Guest house holiday rentals in The Hamptons

We love this place! This is the second time we've stayed, and it's a perfect little bungalow for two. The location in Cherry Grove is ideal, just a minute walk to the shops/bars but still quiet. Comfortable, cozy space. Minimal kitchen but the two burners and pots—not to mention the grill—make it possible to cook a nice meal. Great deal, highly recommend!

Robert is a kind and gracious host. He left a bottle of wine with a charming note upon arrival. We had a few questions about the house and he was very prompt and helpful. The house is a sweet charming little cottage in Montauk on the steps from the beach at central air- it was perfect. We would definitely return in the future.

We loved staying at Christine’s place! Great location, great deck to sit outside and enjoy the weather, and not too far from the beach. She even came in person to be sure check in went smoothly. Definitely would stay here again!

10000/10 recommend. Amazing Airbnb, beautiful pool, near east Hampton, Montauk, Parrish art museum, Dan Flavin institute, longhouse reserve, pollock krasner house. Easy check in, VERY safe neighborhood, Gilliam and her husband were kind and helpful.

If you’re seeking 5 star accommodation, look no further! This unit is exactly what you’re looking for! Candice, our host, was top tier. She was readily available, very clear in instruction, and completely respected our privacy. I utilize Airbnb quite often and I couldn’t have asked for a better stay! Thank you Candice!☺️

This place is very peaceful, in a great area with lots of restaurants and shopping nearby. The guest house is extremely clean and there is no clutter. I really enjoyed my stay here and highly recommend this Airbnb if you ever want to get away to someplace peaceful but close enough where you can find things to do.

If I could rate this stay 10 stars, I would. Geoff welcomed us with open arms. The place was beautiful and equipped with everything you could possibly need including grill equipment, quality sharp knives, a blender, soft beach/pool towels and more. He went above and beyond to ensure the hot tub was clean and perfect for us, that the pool stayed warm, and that we felt at home. He had great local tips and enhanced our weekend every step of the way. You can’t beat this location and the 360° roof deck views. Would stay here again in a heartbeat — best hosts ever!

The pictures really don’t do it justice , the place is adorable. The kitchen has all new appliances, and it has every amenity you could need for a long or short stay.

Great stay overall but only thing wrong was heater was not working properly and the place was very cold

We absolutely loved our stay. Unfortunately, we booked on a much colder day so we weren’t able to take full advantage of the pool— but even then, being able to sit outside in the patio is nice. The family gave us so much privacy. Would absolutely love to come back on a warmer day!

Good amenities in a private, cozy spot. The place was very clean and well-maintained. Liz was great. She met us upon arrival and walked us through everything we needed to know to enjoy our stay. We would definitely stay there again. Excellent experience overall.

Wonderful stay! Thanks for everything!!

We had a wonderful stay at Carrie’s listing. When we first arrived, Carrie was still cleaning up so we were invited inside for a cup of wine. The airbnb had almost everything we needed (minus a microwave) and the property had super friendly chickens and every amenity needed for a stay-at-home vacation. Carrie was even kind enough to have us stay a little past check in to finish some work meetings. We appreciated everything and would recommend this to anyone coming to North Fork :)

Super responsive, friendly host! Great location!

Kate was a very kind, thoughtful and responsive host. She and I had been corresponding before our stay because of a personal issue that threatened to complicate our stay. She was very gracious in all of our interactions. She and her husband made us feel very welcome and at home when we arrived, and throughout our stay. The studio was just what we needed- immaculate, peaceful and private. The location was very convenient to various sites on the island. Kate even allowed us access to her dock, which was a great place to sit and take in the marvelous sunsets the island offers. We will definitely return.

Had the most gorgeous time at Christina and Felipe's guesthouse. It was so cozy and beyond everything that we wanted. I don't think that the photos did justice to how beautifully they've curated the space to feel at home + sprinkles of decor that makes you truly love the Hamptons and the vibe there. Thank you for such a great time. Cannot recommend them enough! If you are looking for a place to stay near SouthHampton or Hampton Bays, THIS is the place to be. What a lovely stay! :)

The cottage was just as described and the pictures were spot on. This is perfect for a get-a-way which is what we did. Had not been back to the area in over 20 years and wanted a convenient place to meet up with family and see the sights. It is just off the Main Road and 2 minutes to Route 48 for quick access to the vineyards, beaches, restaurants and more. If you like oysters, there is an stand right next door. If we decide to go back to Long Island, this will be the one I look for first.

Such a relaxing atmosphere! Quiet and nestled within nature. The view and hot tub were my favorites. The coffee station was an added bonus:) Monica and Stanley were very responsive. If you’re looking for R&R this is the place.

This cottage couldn’t be cuter! Perfect for 4 for a short stay. Spotless, breezy, well decorated, everything brand new, with thoughtful touches like candy jar with gummies and a wine fridge. Location is perfect for exploring the North Fork. John was super responsive and friendly.

Brian is an amazing host, attentive, friendly, and always making sure we had everything we needed. The apartment was exactly as described: very clean and well-equipped with all the essentials. The surroundings were absolutely beautiful and made our stay even more enjoyable. We had a wonderful time and can’t wait to return to Brian’s place!