxes & fees
Entire, new, roomy, village beach house close to beach, park, and town center
Private kitchen
Property grounds
Dining
Terrace/patio
Exceptional
(5 reviews)

Beautiful 4 bedroom house with tranquil gardens close to bay beaches.

East Hampton

8% off
AU$10,412
for 7 nights, 1 home
AU$1,487 per night
includes taxes & fees
Beautiful 4 bedroom house with tranquil gardens close to bay beaches.
Private kitchen
Pool
Living area
Dining
Wonderful
(18 reviews)

PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

East Hampton

8% off
AU$23,484
for 7 nights, 1 home
AU$3,355 per night
includes taxes & fees
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

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  • More quality time

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Take in the waterfront beauty of Orient

Enjoy the museums and other features of Orient. This scenic city is known for its island views, beaches and golfing. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Sightseeing in and around Orient

Do you want to find attractions to see in the area? Venture out of your cosy holiday rental and experience everything that makes Orient a one-of-a-kind holiday spot. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Kontokosta Winery (3.6 mi / 5.8 km)
  • Raphael Winery (10.9 mi / 17.5 km)
  • Pindar Vineyards (11.2 mi / 18 km)
  • Bedell Cellars (11.5 mi / 18.5 km)
  • LongHouse Reserve (12.1 mi / 19.5 km)
  • Peconic Bay Winery (12.4 mi / 19.9 km)

Exploring the natural landscape of Orient

Whether you're an active traveller or just want to appreciate the scenery, Orient is a great place to spend some time outside. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Orient Point County Park (3.6 mi / 5.8 km)
  • 67 Steps Beach (3.7 mi / 5.9 km)
  • Sunset Beach (5.5 mi / 8.9 km)
  • Harvey's Beach (10.5 mi / 16.8 km)
  • LongHouse Reserve (12.1 mi / 19.5 km)
  • Westbrook Town Beach (12.5 mi / 20 km)

Travelling to and around Orient

The nearest airport is in East Hampton, NY (HTO), located 12.6 mi (20.3 km) from the city centre. If you're unable to find a flight that fits your schedule, you can also fly into Fishers Island, NY (FID-Elizabeth Field), which is 16.3 mi (26.2 km) away.

