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

We have been staying here over the last 4 years, when we visit UConn, and will miss it now that our daughter has graduated. Keri is wonderful host, welcoming & accommodating. Her home in the woods is a refuge, comfortable, peaceful, and minutes from campus.

Had booked a girls getaway at Tracy and Patrick’s place and it was perfect, even with gloomy weather! The house perfectly matches all pictures and descriptions and has everything you’ll need and more for the perfect relaxing and fun getaway! We even got a cute surprise visit from their furry friends which is always loved!! There are also shops and beaches a short drive away, we just didn’t happen to go visit because we were enjoying our cozy time at the home. Thank you again Tracy and Patrick:) we would totally recommend and want to come back!

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!

Alexis welcomed us at her gorgeous Airbnb. The place is very well though and practical. It is soothing and relaxing. I would recommend this opportunity anytime, and looking forward to come back soon! Excellent experience for a reasonable price!

We loved our stay! It’s perfect distance to walk to dinner downtown. Off street parking was a huge plus. Brennan gave us a great recommendation upon our arrival! Love the touch of having snacks and drinks in the fridge. Overall perfect place to stay at in Newport!

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 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!

Cabin on Little River met our expectations and more. Myself, 2 sisters and my daughter wanted a quiet getaway. A charming open concept post and beam, pine floors and wood trim, woodstove for winter, deck with charcoal grill. It's very rural and IN the woods ( so bring bug repellant). Even though the host's home is visible you still feel tucked away. Kitchen and bath are modern and clean and the beds and livingroom were very comfortable. The soothing sound of the river is always present. It was relaxing to sit down in the adirondack chairs near its bank. The woods provide a place to walk. Lake is across the road. Glenn informed us of several events nearby that we were really interested in...but we never felt like leaving the cabin! There's a big firepit nearby and wood provided. Glenn is a wonderful host. A fellow artist, I asked to see his studio on the ground level. Even bought a couple small paintings. Do not hesitate to book this place if you are looking for a quiet respite!

I went with a group of girls and it was perfect for what we needed! It was so cute and spacious. It was too cold for us to utilize the roof top deck area but on a warm sunny day it would be perfect! There was plenty of room for all of us to get ready. All the bedrooms were big as well. The location was walkable to everything! Parking was great as well and easy. The host responded to all my questions very quickly. This was one of the best Airbnb’s I’ve ever stayed at. I would definitely recommend!!!

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.

The place was perfect. Eli was super friendly and easy to coordinate with. Great views of the water and a solid home base if the weather isn't cooperating. Really enjoyed the weekend there.

We had a wonderful stay at this Airbnb! Geoff was incredibly accommodating, friendly, and very responsive to any questions we had—communication was smooth and easy from start to finish. The apartment itself was spotless and well-maintained, with everything we needed for a comfortable stay. The location couldn’t have been better—just a short walk to downtown Mystic, where you’ll find great restaurants, shops, and waterfront views. I highly recommend this place and would definitely stay here again!

This place is perfect for a large group with lots of queen size beds. Easy walk to Ocean beach.

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!

We absolutely loved our stay at Milton & Megan's Montauk house! It was perfect for a group of 4 (2 couples) there for a 4 day trip. The house is very quiet & peaceful, with lots of outdoor space, but also very walkable to town. The house was super clean, and everything was very easy to find. The bedrooms had lots of closet space, the TV was easy to set up, and all the amenities listed on the website were accurate. We'd love to come back again and stay. Thanks!

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!