Family-friendly vacation rentals in Litchfield County

Jeannine’s home was an absolute gem! We had our annual girls weekend here and felt right at home. The house was so cozy and warm yet had ample space for me and the girls to sit and chat together. We loved that the house was lived in with family photos and mementos around, rather than being sterile like many other bnbs we’ve stayed in. There was also so much to do in the surrounding area! I would definitely recommend this stay :)

We had an absolutely wonderful time at Stephen’s house! my brother came with his 3 kids and they had so much fun that they didn’t want to leave. There were plenty of activities to keep them entertained, and the pool was perfect. The grill and outdoor space provided exactly what we needed for some enjoyable family time. It was a perfect trip that truly felt good for the soul!

Cannot thank Stephen enough for taking care of us after a major mess up. We were able to get in and relax and enjoy. So grateful for all he did for us on a graduation weekend.

Anna’s place was perfect for two couples and two toddlers - close to Litchfield and a huge yard. The house is well designed and has a ton of space.

The house is beautiful with lots of amenities. The kitchen was nice and big for cooking. We spent a lot if time in the library using the fireplace. The surround sound speaker system was great for listening to music. DeeAnne stays in an attached apartment, but with it’s own entrance/exit. She was not in our way at all during the stay. This house was perfect for our group of 10.

Prana is a cozy, relaxing retreat. Our family had a great time warming ourselves around the fireplace, relaxing in the hot tub, and snoozing in the sauna. It was a great post-Christmas getaway!

This was a beautiful, historic home. The pool/ spa area was perfect for the 8 of us. We spent days lounging in the pool, visiting wineries, Kent, Kent Falls, New Preston and touring the area. We also spent time on the hiking trails that are accessible right from the property. The little town of Washington was quaint and had the basics of what you may need. A Wonderful book store and coffee shop (Marty’s Cafe, their gluten free pastries were fantastic). There was even a small market. We would definitely recommend the G W Tavern for dinner. Gregory was very easy to communicate with and answered all our questions and concerns. Having a full time automatic generator was really wonderful, we had some storms while we were there and the neighbors were without power but we continued on without interruption. Even the house A/C, spa and pool filter and heater were up and running. Our daily visits from all the wildlife and resident spirit were magical. We loved our time here!

We had a fantastic 2-night stay at Jim’s beautiful old home. So clean, so thoughtful & tasteful decorated. Great first sunny day for biking & hiking on Harlem Valley Rail Trail and close to restaurants in town. But also great second day when caught in snowstorm. Jim’s house is warm, cozy, comfortable, perfect for a day to relax, read, watch movies, cook, and enjoy the beautiful view. Thank you and we will certainly come back.

Kathy is amazing! She is kind, responsive, helpful and makes you feel her place is yours! It’s so beautiful and cozy!!! It’s clean and has all the amenities you need! Also all beds are so comfortable!! If you want a cozy warm stay in a peaceful place…. Book now!

My reservation at another property was mysteriously cancelled 3 days before my family's wedding. After 24 hours of back and forth with Airbnb, Mary saved the day and worked with myself and airbnb to get me rebooked into her amazing family home. She was an angel!

Wonderful place to stay, this was our home base for a Christmas visit with family and it was a great and cozy spot to come home to each night. Beautiful back yard!

The place was great! My parents live in the area so it was a nice quick ride to get to their house. The space looked exactly like the pictures. Host was very responsive and very friendly.

We had a wonderful stay at Niva's home in Kent. The house is beautifully decorated and perfectly clean. Niva's place is great-looking and very comfortable. It is just a short walk into the charming town of Kent, CT. Niva was a communicative and friendly host. Thank you, Niva!

We had a great stay at the cottage. Both Laura & Steve were very responsive & genuine. They were really knowledgeable about the area. I feel that they went above & beyond to make it feel like home away from home for the week. Would definitely stay again😊

I will always cherish the two weeks we stayed at Kelly’s cottage. It is a beautiful, cozy home. The fireplace is wonderful and Kelly supplied wood and kindling in the garage. The bathtub is deep. The couch and armchair is extremely comfortable. The bedrooms are beautiful and very comfortable. The kitchen is fully stocked, everything I needed to use was there. I told Kelly that when I next settle in a home I will beg her to come advise me on decorating and use of space, her taste is exquisite.

We spent a long weekend at Stephen’s place in Washington. The property is a beautiful one-of-a-kind property (indoors and out) in a peaceful and private location. This was our second stay with Stephen, he does a great job communicating both before and during the stay. Overall great experience and would definitely recommend to others.

We had a wonderful long weekend stay! Steve was an excellent host, who was very hospitable and responsive, allowing us flexible check in and check out, leaving a thoughtful welcome gift and sending us recommendations for things to do in the local area. We ended up hiking, wine tasting, visiting local restaurants. The home was great for our two kids (12 year old and 3 year old) and we made use of the pool every day! Wish we could've stayed longer but it was the perfect city getaway.

I highly recommend this place. Beautiful house in a great location next to the river. This is the third place I’ve rented from Steve and I think I will continue to rent when the opportunity arises. The house is beautiful with all the amenities you need. With a large group, we particularly liked the big kitchen and 2 large tables for dining. There was a movie room and living room so there was plenty of space. It snowed while we were staying there so we took advantage of it and went sledding in the backyard (sleds were provided). My pup also enjoyed herself with plenty of room to run around. I only wish to come back when the heated pool is open.

We had a fabulous week! The house was immaculate, the property and house itself were just beautiful. There had been a terrible rain storm the night of our arrival. Steve and his team made sure that small issues due to the storm (pool furniture stored for safety, small electrical issue with the stove) were addressed within 24 hours. Steve was away in Europe and still responded immediately to all of our concerns. It was a relaxing and lovely week. We recommended the house to everyone we know!

Absolutely beautiful location, amazing pool. Joseph was a responsive and helpful host. Great stay!

We had a fabulous stay at Fallen Fence for my in-laws 50th anniversary weekend. The home is spacious and the property is stunning.

Stephen is one of the nicest hosts I have ever met. He was extremely responsive and had so many great suggestions for things to do in the surrounding area. Nothing was ever a problem, he clearly takes his host responsibilities very seriously which is refreshing! As for the place, it was as relaxing as we had hoped for, and has enough amenities that you can easily stay put and enjoy the property without needing to rely on outside activities. What a gem. We look forward to returning!

We had a wonderful stay at Stephen’s place. It was perfect in every way!