House holiday rentals in Orient

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Popular amenities for Orient house rentals

House rentals with a pool

Guest favourite
Home in North Fork
5 out of 5 average rating, 35 reviews

North Fork paradise between beaches and vineyards

AndrewRating, 5 stars5 months ago
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!
Superhost
Home in Stonington
4.9 out of 5 average rating, 105 reviews

Homestead Near Mystic, Casinos & Beaches

Sherri Watson Rating, 5 stars4 weeks ago
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!!
Guest favourite
Home in The Hamptons
4.91 out of 5 average rating, 113 reviews

Private & Pristine with Pool and Kid’s Playard

BridgetRating, 5 stars1 week ago
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!
Superhost
Home in The Hamptons
4.94 out of 5 average rating, 131 reviews

Peaceful Retreat in Immaculate Architect’s House

JessikahRating, 5 stars1 month ago
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!
Guest favourite
Home in The Hamptons
4.96 out of 5 average rating, 106 reviews

Stylish+Modern Cape w/Saltwater Pool-5min to Beach

JessicaRating, 5 stars2 weeks ago
Great spot in Hampton Bays! The house was as described and in a very cute and walkable neighborhood. Super close drive to the beach and a couple of local restaurants and eateries. Loved how private the spot felt too! David’s done a wonderful job with the backyard, so you get the comfort of having close neighbors without the intrusiveness. Pool was awesome. We definitely enjoyed it!
Superhost
Home in The Hamptons
4.84 out of 5 average rating, 100 reviews

East Hampton Oasis - Pool and Hot Tub

MaryRating, 5 stars1 week ago
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!!
Guest favourite
Home in Manorville
4.98 out of 5 average rating, 255 reviews

Ultimate House with Heated Pool, Hot Tub and Sauna

SolomonRating, 5 stars1 month ago
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!
Guest favourite
Home in The Hamptons
4.86 out of 5 average rating, 268 reviews

Exclusive Sag Harbor Compound

Amy RoseRating, 5 stars2 weeks ago
Ben is a super host. His home is absolutely beautiful and well managed. His thoughtful recommendations and well timed check ins and reminders were the height of polished professionalism. We felt right at home, down to the bins of toys in the living room that our toddler and baby played with every day.

Weekly house rentals

Guest favourite
Home in North Fork
5 out of 5 average rating, 18 reviews

Newly renovated farmhouse - steps to Village

Sarah JaneRating, 5 stars1 month ago
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!
Top Guest favourite
Home in Niantic
4.99 out of 5 average rating, 68 reviews

The Beach House (Costa Casa Pelo Mar)

JenniferRating, 5 stars4 days ago
Rosemary was an excellent host and the home was clean, well stocked and felt very comfortable as a home away from home while traveling. We especially enjoyed the community’s private beach, using the provided parking pass, which was clean and calm water for children. After checkout I had left a pair of glasses and Rosemary let me know right away and assisted me in retrieving them before we left town which was much appreciated. The amenities for staying with a child were so helpful (changing table, pack & play, high chair, baby gate for stairs, beach toys). Would definitely recommend. Thank you!
Top Guest favourite
Home in East Lyme
4.99 out of 5 average rating, 73 reviews

Adorable Beach Cottage - Private Beach Association

MaryRating, 5 stars1 week ago
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!
Guest favourite
Home in North Fork
4.95 out of 5 average rating, 44 reviews

modern 3 bedroom home with fireplace

MarielleRating, 5 stars1 month ago
We had a wonderful stay in Greenport! The house was comfortable and very well kept. Everything was pristine. The location was great- a few short blocks into town for shops and restaurants. We had an issue with the fire detector sounding and Kim was kind enough to compensate us for the issue. She is a great and responsive host. Would definitely stay here for our next visit!
Guest favourite
Home in The Hamptons
5 out of 5 average rating, 9 reviews

Oh Buoy! Charming Cottage Steps to Beach | Firepit

AveryRating, 5 stars3 weeks ago
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!
Guest favourite
Home in South End
4.97 out of 5 average rating, 29 reviews

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub

NigelRating, 5 stars5 days ago
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.
Guest favourite
Home in Old Saybrook
4.72 out of 5 average rating, 223 reviews

The Cottage

KatieRating, 5 stars2 weeks ago
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.
Top Guest favourite
Home in North Fork
5 out of 5 average rating, 13 reviews

Long Island home w/ large pool

AllieRating, 5 stars2 months ago
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!

Private house rentals

Top Guest favourite
Home in North Fork
5 out of 5 average rating, 23 reviews

Elegant Greenport Victorian -Winter Harbor House

BrianRating, 5 stars8 months ago
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!
Guest favourite
Home in Westbrook
4.96 out of 5 average rating, 26 reviews

Barnacle Bay Beach House

AshlynRating, 5 stars4 days ago
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!
Top Guest favourite
Home in The Hamptons
5 out of 5 average rating, 31 reviews

Montauk Village

RyanRating, 5 stars1 week ago
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.
Guest favourite
Home in The Hamptons
5 out of 5 average rating, 49 reviews

East Hampton Rental w/ Pool, Moments to Amenities

JessicaRating, 5 stars1 week ago
This house was even better than I expected ! The pool was big. Perfect for a weekend with friends/family. Peaceful. House was well equipped with everything that we needed. Clean. Fast WiFi. Close to Sisi restaurant which is stunning. I enjoyed my stay here. Highly recommend it! A++
Top Guest favourite
Home in Old Lyme
5 out of 5 average rating, 21 reviews

Sky of Blue, Sea of Green

KaylaRating, 5 stars3 days ago
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!
Superhost
Home in The Hamptons
4.77 out of 5 average rating, 52 reviews

East Hampton: Clearwater Beach Pass

MeganRating, 5 stars1 month ago
My friends and I booked Renee’s place for a relaxing getaway weekend. The house was exactly what we needed, clean, private, and full of everything we needed. Renee was responsive and flexible and overall just a wonderful host. We would stay here again in a heartbeat!
Guest favourite
Home in East Lyme
4.93 out of 5 average rating, 29 reviews

Stylish Retreat Waterviews

HillaryRating, 5 stars2 weeks ago
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!
Guest favourite
Home in North Fork
4.95 out of 5 average rating, 40 reviews

Walk to town, Greenport Village - Harbor Views

JRating, 5 stars3 weeks ago
What a great space! Jackie was super responsive to any questions. Perfect location. With great outdoor space. We would definitely go back!

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