Family-friendly vacation 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!

Patrick and Tracy were wonderful to rent from and the house was great. We had 5 adults and everyone slept comfortably. The patio was a great experience with the pool, hot tub and great outdoor seating. We loved the area and would return in a heartbeat if the dates are open for next year’s trip.

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!

Kyra was an amazing host and we loved staying in her home! She has clearly done so much work to make it feel comfortable for groups, cozy for relaxing, and worth the listed price. Her attention to detail was very clear - tons and tons of soft towels, beach towels, great shampoo and toiletries, ample cookware that was very high quality, spices for cooking, and lots of pool toys. We got lucky enough to go at a time when a local farm had a weekend of family events. We ate fresh strawberries, had local beer, and toured local antique shops. This was the best Airbnb experience we’ve had and would definitely return!

Stay was great, enjoyed the Spa and the hot tub ! I wish the hot tub closing times were posted somewhere but other than that it was great ! Fire place was a also very cool and the fire starter that is supplied was very helpful

Sort of magical old house, dripping with character and quirks. Great stove and grill and a big dining room Gori Cooking and gathering. Super nice hosts. Nice walk to a nice park nearby. We really enjoyed being there. If you have a reason to be in Norwich, this is a cool place!

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

Great spot. Tons of things to do in walking distance. Cute apartment with everything you could need. Responsive and friendly host.

We had a wonderful stay! The location couldn’t be better and the home was so comfortable and welcoming. All the information was clear and James was very responsive. We would definitely stay again!

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.

This home was perfect. Loved that it is dog friendly. Its location to the surrounding cities and attractions will be the reason I will rent this home again.

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!

Kathleen’s home is quaint, comfortable and offered outstanding views. Kathleen was friendly, very responsive and excited about her family home and the area. We highly recommend her home. Tom and Barbara

This was our fourth stay at Regina’s place! It’s truly the perfect cozy getaway. This spot has become our favorite place to relax, recharge, and feel right at home. Thank you for having us, Regina! You made our last-minute birthday getaway outstanding.

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

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

We had an excellent stay while attending our son's graduation at UCONN. The place was clean and homey, perfect when traveling back and forth. Our plans changed and we did not bring our dog, and Ashley was kind enough to refund us. My son goes back to UConn in the fall for his master's, and we know where we will stay again next May.

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!