A lighthouse on a rocky outcrop with a boat in the water.

Orient Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Orient vacation rentals

Terrace/patio

1. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (297 reviews)
"Great condo. Very nice location and grounds."
United States
William
$266 nightly
The price is $304
Nov 1 - Nov 2
Total with taxes and fees
Cliffside Resort Condominiums
A modern house with a deck, outdoor seating, and a fire pit.

2. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (65 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
$222 nightly
The price is $254
Oct 13 - Oct 14
Total with taxes and fees
North Fork Resort
A beach with people relaxing on chairs and sunbathing.

3. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (27 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
$223 nightly
The price is $255
Nov 1 - Nov 2
Total with taxes and fees
Harbor Heights
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

4. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (55 reviews)
"Very wonderful location so close to the train station will come back soon"
United States
Julian V.
$223 nightly
The price is $255
Nov 2 - Nov 3
Total with taxes and fees
The SandPiper
A spacious hallway with high ceilings, arched columns, and chandeliers.

5. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,415 reviews)
"Excellent service, beautiful property, accommodating staff."
United States
Maria
$168 nightly
The price is $192
Nov 2 - Nov 3
Total with taxes and fees
Montauk Manor
Room

6. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (326 reviews)
"Easy access to the beach. Perfect weather. Nicely furnished and updated rooms and bathrooms. The gym is tiny- not much equipment. The location is perfect for Montauk and Amagansett. The staff were very nice and hard working."
United States
Gaurang J
$167 nightly
The price is $190
Oct 26 - Oct 27
Total with taxes and fees
Windward Shores Ocean Resort
A beach with people relaxing, a pier extending into the water, and a clear sky.

7. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Pipes Cove
10.0 out of 10, Exceptional, (34 reviews)
"We had a wonderful stay in Greenport! The location was absolutely perfect, and one of the things we loved most was being able to walk to town and the beautiful harbor. Everything was so conveniently located, from the charming shops and wonderful restaurants to the lovely waterfront, making it easy to enjoy everything Greenport has to offer without needing to drive. We would happily stay here again and highly recommend this place to anyone looking for a wonderful Greenport getaway!"
United States
Nino
$337 nightly
The price is $385
Nov 1 - Nov 2
Total with taxes and fees
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

8. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (50 reviews)
"Great location and nice spot."
United States
Kerri L.
$216 nightly
The price is $247
Nov 9 - Nov 10
Total with taxes and fees
Aqua Vista
Room

9. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
8.8 out of 10, Excellent, (256 reviews)
"Great right on the beach property with nice pool."
United States
Julian
$159 nightly
The price is $182
Oct 13 - Oct 14
Total with taxes and fees
Driftwood Resort
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

10. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (61 reviews)
"We enjoyed our stay"
United States
JM B.
$183 nightly
The price is $207
Oct 21 - Oct 22
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
A stone pier leading to a beach with houses in the background.

11. Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (62 reviews)
"A beautiful little beach cottage that was just what the doctor ordered. A great place to unwind and take in the sea air."
United States
Emily M.
$241 nightly
The price is $272
Oct 19 - Oct 20
Total with taxes and fees
Insta-worthy Couples Retreat: Perfect for romantic getaway!
An outdoor dining area with hanging lights, palm trees, and a bar.

12. American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.4 out of 10, Exceptional, (6 reviews)
"Great place! So nice."
United States
Paul F.
$268 nightly
The price is $306
Oct 14 - Oct 15
Total with taxes and fees
American Beech in Greenport - Petite King Room 7
A wooden pathway leading to a beach with scattered rocks and greenery.

13. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
$393 nightly
The price is $449
Nov 3 - Nov 4
Total with taxes and fees
Beach Block Hideaway
Room

14. Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (456 reviews)
"The room was very clean and spacious."
United States
Jadana
$151 nightly
The price is $173
Oct 26 - Oct 27
Total with taxes and fees
Montauk Oceanside Suites
A dining area with a round table, six chairs, and a chandelier.

