Orient vacation rentals

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Top-rated vacation rentals in Orient

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Superhost

A serene beach view features soft sandy shores leading to calm waters. A small wooden bench is positioned in the foreground, while a sailboat glides gracefully on the horizon. Gentle waves can be seen lapping at the shoreline under a clear blue sky.

Home in Woodmont

4.92 out of 5 average rating, 26 reviews

Light-filled Beach House Steps from the Sand

FayeRating, 5 stars20 months ago

Mougeh's place is a lovely home with ample space, toys, books, games for entire family, within walking distance to the beach, and four mile drive to all shopping needs. The reason for the three star rating given in the "clean house" question was because when we arrived we noticed dog hair in the living area. We contacted the host and immediately the next day the cleaning service arrived and cleaned it. We were refunded the cleaning fee. Mougeh is very caring and responsive to her guests's needs.

Guest favorite

A waterfront gazebo is depicted, featuring a round table adorned with a vase of flowers. Two white chairs are positioned around the table, and autumn foliage adds warmth to the scene, with the glistening water visible in the background.

Villa in New London

4.86 out of 5 average rating, 28 reviews

Waterfront Holiday Vacation Villa New England

SallyRating, 5 stars4 days ago

We loved our stay. Very clean, professionally decorated, quiet and comfortable. There are only a few steps to navigate in the home, so that was a plus for our group as well. Would definitely choose to stay there again. Thank you!

Guest favorite

Home in East Hampton

4.95 out of 5 average rating, 205 reviews

Rex- East Hampton Cottage- 5 stars

AlexRating, 5 stars7 months ago

Great stay! My kids really enjoyed exploring the property and admiring the boats in the marina. Place also had everything we needed as far as kitchen supplies, linens, etc.. Our host was also very friendly and responsive. Would definitely come out here again for another wonderful escape from the big city!

Top guest favorite

An outdoor seating area surrounded by lush greenery features six blue Adirondack chairs arranged around a central fire pit. Soft lighting is provided by string lights overhead, creating a cozy atmosphere. Colorful plants are planted around the gravel surface, enhancing the natural setting.

Apartment in Hampton Bays

5 out of 5 average rating, 47 reviews

Hampton Studio

DonaldRating, 5 stars6 months ago

There are not enough stars to give to Nancy and her air b&b. This was our first experience with the app. The room was better than advertised. But what made this even more special was Nancy herself. What a sweet, kind woman. We plan on going back often. Not only to explore the Hampton area. But to make sure we have a drink around the fire pit with Nancy and her husband. Thank you again Nancy. You were awesome.

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What guests are saying

Direct Shoreline Long Island Sound Waterfront

4.95 out of 5 average rating, 80 reviews7 months ago

Our visit was utilitarian. We needed accommodations for us, our grown children and grandchildren and a dog. But the site of the cottage, its charm, its comfort made us wish we were staying another week. James' thoughtfulness went beyond any other Airbnb hosts' that we've experienced. Everything we might need if we were staying 10 days was there, clean, labeled. Thank you, James.

Cottage in Guilford

What guests are saying

Stylish Beach Getaway: pool & walking location

5 out of 5 average rating, 9 reviews6 months ago

Maher’s house was an amazing peaceful experience. I enjoyed my time there and he had great recommendations to restaurants and activities! He was very responsive with all questions we had. I will totally stay here in the future if I can get the chance again!! Thank you Maher!!

Home in North Fork

What guests are saying

Black Point Retreat - Entertain & Enjoy the Beach!

5 out of 5 average rating, 10 reviews7 months ago

Our group had a wonderful stay at this beautiful, spacious home. It was spotlessly clean and well stocked with supplies. The 7 of us enjoyed gathering around a spacious table to play games in the bright roomy sunroom. It led out to a very nice patio with a comfy wicker couch and chairs. The host was very prompt in responding to us and was quick to satisfactorily address our questions. We had a wonderful,memorable time!

Home in East Lyme

What guests are saying

Grand Hide-A-Way Central to Mystic and Vineyards

4.98 out of 5 average rating, 91 reviews2 weeks ago

This house was perfect for our family weekend (parents, siblings, grandkids) trip to Mystic Seaport. The finished basement was perfect for the teenagers to have their own space. The house was spacious & well appointed. Ashley was very helpful & responsive. We would definitely stay here again. Thank you Ashley!

Home in Stonington

What guests are saying

The Sandy Shack - Coastal Escape

4.9 out of 5 average rating, 21 reviews6 days ago

As a native long islander I enjoy finding great properties I can bring my family to to take advantage of all long island has to offer. This was the DREAMIEST beach bungalow!! The bedroom with the two beds was just my favorite room especially since we visited off season. You cannot beat this location. I can't wait to book again during high season! Thanks for sharing your home with us !!

Home in North Fork

What guests are saying

Captains Quarters | July avail!

5 out of 5 average rating, 16 reviews1 month ago

This house served our family very well for a multi-month stay. The house and property are just like the photos and all the amenities were great to have. Would recommend staying here if you are looking for a quiet place near the water in East Hampton. Petra was always very responsive with anything we needed and was an excellent host.

Home in East Hampton

What guests are saying

Exquisite Spacious Waterfront Modern-Sleeps 8

4.83 out of 5 average rating, 163 reviews6 months ago

We spent a week at Joe‘s house and couldn’t be happier. The house, property, and surrounding area was amazing. Everything was super clean, and you won’t find a spot like this anywhere else. The master bathroom is incredible. Already trying to figure out how I can replicate that shower in my own house lol. would recommend this place 100%

Home in Bayport

What guests are saying

2 Bedroom Hamptons Waterfront Cottage Rental

5 out of 5 average rating, 21 reviews9 months ago

A quaint cottage that was sparkling clean. Access to the Peconic from a private dock with the available kayaks and canoes. There is a pristine built-in pool with new decking. There was a 10 minute drive to Hampton Bays town with great restaurants, grocery and shopping.

