Orient Holiday Rentals

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Holiday Rentals in Orient

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1243)
"I had the best time and highly recommend this hotel!"
The price is NZ$613
includes taxes & fees
1 Sept - 2 Sept
Montauk Manor

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (407)
"great place to stay"
The price is NZ$405
includes taxes & fees
10 Sept - 11 Sept
Montauk Oceanside Suites

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (274)
"The front desk was great !!"
The price is NZ$530
includes taxes & fees
1 Sept - 2 Sept
The Surf Club

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (238)
"Had a great time. Will be back"
The price is NZ$722
includes taxes & fees
11 Sept - 12 Sept
Cliffside Resort Condominiums

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (291)
"Easy checking in and out Easy access few steps to beach from first floor unit "
The price is NZ$362
includes taxes & fees
14 Sept - 15 Sept
Windward Shores Ocean Resort

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (229)
"Great place to stay for small family "
The price is NZ$394
includes taxes & fees
24 Sept - 25 Sept
Driftwood Resort

Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill

8.8 out of 10, Excellent, (26)
"This adorable, cozy cottage was perfect for our family getaway to Montauk. We have tried various rentals and hotels each summer and Robert’s cottage was by far our favorite. It fit our family of 5 perfectly, with enough room that we didn’t feel on top of each other. The decor was light and airy and just what we were hoping to find. From the awesome location, just a walk to the ocean, to the indoor pool and back up to a comfortable stay, our entire family agree that we can’t wait to return!...
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 star property
9.6 out of 10, Exceptional, (13)
"Tucked away in a quiet residential area. Rooms were clean and kitchenette was well equipped. Private parking spot in the driveway next to the cottage was a bonus. Highly recommended!"
The price is NZ$945
includes taxes & fees
8 Sept - 9 Sept
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Charming houseboat in pleasant New London with AC, WiFi

9.6 out of 10, Exceptional, (10)
"Very nice people. Boat was roomy and well stocked but dirty. Toilet pump was broken and made loud noises all night. We were not informed this was an issue til checkout. Some other small issues "
The price is NZ$551
includes taxes & fees
28 Aug - 29 Aug
Charming houseboat in pleasant New London with AC, WiFi

MONTAUK MANOR-DELUXE STUDIO APARTMENT

9.8 out of 10, Exceptional, (70)
"We were so excited to come back to this property after our lovely stay in february! We had an amazing time again and loved it! "
MONTAUK MANOR-DELUXE STUDIO APARTMENT

Safari Tent Glamping,S10-CedarPt, East Hampton, NY

The price is NZ$487
includes taxes & fees
1 Sept - 2 Sept
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Thames River Retreat · CT College+Casinos+USCGA

10.0 out of 10, Exceptional, (8)
"We found this home a perfect combination of being able to get away but also convenient to restaurants, stores, and activities. The view could not be beat and the house was clean and comfortable."
The price is NZ$1,009
includes taxes & fees
28 Aug - 29 Aug
Thames River Retreat · CT College+Casinos+USCGA

Offshore Residences

4.0 star property
The price is NZ$1,731
includes taxes & fees
2 Sept - 3 Sept
Offshore Residences

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (72)
"In the Hamptons working a Vintage market so I barely got to enjoy this incredibly gorgeous home, but it was perfect for just me and the host were absolutely delightful so friendly and accommodating they even let me sleep in which I haven’t had a chance to do in sometime so that was much appreciated I rested better than I have in months in this sweet cottage on a beautiful property. They made sure I was taken care of while giving me speciation enjoy some much needed quiet time. It’s a stunning...
Fairy Tale Guest Cottage in Magic Garden by Pool

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

10.0 out of 10, Exceptional, (93)
"Beautiful house with lots of light and comfort. Excellent quiet location by the ocean with outstanding communication with the host who answered all pertinent questions and addressed all outstanding issues. "
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

Coastal Retreat • 2BR Near Beaches & Mystic

10.0 out of 10, Exceptional, (2)
"Nice clean place, has everything you need and is in a great location!"
The price is NZ$563
includes taxes & fees
27 Aug - 28 Aug
Coastal Retreat • 2BR Near Beaches & Mystic

Amazing Ocean Front 2 Story Home, Steps Away From The Water

9.8 out of 10, Exceptional, (97)
"This is our 2nd time renting the home and we have booked for a third. Cindy is a fantastic host and her beach house is a perfect getaway. Family enjoyed every minute. "
Amazing Ocean Front 2 Story Home, Steps Away From The Water

The Stern at Soundview · Beach+Ocean+Sunrise

2.0 star property
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
The price is NZ$317
includes taxes & fees
27 Aug - 28 Aug
The Stern at Soundview · Beach+Ocean+Sunrise

A Tiny Escape - Charming Eco-Friendly Retreat Awaits in Stonington

10.0 out of 10, Exceptional, (1)
"We visited here for a weekend in the Mystic area. Our daughter joined us for an evening and the home was cozy and comfortable for 3 adults. The check in process was seamless and communication with the host was always timely. They thought of everything to make our stay enjoyable and everything was within arms reach. The home is located in a great spot and enabled us to enjoy many surrounding areas. Pawcatuck/Westerly, Mystic, Watch Hill... all were very close so this was a perfect base of...
The price is NZ$639
includes taxes & fees
15 Sept - 16 Sept
A Tiny Escape - Charming Eco-Friendly Retreat Awaits in Stonington

Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!

10.0 out of 10, Exceptional, (10)
"Such a fun, beautiful and unique stay. Would love to stay again!"
The price is NZ$684
includes taxes & fees
2 Sept - 3 Sept
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!
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

Find out more about Orient

Find out more about Orient

Everything you need to know about Orient holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Orient holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Orient holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Orient holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Orient holiday rentals we have selected for you start as low as NZ$317 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Orient rentals

At Expedia, we put the best Orient holiday 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 holiday.

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. 

Frequently asked questions

Can I find holiday rentals in Orient?

Yes, there are holiday rentals close to the most popular sights in Orient, or you can select a more secluded option if you're looking for a relaxing stay. 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 are some of the best holiday rentals that Orient has to offer?

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor : This holiday home rental outside of Orient offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a patio, a garden and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Orient?

With 22 Expedia holiday rentals, you're guaranteed 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 Island's End Golf & Country Club are other places worth a visit.

What are holiday rentals like in Orient?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Orient. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from public hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for a small group gathering.