Family-friendly holiday rentals in Charlestown

Our stay was peaceful located in a great place , the home its self was perfect if we come back next year we will book this place again

The place was quiet, surrounded by beautiful woods, and truly relaxing—it was exactly what I needed. The bed was incredibly comfortable, and I slept so well each night. I also appreciated how responsive the host was to my questions via text. I would love to stay there again in the future. Thank you so much!

We thoroughly enjoyed our time at the cottage. It was so very peaceful and we loved being literally right around n the water! Slept amazingly well and the cottage was just lovely! Robert was also a great host. 5 stars all around and we hope to return again!

Went with family for a weekend trip. Tracy and Patrick’s home is lovely, very beautiful and well maintained. And everyone enjoyed including my kid who found a lot of toys to play.

This spot was a great find. Hadn't been to Shelter Island before. I found the location super convenient. Literally every place I went was 5 mins on GPS from her house. She was very clear about everything, responsive to emails, and everything was as described, however the pictures don't do it justice. Beautiful home and pool, people came to clean the pool early one morning during the stay and were not disruptive at all. There were beach chairs, umbrellas, pool floaties, games, netflix, literally everything you could want or need. Loved our stay!

Very cute tucked away villa, with pool/hot tub, close to Mohegan Sun. The host was very responsive and the villa was clean and nicely decorated. Would love to come again :-)

Great location, close to everything. The house was roomy and comfortable. The porch was nice to hang out on and the jacuzzi and cabana were a fun plus. I recommend this home for your Greenport stay

I can’t say enough wonderful things about this incredible home! Surrounded by peaceful woods with snow on the ground, many birds, and the occasional deer wandering by, I felt completely connected to nature. It was the perfect winter getaway I needed from the city. The house was impeccably clean with all the essentials - a well stocked kitchen, an impressive vinyl collection and sound system, and a variety of interesting books and magazines throughout. There’s also a generous-sized TV with all my favorite streaming services, making it easy to unwind and enjoy my downtime. This home brought back fond memories of a lake cabin I spent many summers at but with a much more chic, spacious, and cozy vibe. With it's warm wood finishes and large windows that filled the rooms with sunlight, it perfectly blends nostalgia with modern comfort. I wholeheartedly recommend this place to anyone seeking a serene escape!

This was a fabulous destination! We were looking for a big place to have a special anniversary party weekend with extended family, and this house had everything we needed. Plenty of bedrooms upstairs and first floor, many common gathering areas, large kitchen and dining room tables, and lots of Space. (And this doesn't even include the explorable property outside.) The dozens of photos in the listing were very helpful, as well as the detailed descriptions. We had specific needs for elderly relatives with disabilities, and owner Lynne was so responsive in her replies to my many messages with varied questions. Truly, Lynne, you deserve a gold star from Airbnb for promptness and offering up ways and help that made our stay both easier and fulfilling.

Lovely spot for 2 families with young kids and dogs! Had gates at the stairs, a pack and play, and a high chair for baby. Super walkable location. Would come back!

This home is gorgeous and filled with timeless artifacts and family heirlooms. Beautiful spots to sit outside with a morning coffee. My partner and I made a point of staying in and cooking one night because we felt right at home and wanted to appreciate the ambiance. We enjoyed the privacy and proximity to Newport very much as well. Well outside any potential chaos of downtown yet only a couple minute drive to Easton Beach. Thank you so much!

We had a wonderful family stay a this home to visit some local kid attractions including the aquarium. Hope is a fantastic host - great communication, friendly and accommodating. The house itself was roomy for our group. It was clean and very well appointed with all the basics you need to be comfortable. The four king sized beds was really nice. No fighting over rooms! Our kids enjoyed the chalk and bubbles that were left outside and playing in the yard. The deck is also a nice space although we didn’t get to use it due to weather. I would definitely recommend this home.

Wonderful weekend stay at Kathleen’s oceanfront cottage. Charming neighborhood makes you consider moving to Newport if you could afford it! Loved our stay and would love to return in the future. Kathleen is a superb and welcoming host.

A nice stay for a family gathering in the area. It worked well for us.

We had a great stay a CasaBungo. The location was easily within walking distance to town, the beach and great restaurants. We loved being able to bring our dog and having her play in the fenced in yard. All the necessary houseware was there for our needs. I love an Air B and B with a good bed and these beds were top notch, super comfy with quality linens. We will definitely be back!

Eli’s place is a peaceful haven to rest and recharge. My kids weee coming straight from their finals and really needed that time of serenity to recharge before heading back to their busy summer internships. Waking up to the breathtaking sunrise views with a cup of coffee was healing to the soul. Eli was a wonderful host, very kind and super helpful. He even left a gift card for a local coffee place so that we would know which beach to access with a cup of coffee in hand. My only suggestion for improvement was to add blackout curtains in the bedrooms for days you want to sleep in or go back to bed after watching the sunrise. Other than that, everything was perfect. Thank you Eli for a wonderful and memorable stay!

Beautiful, relaxing, clean Airbnb. Had an issue with the shower, which can happen anywhere, Mk was super responsive and came over quickly. Loved loved loved our stay here. Didn’t use the swimming pool due to weather but the screened deck with the Fire Pit and the superb game room saved the day. Thank you for hosting us will be back

Thank you so much! Really enjoyed my time in brooklyn.

The hosts Marybeth and Douglas were so welcoming to us and accommodated our request to check- in earlier than scheduled! They were very friendly and provided extra stuff to make our stay feel so homely and comfortable! Everyone of us (13 people) truly enjoyed our stay at their beautiful, spacious and historical home!

John was a perfect host! Friendly, responsive and made us feel welcome. I took my 9 year old son and we had a great time fishing off the dock and kayaking. The kitchenette is lacking if you want to cook any meals but it didn’t matter in our case. Absolutely beautiful location!

Absolutely perfect. The house provides everything we needed for a great visit. Easy walk to the local beaches. Would definitely return if given the opportunity.

We had a lovely stay at Eric's home. The home exceeded our expectations and we felt right at home. The decor was warm and inviting. Everything you could possibly need was in the stunning, modern kitchen. The beds were all comfortable and we slept very well. The property was very peaceful. We enjoyed seeing deer, turkeys and hawks each day. The fixtures in the home were modern, clean and high-end. It was great being so close to Greenport with it's wonderful restaurants and shops. We can't wait to return.

Just had a wonderful stay at Robert’s place! The place was impeccably clean, and Robert was incredibly responsive and friendly throughout our visit. While the manor has a charmingly vintage vibe and could use a bit of modernization, we truly enjoyed our time there. The warmth of the atmosphere made it feel like a home away from home. We recommend for anyone looking for a cozy getaway!

Fantastic weekend spent in Montauk! Close to everything. Matthew was quick to respond to my questions before we arrived. Would defiantly book again!