Monthly Rentals in Shelter Island

Had a wonderful stay at this beautiful home on the North Fork. Stayed off-season-calm, peaceful and relaxing setting with breathtaking views of the bay. The cottage had everything I needed and felt cozy and welcoming immediately. And very clean. Andrew was friendly, efficient and well organized. I highly recommend this cottage to anyone looking for some R and R!

Absolutely gorgeous spot on Shelter Island! Everything you could possibly want - and I do mean EVERYTHING - in a lovely house. Fully stocked kitchen, bathtub, workout room, fire pit - the list goes on! So close to grocery, wine store, restaurants. The nicest and most attentive hosts, as well. Total gem that we will be coming back to. 🥰

This is a great house on Shelter Island. Our family loved the pool and the basement TV room. The host was accommodating and responsive. Highly recommend!

Michaela is a super host - for sure! Easy to communicate with. She's kind and patient. Very responsive to the needs of her guests. I would not hesitate to stay here again! The street is quiet, there's a pond in the backyard which attracts all kinds of birds, deer and turkeys. I thoroughly enjoyed the amazing living room with piano. The stores and restaurants are near by and food is easily procured. Michaela has a welcome notebook which lists all the go-to spots on the Island. A true treasure. I will definitely stay here again.