Orient holiday rentals

We found 3,130 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:6 Nov - 13 Nov

Dining
Living area
Living area
Exterior
Exceptional
(9 reviews)

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

Orient

8% off
AU$16,973
for 7 nights, 1 room
AU$2,425 per night
includes taxes & fees
Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach
Interior
Exterior
Dining
Living area
Exceptional
(67 reviews)

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

Westbrook

8% off
AU$9,947
for 7 nights, 1 home
AU$1,421 per night
includes taxes & fees
Brand New, Villa Je t’aime, Across the Street from the beach, Sleeps 6 adults
Beach
Exterior
Living area
Private kitchen
Wonderful
(58 reviews)

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

Old Lyme

8% off
AU$3,598
for 7 nights, 1 cottage
AU$514 per night
includes taxes & fees
2bdr Beachfront; 11A first floor; Old Colony Beach, Old Lyme CT
Chef kitchen with breakfast area on 2nd floor
Dining table and picnic table
water view
Main Entrance
Heated pool with gorgeous water and natural wetland view
Exceptional
(35 reviews)

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

Southampton

8% off
AU$12,320
for 7 nights, 1 home
AU$1,760 per night
includes taxes & fees
Luxurious Waterfront Retreat in Southampton: Breathtaking Views, Pool, and More!
Private kitchen
Pool
Exterior
Dining
Exceptional
(5 reviews)

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

Hampton Bays

8% off
AU$14,369
for 7 nights, 1 home
AU$2,053 per night
includes taxes & fees
Newly Built Hamptons House, Pool, Beach Access + Easy Access of Montauk Highway
The Harbor
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$11,900
for 7 nights, 1 home
AU$1,700 per night
includes taxes & fees
Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
Living room looking into Kitchen
Exterior
Living room with Queen size pullout Bed
Private backyard to enjoy grilling, Cornhole or toasting smores over campfire
Exceptional
(48 reviews)

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

Niantic

7% off
AU$2,059
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
Spacious Main Floor Living room
Exterior
Pool
Large Dining/Kitchen Space
Exceptional
(11 reviews)

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

Southold

8% off
AU$14,063
for 7 nights, 1 home
AU$2,009 per night
includes taxes & fees
New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!
Lower deck With Pool, 9 Loungers, plus 6 pool-chairs. Upper deck dining seats 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$14,365
for 7 nights, 1 home
AU$2,052 per night
includes taxes & fees
Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool
Parlor by fireplace
Inner Hall
Entry Hall
Whitefield Rock and rear view of Ludington House (Whitefield Suite is at left)
Exceptional
(20 reviews)

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

Old Lyme

10% off
AU$21,110
for 7 nights, 1 home
AU$3,016 per night
includes taxes & fees
Ludington House, Historic CT Shoreline Mansion filled with luxury and antiques
Exterior
Terrace/patio
Living area
Living area
Exceptional
(8 reviews)

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

Water Mill

8% off
AU$55,087
for 7 nights, 1 home
AU$7,870 per night
includes taxes & fees
Stunning fall sunsets, coveted location on Mecox Bay - recently furnished
Living area
Pool
Dining
Terrace/patio
Exceptional
(16 reviews)

PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

East Hampton

8% off
AU$23,326
for 7 nights, 1 home
AU$3,332 per night
includes taxes & fees
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
Interior
Living area
Exterior detail
Dining
Exceptional
(34 reviews)

Cottage near the beach

Niantic

7% off
AU$2,476
for 7 nights, 1 cottage
AU$354 per night
includes taxes & fees
Cottage near the beach
Dining
Living area
Living area
Beach
Exceptional
(25 reviews)

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

Niantic

11% off
AU$4,760
for 7 nights, 1 home
AU$680 per night
includes taxes & fees
PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS
living room
Dining
Pool
outdoor shower
Exceptional
(60 reviews)

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

Southampton

8% off
AU$19,879
for 7 nights, 1 home
AU$2,840 per night
includes taxes & fees
Southampton Village Renovated Sun-filled Charming Home, Heated Salt water Pool
Bedroom 2
Interior
Fully stocked kitchen - coffee, tea, sugar, creamer, pantry staples
Exterior detail
Exceptional
(32 reviews)

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

Waterford

8% off
AU$3,230
for 7 nights, 1 cottage
AU$461 per night
includes taxes & fees
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Exterior
Outdoor dining
More vineyard views
Living area
Exceptional
(24 reviews)

Vineyard View, Bike to the Most Beautiful Beach

Mattituck

8% off
AU$9,894
for 7 nights, 1 home
AU$1,413 per night
includes taxes & fees
Vineyard View, Bike to the Most Beautiful Beach
Exterior
Living area
Private kitchen
Living area
Exceptional
(29 reviews)

Incredible Beachfront Home w/ Private Beach!

