Kid-friendly holiday rentals in Greenport West

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!

Beautiful house, perfect for a getaway to the north fork. Very close to a beach. Very clean and comfortable. Elizabeth is a great host. Highly recommend.

Kristin’s house was perfect!!! It was even more beautiful in person and had absolutely everything we needed to have the best stay at Greenport! Not only was it beautiful, but it was also in the best location, making it easy to get to and from the Main Street and wineries! I traveled with 8 friends and we all said we’d book again without a doubt! Thank you Kristin for an unforgettable stay!

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.

Wonderful weekend stay. Charming.

had an amazing time staying at Jessica's house. the place is close to everything, very convenient. Jessica is very quick to respond and flexible with check in and check out. Will definitely come back

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.

We had a lovely stay at Eric's home. The home exceeded our expectations and we felt right at home. The decor was warm and inviting. Everything you could possibly need was in the stunning, modern kitchen. The beds were all comfortable and we slept very well. The property was very peaceful. We enjoyed seeing deer, turkeys and hawks each day. The fixtures in the home were modern, clean and high-end. It was great being so close to Greenport with it's wonderful restaurants and shops. We can't wait to return.

We had a great weekend at Nicholas’s place. It was very peaceful in the woods, and we enjoyed using the record player and looking through the books spread throughout the studio. Nicholas was very responsive when I texted with questions and we used his provided recommendations to find breakfast and dinner. We’d definitely stay here again!

I can’t say enough good things about our stay at Holly’s place! We were traveling with 2 adults, an 18 year old and significant other and 2 teenagers and the amount of space was perfect! Everyone had room to spread out. The apartment had all the things you love about old homes, but all the updates that make life easier. The homemade banana bread that Holly left for us was such a personal touch and it was delicious. Erica greeted us with a warm welcome even though we arrived well past midnight. My daughter enjoyed reading in the cozy sitting area by the window. It was fun to watch the Hallmark movie that was filmed there. We fast forwarded the cheesy parts and enjoyed seeing the house in the movie. The area is peaceful and quaint. There’s a Dunkin about 5 minutes away, too which made our early mornings a little easier. Highly recommend if you’re traveling with a family!

This was my second time staying in Paris' cottage and it was just as charming and lovely as the first time. The cottage is set back from the road, nestled in a charming neighborhood. It's a very comfortable, quiet and peaceful place with a beautiful view and privacy. The center of Sag Harbor - with shops, restaurants and a sweet movie theater - are all walking distance from the cottage! Thank you for another great stay, Paris!

Very clean and comfortable! Tatenda is so sweet and responsive. Walkable to Yale and great restaurants, but also includes covered, safe parking in the building. We had fun grilling a dinner by the outdoor pool. Well-equipped workout rooms and the coffeemaker in the lobby was amazing offering a variety of options. We enjoyed everything about this Airbnb and will likely be back! Thank you Tatenda and Hyatus!

It was such a pleasure spending a weekend in Claire’s studio. The studio is very clean and comfortable, and my wife and I particularly appreciated the kitchenette, which allowed us to prepare a dinner one night and make our own pour-over coffee in the morning. We also loved hearing the birds as we woke up in the morning. And the location is terrific—an easy walk to the Southhold town center and a quick drive to other surrounding attractions like Greenport, nearby beaches, and wineries. Highly recommend!

It was a great stay, my second time staying here and Roisin is quick over communication and answering all the questions we had. Overall, great location and easy to get to!

Great venue. Hope to be back next year!

Lori's place lived up to all of my expectations. It was very comfortable and well appointed. While it is right in the center of the little village, it still maintained a great sense of peace and privacy. I highly recommend this place as a lovely respite in the charming town of Chester.

Great spot and at a really good price. Was visiting for a Yale event and was near enough to feel close without being too close to downtown. The area around the place is also super cute and not one I had explored previously. Huge plus for some good coffee shops nearby and of course Pepe’s. Camila was a great and responsive host. 10/10 would recommend Camila and this spot.

Mark's place was exactly what I was looking for to ring in the New Year in style, comfort and complete relaxation! I was able to start each day with a quiet cup of coffee and then head directly to the beach for a long morning walk (just a short drive away). Montauk Manor is an absolute hidden gem for a winter break and the indoor pool and hot tub are a rare find in the Hamptons. Check-in/out could not have been any easier and the Manor staff are wonderfully welcoming and friendly. There were still a good number of local shops open, including Left Hand Coffee. 100% recommend for all seasons and will eagerly book again!

The location is fantastic, the beach is wide, sandy, well kept, with a couple bar/restaurants just a short walk. The room is compact but was very clean with a comfy bed and good water pressure for showering off the sand. Host is responsive. Checkin instructions are clear and worth paying close attention to the because the blocks between shore rd and the beach only interconnect within each beach club.

Harper House was absolutely beautiful! It is in the perfect spot in mystic to walk to pretty much everything! We walked to dinner and lunch everyday as well as the shops. Food is great in this area and the hosts left us some great recommendations. Highly recommend to anyone looking to stay in mystic!

We loved Montauk - low key, wild and upmarket at the same time. This apartment was perfect, super quiet yet near everything and loved seeing wild deer from the terrace

Lisa and I enjoyed our stay at Laurens place. Felt right at home. Very clean, open space. We had the best time and did not want to leave. We will be back for sure.

Had a wonderful stay with my family. Clean, comfortable, great location. Good communication. Had a little trouble with the front door first day but someone was available quickly to help. A+

We had a great time at Adam’s place! The apartment was cozy, clean, and comfortable — perfect for a relaxing getaway. It’s just a quick 5-minute drive to Sag Harbor, which made it super convenient.