Holiday Homes in Town of Southold Town

"We stayed at this house for 3 days at the beginning of the season. It’s very close to everything in town and was very thoughtfully designed and maintained. It was absolutely perfect, especially the amazing garden. Highly recommended."

"Spacious comfortable and inviting home. Well-stocked everything. Lovely outdoor spaces and gracious hosts."

"We've found that fall is a great time to visit the North Fork and the property was the perfect place for relaxing. Even when the weather was bad, we had the indoor fireplace to add ambiance and then the outdoor firepit when the weather cleared up. The views are fantastic and so nice to sit outside and relax at night. Had a couple of quick questions come up but got responses very quickly and it didn't interrupt the trip. We had a great time."

"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 listing was exactly as described and was a great little apartment in Greenport with everything we needed. About a 10 minute walk to downtown area which was very convenient. It sits on a busy street so there is some noise from the road but it did not bother us too much and the host provided noise machines in the bedrooms which was very helpful. Overall I recommend this apartment and would definitely stay in the future!"

"Very nice property that is incredibly well maintained. We had a nightmare experience on Cape Cod two summers ago and this was just the opposite. Laura was super responsive and the home was everything you see in the photos with absolutely everything we needed for our stay."

"My oldest daughter did a little getaway during the week and we fell in love with our accommodations! Clean, priced right and close to town. But maybe the best part was the clear communication and attention we recvd from our host. Everything went smooth. This immaculate home came with everything we were looking for. Outstanding!!!! Definitely recommend."

"My family had a beautiful stay in this home right on Peconic bay! The home was huge and stunning with gorgeous landscaping in the front and the beach only steps away across the lawn in the back. We especially loved enjoying the views across the bay from in the hot tub. This home is ideal for a small family reunion, with ample space and bedrooms, especially with the separate carriage house which really is its own mini apartment-- the listing actually sort of undersells it! Communication from the...

"Perfect spot for a weekend on the North Fork"

"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!"

"Lovely home set right off the water with a sprawling yard. Unfortunately the weather was not on our side but the town had so many wonderful shops and amazing places to eat that we didn’t miss a beat. The house was clean and comfortable set in a beautiful neighborhood ."

"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!!"

"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."

"We had a wonderful pre season get away for a couple of days. The apartment was newly renovated and really clean and comfortable. Cute walkable main street nearby with restaurants and shopping. Nice little beach nearby if you have little kids. We took the ferry to Shelter Island and the south ferry to the Hamptons. We are looking forward to coming back to do the winery tastings. We rust ran out if time. The host was great and responsive."

"My family had a lovely weekend in this lovely home! It was well located, well stocked, clean and spacious. Kathy was a super responsive and helpful host. We loved our stay!"

"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...

"We had a lovely time at this rental not only because of its amazing location to downtown/local wineries, but its stunning design and aesthetic. We could have just stayed inside to enjoy the fireplace & glorious seating. Beds/amenities were fantastic. Hosts were very responsive and helpful. Highly recommend."