Orient Point Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Vacation Rentals in Orient Point

Our top choices for Orient Point vacation rentals

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1239)
"I had the best time and highly recommend this hotel!"
The price is CA $412
CA $498 total
includes taxes & fees
Sep 1 - Sep 2
Montauk Manor

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (405)
"great place to stay"
The price is CA $275
CA $330 total
includes taxes & fees
Sep 3 - Sep 4
Montauk Oceanside Suites

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (273)
"The front desk was great !!"
The price is CA $467
CA $609 total
includes taxes & fees
Sep 10 - Sep 11
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 CA $460
CA $586 total
includes taxes & fees
Sep 11 - Sep 12
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 CA $232
CA $295 total
includes taxes & fees
Sep 14 - Sep 15
Windward Shores Ocean 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

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (229)
"Great place to stay for small family "
The price is CA $284
CA $370 total
includes taxes & fees
Sep 3 - Sep 4
Driftwood Resort

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 star property
9.6 out of 10, Exceptional, (13)
"Great place! Great communication with property owner!"
The price is CA $422
CA $796 total
includes taxes & fees
Aug 25 - Aug 26
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Regency Inn and Suites - RS Handicapped Non Smoking Double Bed Hearing

6.0 out of 10, (5)
"The listing states a 1 bedroom, don’t be confused thinking there is a room with a door and then another room, as it’s just a single room with a bed. There was one gentleman that was very blunt and rude with his words. I unfortunately dealt with him prior to my visit, via phone, and once I got there. However, I had interaction with two others and the experience with them was very pleasant! Breakfast staff was extremely welcoming and friendly! (They check your paper for breakfast- be sure to bring...
The price is CA $121
CA $167 total
includes taxes & fees
Aug 31 - Sep 1
Regency Inn and Suites - RS Handicapped Non Smoking Double Bed Hearing

Charming houseboat in pleasant New London with AC, WiFi

9.8 out of 10, Exceptional, (7)
"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 CA $208
CA $447 total
includes taxes & fees
Aug 23 - Aug 24
Charming houseboat in pleasant New London with AC, WiFi

MONTAUK MANOR-DELUXE STUDIO APARTMENT

9.8 out of 10, Exceptional, (69)
"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

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 CA $265
CA $809 total
includes taxes & fees
Aug 28 - Aug 29
Thames River Retreat · CT College+Casinos+USCGA

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (71)
"We had a wonderful vacation at the Fairy Tale Guest Cottage. The location was awesome and we loved the accommodations, especially the fancy bathroom. Mark and Eunyoung are impeccable hosts. Would absolutely stay again!"
Fairy Tale Guest Cottage in Magic Garden by Pool

Walk to town, Bike to beach, Private pool oasis !

10.0 out of 10, Exceptional, (18)
"Nice house with very great outdoor. Well located, with the bikes, we can access the beaches, the city center and some restaurants very easily."
Walk to town, Bike to beach, Private pool oasis !

NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day

4.0 star property
9.6 out of 10, Exceptional, (134)
"Loved our stay and will be back"
NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day

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

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 CA $107
CA $273 total
includes taxes & fees
Sep 2 - Sep 3
The Stern at Soundview · Beach+Ocean+Sunrise

Regency Inn and Suites - Non Smoking King

8.0 out of 10, Very good, (3)
"Desk clerk was wonderful. Made sure my stay was everything that I needed."
The price is CA $121
CA $167 total
includes taxes & fees
Aug 31 - Sep 1
Regency Inn and Suites - Non Smoking King

Sag Harbor Suite by the Beach

8.8 out of 10, Excellent, (10)
"Trvis and Alice are great host and the property was a great place to stay close to the beach and downtown Sag Harbor."
Sag Harbor Suite by the Beach

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 CA $248
CA $365 total
includes taxes & fees
Sep 1 - Sep 2
Shoreline Oasis
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Orient Point Hotel Reviews

Frequently asked questions

Can I find a vacation rental in Orient Point?

Yes, there are vacation rentals near top attractions in Orient Point, or you can go with a secluded option if you want a relaxing place to stay. Orient Point is known for its waterfront and parks.

What are some of the best vacation home rentals in Orient Point?

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor : Visitors like this Orient Point vacation home rental. It offers an outdoor pool, a fireplace, and a barbecue grill 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 a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Orient Point?

With 12 Expedia vacation rentals, you're sure 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 larger area.

What’s a vacation rental in Orient Point like?

Vacation rentals are private properties you can stay in for short or long periods in Orient Point. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for a family trip.