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Orient Vacation Rentals

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Our top choices for Orient vacation rentals

1. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (284 reviews)
"Great place!"
United States
Christine
The price is CA $425
CA $610 total
includes taxes & fees
Sep 7 - Sep 8
Cliffside Resort Condominiums

2. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (48 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is CA $436
CA $498 total
includes taxes & fees
Sep 17 - Sep 18
North Fork Resort

3. Grey comfort room

Grey comfort room
New London
10.0 out of 10, Exceptional, (1 review)
"Muy bien servicio"
United States
Eduin Vicente
The price is CA $81
CA $161 total
includes taxes & fees
Aug 31 - Sep 1
Grey comfort room

4. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (22 reviews)
"Close to the train, beach and restaurant, very convenient on foot"
United States
Nigel
The price is CA $271
CA $530 total
includes taxes & fees
Sep 13 - Sep 14
Harbor Heights

5. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (47 reviews)
"Lovely place, very clean, host was very responsive. Thanks so much!"
United States
Marie H.
The price is CA $271
CA $530 total
includes taxes & fees
Sep 10 - Sep 11
The SandPiper

6. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Pipes Cove
10.0 out of 10, Exceptional, (28 reviews)
"We had a great stay!! "
United States
Callie E.
The price is CA $340
CA $709 total
includes taxes & fees
Sep 7 - Sep 8
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

7. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (8 reviews)
"Everything about Beach Block Hideaway was perfect! The house was absolutely immaculate, the kitchen well stocked with plenty of kitchenware, beds very comfortable. Easy walk to town. We have stayed at a number of homes when visiting Greenport over the years but this place is truly the best - highly recommend! "
United States
maureen f.
The price is CA $409
CA $758 total
includes taxes & fees
Sep 8 - Sep 9
Beach Block Hideaway

8. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (41 reviews)
"Nice clean space, well appointed and easy walking access to downtown area."
United States
Molly G.
The price is CA $271
CA $530 total
includes taxes & fees
Sep 8 - Sep 9
Aqua Vista

9. American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.4 out of 10, Exceptional, (6 reviews)
"Great place! So nice."
United States
Paul F.
The price is CA $429
CA $617 total
includes taxes & fees
Sep 7 - Sep 8
American Beech in Greenport - Petite King Room 7

10. Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (13 reviews)
"yes the house had everything we needed"
United States
patricia m.
The price is CA $1,317
CA $2,100 total
includes taxes & fees
Sep 10 - Sep 11
Beachfront Greenport Villa

11. Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount
Shelter Island
10.0 out of 10, Exceptional, (57 reviews)
"Really great property, had a relaxing lovely time!"
United States
Nava S.
The price is CA $1,161
CA $2,059 total
includes taxes & fees
Sep 15 - Sep 16
Work and Play Special! Extended Stay Discount

12. Safari Tent Glamping,S4-CedarPt, East Hampton, NY

Safari Tent Glamping,S4-CedarPt, East Hampton, NY
East Hampton
The price is CA $268
CA $408 total
includes taxes & fees
Aug 18 - Aug 19
Safari Tent Glamping,S4-CedarPt, East Hampton, NY

13. Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Old Saybrook
9.8 out of 10, Exceptional, (40 reviews)
"Enjoyed our stay"
United States
Nicole L.
The price is CA $1,665
CA $2,496 total
includes taxes & fees
Sep 6 - Sep 7
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

14. Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
9.0 out of 10, Wonderful, (2 reviews)
"Absolutely Beautiful view The vibe and food was great. Just beware of the tics."
United States
Christina V.
The price is CA $298
CA $449 total
includes taxes & fees
Aug 20 - Aug 21
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

15. The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
9.0 out of 10, Wonderful, (4 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is CA $229
CA $423 total
includes taxes & fees
Sep 14 - Sep 15
The Stern at Soundview · Beach+Ocean+Sunrise

16. Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Old Saybrook Center
9.6 out of 10, Exceptional, (51 reviews)
"Great spot easy walk to the water and very close to town!"
United States
Genevieve G.
The price is CA $729
CA $1,211 total
includes taxes & fees
Aug 18 - Aug 19
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

17. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (52 reviews)
"We enjoyed our stay"
United States
JM B.
The price is CA $156
CA $303 total
includes taxes & fees
Sep 15 - Sep 16
1-bedroom cottage with Grove Beach 🏖️ access.

18. Safari Tent Glamping,S5-CedarPt, East Hampton, NY

Safari Tent Glamping,S5-CedarPt, East Hampton, NY
East Hampton
8.6 out of 10, Excellent, (4 reviews)
"We loved our tent, the view was great. The bed was super comfortable. We will definitely come back and hopefully stay longer. Also, the pizza is so good as was the watermelon Margherita."
United States
Jennifer
The price is CA $268
CA $408 total
includes taxes & fees
Aug 18 - Aug 19
Safari Tent Glamping,S5-CedarPt, East Hampton, NY

19. Cozy spacious bedroom with king size bed, only half mile to Rt.95, private bath

Cozy spacious bedroom with king size bed, only half mile to Rt.95, private bath
New London
10.0 out of 10, Exceptional, (13 reviews)
"Parking was easy and the room was the right siz."
United States
Vicente B.
The price is CA $150
CA $200 total
includes taxes & fees
Aug 18 - Aug 19
Cozy spacious bedroom with king size bed, only half mile to Rt.95, private bath

20. Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Waterford
10.0 out of 10, Exceptional, (32 reviews)
"The stay was great and the host was more than kind and very helpful! "
United States
Jenna K.
The price is CA $444
CA $751 total
includes taxes & fees
Aug 25 - Aug 26
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
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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Top Orient Hotel Reviews

Find out more about Orient

Everything you need to know about Orient 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 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Orient vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Orient. 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 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 vacation rentals we have selected for you start as low as CA $303 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Orient rentals

At Expedia, we put the best Orient 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 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 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. 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 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?

The Hampton Sack a cheerful relaxing beach cottage: This vacation home rental outside of Orient is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Orient?

With 17 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 Point County Park and Truman's Beach are a couple of scenic spots to enjoy the outdoors, whereas Oysterponds Historical Society is one of the cultural attractions. While here, Orient Beach State Park and Little Bay 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.