Guesthouse in Hampton Bays

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Popular amenities for Orient vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Orient's top sights

Orient Beach State Park62 locals recommend

Duryea's Orient Point20 locals recommend

Orient Point Ferry20 locals recommend

Orient Country Store13 locals recommend

Orient Point Lighthouse8 locals recommend

Eagle's Neck Paddling Company6 locals recommend

Other great vacation rentals in Orient

Superhost

Large windows allow natural light to fill the open living space, showcasing the stunning view of the Great South Bay. A comfortable sofa with decorative pillows faces the water, complemented by a dining area nearby. Warm wood tones enhance the cozy atmosphere of the room.

Cabin in Shirley

4.87 out of 5 average rating, 153 reviews

A-Frame cabin with private beach & epic sunsets

JenniferRating, 5 stars1 week ago

Amber’s place was immaculate and stunning. This was my 2nd time staying and it was just as magical! The place had plenty of space for a family of 3 and the washer/dryer was very convenient. We had a great time and would stay here again!

Top guest favorite

Cottage in Guilford

4.99 out of 5 average rating, 136 reviews

"Red House on the Knoll" at Indian Cove

MaryRating, 5 stars1 week ago

My family and I loved staying at Gail’s place! We grew up in Madison and were back for a visit. It was such a great place and allowed us to re-live many fond memories of growing up in the area!

Superhost

A serene beach scene captures gentle waves lapping at smooth stones along the shoreline. Soft, sandy areas are visible in the distance, with greenery lining the coast. A cloudy sky provides a soft light over the tranquil waters.

Home in Waterford

4.94 out of 5 average rating, 18 reviews

Summer Beach Cottage Harknes, Ocean Beach N

JenniferRating, 5 stars7 months ago

It was a perfect spot for our little family vacation. We were so close to a few really nice beaches and the area is a short drive to mystic aquarium and village. Patsy and family are very nice and gave some great suggestions for activities in the area.

Guest favorite

A shoreline is depicted with a mixture of smooth, round pebbles covering the sand. Gentle waves are seen rolling onto the beach, and a colorful sunset fills the sky, casting reflections over the water's surface.

Cabin in Rocky Point

4.89 out of 5 average rating, 484 reviews

Great little place just for a couple

AllaireRating, 5 stars4 days ago

We had a great time staying with Marina. The space was so clean and the perfect size for two adults and our senior pup. The outdoor space was beautifully landscaped and the beach was only a 5 minute walk. We would definitely come back!

Guest favorite

A spacious outdoor area is highlighted by a refreshing pool surrounded by lounge chairs. The pool house, featuring a white exterior, sits in the background amidst lush greenery. Flower pots and garden plants frame the scene, enhancing the tranquil environment.

Guesthouse in Shelter Island

4.96 out of 5 average rating, 27 reviews

Sleek and Chic cottage/Pool House

YuryRating, 5 stars11 months ago

Perfect getaway in Shelter Island! The pool house is as amazing as it looks in the listing :) Cute house on a beautiful, peaceful and very private green lot. Primael was very welcoming and responsive. She was also very flexible in terms of our check in and check out. Everything went super smoothly. We enjoyed our stay a lot!

Guest favorite

A charming beachside home is showcased, featuring a wrap-around porch with seating. The sandy beachfront extends along the water's edge, and a clear blue sky overhead enhances the coastal atmosphere. Nearby houses are visible, offering a sense of community along the shore.

Home in Woodmont

4.98 out of 5 average rating, 43 reviews

Beachfront paradise- come, stay, relax!

TheoRating, 5 stars3 months ago

we rented La Spiaggia in December, and while it's mostly going to be more beautiful and better in the summer (since it's a beach house) it was still perfectly fine in the winter; well insulated and with good strong heaters. speaking of the beach I can't stress enough of how close this place is to the water; I'm talking literally ten steps to the sand. I would certainly recommend the place as a great summer getaway!

Top guest favorite

Home in Old Saybrook

5 out of 5 average rating, 49 reviews

Great Hammcock Getaway, Nearby beaches, Hot tub

DavidRating, 5 stars1 month ago

What a beautiful place and conveniently located. The house was wonderful decorated, was very comfortable and definitely was a relaxing place to get away. Irina was a wonderful host and the home had many wonderful amenities to offer.

Guest favorite

Home in Mystic

4.88 out of 5 average rating, 8 reviews

Family Friendly Mystic Retreat - Close To Town

VirginiaRating, 5 stars3 weeks ago

Cory and Dani have a beautiful and welcoming home. It is immaculate and very comfortable. The neighborhood is peaceful. They kindly responded quickly to my inquiries and request. I highly recommend their home.

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Orient vacation rentals

Top-rated vacation rentals in Orient

Modern Farmhouse Oasis in GP Village

Direct Shoreline Long Island Sound Waterfront

Stylish Beach Getaway: pool & walking location

Black Point Retreat - Entertain & Enjoy the Beach!

Grand Hide-A-Way Central to Mystic and Vineyards

The Sandy Shack - Coastal Escape

Charming New Beach Cottage

Vacation at the Beach: Entire Home

Captains Quarters | July avail!

Exquisite Spacious Waterfront Modern-Sleeps 8

2 Bedroom Hamptons Waterfront Cottage Rental

Cottage by the beach

Vacation rentals for every style

Popular amenities for Orient vacation rentals

Stay near Orient's top sights

Other great vacation rentals in Orient

Destinations to explore