Holiday rentals with a kayak in Southold

This house is a gem! I came to stay a week in off season with my dog, Rollo. The location is breathtaking, right on the Long Island Sound. We had a great time exploring the beach, looking for all the biodiversity in the birds and sea creatures, watching the boats, and this place is relatively close to an airport so watching the planes land and take off was awsome as well. We came for privacy, and I expected the beach to be a little more private than it was due to my dog's reactivity. But the neighbors did not seem to have issues with us, and once you are close to the water, especially in low tide, the beach is pretty open for all the locals. Walking around, the locals all waved and said hello. Not too many restaurants close by, but the Lobster Shack down the road had good food! Would stay again! The deck alone was worth it!

We would stay again. The cottage is well maintained. It was nice to have some basic cleaning supplies so you can touch up if needed. Toiletries, laundry supplies, coffee pods, nice touches, felt like home.

Amazing house that could not be any closer to the beach. Super well thought out house with very nice appliances and finishes. Kids and parents alike had a great time and will look forward to visiting again. A real gem!

Beautiful home! Great location! Spent quality family time during Memorial Day weekend. So much to do on Northfork. Nicole was a pleasure to deal with.

I would highly recommend Melissa's place in Jamesport. It was a great location with room to enjoy with some family members including children. It was perfect with some toys and a big outdoor area (and a private beach!) for us all to spend some time together while visiting family in the area. Melissa was accommodating and clear in her directions and gave us a warm welcome with a greeting basket, information about the area and coffee! The location is lovely and everything about the house was fun and comfortable. Thanks!

This place is a gem! When we arrived the home was spotless and exactly as pictured. It seemed brand new and in excellent condition. The hosts were very kind and helpful and even gave us a bottle of wine and left bottled water in the fridge. The beds were so comfortable and the home was stocked with everything we needed. Our young kids loved swimming in the beautiful pool and we enjoyed exploring the rest of the picturesque property—so cool to see the wild turkeys walking around. We had a wonderful vacation and hope to return one day!

Steven and Sylvia are great hosts. The house was very accommodating to our needs. The house invited us to engage in fun activities such as roasting marshmallows, playing pool, and kayaking. The house also provided us a beautiful view of the ocean and the wildlife. We truly enjoyed our stay and wish we could stay even longer.

My extended family (6 adults and 6 kids) had a wonderful stay! The house was gorgeous and in a perfect location for all of our activities!! We felt right at home and there was plenty of room for all of us. The view was simple amazing and we enjoyed walking around the neighborhood. We would recommend this house!

We very much enjoyed staying in Meredith’s place. The cottage is surrounded by trees so it feels secluded and peaceful. The cottage is elegantly decorated; there were so many nice books around which we enjoyed checking out. Meredith was so nice and responsive. We will definitely go back.

Great stay, Maureen is very communicative and super helpful. Beautiful views

Prachtig gelegen vakantiehuis op loopafstand van strand. Fijn huis en fijne omgeving!

Peaceful and beautiful water views. We enjoyed relaxing on the deck and the kids loved playing in the water and on the sand bar despite the rocky beach. The house was welcoming and well stocked. It was very warm especially upstairs and took a while to cool down even with all the wall units on. The host was helpful and responsive whenever we reached out. Overall it was a lovely getaway spot!

Simply wonderful spot! We will try to come back! The personal touches were great. Shampoo and conditioner! Make up wipes! Plenty of toilet paper and so on. Traveling guests really appreciate those small things. Thank you!

We had a fabulous weekend at this lovely cottage. Located on a remote peninsula surrounded by the glistening water we couldn’t have asked for a nicer experience. The amenities were both convenient and thoughtful. Although we chose to dine out, the kitchen was very modern with upscale appliances and an espresso machine. We did bbq on our last night and had a great end to our 4 night stay!

Wonderful bay side cottage! Stayed here for a long weekend with my husband and in laws. It’s a great location!! Water views, walkable cute neighborhood, and 20 mins from some of the bigger towns (Jamesport & Greenport) Place was clean and a fully stocked kitchen made it easy to stay in and grill out.

We absolutely loved our stay in Clinton! The apartment was beautiful and clean with an amazing view. We tried lots of local hot spots and had a great swim at nearby Hammonasset. Communication and instructions were excellent. We look forward to returning!