Holiday Rentals in Orient

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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, (1090)
"Very clean "
The price is €164
includes taxes & fees
8 Jan - 9 Jan
Montauk Manor

Montauk Oceanside Suites

3.0 star property
8.4 out of 10, Very good, (351)
"Location, location..."
The price is €160
includes taxes & fees
8 Jan - 9 Jan
Montauk Oceanside Suites

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (266)
"I recently had a wonderful stay at this property, and I can't recommend it enough! Although it takes less than a 10-minute drive into Montauk, it's perfect. The room we stayed in was very clean and spacious, providing all the comforts we needed. The property is exceptionally well-maintained, and it's clear that the staff takes pride in their work. From the friendly service to the beautifully kept grounds, everything contributed to a very pleasant experience. One of the highlights was the...
The price is €145
includes taxes & fees
20 Jan - 21 Jan
Windward Shores Ocean Resort

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (207)
"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

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (212)
"Well kept. Everything in good working order. Easy check in/out. Very good communication. Enjoyed our second time here. "
Driftwood Resort

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

Montauk Mansion INDOOR + OUTDOOR POOLS

9.6 out of 10, Exceptional, (88)
"Well kept unit. Easy access. Very quiet. Pool and spa area beautiful "
Montauk Mansion INDOOR + OUTDOOR POOLS

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

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

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

9.8 out of 10, Exceptional, (193)
"Our stay was great! Bobby was there when we arrived to show us around. The cottage was comfy and cozy. It was a great place to relax and enjoy the beauty of the water on either of the 2 decks or from the hot tub. The beds were comfortable "
The price is €231
includes taxes & fees
16 Jan - 17 Jan
Lakeside cottage overhanging the water, beautiful window views across the lake

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

8.8 out of 10, Excellent, (22)
"everyone associated with the property is great from owner to local mananger. house is quiet and on a beautiful piece of property"
Amazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages

Newly Renovated Montauk Condo with Ocean Views!

9.8 out of 10, Exceptional, (74)
"Montauk has been our Happy Place for many years. We feel fortunate to have discovered this charming condo. Comfortable-feels like home. Immaculate. Consideration went into the details. Luxurious towels. Fantastic location near beach. And owner is a pleasure, right on top of communication. This place made our visit even Happier. Highly recommend. Thank You! Lynn"
Newly Renovated Montauk Condo with Ocean Views!

Mid-Century Winter Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!

10.0 out of 10, Exceptional, (81)
"Very relaxing place to stay 2 minutes from the beach and fabulous sunsets. Property was spotless with tons of room. "
Mid-Century Winter Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!

Montauk Cozy Beach Studio. Walk to private ocean beach & always pet friendly!

10.0 out of 10, Exceptional, (2)
"Lovely to be away in a spot just hidden enough to be accessible from the main road but not close to it. Near to the beach but not on top of it. Perfect! Quiet, woody, peaceful, restful and pet friendly. A hidden gem. The only thing I regret is not having time to stay longer."
Montauk Cozy Beach Studio. Walk to private ocean beach & always pet friendly!

Holiday Specials!!!/Out Door Theater Fire Pit/ Bocce court- WATCH VIDEO!!!

10.0 out of 10, Exceptional, (34)
"This home is quintessentially charming! I arrived late at night, alone. It has a charming curved drive in and there sat the wood home with a large front porch and Forrest behind it. It seemed like little house on a prairie with the porch and dormer windows. The motion lights went on immediately, which I was grateful for. There is a narrow stairwell up to 3 bedrooms, as is customary in older style homes. High ceilings and windows everywhere enhance this property. When I woke there was a family of...
Holiday Specials!!!/Out Door Theater Fire Pit/ Bocce court- WATCH VIDEO!!!

Cape Cod home in great location! Walk to downtown

9.4 out of 10, Exceptional, (142)
"The house was clean and had a cozy feel. Good location too, with a lot of restaurants/ neat stores nearby. I would definitely recommend this if you're looking to go on vacation to Connecticut."
Cape Cod home in great location! Walk to downtown

Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

9.8 out of 10, Exceptional, (105)
"Lovely rental; very easy to work with property manager. Clean, close to ocean - would rent again"
The price is €493
includes taxes & fees
3 Feb - 4 Feb
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

Super Cute & Cozy Apartment in Downtown Mystic!

9.8 out of 10, Exceptional, (66)
"It is a cute, but tiny apartment. Very short walk to "downtown" Mystic and the Seaport. There is another apartment above it so at times you'll hear voices and footsteps. The heat hadn't been turned on, so the 1st nite was chilly but the property manager quickly addressed that."
The price is €174
includes taxes & fees
8 Jan - 9 Jan
Super Cute & Cozy Apartment in Downtown Mystic!
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, (2289)
"Good seevice"
The price is €105
includes taxes & fees
14 Jan - 15 Jan
Hyatt Place Uncasville - Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

2.5 star property
8.8 out of 10, Excellent, (1614)
"Very close to the casino, with a free shuttle!"
The price is €83
includes taxes & fees
13 Jan - 14 Jan
Microtel Inn & Suites by Wyndham Uncasville Casino Area

Hilton Mystic

3.5 star property
8.4 out of 10, Very good, (1011)
"Great stay!"
The price is €122
includes taxes & fees
20 Jan - 21 Jan
Hilton Mystic
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.

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?

Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready: This holiday home rental outside of Orient is located on the beach, and has an outdoor pool, a fireplace 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. 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?

With 21 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, Orient By The Sea Marina 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.