Thimble Islands vacation rentals

Ed was great at communicating, house was everything we could have asked for. Would definitely book again!

Truly home sweet home. Just walk in and relax. Fully stocked kitchen including milk, eggs, butter and pastries so no need to rush out to go grocery shopping. Convenient to New Haven yet completely quiet neighborhood for resting and taking walks.

Our family opted for a trip to New London to reconnect with our family for Thanksgiving. We were able to utilize the beautiful dining room for our dinner . We loved staying at Rosa’s place and were very comfortable . Just a note - there is only one bathroom and it is on the second floor ( as are all the bedrooms) We made this work but can be difficult with a larger family . It would definitely not deter me from booking again! This place was beautiful. The surrounding area and ease of access was comforting ! Would definitely stay here again .

Laurie s place is very nice, spacious and clean. Plenty of space to eat, hang out and 2 bath. The fenced in yard is great for dogs or kids. We weren't in full summer season so we're not taking advantage of the beach and water options but they offer alot. Allowed for an early check in which was great as we were in town for a memorial service.

What an amazing host. Jenns communication is spot on. She is very accommodating and was understanding and went above and beyond for our family. In the unusual situation that we were in, not only that, but she provided us with additional garbage bags and toilet paper and other things that we needed in the home, most hosts do not do that. her home is very warm and Welcoming and inviting and made us feel right at home. If I could rate her three hundred stars, I would, she is truly and honestly, a superhost.

Our family had an amazing stay at this location. Loved that all the switches were clearly labeled as we have had trouble figuring out lighting in other locations. What a great touch! Wonderful yard and the basement was fun for all ages. This location was perfect for us as we have family all over the island. Lots of stores locally for anything you need. Highly recommend!

This was our second stay at Judie's place. The house is immaculately clean, from easy check in, instructions left, comfortable beds, location is amazing, walkable into town. Showers are great, I could go on and on about how great the space is. We will definitely stay here again when back in Greenport.

My family and I had a very relaxing stay at this place. Cozy with plenty of amenities. PAPA, the neighborhood cat likes to visit in the morning on the front deck and he’s a very good boy. Bring him treats.

Great place to stay clean and close to the event we went to… they were helpful and allowed us to stay 1 hr longer for our convenience… there was only one TV in the house so if you have kids make sure they have their tablets or they will control the one TV other than that it was enough space for us…. Thanks

Amber’s place was immaculate and stunning. This was my 2nd time staying and it was just as magical! The place had plenty of space for a family of 3 and the washer/dryer was very convenient. We had a great time and would stay here again!

My family and I loved staying at Gail’s place! We grew up in Madison and were back for a visit. It was such a great place and allowed us to re-live many fond memories of growing up in the area!

It was a perfect spot for our little family vacation. We were so close to a few really nice beaches and the area is a short drive to mystic aquarium and village. Patsy and family are very nice and gave some great suggestions for activities in the area.

The property was cozy and clean with great graden sitting are and almost everything you could need. Only qualm was that the property was advertised to have a fence but there isn’t one, there is a hedge but not a gate to make an enclosed space for a dog. This isn’t a huge deal because the beach is so close and great for walks just a minor disappoint other than that the place is incredibly cozy and we would be happy to stay here again

Perfect getaway in Shelter Island! The pool house is as amazing as it looks in the listing :) Cute house on a beautiful, peaceful and very private green lot. Primael was very welcoming and responsive. She was also very flexible in terms of our check in and check out. Everything went super smoothly. We enjoyed our stay a lot!

we rented La Spiaggia in December, and while it's mostly going to be more beautiful and better in the summer (since it's a beach house) it was still perfectly fine in the winter; well insulated and with good strong heaters. speaking of the beach I can't stress enough of how close this place is to the water; I'm talking literally ten steps to the sand. I would certainly recommend the place as a great summer getaway!

What a beautiful place and conveniently located. The house was wonderful decorated, was very comfortable and definitely was a relaxing place to get away. Irina was a wonderful host and the home had many wonderful amenities to offer.