Orient Holiday Rentals

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Our top choices for Orient holiday rentals

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (252 reviews)
"Convenient parking and proximity to all."
United States
Rosemaria
The price is NZ$468
includes taxes & fees
31 May - 1 June
Cliffside Resort Condominiums

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.0 out of 10, Wonderful, (14 reviews)
"Great stay & great staff!"
United States
James
The price is NZ$412
includes taxes & fees
18 May - 19 May
North Fork Resort

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (312 reviews)
"We always stay at the Windward Shores when we go to Montauk. It is a beautiful, clean and comfortable place, and the price is great!"
United States
Joseph
The price is NZ$390
includes taxes & fees
21 May - 22 May
Windward Shores Ocean Resort

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,346 reviews)
"Had a wonderful stay"
United States
Meghan
The price is NZ$377
includes taxes & fees
18 May - 19 May
Montauk Manor

The Tiny Cottage on The Pond

The Tiny Cottage on The Pond
Oakdale,
10.0 out of 10, Exceptional, (8 reviews)
"Host was extremely nice and responsive. Cottage is so cute I can't wait to come back in the summer! Nice and private little place and adorable goats! If you're looking for a quiet, cute little getaway this is the place to go! Thank you Thomas for the hospitality!!"
United States
Sharon O.
The price is NZ$359
includes taxes & fees
17 June - 18 June
The Tiny Cottage on The Pond

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (42 reviews)
"We had such a wonderful one night stay at Shalom Cottage! The place was absolutely beautiful—so cozy, clean, and thoughtfully decorated. Raj, the host was truly amazing! He was kind, responsive, and made sure we had everything we needed from start to finish. We felt so welcomed and comfortable the entire time. We would definitely love to stay here again and highly recommend it to anyone! "
United States
Alexis F.
The price is NZ$404
includes taxes & fees
18 May - 19 May
1-bedroom cottage with Grove Beach 🏖️ access.

Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village

Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village
Stonington
9.8 out of 10, Exceptional, (178 reviews)
"A bright and cozy vibe as well as being thoroughly equipped with everything to make our stay comfortable.We appreciated the winter escape and enjoyed Stonington, Mystic, and Westerly. A lovely stay!"
United States
Dawn R.
The price is NZ$423
includes taxes & fees
19 May - 20 May
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village

Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (6 reviews)
"Host was very responsive. Property as described. We would stay again! "
United States
john18250
The price is NZ$758
includes taxes & fees
18 May - 19 May
Rogers Lake House (87) · CT College+Beach+USCGA

Charming 2-bedroom house with WiFi, AC in lovely Waterford

Charming 2-bedroom house with WiFi, AC in lovely Waterford
Waterford
10.0 out of 10, Exceptional, (1 review)
"The home was very clean and welcoming."
United States
Michelle M.
The price is NZ$643
includes taxes & fees
18 May - 19 May
Charming 2-bedroom house with WiFi, AC in lovely Waterford

Lakefront Boho Tiny House

Lakefront Boho Tiny House
East Lyme
10.0 out of 10, Exceptional, (4 reviews)
"Every thing was amazing "
United States
Annaliaa C.
The price is NZ$475
includes taxes & fees
20 May - 21 May
Lakefront Boho Tiny House

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (3 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is NZ$470
includes taxes & fees
25 May - 26 May
The Stern at Soundview · Beach+Ocean+Sunrise

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (238 reviews)
"Wonderful location, right on the beach. The staff was kind and welcoming. The property was beautiful with a pool, playground, tennis and basketball courts, cornhole, etc. Very family friendly. Some walkable restaurants nearby and a quick 5-10 minute drive into town where a lot of the restaurants and shops are. We did have ants all in our food one day but the staff addressed it quickly "
United States
John
The price is NZ$361
includes taxes & fees
18 May - 19 May
Driftwood Resort

Cozy Lakefront Tiny House

Cozy Lakefront Tiny House
East Lyme
10.0 out of 10, Exceptional, (3 reviews)
"It was a peaceful and quant "
United States
Patricia M.
The price is NZ$466
includes taxes & fees
18 May - 19 May
Cozy Lakefront Tiny House

Cozy 3-bedroom house near Mystic and Mohegan & Foxwood Casinos!

Cozy 3-bedroom house near Mystic and Mohegan & Foxwood Casinos!
Montville
10.0 out of 10, Exceptional, (6 reviews)
"great place to stay"
United States
christopher
The price is NZ$640
includes taxes & fees
31 May - 1 June
Cozy 3-bedroom house near Mystic and Mohegan & Foxwood Casinos!

Beach Cottage, private beach and pass

Beach Cottage, private beach and pass
East Lyme
10.0 out of 10, Exceptional, (11 reviews)
"It was PERFECT way to spend USCGA Parent’s Weekend!!"
United States
Kerri G.
The price is NZ$1,206
includes taxes & fees
30 May - 31 May
Beach Cottage, private beach and pass

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

Lakeside cottage ON the water with beautiful views up the lake!
Ledyard
9.8 out of 10, Exceptional, (198 reviews)
"We had a wonderful stay at the cottage! It was so cozy and peaceful, exactly what we were looking for. Mini splits kept our rooms toasty on the cold night, and we had everything we needed. Our host was super communicative and helpful. Would definitely stay here again!"
United States
Anonymous traveller
The price is NZ$591
includes taxes & fees
19 May - 20 May
Lakeside cottage ON the water with beautiful views up the lake!

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

Lakeside cottage overhanging the water, beautiful window views across the lake
Ledyard
9.8 out of 10, Exceptional, (227 reviews)
"wonderful place to stay. the pond is beautiful. plenty to do nearby "
United States
Mike
The price is NZ$546
includes taxes & fees
18 May - 19 May
Lakeside cottage overhanging the water, beautiful window views across the lake

Upscale Apartment in Mystic 7 Minute Walk to Drawbridge

Upscale Apartment in Mystic 7 Minute Walk to Drawbridge
Stonington
10.0 out of 10, Exceptional, (22 reviews)
"Beautiful, quiet, close to town!! Really enjoyed our stay. "
United States
Maureen F.
The price is NZ$704
includes taxes & fees
25 May - 26 May
Upscale Apartment in Mystic 7 Minute Walk to Drawbridge

Adorable Cottage with Cottage porch, walk to water & town

Adorable Cottage with Cottage porch, walk to water & town
Westbrook Center
8.8 out of 10, Excellent, (6 reviews)
"Great host and property"
United States
Kevin K.
The price is NZ$790
includes taxes & fees
18 May - 19 May
Adorable Cottage with Cottage porch, walk to water & town

Tranquil Farmhouse Retreat

Tranquil Farmhouse Retreat
Montville
9.8 out of 10, Exceptional, (22 reviews)
"We had a great stay during the Thanksgiving holiday. We were able to enjoy the space of the house and the close proximity to Mohegan Sun."
United States
Allison R.
The price is NZ$1,405
includes taxes & fees
1 June - 2 June
Tranquil Farmhouse Retreat
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Orient holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Orient holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Orient holiday rentals we have selected for you start as low as NZ$340 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 holiday 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 holiday.

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 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?

Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village: This holiday home rental outside of Orient is located near the beach, and has a private garden, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Orient?

With 16 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.