Frequently asked questions

What is the best area to stay in Orient when booking a holiday rental?
When considering a holiday rental in Orient, New York, a popular area to stay is along the scenic waterfront. This charming neighbourhood offers a tranquil atmosphere, superb for those looking to unwind and enjoy the natural beauty of the region. Here, you can find a selection of properties, including quaint cottages and more modern homes, providing a variety of choices for different preferences.A highlight of staying in this area is the proximity to Orient Beach State Park, where visitors can relish stunning views of Gardiners Bay and engage in outdoor activities such as swimming and hiking. Additionally, the historic Orient Point Lighthouse stands as an iconic landmark, offering picturesque views and a glimpse into the area's maritime history.
Where are the best areas for renting a beach house in Orient?
For renting a beach house in Orient, the idyllic shoreline along Orient Beach is a prime location. This area offers beautiful waterfront properties that provide direct access to sandy beaches and stunning views across the Long Island Sound. Many beach houses in this vicinity come equipped with amenities such as private decks or patios, outdoor grills, and spacious living areas, great for families or groups seeking a relaxing getaway.Additionally, the nearby Orient State Park features scenic walking trails and picnic areas, allowing visitors to immerse themselves in nature while enjoying the coastal surroundings. Rentals in this area often include features like fully stocked kitchens, laundry facilities, and sometimes even outdoor showers to rinse off after a day at the beach. The charming local community also offers quaint shops and eateries, adding to the appeal of a beach house rental in Orient.
What is the most popular type of holiday rental accomodation in Orient?
In Orient, holiday houses are the most popular type of holiday rental, with around 22 available throughout the charming area. These properties often feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups seeking a comfortable stay. Many holiday houses also include outdoor spaces such as gardens or patios, great for enjoying the serene surroundings. Additionally, several cottages and villas can be found, providing alternative options for those looking for a more quaint or luxurious experience.
Are there any family house rentals in Orient?
In Orient, New York, there are several family-friendly house rentals available, with around 11 options to choose from. This charming area boasts picturesque scenery and a peaceful atmosphere, making it ideal for families seeking a relaxing getaway. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces that may include gardens or patios for children to enjoy.Visitors can easily access nearby attractions, such as the stunning beaches of Long Island Sound, superb for a day of sun and sand. Additionally, the Orient Point Ferry offers a scenic ride to Shelter Island, enhancing the overall experience for families looking to explore.
Can I rent a holiday home with a pool or hot tub in Orient?
In Orient, New York, there are several holiday homes available for rent that feature pools and hot tubs. This picturesque area, located on the North Fork of Long Island, offers a tranquil escape with its charming coastal scenery and proximity to beautiful beaches. Many of the properties come equipped with private pools, inviting hot tubs, and spacious outdoor areas great for relaxation and entertaining.Travellers can also expect amenities such as fully equipped kitchens, comfortable living spaces, and sometimes additional features like outdoor dining areas and fire pits, creating an ideal setting for family gatherings or romantic getaways.
Are there pet-friendly house rentals in Orient?
In Orient, there are several pet-friendly house rentals available, making it an excellent destination for travellers with furry companions. The area is known for its picturesque landscapes and tranquil atmosphere, allowing for a peaceful retreat. Many of the holiday homes here come equipped with amenities such as spacious backyards, outdoor seating areas, and fully stocked kitchens, great for families or groups.Orient is located near the scenic North Fork of Long Island, providing easy access to beautiful beaches where pets are often welcome. The surrounding areas also feature charming parks and walking trails, ideal for leisurely strolls with your pet.
Are there any remote work holiday rentals in Orient?
In Orient, New York, there are several remote work holiday rentals available, with around 26 options for those looking to combine work and leisure. This charming hamlet, located at the tip of Long Island, offers a peaceful environment with beautiful views of the surrounding waters. Many properties come equipped with essential amenities for remote work, including Wi-Fi and dedicated office spaces featuring desks and chairs, ensuring a productive stay.Travellers can enjoy the tranquillity of the area while being close to local attractions, such as the scenic Orient Beach State Park, which is ideal for relaxation during breaks. The nearby vineyards and quaint shops in the region provide a delightful way to unwind after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Orient?
In Orient, popular holiday rental amenities include kitchens, which are essential for those looking to prepare their own meals, and decks or patios that provide outdoor spaces for relaxation and enjoying the scenic surroundings. Many rentals also feature blenders, making it easy to whip up smoothies or cocktails during your stay. A fireplace is another sought-after amenity, offering warmth and a cosy atmosphere, particularly in cooler months. Additionally, porches or lanais are common, allowing guests to soak in the fresh air while surrounded by the natural beauty of the area.
When is the best time to visit Orient for a holiday rental?
The best time to visit Orient for a holiday rental is during the peak season from June to August, with July being the most popular month. This vibrant time of year attracts visitors eager to enjoy the charming coastal atmosphere and partake in various outdoor activities. With warm temperatures averaging around 25 to 30 degrees Celsius, it's great for beach outings, sailing, and exploring local vineyards.During these summer months, you'll find plenty of opportunities for sightseeing, from the picturesque beaches to the historic lighthouse, all while enjoying the lively local events and festivals that characterise this seaside town. The inviting climate makes it ideal for leisurely walks along the waterfront or indulging in fresh seafood at local eateries.For those looking for a more budget-friendly experience, consider visiting in December. While the temperatures drop to around 0 to 5 degrees Celsius, this quieter time allows for peaceful exploration of the area, including winter strolls and the opportunity to enjoy the festive holiday spirit without the summer crowds.Ultimately, your choice of timing will depend on whether you prefer the bustling energy of summer activities or the tranquil charm of the off-peak season.
Are all fees included in the Orient 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 holiday homes with parking?
Stayz offers a wide selection of holiday homes in Orient 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 holiday homes?
You can find great discounts on holiday homes in Orient 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 holiday home booking on Stayz?
To find Orient 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?
A long-stay holiday home in Orient 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 holiday home?
Book your Orient 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?
Prices for holiday homes in Orient 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 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.