Thimble Islands vacation rentals

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

This was our second time back to the pool house and it was amazing, again. We thinks of everything to make you feel welcome. Milk and eggs in the fridge. Muffins and croissants waiting for you. Pristine home. Fully stocked kitchen. I was even able to host a few family members for Christmas dinner and had everything I needed to make a lovely dinner. We also travel with two dogs and Sue is so accommodating, making our pups feel right at home. Thank you, Sue, for making our holidays away from home so peaceful and enjoyable.

This home is beautiful and so spacious! Proximity to East Hampton and Springs, yet very private and peaceful. Couldn’t recommend enough!

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 .

We were so excited to find this house available again. We were here a few years ago and always wanted to return. It was just as wonderful as we remembered. Iris is a great host. She meets every request with prompt enthusiasm. We highly recommend her and this beautiful home.

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.

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.

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

A beautiful home- super comfortable and spacious. It is outfitted with everything you could need. Peaceful location (we stayed in spring/winter- can’t speak to what it would be like in season). Lovely views. Easy to get into town by car (3-5 minutes!). Host was excellent - responsive to any questions or inquiries

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!

June and her bungalow emanated an inviting warmth from the very beginning. My partner and I were looking for a peaceful getaway with our pup, and we were thrilled to see such a beautiful, affordable, pet friendly option by the water. I then saw that it was just 15mins from my grandmother in Waterford, so we would be able to visit with her, too! We exchanged friendly messages right after booking, and I immediately felt confident and comfortable with our decision to stay at her place. June was incredibly thoughtful and seemed to think of everything! She sent a message earlier in the week ahead of the booking to let us know she was preparing for our stay and to share excitement on the beautiful forecast. She was flexible and communicative on check in/check out times, and wished us well throughout her stay. We felt truly at home upon arrival. You can tell this bungalow has been loved and cared for, and that many good times have been shared. Very positive and serene energy. 🌅♥️🐾

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.

We had a great time staying with Marina. The space was so clean and the perfect size for two adults and our senior pup. The outdoor space was beautifully landscaped and the beach was only a 5 minute walk. We would definitely come back!

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!