
House holiday rentals in Orient
Find and book unique houses on Airbnb
Top-rated house rentals in Orient
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Orient house rentals
House rentals with a pool

North Fork paradise between beaches and vineyards
We had a lovely stay at Karine’s cute house! The kitchen was very nicely outfitted, beds were super comfortable, and the big wood-burning fireplace was excellent! We appreciated all the cool artwork around the house, and Karine’s wonderful photography book! We got to enjoy lots of bird life, and we were lucky to have a bit of snow. What a beautiful and peaceful spot. We can’t wait to come back in warmer weather to enjoy the pool and lovely big deck and yard!

Homestead Near Mystic, Casinos & Beaches
This was the perfect spot for what we were looking for as my son graduated from Conn College. The host was very responsive to my questions and flexible with check in times which we needed. House was exactly what was described and we had a wonderful time. Thank you!!

Private & Pristine with Pool and Kid’s Playard
Marta could not have been more accommodating! She was responsive and provided everything we needed. She even went the extra mile and insta cart-ed garbage bags and paper towels when we ran out. She could not have been a kinder host! We had the best weekend and would HIGHLY recommend staying at Marta’s place! We will definitely be back!

4 BD w/ Heated Pool in E Hampton, Fully Furnished
Ashton’s house a very comfortable and extremely clean home. It is spacious, allowed tremendous privacy and met our needs perfectly for an amazing family vacation. Everything was just as explained with no surprises. Great stay and a very accommodating host.

Peaceful Retreat in Immaculate Architect’s House
Michael’s place was amazing, means a few friends stayed this weekend for my birthday. He was always willing to help and very accommodating! The house itself is so beautiful and had everything we needed! It was our first time in The Hamptons and he gave us tons of recommendations!

East Hampton Oasis - Pool and Hot Tub
We had the most beautiful weekend stay at Tim’s home! Everything is accurately described and the pool and hot tub were amazing!! All the beds were very comfortable. Was perfect for a 5 girl weekend getaway!! Tim was incredibly communicative and checking in was a breeze. The location is PERFECT in East Hampton!! So many amazing restaurants and bars nearby. 100% will stay here again for my next Hamptons trip. Thank you so much Tim!!

Ultimate House with Heated Pool, Hot Tub and Sauna
This Home was Amazing!! Anastasia is Phenomenal, I could see why they are Super Hosts. Their home is Beautiful and very clean. It’s filled with amenities! all that are in the description. So much so we didn’t even get a chance to take advantage of them all. We were only there for two days. Next time it’ll be much longer. I love this place!

Long Island home w/ large pool
Beautiful house, even nicer than the photos. Great location to tour local wineries and close to the greenport’s Main Street! The house is stocked with plenty of cooking utensils and has whatever you might need. Would definitely consider coming back in the summer to enjoy the backyard when the pool is open!
Weekly house rentals

Elegant Greenport Victorian -Winter Harbor House
Erica and Janson's place was perfect for our group of eight to attend a wedding in the Hamptons. You cannot get closer to the North Ferry to Shelter Island and there are many restaurant and shopping options within walking distance... the pizza place next door is open late, PORT restaurant (across the street!) is great for waterfront drinks and dinner. While we didn't use it, the LIRR station from Manhattan is also 500 feet from the front door. Ample parking was appreciated and the place was spotless. Thank you Erica and Janson!

Newly renovated farmhouse - steps to Village
Cannot say enough great things about this house. I’ve stayed in many AirBnBs and other home rentals over the years and this was one of my absolute favorites. The house is beautifully updated and was extremely clean. The kitchen and bathrooms are gorgeous and have everything you need. Beds were so comfortable and the room darkening shades are a rare find in a vacation rental. Close to Greenport town and lots of wineries. Backyard was beautifully landscaped and was amazing for our dogs to run around. We will definitely stay here again!

Montauk Village
Ashley’s location was amazing and the entire layout was efficient. The automated blinds and Sonos wireless surround system were amazing highlights of the property. The hot tub worked flawlessly and the amenities were well stocked. Ashley’s house is well stocked to host a private dinner party for guests with the large prep sink and counter areas. The newly renovated kitchen cabinets all had slow closure mechanisms and the dual oven microwave was a nice touch. The dual shower head in the downstairs bathroom was a useful amenity as well.

Adorable Beach Cottage - Private Beach Association
Sandy and Ian were perfect hosts! Quick to respond to any queries and extremely welcoming. The cottage was clean and well stocked with all needed supplies. I cannot express how happy we were with our stay. Thank you once again Sandy and Ian for making our stay comfortable and stress-free!

