Search Vacation Homes in Southold

"Very relaxing place to stay 2 minutes from the beach and fabulous sunsets. Property was spotless with tons of room. "

"Enjoyed this house in a great location. It was perfect for attending a family wedding!"

"Had a great stay! Everything about the stay was perfect. Place was all that we expected and more. Host was easy to reach and very responsive. "

"Perfect getaway for a group of ladies spending a snowy night catching up away from our spouses and kids. Cozy fireplace, beautiful home, ample space and in a great location. Highly recommend!"

"Margaret is just wonderful. We felt like we were staying at a dear family member’s home. Stayed in her very private upstairs suite and it was perfect for me, my wife and our pup. He had a blast running around the yard, meeting the chickens going to the bay beach etc. We had the best time! Thank you Margaret!!"

"We had an amazing stay. This was the perfect weekend trip for us with our pups to celebrate our husky's 10th birthday(he has terminal cancer and we werent sure we would be celebrating this milestone with him). House was very clean and welcoming. Beach is just a short walk (or drive in the cold). The kids loved the ping pong table and being able to walk down to the beach. Host was easy to get ahold of if needed. Would definitely stay again."

"We loved our stay in this home! It was the perfect size for our extended family. It was well appointed. The kids loved playing in both levels of the garage. The kitchen had everything we needed. The beds were all comfy. We even took a dip in the cold pool! The owner was responsive to our requests and met all of our needs. I highly recommend this home!"

"Family friendly, clean and well-stocked house with nice deck and pool for entertaining. It has personality. Well stocked kitchen (note - includes french press and a pod system but you need to bring your own pods; no coffee maker or kettle at time of our stay). Plenty of spices and condiments and entertaining ware as this is also their vacation home. Conveniently located near the highway and walkable to commercial area and 10 min drive to nearest beaches (it does back up to highway so gets road...

"This property is beautiful and the house is spacious and well equipped for a wonderful stay. The host was attentive and easy to contact when it was necessary. Such a fantastic choice for a stay in a delightful town. "

"Beautiful classic farmhouse with all the modern amenities including high speed internet, great kitchen and brand new heating/AC so you can enjoy all the comforts of a 5 Star Resort. Conveniently located within walking distance to the Palm, Movie Theatre and the bus stop to NYC. Beverly Leopold was a very conscientious and hospitable host. Highly recommend!"

"Susan's place was perfect for my family to visit the neighborhood where I grew up! It was clean, comfortable and had everything we needed. It's also a few steps from the beach and the amenities GNB has to offer."

"Wonderful property combining original details with modern amenities. Well located near the town green and shops. We would definitely stay here again."