Mattituck

7% off
AU$5,246
for 7 nights, 1 cottage
AU$749 per night
includes taxes & fees
Incredible Beachfront Home w/ Private Beach!
Interior
Interior
Exterior detail
Room
Exceptional
(139 reviews)

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

Old Saybrook

8% off
AU$5,232
for 7 nights, 1 home
AU$747 per night
includes taxes & fees
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
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$3,788
for 7 nights, 1 cottage
AU$541 per night
includes taxes & fees
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Living/dining space
Facade
Zepherine Drouhin, c. 1868 French thornless rose cultivar famed for its scent
Front yard closeup
Exceptional
(22 reviews)

Private Hamptons cottage in ideal Amagansett location

Amagansett

8% off
AU$7,608
for 7 nights, 1 cottage
AU$1,087 per night
includes taxes & fees
Private Hamptons cottage in ideal Amagansett location
local marinas
Saybrook Point Cottage
Living Room
Park like grounds
Exceptional
(143 reviews)

Saybrook Point Cottage - Charming and Private

Old Saybrook

15% off
AU$2,170
for 7 nights, 1 cottage
AU$310 per night
includes taxes & fees
Saybrook Point Cottage - Charming and Private
Main living room and dining room
Dining
Interior
Interior
Exceptional
(27 reviews)

9BR Sag Harbor PRIVATE w/ Pool-Tennis- B-ball- HotTub

Sag Harbor

8% off
AU$20,543
for 7 nights, 1 home
AU$2,935 per night
includes taxes & fees
9BR Sag Harbor PRIVATE w/ Pool-Tennis- B-ball- HotTub
Dining area
Large pool heated pool
Kitchen
Exterior
Exceptional
(20 reviews)

Charming, spacious 3 bedroom, 3 bath East Hampton Springs house

East Hampton

7% off
AU$7,294
for 7 nights, 1 home
AU$1,042 per night
includes taxes & fees
Charming, spacious 3 bedroom, 3 bath East Hampton Springs house
  • 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)
  • 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)
  • Elizabeth A. Morton National Wildlife Refuge (11 mi / 17.7 km)
  • LongHouse Reserve (12.1 mi / 19.5 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 most popular type of holiday home accommodation in Orient?
Based on our research, houses are the most sought-after property type in Orient. But as you might expect, everyone's idea of the perfect 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?
The average price for a holiday home in Orient is based on a number of factors, including length of stay, season and property type. Whether you're in search of a sprawling villa with space for extended family or a cosy cabin for just you and your sweetheart, just add your travel dates to find stays with unbeatable value.
How much does it cost to rent a beach house in Orient?
The average price for a holiday home by the beach in Orient depends on when you're going and the size and style of property you're searching for. You can find prices easily and quickly on Stayz by entering your preferred travel dates and destination. Then use the filters to pick the number of bedrooms and amenities essential to you, like WiFi, air conditioning and a pool.
What are popular home amenities in Orient?
Some of the most popular home amenities people look for in Orient include a barbecue grill, a beach view and an ocean view. Whether you're hitting the road with family, your besties or even pets, Stayz holiday homes have the best amenities for fun and relaxation with your loved ones.
What are the top attractions for families in Orient?
Keep your kids entertained at these leading family-friendly attractions in Orient:
  • 67 Steps Beach
  • Orient Beach State Park
  • Railroad Museum of Long Island
Are there holiday homes with WiFi in Orient?
Orient has 10 holiday homes with WiFi, so you can stay connected when you're away. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movie blockbusters to sending emails, these Stayz homes will keep you online.
How old do you have to be to rent a holiday home in Orient?
We advise checking with the Orient holiday home you're considering on Stayz as the minimum age varies. However, it's normally 16, 18 or 21.
How long can I rent a holiday home in Orient for?
How long you can book a holiday home in Orient varies according to the property. Simply enter your preferred travel dates to see a list of options offering extended stays. With a range of amenities such as kitchens and air conditioning, as well as some offering weekly or monthly discounts, you're sure to find somewhere just right to call your home away from home in Orient.