Orient Point Holiday Rentals

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Holiday Rentals in Orient Point

Our top choices for Orient Point holiday rentals

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1245)
"I had the best time and highly recommend this hotel!"
The price is AU$548
includes taxes & fees
11 Sept - 12 Sept
Montauk Manor

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (407)
"great place to stay"
The price is AU$303
includes taxes & fees
1 Oct - 2 Oct
Montauk Oceanside Suites

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (239)
"Had a great time. Will be back"
The price is AU$646
includes taxes & fees
11 Sept - 12 Sept
Cliffside Resort Condominiums

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (275)
"Very close walk to the beach great for little ones "
The price is AU$474
includes taxes & fees
3 Sept - 4 Sept
The Surf Club

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 AU$295
includes taxes & fees
21 Sept - 22 Sept
Windward Shores Ocean Resort

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (230)
"Great place to stay for small family "
The price is AU$351
includes taxes & fees
30 Sept - 1 Oct
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 AU$627
includes taxes & fees
9 Sept - 10 Sept
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

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

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 AU$499
includes taxes & fees
7 Sept - 8 Sept
Charming houseboat in pleasant New London with AC, WiFi

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

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 AU$569
includes taxes & fees
1 Oct - 2 Oct
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!

Shoreline Oasis

9.2 out of 10, Wonderful, (7)
"A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!"
The price is AU$402
includes taxes & fees
7 Sept - 8 Sept
Shoreline Oasis

Offshore Residences

4.0 star property
The price is AU$1,532
includes taxes & fees
1 Oct - 2 Oct
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

Thames River Retreat · CT College+Casinos+USCGA

10.0 out of 10, Exceptional, (9)
"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 AU$1,322
includes taxes & fees
30 Sept - 1 Oct
Thames River Retreat · CT College+Casinos+USCGA

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

10.0 out of 10, Exceptional, (29)
"Our trip was amazing, the pool was in perfect condition and the house had everything we needed. Would definitely stay here again!!"
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

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 AU$287
includes taxes & fees
3 Sept - 4 Sept
The Stern at Soundview · Beach+Ocean+Sunrise

Cozy spacious bedroom with queen bed, only half mile to Rt.95, exclusive bath

10.0 out of 10, Exceptional, (5)
The price is AU$191
includes taxes & fees
7 Sept - 8 Sept
Cozy spacious bedroom with queen bed, only half mile to Rt.95, exclusive bath

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

9.8 out of 10, Exceptional, (97)
"This is a great place to stay in Greenport. It has a private beach and is quiet and friendly. It's a 2-minute drive to town and shops, but you will want to spend your time enjoying the beautiful waterfront views."
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
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 Point Hotel Reviews

Find out more about Orient Point

Find out more about Orient Point

Everything you need to know about Orient Point 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 Point 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 Point holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Orient Point holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Orient Point. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Orient Point 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 Point holiday rentals we have selected for you start as low as AU$191 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Orient Point rentals

At Expedia, we put the best Orient Point 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 Point 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 Point 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 Point. 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 a holiday rental in Orient Point?

Yes, there are holiday rentals close to the most popular sights in Orient Point, or you can select a more secluded option if you're looking for a relaxing stay. Orient Point is known for its waterfront and parks.

What are some of the best holiday rentals that Orient Point has to offer?

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor : This holiday home rental outside of Orient Point 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 Point?

With 13 Expedia holiday rentals, you're guaranteed to find just the right place for your Orient Point stay.

What’s there to see and do in Orient Point?

Orient Point County Park and Little Bay are a couple of lovely local spots to get outside and enjoy nature. Orient Beach State Park and Kontokosta Winery are a couple of places you'll find in the wider area.

What’s a holiday rental in Orient Point like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Orient Point. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for a small group gathering.