15. Year round Jacuzzi - Blackberry East Hampton Home

Year round Jacuzzi - Blackberry East Hampton Home
East Hampton
9.2 out of 10, Wonderful, (7 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
$1,218 nightly
The price is $1,291
Oct 13 - Oct 14
Total with taxes and fees
Year round Jacuzzi - Blackberry East Hampton Home
A rocky shoreline with a beach and ocean in the background.

16. The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
8.4 out of 10, Very good, (6 reviews)
"If you are looking for a place to sleep, this place is ok. No place to sit down or put anything down. Just a bed and an old beat up tiny side table. Refrigerator is tiny, needed to be cleaned and defrosted. Stains in the bathroom ceiling tiles and the smell of Marijuana at night. Hot plate and microwave present but did not use. The entryway and stairs were dirty and could use a coat of paint and trim. The beach was the highlight and a very short walk. Definitely not worth the $$$ we paid."
United States
Janine
$236 nightly
The price is $267
Oct 13 - Oct 14
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise
A wooden deck with a red chair and a table, a tent, and a grassy area in the background.

17. Safari Tent Glamping,S4-CedarPt, East Hampton, NY

Safari Tent Glamping,S4-CedarPt, East Hampton, NY
East Hampton
Safari Tent Glamping,S4-CedarPt, East Hampton, NY
A spacious living area with a large bed, a dining table, and a kitchen in the background.

18. Unit 1021: Studio | 2nd Floor-Pool View | Starfish

Unit 1021: Studio | 2nd Floor-Pool View | Starfish
Napeague
9.8 out of 10, Exceptional, (6 reviews)
"Comfortable accommodations, easy access to pool and beach, close to restaurants, quiet."
United States
Liana T.
$368 nightly
The price is $419
Oct 13 - Oct 14
Total with taxes and fees
Unit 1021: Studio | 2nd Floor-Pool View | Starfish
A two-story house with a front porch, a balcony, and a driveway.

19. Grey comfort room

Grey comfort room
New London
9.6 out of 10, Exceptional, (4 reviews)
"Nice place"
United States
JACQUELINE FELICIANO
$104 nightly
The price is $116
Oct 13 - Oct 14
Total with taxes and fees
Grey comfort room
Living area

20. The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (303 reviews)
"Staff are nice"
United States
na
$257 nightly
The price is $294
Oct 26 - Oct 27
Total with taxes and fees
The Surf Club
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Orient Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Beautiful place. Staff were very helpful and polite."
Deborah 1-night trip
Posted 13 hours ago
Water's Edge Resort & Spa

Find out more about Orient

Everything you need to know about Orient vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Orient vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Orient vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Orient vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Orient. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Orient in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $173 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Orient rentals

At Expedia, we put the best Orient vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Orient rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Orient vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Orient. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Orient?

Yes, we offer vacation rentals near popular attractions in Orient, or you can choose a more secluded option if you're looking for relaxation. Orient is known for its waterfront and golf courses. Make sure you have time to check out the parks and bars during your trip.

What's the top vacation rental that Orient has to offer?

Amazing Ocean Front 2 Story Home, Steps Away From The Water: This vacation home rental outside of Orient is located on the beach and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the books in this rental home to help you unwind.

How many vacation rentals are there in Orient?

With 17 Expedia vacation rentals, you're sure to find just the right place for your Orient stay.

What can I see and do in Orient?

Orient Point County Park and Truman's Beach are a couple of scenic spots to enjoy the outdoors, whereas Oysterponds Historical Society is one of the cultural attractions. While here, Orient Beach State Park and Little Bay are other places worth a visit.

What are vacation rentals like in Orient?

Vacation rentals are private accommodations you can stay in for several days or longer in Orient. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can provide a sense of safety away from shared hotel elevators and busy front desks while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for family gatherings.