Holiday Homes in Town of Southold Town

"Got away for a girls weekend and this was perfect. It was close to wineries, and a short Uber away to Greenport. The house was comfortable, clean, and private with enough space for all 8 of us. The outside was also beautiful- right on the water. Highly recommend!!"

"Perfect spot for a weekend on the North Fork"

"We had the best time visiting Sam & Matt’s place in Southold. The house is the perfect size for us- 3 adults and 3 kids plus 2 dogs. And it was an ideal location to explore all the north fork has to offer. We can’t wait to return!"

"Great stay and wonderful property. The first stay that didn’t have a book and list full of restrictions and checkout instructions. After a whirlwind weekend celebrating our daughter ‘s engagement, this was a welcomed surprise! Everyone enjoyed their stay, including our two labs. Great fenced in yard that gave them plenty of room to exercise. We will be back!"

"This was a great house! Everythingwas perfect, the house was very clean and David was incredibly accomodating to all our requests and provifed great recommendations for places to visit. We will definitely be back"

"Lovely home, right on the bay, super clean, very well , wonderful owner."

"Such an amazing and flawless experience! The whole process of checking in and instructions, plus the homeowner gave us recommendations for places to eat and fav wineries! The cottage was so cute, so so clean, so spacious. It was the perfect cottage for our girls weekend!! The location was beautiful! We walked to the beach in the morning and it was gorg!! It has a private lawn & outdoor space, that we were able to hang out in. We really felt at home the entire weekend!! I would highly recommend &...

"Had friends and family at whitecap for a wine weekend. House was beautiful and clean. Close to so many vineyards and the walk to the beach was amazing. Can’t wait to stay again!"

"The house was well kept and very organized. We loved the way everything was labeled and the clear directions provided. Kim was a great hostess and provided us with a timely response with any of our questions. We had an amazing time and were extremely happy and satisfied with our overall experience."

"Our stay was wonderful! The check-in process was smooth, the home was clean and the location was perfect! We look forward to visiting again!"

"The house was great but the back yard was sensational . we enjoyed every inch from the large patio to the pool to the basket ball court. There was something for every age group . My family enjoyed it all especially my grandchildren ages 3 to 12 . And after the children went to bed the adults sat around the fire pit for a lively evening . Great vacation !"

"We spent the last few weeks of summer in this beautiful home! We didn’t want to leave at the end of our stay. Beautiful, spacious and well decorated with a gorgeous backyard and pool. And a great location too! We took nightly walks to the beach to watch sunset and rode bikes through the neighborhood. Close to Greenport village and some of our favorite vineyards. Our kids loved the bunk beds in the kids room and the trampoline in the backyard. This house has everything you need though for a fun...

"Perfect home and location near the vineyards and restaurants"

"Nicely redone house with a cottage feel well located in North Fork wine country. Not a large place but plenty of room for two adults and two kids. Stairway to the upstairs bedrooms/bath are non standard and could be a challenge for some folks. Communication between VACASA and local rep was not good. We were notified we could get into the house early and when we arrived the local rep was there cleaning and was unaware of the early check in notice. Not a big deal but also not ideal.Overall the...

"We stayed at this lovely home in Greenport. It was very close to shops and restaurants, but very peaceful and a great location for exploring the North Fork. The house and rooms were bright and comfortable, and the decor was very tasteful."

"This was the perfect Christmas House for our family while celebrating a 100th Family Birthday nearby. This is a beautifully appointed and true to period Victorian. The home is immaculate and incredibly well tended. The hosts were lovely and very responsive. This was a special stay and made more so by the wonderful surroundings and ease to town. We would stay here again."

"A group of 8 women had a wonderful weekend visiting vineyards and this was the perfect location! The house was extremely clean and well stocked with everything we needed. Great communication with host, thank you!"

"Everything was just like it was stated. Beside the bad weather, we couldn't have gotten something my perfect for the 7 of us. Plenty of room for us to enjoy our time. Will return!"

"This spot is where you want to be if you love the chill North Fork vibe and small town feelings from Mattituck to Orient Point. We will be back- actually we wish we were still there!! :)"

"It was lovely having my family stay at Jackie's home for a family wedding in Greenport. The home accommodated our large group and was a close walk to town as well! Jackie was communicative when we needed prior to reservation and we would recommend this stay to anyone who is looking for a lovely time in Greenport!"