Sky of Blue, Sea of Green
This house had so many amenities and was exactly as described! We enjoyed having access to grills, a hot tub, game room, and all of the household/beach necessities! The house and game decor were super cute and the adults loved the competitive scrabble game on the wall. There was a small ant problem in the kitchen (which the owner was aware of) that was there despite attempts to keep the dishes and garbage can clean, but that was our only minor complaint. Overall, loved the place and would consider staying here again!

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
This is one of the most soulful places to stay on Long Island, Greenport, our second visit. A true family gem with laidback vibes and stylish features.

Oh Buoy! Charming Cottage Steps to Beach | Firepit
Ann Marie must be one of the top hosts on the app. She was the most responsive and caring person assuring our stay was up to her high standards. The property was suited our needs very well, was close to the beach, and only a short drive away from the main strip in town. Everything was clean and prepared for our arrival with meticulous attention to detail. We would certainly stay here again in the future!

The Cottage
This was the perfect place to stay for our weekend get away. It’s a great location close to a lot of restaurants, shopping, and beaches. We had everything we needed and the beds were very comfortable. We would definitely stay there again.
Private house rentals

Salt & Sea House - Near wineries, farms, & beaches
We had a wonderful stay! The master suite is huge and the bathroom is dreamy. We didn’t really use the backyard bc it was winter but it was great for our pup! Kitchen was small but did the job (no microwave). We had issues with streaming on the “guest” accounts but we always travel with our own firestick so we were fine. The beds were super comfortable (firm memory foam type) but it was quite bright in the upstairs bedrooms in the morning bc several of the windows had no covering so if you need a blackout situation for little ones pack accordingly. We were able to put the provided pack and play in the closet which was fine for us! We would definitely recommend and return!

Modern Farmhouse Oasis in GP Village
Luigi was an excellent host, super responsive and a pleasure to interact with. The house is beautiful, super clean and well appointed. The beds were very comfortable and created the perfect sleep environment. Close walking distance to all the Greenport activities. I would absolutely stay here again and highly recommend staying here.

The Big Easy... A gentle, slow and easy going stay
Dave was an amazing host. Incredibly responsive, everything was clearly communicated, and very helpful. The house was perfect for our family--great location near the beach with shops/restaurants nearby. Highly recommend!

Barnacle Bay Beach House
My husband, dog, and I LOVED our stay here- so much that Danielle accommodated for us to stay an additional day! It was the perfect location. Private enough where we felt secluded, but yet right off of a main road with so many great restaurants to walk to! The beach was about a 5 minute walk, and left us with the perfect spot and feeling like we had the beach completely to ourselves the days we were there. We are already talking about going back, and can’t wait to plan our next trip. Thanks so much!

Cedar Hot Tub, Suana, Heated Pool walk to water
Our family had the most amazing weekend at this home. Benjamin was very responsive and accommodating. There was not a detail missed in the home and outdoor environments. Even though it rained we had a full day of entertainment at the home. You will not be disappointed.

Stylish Retreat Waterviews
From the kayaks to the coffee, our stay was glorious! I loved waking up every morning to the gorgeous view of the Niantic River. The indoor and outdoor spaces were comfortable and there are so many amenities. Location is perfect- a short walk to the boat dock and back entrance to the Oswegatchie Hill Trail. I’d love to go back!! Thank you Cindy!

Le Petit Cottage, Southold, NY
We had a lovely stay fro our rainy June weekend. Southold is a quaint town with some excellent local places and fine dining as well. Took a trip to shelter island with the car on the ferry. Went to a cool vintage store in Greenport. Bed and space were super comfy & cozy. Book this spot you won’t be disappointed! Looking forward to visiting again in full summer weather:)

Walk to town, Greenport Village - Harbor Views
What a great space! Jackie was super responsive to any questions. Perfect location. With great outdoor space. We would definitely go back!
Destinations to explore
- The Hamptons Holiday rentals
- Long Island Holiday rentals
- Plainview Holiday rentals
- East River Holiday rentals
- New York Holiday rentals
- Hudson Valley Holiday rentals
- Boston Holiday rentals
- Jersey Shore Holiday rentals
- Pocono Mountains Holiday rentals
- South Jersey Holiday rentals
- Philadelphia Holiday rentals
- Washington Holiday rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Beach
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- Napeague Beach
- Shinnecock Hills Golf Club
- Walnut Public Beach
- TPC River Highlands
- Point Judith Country Club
- Ocean Beach Park
- Woodmont Beach
- Amagansett Beach
- Blue Shutters Beach
- Jennings Beach
- Seaside Beach
- Silver Sands Beach
- Bushnell Park
- Quotonset Beach
- Ninigret Beach
- Outer Beach at Smith Point County Park
- Groton Long Point South Beach