Vacation Rentals in Orient, NY: Compare 10+ Sites & Save

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166 Best Vacation Rentals in Orient (Starting from $118)

BayFront Cottage
BayFront Cottage
Villa
Orient, NY, USA
2.4k from Orient center

Parking, Air Conditioner, Ocean View, View, Internet, Child Friendly

3 Bedrooms6 Guests
New to Booking
$306
Average price / night
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Orient Point Vacation Home Saltwater Pool and Five Bedrooms Book Summer Now
Orient Point Vacation Home Saltwater Pool and Five Bedrooms Book Summer Now
House
Orient Point, NY, 11957, United States
1.3k from Orient center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

5 Bedrooms10 Guests
9.6

Exceptional

5 reviews

$1370
Average price / night
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Lagoon Lodge: North Fork,Charming 3Br, Waterfront
Lagoon Lodge: North Fork,Charming 3Br, Waterfront
House
East Marion, NY, USA
5.7k from Orient center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Beach, Places to stay

3 Bedrooms8 Guests
New to Booking
$550
Average price / night
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Beachfront vacation Dream house in Long Island Sound.
Beachfront vacation Dream house in Long Island Sound.
House
Orient, NY, 11957, United States
1.4k from Orient center

AC, Arcade, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking

4 Bedrooms8 Guests
9.8

Exceptional

61 reviews

$859
Average price / night
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Lavender Bay Breezes - Private Bay Beach Community
Lavender Bay Breezes - Private Bay Beach Community
House
Orient, New York, USA
6.5k from Orient center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Beach, Places to stay, Accessible hotels

4 Bedrooms8 Guests
New to Booking
$312
Average price / night
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Charming Country Home sits on a 3-acre property in Bucolic Orient.
Charming Country Home sits on a 3-acre property in Bucolic Orient.
House
Orient, NY, 11957, United States
1.8k from Orient center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

98 reviews

$637
Average price / night
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Shelter Island Retreat with Outdoor Pool!
Shelter Island Retreat with Outdoor Pool!
House
Shelter Island, NY, USA
7.4k from Orient center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings

5 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1119
Average price / night
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Private Vineyard Estate in Orient Village w Pool / AC / Walk to Beach & Town
Private Vineyard Estate in Orient Village w Pool / AC / Walk to Beach & Town
House
Orient, NY, 11957, United States
1.9k from Orient center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms6 Guests
New to Booking
$1909
Average price / night
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Bright Apartment - half Mi to Greenport Harbor!
Bright Apartment - half Mi to Greenport Harbor!
Apartment
Greenport, NY, USA
7.9k from Orient center

Apartments, Accommodations, Parking, Spa, Lodgings, Vacation rentals, Places to stay, Family

1 Bedroom2 Guests
9.8

Exceptional

14 reviews

$236
Average price / night
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Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home
Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home
House
Orient, NY, 11957, United States
2.2k from Orient center

AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
9.4

Superb

10 reviews

$2299
Average price / night
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Quaint DT Greenport Apt - 2 Mi to Shelter Island!
Quaint DT Greenport Apt - 2 Mi to Shelter Island!
Apartment
Greenport, NY, USA
7.9k from Orient center

Apartments, Accommodations, Parking, Spa, Lodgings, Vacation rentals, Places to stay, Family

1 Bedroom2 Guests
10.0

Exceptional

2 reviews

$208
Average price / night
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Orient Village — Historic Bayfront Cottage — 2025 Season
Orient Village — Historic Bayfront Cottage — 2025 Season
Cottage
Orient, NY, 11957, United States
2.4k from Orient center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

24 reviews

$424
Average price / night
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Charming Greenport Gem 1, 1 Mile to Ferry!
Charming Greenport Gem 1, 1 Mile to Ferry!
Apartment
Greenport, NY, USA
8.1k from Orient center

