House holiday rentals in Cutchogue

Staying at Amy's place was perfect for my friends and I while we're out on the North Fork for a wedding. Amy was very responsive with any questions we had. We were all very comfortable in the main living area as well as our bedrooms. The house was conveniently located to the wedding venue and my friends were also very happy that it was located near some pickleball courts. Thank you Amy for a wonderful stay.

Great host, great house with a bunch of fun things to do walking distance. Would definitely recommend and will 100% be booking again!

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!

Maher’s home is so elegant and mid —such great taste. He was such a kind host and so very easy to communicate with. The pool was lovely and the garden and back so pretty. We had a brilliant time! Thank you.

Our hosts were amazing. They responded quickly. They were very welcoming to us and provided easy-to-follow instructions. The location was great and the house was lovely. I would definitely stay here again.

Absolutely loved our stay and the hospitality of the host, Kate. The house was very nice and the property is very private. Highly recommended! Thanks Kate!

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!

Christine's place was nice and clean! We especially loved the fire pit and the pool. Upon arrival of the AirBNB Christine was waiting to meet us and show us around. This was something that was new to me in my AirBNB experience, but it was honestly so nice and so was she! Christine let me know that I could communicate with her for anything that was needed and asked for recommendations to make her place better. This place was so well-equipped, close to everything and it comfortably fit me and my 6 other friends! I would definitely book again with Christine.

Loved Kenneth’s house. Perfect for my wife & I to get away and explore the north fork for a weekend. Great location Private house Clean Comfy Walkable to Kenneys beautiful beach sunset Drivable/uberable to key winery or Greenport locations if needed Exactly what we were looking for as a mini couples getaway Would highly recommend; likely a returning customer Kenneth was responsive and pleasant with clear instruction 5 stars!

Erica’s place was amazing!! Super quiet neighborhood, nice walk to the beach, very clean and well accommodating for our group. Would definitely come back here!

Had a best friend’s wedding at a local vineyard and this location was perfect! Easy to find with large driveway and private property. Beautiful home, very clean, and responsive host (and has a property manager who lives right down the road and was able to help for a small few things)! Yard is stunning! Can’t recommend this beautiful place enough!

our group found this place when planning a trip to Montauk, and while we did make it to Montauk as well, Greenport was also a pleasant surprise. Great community and quaint town! The place was amazing too! clean rooms, very cozy. And a complimentary wine bottle! Highly recommend!

Perfect location. Great neighbors. Nice backyard. Close to Macary vineyards

We had such a fantastic stay in Cutchogue! The house is stunning, spacious and perfect for a group looking to enjoy North Fork wine country or the surrounding areas. All weekend we kept saying we would love to come back someday!

Jennifer’s place is great and in an amazing location. We loved it and it was perfect for the weekend. Very clean, spacious and great backyard.

Hi, we had a great stay with plenty of space for all of us. We all loved the fresh flowers on the living room table. The roses were a beautiful touch! The place was very clean to which my mother-in-law said it at least 4 times a day! LOL The bedrooms were set up so neatly when we arrived (very impressive). The kitchen had all the necessary utensils we needed and more. Great weekend! Thank you.

Second year renting this house and it once again was incredible. The house, yard, pool and deck were perfect for our young family and dog. Spencer was incredibly communicative throughout the process and we enjoyed many of his listed recommendations! Southold is an amazing area and Seasound is the perfect oasis to stay while enjoying the Northfork!

This is a very clean and comfortable house with good quality linen and towels. There is minimal clutter and the place is well furnished with everything you need in the kitchen. The house gives off very good vibes. The view from the French windows across the deck to the little bay is exquisite. All in all, highly recommended.

Sophia and Gus were great hosts. We had an issue with one of the AC units when we first got there and they immediately came over and fixed the problem. Sophia was very responsive to any questions we had and gave some great recommendations. The house was a very short 2 minute walk to the beach and there are no buildings between the house and the beach. Like most of the beaches around there they have small rocks which is fine. Sophia has beach chairs and an umbrella. As you can see in the pictures the bedrooms are a bit small but the beds are very comfortable. There is very limited cell service but there is wi- fi in the house so as long you are in the house calls are not a problem. Overall the house was a great place to stay and I would highly recommend it. Sophia and Gus are wonderful hosts

Had a lovely time in the Hamptons! Tasha was an amazing host- easiest check in/out, very responsive, and gave great recommendations for places in the area. Would love to stay here again!

We loved the home, we stayed with another couple, great walkability to a nice coffee place and several good restaurants. Perfect spot to explore the North fork and even the South fork. The big yard was a big plus, especially since it was completely fenced it which our dogs very much enjoyed (as did we). We would definitely come back!

We had a wonderful stay at the (Chel)sea. Chelsea herself met us up on arrival to showed us around, and she was super friendly & welcoming. The beds were really comfortable, the sea breeze was relaxing and despite our weather being a bit rainy, the proximity to the water and private beach made this a true retreat! Walkable area, natural surroundings and a lovely restaurant (La Plage) at the end of the road. Kudos to the cleaning staff who left sweet touches throughout. We'd love to stay here again!

We have had several family vacations on the North Shore now, but this was beyond our expectations. Pretty much a private beach on LI Sound in your backyard. Amazing layout with a wrap around deck with three daybeds for lounging outside among the tall hardwood trees and listening to the waves. Hammocks, hot tub and sauna below with a private gym and knocked out theater setup for streaming movies. There were 5 adults and two three year olds on this trip so the 3 full baths were great. The house felt like home for 7 great days and nights. Rainy days were filled with train museums, an aquarium and butterfly gardens and a fabulous library. And the North Atlantic waves are a 25 minute drive. Oh , and everyone said the beds were super comfortable.

We really enjoyed our stay here. The house was beautiful, extremely clean and perfect for our group. It had everything we needed and is in a great location - next to the beach and walkable to a grocery store, Starbucks, etc. We will definitely be staying here again would 100% recommend!