Pet-friendly vacation rentals in Shelter Island

We had a fabulous stay at this adorable cottage. It had everything we needed and more. Great spaces indoors and out to hang out, walkable to one of our favorite wineries, other wineries & restaurants close by. Appreciated having a tandem kayak to use & explore Goose Creek. Enjoyed watching birds, including Baltimore oriole parents in a nest in the backyard. Would return again. Thank you!

Kristin’s house was perfect!!! It was even more beautiful in person and had absolutely everything we needed to have the best stay at Greenport! Not only was it beautiful, but it was also in the best location, making it easy to get to and from the Main Street and wineries! I traveled with 8 friends and we all said we’d book again without a doubt! Thank you Kristin for an unforgettable stay!

I have a lovely time at this charming home. It was exactly as pictured and advertised. The home is warm and inviting and I was very comfortable throughout my stay. The backyard has a beautiful view of a lake. I spent quite a bit of time on the rear deck reading and getting distracted by that view. Locally there is Greenport Village, Orient Point State Park and Inlet County Park to name a few of my favorite outings. Thank you to my host for being so responsive when I called with a minor issue one late evening. I hope to return for another stay one day in the future.

We had a wonderful stay! The master suite is huge and the bathroom is dreamy. We didn’t really use the backyard bc it was winter but it was great for our pup! Kitchen was small but did the job (no microwave). We had issues with streaming on the “guest” accounts but we always travel with our own firestick so we were fine. The beds were super comfortable (firm memory foam type) but it was quite bright in the upstairs bedrooms in the morning bc several of the windows had no covering so if you need a blackout situation for little ones pack accordingly. We were able to put the provided pack and play in the closet which was fine for us! We would definitely recommend and return!

The house was clean, well-decorated, had all the things we needed, and private, with a long wooded lot leading down to the bay. We women friends were totally comfortable there. When we couldn’t find the entrance to the driveway off the main road, she stayed on the phone & directed us until we found it. Excellent choice!

Just returned from an awesome stay at Travis’s cottage. Travis and Morgan are great hosts and were very helpful with providing local suggestions and prompt communication. The property is great and was the perfect home base for our first trip to the North Fork. The location is ideal: quiet, charming, and centrally located to everything (wineries, beaches, breweries, farms, and great restaurants in Mattituck and the nearby towns). As a family with two young kids (6 y/o and 18 months), the fenced yard was a huge bonus - private, peaceful, and perfect for relaxing while the kids played safely. The house itself is cozy, clean, and full of character. We’d absolutely stay again on our next visit to the area.

Dewey’s place is such a dream! Everything is freshly renovated and just feels so crisp, clean, and stylish. You can tell so much love went into the design it’s the perfect mix of modern and cozy. We felt right at home the second we walked in. The kitchen is gorgeous, the bathrooms are spa-like, and every little detail was just so well thought out. Dewey was the sweetest host super responsive and made everything totally seamless. The location is amazing too quiet and peaceful, but still close to all the fun spots (beach, town, restaurants). We didn’t want to leave! Already planning our next trip back. If you’re thinking about booking, do it you’ll love it just as much as we did!

Absolutely beautiful home and wonderful experience!! The host was quick to respond and the amenities were excellent. There was zero lack! Would definitely return for another stay!

Marta could not have been more accommodating! She was responsive and provided everything we needed. She even went the extra mile and insta cart-ed garbage bags and paper towels when we ran out. She could not have been a kinder host! We had the best weekend and would HIGHLY recommend staying at Marta’s place! We will definitely be back!

Ashton’s house a very comfortable and extremely clean home. It is spacious, allowed tremendous privacy and met our needs perfectly for an amazing family vacation. Everything was just as explained with no surprises. Great stay and a very accommodating host.

Maher’s home is so elegant and mid —such great taste. He was such a kind host and so very easy to communicate with. The pool was lovely and the garden and back so pretty. We had a brilliant time! Thank you.

