Family-friendly holiday rentals in Stamford

We loved our stay. They provided everything you need plus more. So comfortable, lovely ambiance and the sauna and hot tub were fantastic. We came on a rainy day and still had a great time. Location is 10/10. Loved the calmbucha. Highly recommend!

Anthony is the best host I’ve ever had! So friendly, welcoming, and super responsive. He has clearly poured ample love and care into the space—it is immaculate, stylish, well-equipped, and truly an easy Williamsburg oasis!

My family of 8 adults needed a place to stay near a wedding at Glynwood. This wonderful spot was minutes away from the farm and town. The number of bedrooms and bathrooms gave everyone the privacy desired while the well equipped kitchen and living rooms had plenty of space for gathering. The house and land are beautiful, including the trail. Paula was easy to communicate with and my whole family felt comfortable and happy with the spot. Highly recommend!

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.

Victoria's place was wonderful! It was spacious and comfortable and gave our family plenty of room to spread out and enjoy our visit. Victoria was a very responsive host and made check in and check out stress free and easy! There was ample parking for our cars and the house was private - it was the "house behind the house" so we weren't subject to busy traffic noise on the street. (Got a little confusing for DoorDash drivers but we worked it out :D). I will book this same place next time I am up for an extended weekend with the family. Highly recommend!

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.

My wife and I had a great stay at Paul’s place. Very clean and just as described. Look forward to staying again in the future.

Surprised my girlfriend with a weekend get away for her birthday and she was thrilled. Evelina and John are great host and their place is warm and welcoming. We loved the lake, and the quiet serenity of the location is perfect for a weekend trip from the city. Also loved the kitchen which made cooking in a breeze because how thoughtfully organized it was. Although our stay was short we did find time to take the canoes out explore the lake and take a refreshing dip. Our only complaint was that our stay wasn’t longer, and we’re both looking forward to coming back !

Clean, spacious, private basement apartment with some natural light. Very comfortable bed. Lovely backyard. Quiet, green residential neighborhood. Within 10 minute driving distance from Port Jefferson town center.

The Captain’s Cottage was the perfect stay for us. We had a last minute request that Nicholas was quick to accept and had all details readily available. The cottage was well maintained, shower had great water pressure, cute private space out back for grilling, and a cozy bed. Just far enough away from the farm store to be quiet but close enough to walk to enjoy their food and beverages. The farm store was prompt, the food was fresh and clearly made with love so you better not miss it. The cottage offered the peace and comfort we needed after saying goodbye to a dear friend. We hope to return and are grateful for the kindness shown to us and our pug.

Our stay was perfect from start to finish! Checking in was a breeze and Jennifer the host was welcoming and super friendly! We stayed with our 8 year old daughter and we had plenty of space for all of us. My daughter loved the pull out bed and felt right at home. Every room was equipped with anything we may need, plus many extras! One of the best parts was that there were beach chairs, umbrellas, towels, ect so we did not have to bring any. We were close to the beaches, restaurants and train station which we utilized going to NYC for a day. We traveled to attend a concert at Jones Beach and we were so happy with how close it was to the home. Everything was perfect, we wished we could’ve stayed longer and would love to return! Jennifer was the best host!

This place is truly a gem! We enjoyed swimming in the waterfalls and relaxing under the trees. We can’t wait to return. The house is also lovely with lots of interesting and quirky touches that we enjoyed. Incredibly well stocked kitchen and everything we could want!

We have stayed at Erik's place 4 or 5 times now. It's perfect, has everything you need. It is centrally located to surrounding towns. Erik and his parents are very friendly and always responsive. I highly recommend staying there!

Beautiful chalet with even better views - perfect for a calm and peaceful get away from the city, near hiking trails and 7 min from town for restaurants, had a great weekend and hope to be back soon

I loved my stay here!! The backyard area is absolutely stunning!!

This place is like heaven!! Charming and beautiful views of Greenwood Lake. The beds were super comfortable and the place was well equipped with everything you could need. Great communication with our hosts. Highly recommend this place!!

My girlfriend and I had a great stay here. The place was cozy, well-equipped, and perfect for a relaxing getaway. The outdoor area was the true highlight — from the spacious patio to the beautifully maintained landscaping, the property felt peaceful and private. There’s also a pool that looked amazing, even though we couldn’t enjoy it due to the weather. We had some trouble during check-in after a delayed flight and arrived around midnight, but the property owners were just a phone call away and quickly helped us get settled, which we really appreciated. Overall, it was a great experience and we’d absolutely recommend this spot to anyone looking for a quiet, scenic place to unwind.

We were absolutely charmed by this stunning house, surrounded by breathtaking nature and offering incredible views—especially over the lake. Every corner is filled with character and warmth, making it feel like a true hidden gem. A huge thank-you to our wonderful host Sandy, who was incredibly thoughtful and proactive throughout our stay. We couldn’t have asked for a better experience. We’ll be back without a doubt!

This is a lovely house very close to New Paltz. We had a nice long weekend with the kids and loved spending time in the pool. Susan was a great host. No complaints!

The pool house is so cute and the outdoor patio is gorgeous and the perfect place to relax. Great place to stay if you want to stay near New Haven but also want to enjoy quiet away from the city. Sue is a responsive and very generous host!

We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!

This is a beautiful place. Second time we’ve stayed there and I would like to come again next year!

Had a very enjoyable time during my stay. Hosts were very helpful, friendly, accommodating, and responsive. Gave lots of great recommendations for dinner spots and shopping. The house was very comfortable, clean, and cute. Will definitely be booking again!

The place worked perfectly for what I had needed. Travel a lot for work, and this time my wife and son came to visit for a few days of the stay. Host was very nice and helped us with accommodations and recomendations of local eateries. Very much enjoyed our time here, would stay again.