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Orient Holiday Rentals

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Our top choices for Orient holiday rentals

1. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (50 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is NZ$612
includes taxes & fees
20 Sept - 21 Sept
North Fork Resort

2. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (285 reviews)
"Great place!"
United States
Christine
The price is NZ$740
includes taxes & fees
9 Sept - 10 Sept
Cliffside Resort Condominiums

3. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (48 reviews)
"Lovely place, very clean, host was very responsive. Thanks so much!"
United States
Marie H.
The price is NZ$630
includes taxes & fees
10 Sept - 11 Sept
The SandPiper

4. 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 NZ$643
includes taxes & fees
14 Sept - 15 Sept
Aqua Vista

5. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (23 reviews)
"Close to the train, beach and restaurant, very convenient on foot"
United States
Nigel
The price is NZ$643
includes taxes & fees
15 Sept - 16 Sept
Harbor Heights

6. 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 NZ$366
includes taxes & fees
15 Sept - 16 Sept
1-bedroom cottage with Grove Beach 🏖️ access.

7. 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 NZ$749
includes taxes & fees
8 Sept - 9 Sept
American Beech in Greenport - Petite King Room 7

8. 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 NZ$543
includes taxes & fees
25 Aug - 26 Aug
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

9. 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 NZ$855
includes taxes & fees
15 Sept - 16 Sept
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

10. Safari Tent Glamping,S7-CedarPt, East Hampton, NY

Safari Tent Glamping,S7-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (1 review)
"Thank you Cedar Point for the great accommodations. We were fortunate to have a Tent right on the Bay, great views and good times."
United States
Vasilios
The price is NZ$531
includes taxes & fees
13 Sept - 14 Sept
Safari Tent Glamping,S7-CedarPt, East Hampton, NY

11. Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (60 reviews)
"A beautiful little beach cottage that was just what the doctor ordered. A great place to unwind and take in the sea air."
United States
Emily M.
The price is NZ$474
includes taxes & fees
15 Sept - 16 Sept
Insta-worthy Couples Retreat: Perfect for romantic getaway!

12. 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 NZ$510
includes taxes & fees
14 Sept - 15 Sept
The Stern at Soundview · Beach+Ocean+Sunrise

13. 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 NZ$884
includes taxes & fees
9 Sept - 10 Sept
Beach Block Hideaway

14. 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 NZ$243
includes taxes & fees
23 Aug - 24 Aug
Cozy spacious bedroom with king size bed, only half mile to Rt.95, private bath

15. Safari Tent Glamping,D28-CedarPt, East Hampton, NY

Safari Tent Glamping,D28-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (4 reviews)
"First time glamping with my boys and had a great time."
United States
Massimo P.
The price is NZ$552
includes taxes & fees
1 Sept - 2 Sept
Safari Tent Glamping,D28-CedarPt, East Hampton, NY

16. Cozy Lakefront Tiny House

Cozy Lakefront Tiny House
East Lyme
10.0 out of 10, Exceptional, (4 reviews)
"gorgeous tiny home on a tranquil lake!"
United States
Richard R.
The price is NZ$528
includes taxes & fees
16 Sept - 17 Sept
Cozy Lakefront Tiny House

17. Safari Tent Glamping,S3-CedarPt, East Hampton, NY

Safari Tent Glamping,S3-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (3 reviews)
"The store was great and the upgrades were perfect. The pizza was excellent and hope to be back soon"
United States
Joseph
The price is NZ$533
includes taxes & fees
1 Sept - 2 Sept
Safari Tent Glamping,S3-CedarPt, East Hampton, NY

18. 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 NZ$196
includes taxes & fees
2 Sept - 3 Sept
Grey comfort room

19. Safari Tent Glamping,D30-CedarPt, East Hampton, NY

Safari Tent Glamping,D30-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (1 review)
"Live music, small bar, pizza and friendly staff."
United States
Bibek
The price is NZ$564
includes taxes & fees
13 Sept - 14 Sept
Safari Tent Glamping,D30-CedarPt, East Hampton, NY

20. Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (12 reviews)
"We had a wonderful girls weekend in Greenport. The house was perfect for the three of us. Loved the location. We didn’t get to use the back area due to the weather, but it looked so inviting. Next time!"
United States
Melissa A.
The price is NZ$1,151
includes taxes & fees
17 Sept - 18 Sept
Renovated Townhouse walk to all
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Orient holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Orient. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Orient. Seeing all the best attractions is bound to make you fall in love with Orient. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Orient short-term rentals, that won’t be hard to do.

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?

The Hampton Sack a cheerful relaxing beach cottage: This holiday home rental outside of Orient is equipped with a BBQ, 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 holiday rentals are there in Orient?

With 17 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 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 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.