Great spot in Hampton Bays! The house was as described and in a very cute and walkable neighborhood. Super close drive to the beach and a couple of local restaurants and eateries. Loved how private the spot felt too! David’s done a wonderful job with the backyard, so you get the comfort of having close neighbors without the intrusiveness. Pool was awesome. We definitely enjoyed it!

We had the most beautiful weekend stay at Tim’s home! Everything is accurately described and the pool and hot tub were amazing!! All the beds were very comfortable. Was perfect for a 5 girl weekend getaway!! Tim was incredibly communicative and checking in was a breeze. The location is PERFECT in East Hampton!! So many amazing restaurants and bars nearby. 100% will stay here again for my next Hamptons trip. Thank you so much Tim!!

Yvonne's place is wonderful, we spent six days there on a family vacation to celebrate a graduation and it was a perfect spot for a crowd. The description and pictures are spot on (maybe even better) and the place is very well maintained. The weather was not great - so we landed up staying in more than we anticipated and this was a great spot for that. The kitchen is well stocked, having a barbecue really helped, and the large windows and skylights kept us connected to the outside. Yvonne was also highly responsive in case we needed anything. Highly recommend.

Beautiful house, even nicer than the photos. Great location to tour local wineries and close to the greenport’s Main Street! The house is stocked with plenty of cooking utensils and has whatever you might need. Would definitely consider coming back in the summer to enjoy the backyard when the pool is open!

An ideal location in Southampton, Lori’s house is clean, cozy and peaceful; we thoroughly enjoyed spending our New Years there!

Cannot say enough great things about this house. I’ve stayed in many AirBnBs and other home rentals over the years and this was one of my absolute favorites. The house is beautifully updated and was extremely clean. The kitchen and bathrooms are gorgeous and have everything you need. Beds were so comfortable and the room darkening shades are a rare find in a vacation rental. Close to Greenport town and lots of wineries. Backyard was beautifully landscaped and was amazing for our dogs to run around. We will definitely stay here again!

The home was lovely, a charming Victorian home. We loved the porch swing, spacious kitchen, and antique furniture. The home was a good location, a quick walk to Greenport, and it was nice to park our car and walk into town. Down the street was also a nice beach. It was thoughtful that there were some snacks and water when we arrived. We would stay again!

Dave was an amazing host. Incredibly responsive, everything was clearly communicated, and very helpful. The house was perfect for our family--great location near the beach with shops/restaurants nearby. Highly recommend!

This is the second time we stayed at Kim’s. It was another pleasant experience. Kim is responsive and easy-going. Her home is welcoming and very dog-friendly. We love that Kim has beach access and it is walking distance. The convenience of her home being close to Southampton and Sag Harbor restaurants and shops is a plus. Thanks for having us, Kim. We will be back. xo - Dave, Sasha & Ginger.

Our family had the most amazing weekend at this home. Benjamin was very responsive and accommodating. There was not a detail missed in the home and outdoor environments. Even though it rained we had a full day of entertainment at the home. You will not be disappointed.

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!

We had the most wonderful and peaceful fall weekend at Brooke’s cozy cottage to celebrate our anniversary, and it was truly unforgettable! The cottage itself is beautifully decorated and felt like a warm home away from home. Brooke went above and beyond to make our stay special, leaving us complimentary champagne and wine to kick off our celebration. The location was perfect for enjoying the crisp fall air and stunning foliage, providing the peaceful retreat we were hoping for. We can’t recommend this place enough and will definitely be back for another stay!

Spent to my birthday here with my husband, dogs and toddler. Had my gender reveal birthday cake, outback under the sunset. Truly magical.✨ The backyard was ideal. Was able to tie the dogs to the deck with a 20 foot leash. It kept them contained to the backyard & away from beach goers on foot and other dogs. The dunes kept the backyard private you’re not staring at your neighbors. Felt so secluded. I also have some mobility issues and you couldn’t ask for an easier way to enjoy the beach & get your toes in the sand. The house & deck are spacious and easy to navigate with a walker. Was able to add extra days to our stay. Would 100% stay here again.