Orient holiday homes

We found 3,083 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:18 Dec - 25 Dec

Pool
Living area
Living area
Exterior
Exceptional
(12 reviews)

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

Orient

7% off
NZ$22,793
for 7 nights, 1 room
NZ$3,256 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
NZ$4,445
for 7 nights, 1 cottage
NZ$635 per night
includes taxes & fees
2bdr Beachfront; 11A first floor; Old Colony Beach, Old Lyme CT
Pool
Dining
Private kitchen
Pool
Exceptional
(6 reviews)

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

Hampton Bays

8% off
NZ$17,652
for 7 nights, 1 home
NZ$2,522 per night
includes taxes & fees
Newly Built Hamptons House, Pool, Beach Access + Easy Access off Montauk Highway
2nd floor deck with additional dining and leisure seating.
Dining table and picnic table water view
Heated pool with gorgeous water and natural wetland view
Main Entrance
Exceptional
(38 reviews)

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

Southampton

8% off
NZ$18,868
for 7 nights, 1 home
NZ$2,695 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
Main Kitchen/Dining/Living Room
Main Kitchen/Dining/Living Room
Exceptional
(9 reviews)

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

Niantic

8% off
NZ$10,591
for 7 nights, 1 home
NZ$1,513 per night
includes taxes & fees
Luxury Beach House in Giants Neck Beach - Perfect for Large Families!
Patio
Private kitchen
Dining Room
The Harbor
Exceptional
(102 reviews)

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

Sag Harbor

15% off
NZ$15,736
for 7 nights, 1 home
NZ$2,248 per night
includes taxes & fees
Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
Exterior
Terrace/patio
Living area
Living area
Excellent
(10 reviews)

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

Water Mill

8% off
NZ$67,957
for 7 nights, 1 home
NZ$9,708 per night
includes taxes & fees
Stunning fall sunsets, coveted location on Mecox Bay - recently furnished
Exterior
Pool
Master bedroom with ensuite bathroom
Outdoor dining
Exceptional
(28 reviews)

Spacious New 4 Bedroom Home With Pool on 2 Acre Property

Peconic

8% off
NZ$15,220
for 7 nights, 1 home
NZ$2,174 per night
includes taxes & fees
Spacious New 4 Bedroom Home With Pool on 2 Acre Property
Outdoor dining
Living area
Exterior detail
Dining
Exceptional
(39 reviews)

Cottage near the beach

Niantic

7% off
NZ$3,038
for 7 nights, 1 cottage
NZ$434 per night
includes taxes & fees
Cottage near the beach
park-like grounds
Living area
An elegant dining room (to 10 ppl, joins kitchen +8 and outdoor dining +10,)
Lower deck With Pool, 9 Loungers, plus 6 pool-chairs. Upper deck dining seats 10
Exceptional
(26 reviews)

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

Southampton

30% off
NZ$17,647
for 7 nights, 1 home
NZ$2,521 per night
includes taxes & fees
Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool
Interior
Beach
Living area
Room
Exceptional
(28 reviews)

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

Niantic

11% off
NZ$6,883
for 7 nights, 1 home
NZ$983 per night
includes taxes & fees
PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS
Exterior
Outdoor dining
Living area
Welcome to Vineyard View
Exceptional
(26 reviews)

Vineyard View, Bike to the Most Beautiful Beach

Mattituck

8% off
NZ$12,715
for 7 nights, 1 home
NZ$1,816 per night
includes taxes & fees
Vineyard View, Bike to the Most Beautiful Beach
Living area
Living area
Interior
Pool
Exceptional
(14 reviews)

PERFECT GETAWAY East Hampton / Sag Harbor

East Hampton

7% off
NZ$13,830
for 7 nights, 1 home
NZ$1,976 per night
includes taxes & fees
PERFECT GETAWAY East Hampton / Sag Harbor
Pool
Dining
kitchen
living room
Exceptional
(60 reviews)

