Orient Point Vacation Rentals

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Vacation 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 CA $407
CA $492 total
includes taxes & fees
Jun 3 - Jun 4
Montauk Manor
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, 237 reviews
"Good family friendly resort! Hope it’s a heated pool.. Easy Check-out before 11:00 am!"
The price is CA $329
CA $405 total
includes taxes & fees
Jun 2 - Jun 3
Windward Shores Ocean Resort
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The Surf Club
3.5 star property
8.4 out of 10, Very good, 220 reviews
"Very nice location and nice condo"
The price is CA $322
CA $441 total
includes taxes & fees
Jun 17 - Jun 18
The Surf Club
Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very good, 299 reviews
"It was so close to town!"
The price is CA $264
CA $315 total
includes taxes & fees
Jun 4 - Jun 5
Montauk Oceanside Suites
Driftwood Resort
3.5 star property
8.8 out of 10, Excellent, 187 reviews
"Well maintained upscale resort. "
The price is CA $219
CA $279 total
includes taxes & fees
Jun 2 - Jun 3
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 CA $391
CA $506 total
includes taxes & fees
Jun 16 - Jun 17
Cliffside Resort Condominiums
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
10.0 out of 10, Exceptional, 11 reviews
"We really enjoyed our stay in this house. Very safe and clean place to stay. Plenty of parking spaces, logs for fireplace, kitchen accessories. All china is very good quality."
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
9.6 out of 10, Exceptional, 48 reviews
"We had a lovely stay at this home. It was very clean, comfortable and spacious so we could all spread out. We were glad to have a nice warm house to stay in because the weather was terrible! I also went swimming in the warm pool even though it was 60 and raining! Would highly recommend."
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
Private Guest House w/ Deck + Spectacular Views!
10.0 out of 10, Exceptional, 11 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, 63 reviews
"Pictures don’t do it justice! So relaxing. Quiet and clean. Best we could ask for. The deck is great. It was bit cold so we couldn’t use the pool but we would love to be back for the summer! Very close to close to everything but still extremely quiet. Kelly was also an amazing host. She responded quickly and assisted with a parking question we had. Couldn’t ask for anything more. 5 stars!"
Newly Renovated Montauk Condo with Ocean Views!
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!
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
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, 77 reviews
"This property was spacious and well appointed. We had a large family gathering and this property gave us plenty of options for sleeping, eating, gathering and plenty of equipment for entertainment such as bikes, kayaks and paddle boards. I would definitely recommend this property! It was all we needed and much more. We hope to book again!"
Steps From The Beach! Watersports From Your Back Yard. 12 NEW SUP's & Kayaks
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
10.0 out of 10, Exceptional, 28 reviews
"The house was beautiful and comfortable. We enjoyed the property and watching the wildlife. The fire pit was great for a group gathering. We didn't cook but the kitchen appeared well stocked. The house was short on paper products. We left a note for the house manager when we left."
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
9.8 out of 10, Exceptional, 73 reviews
"We enjoyed our stay. No complaints. Great location."
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
Beach House
9.8 out of 10, Exceptional, 43 reviews
"My daughter graduated from coast guard academy so we were staying for several days. The cottage is located in black point in Niantic. So close to the ocean. The cottage was adorably decorated, and very comfortable. Plenty of beds to accommodate a bigger group. Slept very well in comfortable bed. The owner had left some bagels and muffins for us as well. Small but nice kitchen with plenty of room for a family to sit at larger table. My favorite is proximity to water and the daily multiple walks....
Beach House
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
9.4 out of 10, Exceptional, 27 reviews
"Rainy but good weekend"
The price is CA $445
CA $820 total
includes taxes & fees
Jun 13 - Jun 14
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
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
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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

Clarion Inn New London - Mystic
2.5 star property
6.2 out of 10, 1,005 reviews
"Cool"
The price is CA $100
CA $115 total
includes taxes & fees
Jun 18 - Jun 19
Clarion Inn New London - Mystic
Mystic Marriott Hotel and Spa
4.0 star property
8.6 out of 10, Excellent, 1,004 reviews
"Great hotel and excellent service."
The price is CA $217
CA $249 total
includes taxes & fees
Jun 16 - Jun 17
Mystic Marriott Hotel and Spa
Gold Star Inn & Suites
2.0 star property
7.0 out of 10, Good, 1,007 reviews
"."
The price is CA $97
CA $111 total
includes taxes & fees
Jun 16 - Jun 17
Gold Star Inn & Suites
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.

Everything you need to know about Orient Point 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 Point vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Orient Point vacation 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Orient Point vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Orient Point vacation rentals we have selected for you start as low as CA $219 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Orient Point rentals

At Expedia, we put the best Orient Point 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 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 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 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 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?

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

How many vacation rentals are there in Orient Point?

With 11 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 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 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.

Recent reviews of Orient Point properties
Expedia verified reviews