Apartments, Cheap, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Family

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$118
Average price / night
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1.5 Acre Luxury Escape - Saltwater Pool with Water Views
1.5 Acre Luxury Escape - Saltwater Pool with Water Views
Villa
Orient, NY, 11957, United States
2.6k from Orient center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms12 Guests
10.0

Exceptional

4 reviews

$1127
Average price / night
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Cozy Greenport Cottage
Cozy Greenport Cottage
House
Greenport, NY, USA
8.9k from Orient center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms10 Guests
New to Booking
$559
Average price / night
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Private Getaway - corner Home with rights to private beach - Tip of North Fork
Private Getaway - corner Home with rights to private beach - Tip of North Fork
House
Orient, NY, 11957, United States
2.7k from Orient center

AC, Balcony, Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area

3 Bedrooms8 Guests
9.8

Exceptional

29 reviews

$639
Average price / night
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Modern on 9th
Modern on 9th
House
Greenport, NY, USA
9.3k from Orient center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
New to Booking
$403
Average price / night
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Orient Point Waterfront Home – Private Beach & Stunning Views
Orient Point Waterfront Home – Private Beach & Stunning Views
House
Orient, NY, 11957, United States
2.9k from Orient center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms9 Guests
9.6

Exceptional

60 reviews

$904
Average price / night
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Orient Point Family Waterfront Home
Orient Point Family Waterfront Home
House
Orient, NY, 11957, United States
3.1k from Orient center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms10 Guests
9.6

Exceptional

21 reviews

$1439
Average price / night
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Orient Point Cottage with Private Beach
Orient Point Cottage with Private Beach
House
Orient, NY, 11957, United States
3.1k from Orient center

AC, Dryer, Fireplace, Heater, Internet, Kitchen, Laundry, No Smoking, Pool

2 Bedrooms4 Guests
9.4

Superb

6 reviews

$534
Average price / night
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Serene East End Oasis
Serene East End Oasis
House
Orient, NY, 11957, United States
3.1k from Orient center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub

4 Bedrooms8 Guests
New to Booking
$710
Average price / night
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Gorgeous North Fork Farmhouse with Private Beach Rights
Gorgeous North Fork Farmhouse with Private Beach Rights
House
Orient, NY, 11957, United States
3.2k from Orient center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1475
Average price / night
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The Lane House | Private Beach Escape
The Lane House | Private Beach Escape
House
Orient, NY, 11957, United States
3.2k from Orient center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms8 Guests
9.8

Exceptional

20 reviews

$626
Average price / night
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Gorgeous lakefront retreat
Gorgeous lakefront retreat
House
East Marion, NY, 11939, United States
5.3k from Orient center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, No Smoking, Outdoor Space

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$756
Average price / night
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Idyllic North Fork hideaway! Quiet 3 Bedroom cape in East Marion
Idyllic North Fork hideaway! Quiet 3 Bedroom cape in East Marion
House
East Marion, NY, 11939, United States
5.3k from Orient center

AC, Barbecue, Dryer, Fireplace, Internet, Kitchen, Laundry, No Smoking, Outdoor Space

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$537
Average price / night
Check Availability
Quiet 3BR home in East Marion. Private beach access 3 min walk away.
Quiet 3BR home in East Marion. Private beach access 3 min walk away.
House
East Marion, NY, 11939, United States
5.4k from Orient center

AC, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$649
Average price / night
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Waterfront Bungalow w/ Private Beach on Peconic Bay
Waterfront Bungalow w/ Private Beach on Peconic Bay
House
East Marion, NY, 11939, United States
5.4k from Orient center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms7 Guests
9.8

Exceptional

7 reviews

$335
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Orient.

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Frequently Asked Questions

You can explore 166 verified vacation rentals in Orient. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Orient vary depending on the season, property size, and location. Rates typically start from around $118 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Orient include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Orient welcome pets. Currently, 33 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Orient often include amenities such as Fireplace/Heating, View, and Ocean View. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.