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

Southampton

8% off
NZ$24,583
for 7 nights, 1 home
NZ$3,512 per night
includes taxes & fees
Southampton Village Renovated Sun-filled Charming Home, Heated Salt water Pool
Fully stocked kitchen - coffee, tea, sugar, creamer, pantry staples
Interior
Bedroom 2
Exterior detail
Exceptional
(33 reviews)

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

Waterford

8% off
NZ$3,348
for 7 nights, 1 cottage
NZ$478 per night
includes taxes & fees
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Large Dining/Kitchen Space
Exterior
Pool
Spacious Main Floor Living room
Exceptional
(11 reviews)

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

Southold

7% off
NZ$16,305
for 7 nights, 1 home
NZ$2,329 per night
includes taxes & fees
New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!
Kitchen walks out to covered porch across length of entire back
Featured as one of most beautiful poolsides
Hydrangeas blooming all summer.these are the August bloomers
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
NZ$31,971
for 7 nights, 1 home
NZ$4,567 per night
includes taxes & fees
IN THE ViILLAGE OF SOUTHAMPTON POOL,TENNIS,PICKLEBALL COURTS BEACH CHAIRS&BIKES
Living area
Exterior detail
Interior
Exceptional
(11 reviews)

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

Sag Harbor

8% off
NZ$19,194
for 7 nights, 1 cottage
NZ$2,742 per night
includes taxes & fees
Secluded Sag Harbor Cottage - HUGE pool and separate bungalow/pool house
Exterior
Living area
Living area
Property grounds
Exceptional
(29 reviews)

Incredible Beachfront Home w/ Private Beach!

Mattituck

7% off
NZ$6,562
for 7 nights, 1 cottage
NZ$937 per night
includes taxes & fees
Incredible Beachfront Home w/ Private Beach!
Dining
Pool
Terrace/patio
Private kitchen
Exceptional
(17 reviews)

PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

East Hampton

8% off
NZ$28,904
for 7 nights, 1 home
NZ$4,129 per night
includes taxes & fees
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
From the bedroom
Facade
Living/dining space
Zepherine Drouhin, c. 1868 French thornless rose cultivar famed for its scent
Exceptional
(23 reviews)

Private Hamptons cottage in ideal Amagansett location

Amagansett

8% off
NZ$9,539
for 7 nights, 1 cottage
NZ$1,363 per night
includes taxes & fees
Private Hamptons cottage in ideal Amagansett location
Interior
Terrace/patio
Interior
Dining
Exceptional
(19 reviews)

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

Greenport

8% off
NZ$8,386
for 7 nights, 1 home
NZ$1,198 per night
includes taxes & fees
Entire, new, roomy, village beach house close to beach, park, and town center
The front of the house
A view of the house and pool from the creek, looking south
The front porch
The kitchen is all glass with a spectacular view of the pool and creek
Exceptional
(20 reviews)

Unique Southold waterfront luxury home with heated pool on Long Creek

Southold

7% off
NZ$7,797
for 7 nights, 1 home
NZ$1,114 per night
includes taxes & fees
Unique Southold waterfront luxury home with heated pool on Long Creek
Our porch is furnished with plants for a Gilded Age feel
Every season brings special flower blooms
Attention to details and fine workmanship was a sign of wealth both then and now
Second living room once called the "parlour"
Exceptional
(37 reviews)

Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach

Greenport

12% off
NZ$14,360
for 7 nights, 1 home
NZ$2,051 per night
includes taxes & fees
Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • 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)
  • Peconic Bay Winery (12.4 mi / 19.9 km)
  • Wolffer Estates Vineyard (13.5 mi / 21.7 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)
  • Westbrook Town Beach (12.5 mi / 20 km)
  • Hole-in-the-Wall Beach (13.8 mi / 22.2 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 Bookabach.
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 Bookabach?
Bookabach 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?
Bookabach 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 Bookabach, 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 Bookabach?
To find Orient holiday rentals with free cancellation, just use Bookabach'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, Bookabach 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 Bookabach?
Bookabach'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 Bookabach 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. Bookabach offers something for every taste and budget, from affordable homes in Orient to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.