Orient Vacation Rentals

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Our top choices for Orient vacation 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
$239 nightly
The price is $274
May 31 - Jun 1
Total with taxes and fees
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
$203 nightly
The price is $232
May 19 - May 20
Total with taxes and fees
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
$197 nightly
The price is $225
May 17 - May 18
Total with taxes and fees
Windward Shores Ocean Resort

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,343 reviews)
"Had a wonderful stay"
United States
Meghan
$185 nightly
The price is $212
May 21 - May 22
Total with taxes and fees
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.
$133 nightly
The price is $149
May 18 - May 19
Total with taxes and fees
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, (41 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.
$199 nightly
The price is $225
May 18 - May 19
Total with taxes and fees
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.
$223 nightly
The price is $252
May 18 - May 19
Total with taxes and fees
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
$417 nightly
The price is $471
May 19 - May 20
Total with taxes and fees
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.
$337 nightly
The price is $381
May 18 - May 19
Total with taxes and fees
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.
$241 nightly
The price is $273
Jun 10 - Jun 11
Total with taxes and fees
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
$250 nightly
The price is $283
May 25 - May 26
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (237 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
$195 nightly
The price is $223
May 28 - May 29
Total with taxes and fees
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.
$256 nightly
The price is $289
May 18 - May 19
Total with taxes and fees
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
$286 nightly
The price is $324
May 18 - May 19
Total with taxes and fees
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.
$581 nightly
The price is $657
May 27 - May 28
Total with taxes and fees
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 traveler
$338 nightly
The price is $382
May 19 - May 20
Total with taxes and fees
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
$286 nightly
The price is $324
May 17 - May 18
Total with taxes and fees
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.
$366 nightly
The price is $414
May 15 - May 16
Total with taxes and fees
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.
$411 nightly
The price is $465
May 17 - May 18
Total with taxes and fees
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.
$691 nightly
The price is $783
Jun 1 - Jun 2
Total with taxes and fees
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 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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Orient in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $212 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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?

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

How many vacation rentals are there in Orient?

With 16 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.