Orient Point Holiday Rentals

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Holiday Rentals in Orient Point

1.5 Acre Luxury Escape - Saltwater Pool with Water Views
1.5 Acre Luxury Escape - Saltwater Pool with Water Views
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, 1,023 reviews
"Best affordable hotel in Montauk"
The price is NZ$552
per night
6 Jun - 7 Jun
Montauk Manor
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, 238 reviews
"Good family friendly resort! Hope it’s a heated pool.. Easy Check-out before 11:00 am!"
The price is NZ$446
per night
9 Jun - 10 Jun
Windward Shores Ocean Resort
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The Surf Club
3.5 star property
8.4 out of 10, Very good, 222 reviews
"An amazing stay with our girls!!! Can’t wait to go back!"
The price is NZ$460
per night
13 Jun - 14 Jun
The Surf Club
Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very good, 302 reviews
"It was so close to town!"
The price is NZ$300
per night
6 Jun - 7 Jun
Montauk Oceanside Suites
Driftwood Resort
3.5 star property
8.8 out of 10, Excellent, 187 reviews
"Well maintained upscale resort. "
The price is NZ$366
per night
9 Jun - 10 Jun
Driftwood Resort
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, 183 reviews
"Wonderful stay and super clean! Can’t wait to come back. "
The price is NZ$519
per night
27 Jun - 28 Jun
Cliffside Resort Condominiums
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
10.0 out of 10, Exceptional, 12 reviews
"Incredible property, incredible people to work with! We this is our second year in a row renting this house for a holiday weekend, and we look forward to renting every year forward! The house itself is stunning, clean and full of activities from the pool, to the tennis court, to the movie room. Rebecca and Shaun are truly a pleasure, and reply immediately to any questions, requests or needs. They even left us a welcome present for returning this year! Thank you for allowing us to have an annual...
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
Private Guest House w/ Deck + Spectacular Views!
10.0 out of 10, Exceptional, 12 reviews
"Our floors were being refinished so we needed a place to stay for a week with our dog. The cottage was perfect for our needs, with plenty of space to walk our dog."
Private Guest House w/ Deck + Spectacular Views!
Newly Renovated Montauk Condo with Ocean Views!
9.6 out of 10, Exceptional, 64 reviews
"Loved our stay! Perfect location and the place was very clean."
Newly Renovated Montauk Condo with Ocean Views!
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
9.6 out of 10, Exceptional, 49 reviews
"Close to the restaurants and beaches. We enjoyed exploring the nearby areas within 15 to 30 mins drive"
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
Beautiful Family Home Nestled In The Heart Of Sagaponack
10.0 out of 10, Exceptional, 25 reviews
"House was very clean and host was exceptional. Very relaxing place to stay."
Beautiful Family Home Nestled In The Heart Of Sagaponack
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
10.0 out of 10, Exceptional, 73 reviews
"This place exceeded all expectations, offering a perfect blend of convenience and serenity. Situated just moments from downtown, the location provided easy access to the vibrant community, while still offering a peaceful retreat. The highlight of our stay was undoubtedly the private beach access. Tucked away in a tranquil neighborhood, it boasted unparalleled beauty and tranquility. Simply being in the vicinity was a getaway in itself, with breathtaking views that soothed the soul. The...
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
9.4 out of 10, Exceptional, 28 reviews
"We stayed here for a 3 night weekend getaway for our 10th wedding anniversary. Plenty to explore, pool was open and weather was just gorgeous. Apartment was clean & cute, decor a lil outdated. Only complaint was the queen bed was very uncomfortable and made noise every time you moved."
The price is NZ$970
per night
13 Jun - 14 Jun
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
MONTAUK MANOR-DELUXE STUDIO APARTMENT
10.0 out of 10, Exceptional, 55 reviews
"Studio was perfect and grounds of property were breaking. Would definitely stay there again. Got to enjoy Montauk and have a beautiful place to stay."
MONTAUK MANOR-DELUXE STUDIO APARTMENT
Steps From The Beach! Watersports From Your Back Yard. 12 NEW SUP's & Kayaks
9.6 out of 10, Exceptional, 78 reviews
"Good place take a large family. Cute nearby towns."
Steps From The Beach! Watersports From Your Back Yard. 12 NEW SUP's & Kayaks
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
9.8 out of 10, Exceptional, 91 reviews
"Had great time at property. Very close to town and beach. Would highly recommend."
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
70 Year old cottage on 2.8 acres, stunning views and sunsets
70 Year old cottage on 2.8 acres, stunning views and sunsets
Montauk Mansion With Outdoor Pool
9.8 out of 10, Exceptional, 79 reviews
"nice layout, plenty of room, great restaurant on the premises, we had a lovely stay and a great time."
Montauk Mansion With Outdoor Pool
4 bedroom 2.5 bathroom A/C Decks Pvt Beach /HotTub/FirePit
9.8 out of 10, Exceptional, 12 reviews
"Loved the location to the beach and neighborhood. Great for a weekend getaway."
4 bedroom 2.5 bathroom A/C Decks Pvt Beach /HotTub/FirePit
Don't see what you're looking for?
See all available properties in Orient Point
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.

Other types of properties in Orient Point you may be interested in

Ramada by Wyndham Groton
2.5 star property
6.4 out of 10, 1,005 reviews
"Was definitely clean, just needed some updates to the property. No major issues with the stay. Keycards didn’t work at some point, but they fixed the issue immediately. "
The price is NZ$140
per night
10 Jun - 11 Jun
Ramada by Wyndham Groton
Mystic Marriott Hotel and Spa
4.0 star property
8.6 out of 10, Excellent, 1,001 reviews
"We were in town for a family gathering and the convenience and location for us was perfect for our needs!"
The price is NZ$296
per night
19 Jun - 20 Jun
Mystic Marriott Hotel and Spa
Pier Blue Inn Old Saybrook - Essex
2.0 star property
7.6 out of 10, Good, 789 reviews
"Most of these reviews give less than 5 stars because it’s outdated, which it is, but other than that I love my stay. I had no issues. Front desk staff were super friendly. Coffee machine in the room which was nice. Great area and location too, a lot of restaurants in walking distance. They are in the middle of renovations so keep that in mind but I’m excited to come back when it’s completed!! "
The price is NZ$147
per night
9 Jun - 10 Jun
Pier Blue Inn Old Saybrook - Essex
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Orient Point holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Orient Point. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Orient Point. Seeing all the best attractions is bound to make you fall in love with Orient Point. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Orient Point short-term rentals, that won’t be hard to do.

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?

Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool: 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 balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Orient Point?

With 12 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 Orient Beach State Park are a couple of lovely local spots to get outside and enjoy nature. While here, Orient By The Sea Marina and Little Bay are other places worth a visit.

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.

Recent reviews of Orient Point properties
Expedia verified reviews