Family-friendly vacation rentals in Litchfield

Beautiful house, gorgeous and convenient location, excellent host. We had a great stay.

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 :)

This is at least our 4th time staying at what we call "The Farm" and it is our favorite getaway! We even got my brother to drive 1.5 hours out of his way on his family trip to Boston so he could check it out. A rare gem!

What a great relaxing couple of nights. If you are looking to get away from it all- this is a perfect place. 8 minute drive to cute coffee shop and local restaurants. Very quiet area. The house was cozy. I booked a last minute stay and felt I was accommodated to the best of her ability. The home is adorable with a lot of character.

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.

Sweet Dotties Cottage was better than expected. It was right on the water and even had a dock for our boat. It was very clean and exactly as described. The screened in porch was great at night. I highly recommend and will be visiting this property again.

The close-up view of farm animals and cooking farm fresh eggs were most pleasant and enjoyable for our 3 nights in the country. We were there during an April cold spell and enjoyed the warm and cozy nights indoors. Very comfortable bed linens were especially pleasing for a great night's sleep.

Margie’s place is an amazing hidden gem. The inside is very clean and comfortable. The outside is an experience of its own. The lake will drop your blood pressure immediately. Gorgeous surroundings. The dogs are friendly and lovable. We will be back! 👍🏼

Cutest little cottage! Really loved the back porch / deck area. Loved this spot — affordable and perfect for a fall weekend getaway. Jeanine and Keith had lots of cute touches like homemade pumpkin bread and eggs in the fridge. They are also easy to communicate with. The town is very cute, too.

We've stayed several times over the past year or so--Ina's cottage is our favorite weekend getaway from the city. The setting is just right--you can see the sunrise and sunset from its hilltop location, which offers lovely views across the surrounding countryside. Last weekend, we watched bluebirds feeding in the meadows nearby. Inside, the cottage is charming and filled with characterful furnishings and decor. All is immaculate and thoughtfully equipped from kitchen to bathrooms for a comfortable stay. We love the privacy that Ina's space provides with options for good restaurants, swimming, and hiking nearby in surrounding towns. Ina, we loved the pumpkin and gourds in the cottage and thank you again for a delightful stay.

Thank you to Keith for the wonderful experience in renting his beautiful home. Super-responsive, easy check-in, and was available for any questions or suggestions that came up. Keith's home is located in a beautiful area near some amazing local attractions, and was the perfect fit for our needs. What a great week!

My daughter and I loved our stay so much. The setting is so beautiful and peaceful. I loved listening to all the bird song and my daughter loved the fish! Such a cozy, comfortable home. We loved our relaxing time here. Gabriele is a fabulous host, so responsive and so kind. Thank you!!

This was our second time back to the pool house and it was amazing, again. We thinks of everything to make you feel welcome. Milk and eggs in the fridge. Muffins and croissants waiting for you. Pristine home. Fully stocked kitchen. I was even able to host a few family members for Christmas dinner and had everything I needed to make a lovely dinner. We also travel with two dogs and Sue is so accommodating, making our pups feel right at home. Thank you, Sue, for making our holidays away from home so peaceful and enjoyable.

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!

Stephen was very accommodating as we had a reservation canceled last minute. Accommodations were beautiful. Scenic views. Infinity pool was amazing. Very comfortable. Washington is a great town with nice restaurants and shops. We would definitely stay at one of Stephen’s properties again.

Felt right at home, check in was very easy, beautiful place, very friendly enjoyed his place thinking to coming back again my business send me to Connecticut! Thank you!

This wonderful antique home is in a Beautiful spot in the heart of Litchfield CT, and a delight early spring when the fields of daffodils awake! This unique 1793 house has a great view & sunset, fireplace, simple spa/gym making it a gem even when the pool is closed. Nearby the town with lots to offer and local farms for food shopping too. What’s not to love 💛 Bonus is a great host offering a home that is in touch with the realities of rentals, pets and people -not picky, precious or punitive. Happy to recommend and return! Thank you Elizabeth!

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

Ileana was great with getting back to questions we had and making sure that we were able to get into the place seamlessly. It was the perfect weekend get away.

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