Family-friendly holiday rentals in Block Island Sound

We loved staying at this home - it was the perfect place for our group of ten. The outdoor space was definitely the highlight, with the pool & spa being our favorite part of the trip. The only thing to note is that we weren’t supplied quite enough toilet paper or paper towels, though I did not reach out for more - It was the last evening when we ran out and we were leaving early the next morning. The trash requirements were a surprise after booking, but going to the transfer station was easy enough, and it is listed on the house rules. Overall, an excellent stay and would absolutely return!

John went out of his way to ensure we had a great stay. It was a great place that accommodates many and the hot tub was relaxing after a long day of golf.

We had a fantastic girls weekend in Southampton and loved Anthony's cottage. It was so beautifully decorated and cozy. We throughly enjoyed mornings with coffee and books in the sun room.

Abagail was very helpful in getting settled. The house is full of interesting antiques and paintings. There was a wonderful view of the Litchfield Hills and a lot to do outside. It is rustic but it has every convenience of home. Great shower. Must have been a barn but now it is a museum of Art Nueveau treasures and stained glass. Very peaceful and slept great.

My fiancé and I stayed at Lambs hill to celebrate our anniversary. We had the most wonderful time. The views are breathtaking. The wrap around deck with jacuzzi and hammock made our stay calming and serene. I loved seeing the horses and donkeys throughout the day. They made the experience even more special and unique. Charlotte was super responsive and accommodating. We took cabs to Main Street at night for dinner and drinks and it was so close and convenient. I left my heart in lambs hill and can’t wait to return one day.

This was one of the most thoughtful airbnb experiences I have ever had. The attention to detail was extraordinary. Cindy provided everything you could need -- a perfectly stocked kitchen, umbrellas, sunscreen, bug spray, first aid, yard games, pool floats etc. The house was just as charming -- if not more charming -- than the pictures. Super private but also great location with proximity to a CVS, grocery store and main street in East Hampton. Cindy was also very communicative and laid everything out super clearly with great recommendations etc. We are already planning our next trip!

Beautiful inside and out — a peaceful oasis & retreat from everything! Nearby restaurants and hikes but also so quiet and private. Great weekend we will be back!!

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 with off street parking!

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 a lovely stay at Pelham Court on the hottest weekend of the year so far! Our apartment (#7) was clean and quiet, despite being in the middle of downtown. The AC was excellent and very important for that particular weekend. Although there are no views or a balcony for this apartment, the little courtyard at the back entrance is lovely and has some sitting spaces that we used to spend an hour or so reading. The location is great - once parked at the hotel we walked everywhere, including Cliff Walk, mansions and restaurants. Hosts were very responsive and proactively asked if we needed anything prior to leaving in the evening. Great stay!

Great stay! The place was clean, cozy, and just like the photos. The host was kind and helpful. I’d definitely stay here again.

This beautiful property has a special place in our hearts. We stayed in the A frame during COVID and we always wanted to come back. This time we stayed in the main house and it was phenomenal. Wish the weather was better for us to use the pool, but next time! It well worth the price. Only an hr from the city and it feels like a full vacation. Wonderful way to lose time time for a few days. We will be back!

Serene and charming riverfront hideaway. In a residential neighborhood but very quiet. You are 5-10 minutes from great restaurants, shopping, Dennis Beach but it all feels very secluded. We went kayaking every day from the private dock, saw swans, sea lions, and hawks. The space is clean, boho-chic, very comfortable beds, easy to use gas fireplaces. Primary bedroom sitting area/sunroom is dreamy for reading. Kitchen has everything you need. We thought we might miss an ocean/bay view but we didn't at all. Very reasonably priced for the quality. Meg replied to all messages within minutes. We would absolutely come back. Great for a couple or small family.

We had a wonderful time here! What a perfect location. John was so accommodating. Definitely would rent again from him!

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

Great place,very convenient for entire extended family to be in town for college graduation weekend. Very large and open common area and kitchen for gathering for meals and celebrating all together.

Michael’s place was amazing, means a few friends stayed this weekend for my birthday. He was always willing to help and very accommodating! The house itself is so beautiful and had everything we needed! It was our first time in The Hamptons and he gave us tons of recommendations!

Beautiful home, very clean, spacious and comfortable to stay with the family. We used the grill on multiple occasions and it was easy to use. The fire pitt was also enjoyable. The kitchen was well stocked, would bring own source of caffeine if you’re picky with your coffee though. Stephen, the host was very responsive and easy to reach when asked questions. The one thing I would recommend is to check in with the host if the pool is available to use prior to booking. Overall a great experience, would stay with them again.

We LOVED: 1) The location! The driveway is long & sand/gravel but you could drive it in a sedan fine. 2) The amenities! The pack n play was a HUGE lifesaver! 3) This location is mostly child friendly. 4) The view is phenomenal! When we woke up & opened the curtains for the first time, we were in awe! 5) The host was extremely helpful. The hot water went out once, but she was over in 5 minutes to fix it. Some feedback: 1) The windows in the ceiling in the master bed! They're HUGE and BRIGHT. 2) The bugs. Ants. Spiders. It was a struggle. NOW I WILL SAY - I brought this up to the host on day 3 and they were more than willing to come help how they could. The house is located in the middle of the forest, but it was a lot. If it weren't for an m&m left under the nightstand in the bedroom by a previous guest, it probably wouldn't have been so bad. 3) the coffee maker was pretty rough when we got there.. a simple over site by the crew. Overall, I would definitely consider this location again

Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.

We had a lovely stay at Roger and Amy’s place. The location was great - close to Southampton, a short drive from Sag Harbor etc. The home is charming and comfortable. The kids loved the heated pool and spent hours in it every day. Roger and Amy were also super responsive, with advice and help when we needed it including with a very sweet gift for our 3 year old whose birthday we were celebrating. All in - a phenomenal time!

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.

We really enjoyed our time at Elizabeth Jane's place. The home is spacious and quaint, with nice furnishings, a tasteful colonial feel and easy access to downtown Litchfield and the Berkshires. The bucolic setting is lovely - scenic, relaxing and peaceful.