House vacation rentals in Southold

Ashton’s house a very comfortable and extremely clean home. It is spacious, allowed tremendous privacy and met our needs perfectly for an amazing family vacation. Everything was just as explained with no surprises. Great stay and a very accommodating host.

Everything was perfect for our girls weekend. This is the 3rd time we’ve used Laurie’s house and there’s obviously a reason we keep coming back. Can’t wait to go again.

It was a lovely stay. Great location. House felt like a home and had great vibes.

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!

We had a great weekend in Mattituck! The house is in a great location close to the vineyards and we enjoyed relaxing in the beautiful backyard. It was a quiet and a peaceful escape from the city. Fabio was also a kind and informative host.

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.

We had a lively stay at David and Michiko's place. It was a perfect little getaway for 2 young familes of four. The pool was great, and it was a short drive to the beach. Lots of great restaurants around also!

We had a fantastic stay at the Floating Barn! The home was exactly as described—clean, cozy, and uniquely decorated. Everything we needed was provided, including a fully stocked kitchen, pool towels, and fast Wi-Fi. The location was perfect—quiet yet close enough to everything. We especially enjoyed the saltwater pool and guidebook recommendations, including Country View Farmstand (amazing pies)! Andrew and Elizabeth are incredibly responsive and made check-in seamless. You can tell they truly care about their guests’ experience. I’d definitely recommend this spot to anyone visiting the area and can’t wait to return!

Short stay but was perfect for what we needed.

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.

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!

We had a great stay. The house was warm and inviting. Very peaceful and quiet. Plenty of room for the family. Very easy to get to and very close to downtown. I would highly recommend!!! Steve was very friendly and responsive to all our needs!

Ellen’s place was great for the 4 of us! We loved the quiet residential location which was a short drive to good restaurants. We spent a lot of time lounging on the back patio which had comfortable patio furniture. We drove to beaches, and found that a couple further away met our needs better than the local Yacht Club. The beach gear that was provided at the guest house was really helpful. Ellen was a top communicator & provided more snacks and drinks than I’ve ever seen at an AirBNB. I recommend Ellen’s place!

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!

Jamie’s place was very clean and as advertised. He responded very quickly to messages that I sent . There were snacks and waters available when we arrived which is a nice touch. Although we did not actually spend much time at the house (as we were in the area for a wedding )it was perfect for what we needed it for.

This was our wedding day weekend and we were shocked just how well this Airbnb was designed, built and cared for. All of the appliances were high quality, an art TV, a gorgeous shower. My wife and I couldn't have been happier calling this cute cottage home for this special weekend. Thank you Sara!

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!

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!

I have a lovely time at this charming home. It was exactly as pictured and advertised. The home is warm and inviting and I was very comfortable throughout my stay. The backyard has a beautiful view of a lake. I spent quite a bit of time on the rear deck reading and getting distracted by that view. Locally there is Greenport Village, Orient Point State Park and Inlet County Park to name a few of my favorite outings. Thank you to my host for being so responsive when I called with a minor issue one late evening. I hope to return for another stay one day in the future.

Wonderful weekend stay. Charming.

Clean, spacious, and convenient walk to town and beach.

Excellent spot for family and extended family. Peaceful and well appointed. Lots of nice updates and comfortable. Games and pool made it so fun.

Yvonne's place is wonderful, we spent six days there on a family vacation to celebrate a graduation and it was a perfect spot for a crowd. The description and pictures are spot on (maybe even better) and the place is very well maintained. The weather was not great - so we landed up staying in more than we anticipated and this was a great spot for that. The kitchen is well stocked, having a barbecue really helped, and the large windows and skylights kept us connected to the outside. Yvonne was also highly responsive in case we needed anything. Highly recommend.

We had a great mini vacation at this wonderful home. The home is beautiful, clean, comfortable. The property is so pretty, well kept, the deck was inviting for our meals and fun games in the backyard. Great location, near vineyards, restaurants and shops. We will be back.