Orient Vacation Rentals

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Vacation 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, (1084)
"Clean, spacious and very comfy with beautiful views! Can’t wait to stay again in the future "
The price is CA $248
CA $311 total
includes taxes & fees
Dec 24 - Dec 25
Montauk Manor

Montauk Oceanside Suites

3.0 star property
8.4 out of 10, Very good, (347)
"Needs to have someone man the phones…"
The price is CA $195
CA $237 total
includes taxes & fees
Jan 3 - Jan 4, 2025
Montauk Oceanside Suites

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (264)
"Stayed for the second time at Windward and have no complaints. will book again next time I'm in Montauk!"
The price is CA $181
CA $238 total
includes taxes & fees
Jan 5 - Jan 6, 2025
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

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

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

Newly Renovated Montauk Condo with Ocean Views!

9.8 out of 10, Exceptional, (73)
"We love this place! It’s our little home away from home. The location is perfect. Quiet, beautiful sunsets overlooking the water and extremely cozy. Will be our destination for many years to come. "
Newly Renovated Montauk Condo with Ocean Views!

Montauk Mansion INDOOR + OUTDOOR POOLS

9.6 out of 10, Exceptional, (86)
"Beautiful location, resort and spotless."
Montauk Mansion INDOOR + OUTDOOR POOLS

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 CA $157
CA $388 total
includes taxes & fees
Jan 8 - Jan 9, 2025
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

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

Mid-Century Fall 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 Fall 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!

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

9.8 out of 10, Exceptional, (167)
"The Cottage was the perfectly cozy home away from home for our Thanksgiving trip to visit family. Everything was thought of from the towels for the hot tub, to the coffee for the morning. Thanks so much for such a lovely getaway for our family!"
The price is CA $200
CA $443 total
includes taxes & fees
Jan 7 - Jan 8, 2025
Lakeside cottage ON the water with beautiful views up the lake!

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!!!

Super Cute & Cozy Apartment in Downtown Mystic!

9.8 out of 10, Exceptional, (65)
"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 CA $101
CA $270 total
includes taxes & fees
Jan 5 - Jan 6, 2025
Super Cute & Cozy Apartment in Downtown Mystic!

Unbeatable Downtown Mystic Location

9.8 out of 10, Exceptional, (140)
"The location, the charm of the unit is consistent with the Mystic Charm! Fabulous!"
The price is CA $293
CA $564 total
includes taxes & fees
Dec 30 - Dec 31
Unbeatable Downtown Mystic Location
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, (2253)
"I would return great place"
The price is CA $142
CA $163 total
includes taxes & fees
Jan 6 - Jan 7, 2025
Hyatt Place Uncasville - Casino Area

Best Western Mystic Hotel

2.5 star property
8.6 out of 10, Excellent, (77)
"The staff was pleasant room was clean .. handicap accessible. Cose to the Christmas activities. Definitely will stay here next year. "
The price is CA $128
CA $147 total
includes taxes & fees
Dec 24 - Dec 25
Best Western Mystic Hotel

Microtel Inn & Suites by Wyndham Uncasville Casino Area

2.5 star property
8.8 out of 10, Excellent, (1603)
"Great place. Will come again. "
The price is CA $114
CA $131 total
includes taxes & fees
Jan 5 - Jan 6, 2025
Microtel Inn & Suites by Wyndham Uncasville Casino Area
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 vacation rentals in Orient?

Yes, we offer vacation rentals near popular attractions in Orient, or you can choose a more secluded option if you're looking for relaxation. 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's the top vacation rental that Orient has to offer?

Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready: This vacation home rental outside of Orient is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. 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?

With 21 Expedia vacation rentals, you're sure 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, Island's End Golf & Country Club and Truman's Beach are other places worth a visit.

What are vacation rentals like in Orient?

Vacation rentals are private accommodations you can stay in for several days or longer in Orient. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can provide a sense of safety away from shared hotel elevators and busy front desks while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for family gatherings.