Orient Holiday Rentals

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Holiday Rentals in Orient

1.5 Acre Luxury Escape - Saltwater Pool with Water Views

10.0 out of 10, Exceptional, (1)
"Very nice house In great shape and outstanding pool area."
1.5 Acre Luxury Escape - Saltwater Pool with Water Views

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1069)
"Property was beautiful, view overlooking the area was great! Parking was convenient and there were charging spots for electric cars! "
The price is AU$287
includes taxes & fees
2 Dec - 3 Dec
Montauk Manor

Montauk Oceanside Suites

3.0 star property
8.4 out of 10, Very good, (338)
"We stayed here a couple of years ago when it was a different name. It was just ok then. Now, it was absolutely comfortable, clean and very updated. We were pleasantly surprised. The bed was extremely comfortable as well. Looking forward to a return visit. Highly recommend!"
The price is AU$218
includes taxes & fees
3 Dec - 4 Dec
Montauk Oceanside Suites

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (262)
"Lovely seaside accommodations. Very clean and comfortable. The location is perfect. The room was just a short walk from the beach. Just minutes away from downtown Montauk. Having a full kitchen is great."
The price is AU$255
includes taxes & fees
1 Dec - 2 Dec
Windward Shores Ocean Resort

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (206)
"Stove it’s not efficient and refrigerator blocked with the corner of wall"
Cliffside Resort Condominiums

Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms

10.0 out of 10, Exceptional, (18)
"Exceptional property, extremely well designed, location is outstanding; it is a true Hamptons Estate fit ideally for family stays and relaxing experience. "
Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (250)
"The pictures of the property showed the bed in the bedroom facing the window with direct ocean views I was dis appointed to find out the bed was moved and no longer faced the ocean view."
The Surf Club

Amazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages

8.6 out of 10, Excellent, (20)
"We had a great time and will definitely option for a return stay. The house fit our group of 23 comfortably. We enjoyed family dinners on the large picnic table and a nightly bonfire. Our kids ranging in age from 3 to 21 enjoyed boating, kayaking, paddle boarding, fishing, swimming, biking, and many other things that the house and area had to offer. The cottages were just great.  It gave us just enough privacy when needed. Everything was very clean and setup nicely. Everyone enjoyed the boat...
Amazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (212)
"We were visiting our so. And just needed an inexpensive..relatively..place to stay….. this was quite convenient…. We had a good night sleep…took a walk to beach..had a great chat with one of the ‘beach boys’ and thought it was lovely……"
Driftwood Resort

Beautiful Family Home Nestled In The Heart Of Sagaponack

10.0 out of 10, Exceptional, (30)
"Great space and location. We loved the house and enjoyed our stay. "
Beautiful Family Home Nestled In The Heart Of Sagaponack

Unbeatable Downtown Mystic Location

9.8 out of 10, Exceptional, (139)
"Perfect area, few minute walk from the main strip. House is very clean, and very cool staying in such an old and well maintained home. "
The price is AU$408
includes taxes & fees
8 Dec - 9 Dec
Unbeatable Downtown Mystic Location

Montauk Mansion INDOOR + OUTDOOR POOLS

9.6 out of 10, Exceptional, (84)
"Beautiful location, resort and spotless."
Montauk Mansion INDOOR + OUTDOOR POOLS

Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready

9.8 out of 10, Exceptional, (97)
"Nothing negative to say. The owner came to greet us on our arrival, and showed us around the property. The house and grounds are family friendly with safety features for toddlers. Plenty of room for a large group. Parking for one car at the beach, and a short walk if all cannot fit in the car. The two outdoor showers are great when returning from the beach."
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready

Lakeside cottage ON the water with beautiful views up the lake!

9.8 out of 10, Exceptional, (164)
"Great weather and time spent "
The price is AU$399
includes taxes & fees
12 Dec - 13 Dec
Lakeside cottage ON the water with beautiful views up the lake!

Cape Cod home in great location! Walk to downtown

9.4 out of 10, Exceptional, (139)
"Dan’s place is cozy and will remind you of your grandparents house. It is a close drive to area attractions. Once we were back from the day’s adventure, we would play games around the kitchen table. Beds are comfortable. The Deck and backyard are nice areas to hang when it’s nice outside. "
Cape Cod home in great location! Walk to downtown

Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!

9.8 out of 10, Exceptional, (82)
"Everything about this condo is perfect! The views are breathtaking and condo is clean and modern. Would love to come back again. "
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!

Beautiful 2 Bedroom Boho Retreat in Downtown Mystic

10.0 out of 10, Exceptional, (20)
"Very clean. Well equipped kitchen, comfortable bed. Sofa bed couch was uncomfortable. We walked to downtown Mystic. Only half a mile. Vrbo gave us the wrong code for the door lock and I didn't have the email for the host. Fortunately the downstairs guests had the email and we got in."
The price is AU$320
includes taxes & fees
2 Dec - 3 Dec
Beautiful 2 Bedroom Boho Retreat in Downtown Mystic

Lakeside cottage overhanging the water, beautiful window views across the lake

9.8 out of 10, Exceptional, (191)
"Great, cozy place to have a friends getaway! Quiet neighborhood with beautiful views and short distance from the charming town of Mystic!"
The price is AU$378
includes taxes & fees
12 Dec - 13 Dec
Lakeside cottage overhanging the water, beautiful window views across the lake

Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound

9.4 out of 10, Exceptional, (31)
"A great corner condo in the Montauk Manor. Had a wonderful weekend. The condo was clean, and a great size for 3 adults. Got to use all the facilities at the manor. Indoor pool beautiful, sauna. Great restaurant and free shuttle bus to take you to town. Just a great weekend. "
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, (65)
"The place was clean and cozy. The owners could not have been nicer or more accomodating! Thanks for a great stay!"
MONTAUK MANOR-DELUXE STUDIO APARTMENT
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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Other types of properties in Orient you may be interested in

Hyatt Place Uncasville - Casino Area

3.0 star property
9.2 out of 10, Wonderful, (2220)
"Nice place close to Mohegan Sun. Free shuttle or quick Uber ride. "
The price is AU$186
includes taxes & fees
2 Dec - 3 Dec
Hyatt Place Uncasville - Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

2.5 star property
8.8 out of 10, Excellent, (1605)
"Great stay!"
The price is AU$134
includes taxes & fees
9 Dec - 10 Dec
Microtel Inn & Suites by Wyndham Uncasville Casino Area

Best Western Mystic Hotel

2.5 star property
7.2 out of 10, Good, (158)
"Property seemed updated and clean. Not many other guests so our visit was very quiet. Room was comfortable."
The price is AU$196
includes taxes & fees
1 Dec - 2 Dec
Best Western Mystic Hotel
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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?

Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!: This holiday home rental outside Orient is located next to a golf course, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Orient?

With 23 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 Beach State Park and Orient Point County Park are a couple of scenic spots to enjoy the outdoors, whereas Oysterponds Historical Society is one of the cultural attractions. While here, Truman's Beach 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.