Family-friendly holiday rentals in Litchfield

A quiet private property located close to amenities, the city of Hudson, and nature. It is a beautiful and comfortable home filled with creative and tangible care. We enjoyed cooking in the kitchen and spending time on the property over a long weekend stay.

Loved this house! We have stayed in many places all over the world for both business and pleasure. This was a business trip. House was great, location was great. It was cold and rainy so we didn’t get to enjoy the porch, deck or hot tub . Even without these amenities we totally enjoyed the house. Hoping to stay again next time we are in the area. We are in Rhinebeck twice a year for the antiques show in the Fairgrounds . Instructions on house were easy to understand and concise. Great job guys!

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.

What a gorgeous stay. My partner and I celebrated our five year anniversary here and each detail was perfect. The home is wonderfully curated, with stunning art, decor, puzzles, plates, you name it! And by the window, the feeders attract all kinds of birds that I’ve never seen so up close. Woodpeckers, cardinals, chickadees. You hardly need the TV, it’s so entertaining. The place is spotless and serene. And Rosy is so responsive while giving you complete privacy! You can tell she really cares about the experience she provides. If you’re looking to stay in an artfully cozy home, this is the place.

We had a great and easy stay for a quick upstate weekend! The house was clean, cute, and accommodated our family of 7. We unfortunately didn’t get to utilize the outdoors because of the weather. Would definitely recommend this house!

Really nothing negative to say. We appreciate all extra personal touch the hosts left for us. I wish all ABNB locations had the same care and attention to detail for their guests.

The home was absolutely gorgeous and peaceful. It's exactly as described but even more spacious than I expected. They put a lot into making guests feel welcome, including prompt communication, a quick walk through to explain where things are, numerous suggestions for the surrounding area, and even a tray of welcome cookies! I came for a 50k trail race, so the hot tub was a perfect added bonus. I HIGHLY suggest booking this property, and I'll definitely be back to spend some time at the beach.

We loved staying at Anat’s gorgeous home. We’ve been in many spots in the HRV and even Columbia County, but this stood out for being so tranquil and for having such lovely grounds. We enjoyed the Copake Hillsdale Farmers Market and a great meals at Local 111 and Zinneas. Cooking at the house was a breeze and there were more than enough beds and living spaces for our two families to feel so comfortable. Hot tub was lovely! We can’t wait to return.

The best Airbnb we’ve ever stayed at! It truly felt like home—every detail was so thoughtfully taken care of. You have everything you need for a comfortable stay, from a well-stocked space to those little touches that make a big difference. The bed and pillows were super comfortable, and even though it rained, the hosts had dry firewood ready for the fireplace, which made it feel extra warm and inviting. We loved sitting by the lake and even saw a fish jump out of the water—such a magical moment! Communication with the host was excellent from start to finish. And thank you so much for approving our cats to stay with us—it meant the world. If we could give 10 stars, we absolutely would. Highly recommend this place to anyone looking for a peaceful and welcoming getaway. Thank you for an unforgettable stay!

We were stunned by how magical this place was with all it's uniqueness of historic house. Spotless clean, spacious, very friendly owners. Our kids loved running around the back yard and playing board games that were provided. We would definitely come back, the only thing we regret is that we couldn't stay for longer, the area is very picturesque. many thanks!

A lovely place to stay. Beautiful view of the animals and mountains. Host was nice and accommodating.

Ilze and Laurence’s place felt like home away from home. Every morning, we were greeted with chirping birds, clucking hens (was even able to order a dozen eggs straight from their free-range poultry—so organic!)—and a smiling donkey! It is a place were you can find peace and rest for your soul even for just a few days.

This was a lovely cottage and location, part of a private beach community, on a very quiet road, with partial views of the Long Island Sound. Gail was thoughtful to put out a nice welcome basket and some cold sodas and bottle water in the fridge. Perfect spot for two to three people. Close to Guilford main green, dock and nearby Stony Creek and Madison. We didn't make use of the bikes and kayaks bc it rained in the mornings, but we enjoyed one of the two beach just a few minute walk away. Jacob's cove area is a gem.

We lived in the Hudson Valley before retiring to Maine. For the past 4 years, Sarah and Jonathan’s home has provided the perfect spot for return visits with family and friends and a comfortable place away from home. The house is tastefully decorated and provides all that we require for an extended stay. The kitchen is well appointed with utensils, dishware, pans, and a large assortment of appliances. A special feature in the home is the lower level room with a huge wrap-around couch, large screen tv and toys for the kids. In addition, the grounds are beautiful. The outside deck allows for time to enjoy the gorgeous view and the large yard is fun for romps with our little Havanese. Being close to the town is an added bonus: The Tribute Gardens, Marona’s Market, the little French restaurant (Cafe Les Beaux), Stewart’s for ice cream, The Merritt Bookstore + Toystore, various antique shops are places we frequent. Innisfree Gardens and Dover Stone Church are nearby. We love it here!

Monica's home is quiet, spotless, and oh so serene. It's a really pretty duplex with lush grass and trees all around while being only a short walk to Wesleyan, a short walk to downtown Middletown, a short walk even to the Connecticut river. The house is well ventilated, the kitchen is well stocked with staples and equipment. The shower has great water pressure (stronger than we are allowed to have in parched L.A.) We met our hosts outside and they let us know about the Middletown Pride Fest that was taking place the following day. Monica sent me a link for info. It was a blast with a really wonderful vibe that made the whole town feel welcoming to everybody. Just as our hosts certainly are as well. Highly recommend!

Super comfy, and adorable stay! The beds were wicked comfortable and the VHS tapes brought a great deal of comforting nostalgia! Serene backyard- with goldfish we could feed, a resident rabbit chilling near the garden, and even a few frogs! Delicious biscotti made morning coffee even more enjoyable, and the kitchen had everything to make cooking dinner easy and enjoyable! As someone with Kitchen experience, I was very pleasantly surprised that the knives here were actually sharp!! Take that onions! I also loved that some of the doors were hand painted to have a creative flare that really made this place feels special! My favorite were the bubbles on the door in the Master Bathroom! Gabriele was also really kind and fast to respond, and I was just really happy with my stay. I could honestly keep going with praise for this place but I'm running out of characters! Definitely give this place a shot and check out Umpachene Falls, only 20mins away!

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.

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!

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!

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!

Alice’s place was great! We’ll be back again for sure.

We had a wonderful time. The weather was perfect. The view of the water was everything and was accessible from nearly every room. The home was modern and easily accommodated our large group. Yet it was cozy and beautifully appointed with all the amenities you would ever want. It is ideal for children with every toy imaginable. There was a highchair and a pack and play for our toddler and child appropriate dishes. The kitchen was fully equipped and had 2 sinks, 2 dishwashers and 3 tables for dining. The beautiful pool and hot tub were in constant use. Mary is very thoughtful and assembled a ringed binder with important contacts and suggestions for dining, shopping and entertainment. Although there was no beach on the property there are nearby beaches. The towns of Guilford and (nearby) Madison are charming and well worth visiting. Mary was very accommodating and responded promptly to several inquiries.

My brother and I spent an amazing weekend at Natasha & Vince’s peaceful lakeside home. The house was clean and roomy and the location was perfect with easy access to the lake for fishing and swimming during the day and beautiful sunsets at night. A lovely home with kind attentive hosts!