House holiday rentals in Southampton

Beautiful, clean property! Bedrooms were spacious and the beds were so comfortable. We enjoyed the hot tub while the snow fell...its a perfect weekend getaway house. I wish I could come back in the summer to enjoy the pool. AJ was very responsive and provided easy instructions for easy check-in.

Joe's place was perfect for a girl's trip with two 1 year olds. The house was beautiful and had so much personality and warmth. The area was super private and quiet surrounded by nature. Joe was very informative about check in process and recommendations were plentiful.

I stayed at Ashton's place by myself on a visit to see my parents, who also live in Springs. It was everything I could have hoped for. So peaceful, and such a beautiful space. Amazing high ceilings and natural light. The yard is gorgeous, so I can only imagine how lovely it is when the weather is warm. Ashton himself is very responsive and accommodating. I was sad to leave!

Our family enjoyed a wonderful post- Christmas getaway at Jennifer’s beautiful home. The house is fabulous - well- located, pristine , beautifully decorated and well-stocked. It was relaxing and perfect. We did not have much need to reach out (everything was effortless) but when we did, Jennifer was very responsive and helpful. Highly recommend!

Dorina’s home was the calm, peaceful reprieve from the city we were looking for. Her home was so comfortable and she went above and beyond to make sure we had everything we needed. The backyard was a little oasis with a large pool (with floats!), several (6 I think) lounger chairs, two 6 top tables in different areas and a functioning grill. We spent most of our time here! Dorina was fast to respond, helpful with recommendations and overall what you hope to have in a host. We would definitely come back to Dorina’s home!

This house was fantastic! We cooked a full Thanksgiving dinner here! The house was well stocked with everything we needed, from kitchen essentials to paper products. The layout of the house was great. Jane was very accommodating and made things easy for us! The house was immaculate and met all of our needs. I hope it’s available next Thanksgiving! Perfect location! Close to town, yet quiet and private! It was my granddaughter’s first Thanksgiving and I’m so glad we had this house to celebrate in!

House is well represented. Spacious, very clean, and great location. Good for families or groups of friends.

Five stars doesn't feel like enough, if anything I'd say everything was better than we'd expected based on the pictures and the reviews! First, as others have mentioned John was an incredible host, the place was well stocked and had all sorts of snacks and drinks (and a nice bottle of wine); he also bought us dinner and was very good about keeping in touch the whole time we were there. The house was amazing top to bottom, but I have to specifically call out the pool, which was jaw-droppingly beautiful and the perfect temperature despite cold weather outside. We loved the neighborhood and yard to walk our dogs, and the kitchen was great to cook in (made me miss having a gas stovetop). We'll definitely be visiting again, it was the kind of stay that sets a new bar for what to look for in a vacation!

The place was perfect! We had a wonderful girls weekend. Beds were super comfortable, place was spotless and beautifully decorated and quaint! Super easy walk to town and Jillian was a great host with prompt response. We will definitely book again! Thank you Jillian

Lovely, well kept and comfortably furnished. This home has everything you need for a comfortable stay. Owner is helpful and very responsive. Highly recommened!

Location was perfect for us- easy to find and close to things that are important to us (family in area, beach, shopping). Fenced yard made bringing our little dog that much easier- especially during the rainy day! Kitchen was well stocked thankfully as we were cooking Thanksgiving dinner (but not well stocked in the casserole dish, baking tin department-- which is usually not an issue for most people!). Decent coffee was supplied with a Keurig. Beds were comfortable. Everything was clean. I liked that he didn't leave a long list of what we needed to do before leaving as that is often a hardship when trying to leave a house with kids before a long drive. I would definitely stay here again.

Kate's place is an absolute gem! This was our first time to Shelter Island, and we loved the laid-back atmosphere. Kate's home has everything you need to have a relaxing weekend, from the amazing, heated pool to the kayaks on the beach, a 2-minute walk from the house! Having been in the hospitality business for over 25 years I tend to be super critical about cleanliness and amenities offered.....this house does not disappoint! We were a group of 10 attending a winery dinner and decided to stay for the weekend. We only left the house to attend the dinner, the rest of the time we stayed at the house, either in the pool, on the deck BBQing or inside chatting where there are two living rooms and a very well-equipped kitchen. The bedrooms were nicely decorated and comfortable! We would definitely recommend and hope to stay again. :)

The house and area were ideal. I had moved from the area the year before I rented Melissa’s home . My partner and I lived just a mile and 1/2 from the rental. He passed away and this was my first time back on the North Fork. Having lived in the area over 30 years it was great to be back. Melissa’s home was perfect close to all my friends and my partner’s family. The house was ideal with 3 levels it was perfectly suited for me and my two dogs to have our space and my two housemates had their own space. I look forward to possibly renting her home next year as well.

House was great! Diana explained everything clearly so I didn’t need to ask any questions. Would definitely stay again!

A lovely cottage on a quiet street (at least in the fall!). The interior is just beautiful with all the wood floors, walls, ceilings. The kitchen was - unusual! Clearly they had to retrofit an old home to accommodate modern appliances, but all worked well.

Kait was super helpful! She texted me a few days prior mentioning we could check in early! I have never had that happen before! The house was stunning, comfortable beds, well maintained and great location. We forgot a jewelry bag at the house and she sent a photo and arranged for our family members near by to pick it up. Highly recommend!!!

Maura was an excellent host and the home was perfect! We enjoyed the weekend very much and cannot thank Maura enough for her kindness, responsiveness, warm hearted spirit, and for opening up her home to us. Will always keep this spot in mind for future SI adventures!

We had a wonderful stay. Cute and comfortable house in an amazing location. Very comfortable for a family of 4.

Wendy’s house is immaculate, tastefully decorated, very spacious and extremely comfortable. Her instructions were clear and her responsiveness immediate. We would absolutely consider staying there again.

Mike is a great host with helpful recommendations and plenty of advice. The house is amazing. Well located, calm, clean and so convenient. The pool is huge and very deep. Everything is perfect. Felt like at home. We will be back

Great stay! House was exactly as described / in photos. Hosts were extremely responsive and easy to communicate with.

My wife and I really enjoyed our stay in Southampton. The place looked exactly like the photographs (really nice), it had everything we could have needed and it was very clean. Our dog very much enjoyed the fenced in back year. The house is in a great location, we took day trips all over both forks and had a great time. We hope to come back when there are leaves on the trees and the pool is open!

Host is very friendly and polite. she responds to your calls and texts whenever we do, my kid 1 year she has so many things to play in the house and well spent

We must have passed the residence hundreds of times going out Montauk over the past 40 years. What a hidden gem. We were so fortunate to have the opportunity to stay at this location. The home was very well appointed, tidy and clean. What a gem of a home, even in the off season. We would love to return.