Family-friendly holiday rentals in Southbury

My family enjoyed their short stay at Camilla’s apartment. The apartment was a beautiful place.

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

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!

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!

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!

We had a wonderful stay! Gabe was a very welcoming host and shared some great local restaurant recommendations—highly recommend checking out Casa Nova on River Road. His two dogs, Molly and Nate, were also incredibly friendly and added a warm, homey touch to the experience. The apartment was spotless and filled with thoughtful notes that made everything easy. A special surprise was the bag of everything needed to make s’mores left for us—such a sweet and thoughtful gesture! The pool area offered stunning views, and the hot tub was clean and perfect for relaxing. There’s even a hiking trail accessible right from the property, which we unfortunately didn’t get a chance to explore—but it’s a great bonus for future visits. This place truly felt like a little piece of heaven. We’d absolutely stay here again!

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.

Hi, we had a great stay with plenty of space for all of us. We all loved the fresh flowers on the living room table. The roses were a beautiful touch! The place was very clean to which my mother-in-law said it at least 4 times a day! LOL The bedrooms were set up so neatly when we arrived (very impressive). The kitchen had all the necessary utensils we needed and more. Great weekend! Thank you.

We loved our stay here. It was the perfect place for two of us and our dog. The home was just as described, welcoming, cosy and well equipped, and we appreciated all the local recommendations. We enjoyed local walks, the lake, and the great dog park, as well as easy access to Middletown to visit our son. Elisabeth and Daniel were fantastic hosts!

Noel’s third floor apartment is light-filled, spacious, has a cute rustic vibe and is perfectly located. It’s across the street from East Rock Park (great for walks and runs) and walking distance to restaurants and an ice cream shop. The entrance to the apartment is through Noel‘s home – – no private entrance. Parking was incredibly easy—right on the street in front of the house! We enjoyed our stay very much, especially thoughtful touches like breakfast muffins and coffee. The apartment is full of interesting books and games and is very comfortable. Noel is a helpful host.

Juliana and Paul were great hosts! There was a storm the day we arrived and they communicated about the towns power outage before our arrival. They had generators on hand and Paul set up the generator and had many extension cords, flashlights and called local supermarkets/restaurants for us. Luckily the outage was just a few hours. The place was clean and spotless. It was quiet and a short drive into Main Street where you can find restaurants. It is close to many beautiful hikes. We would certainly return as it was a joy to stay in such a peaceful home.

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.

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!

I was apprehensive about not staying in a hotel but this turned out perfect! Saved money not only on the space but also on food as we had access to a full kitchen and a grill. Being able to run a load of laundry meant less we had to pack and less to do when we came back home. All the staff at the farm was friendly, knowledgeable and welcoming. This was such a different experience for our family. The kids loved being about to feed and pet the animals on the farm, and even got to collect chicken eggs! They enjoyed having more space than they would have in a hotel and reading the books and playing the games available. The binders of local things to do/places to eat were so nice to have and everything was labeled well with instructions, such as the grill and dishwasher. We felt at home and secluded at the farm yet still able to do all the tourist things. We visited both Boston and NYC which are both about 2½hr drive. Also drove up the Six Flags New England. 10/10 would recommend!

Skye was really helpful and always responded quickly. This is a private location but if you're looking for stuff to do, Carmel is a short drive to Beacon and Cold Spring. It is very pretty in this area and very woodsy. The space is in the lower level and cool and opens to a private yard with seating.

We had a great time in Cutchogue! It was unexpectedly raining for our entire stay but we still managed to make the most of it— the little guesthouse was a perfect cozy getaway from the city and also super clean.

Everything was perfect for our girls weekend. This is the 3rd time we’ve used Laurie’s house and there’s obviously a reason we keep coming back. Can’t wait to go again.

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!

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!

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!

Yvonne's place is wonderful, we spent six days there on a family vacation to celebrate a graduation and it was a perfect spot for a crowd. The description and pictures are spot on (maybe even better) and the place is very well maintained. The weather was not great - so we landed up staying in more than we anticipated and this was a great spot for that. The kitchen is well stocked, having a barbecue really helped, and the large windows and skylights kept us connected to the outside. Yvonne was also highly responsive in case we needed anything. Highly recommend.

Our second time staying at Maitopia with our cat, just as wonderful in a different warmer season. Tina was super responsive as usual and even accommodated a late checkout. We enjoyed feasting in the kitchen as well as grilling in the yard, floating around in the pool when it was warm enough out, "hiking" with our cat on a leash around the forest on the property, taking baths, streaming music. We didn't leave the property much, but it was a fun highlight to get a few local produce items at nearby Greig farm and meet the adorable goats. One tip- bring an eyemask if you're sensitive to light in the mornings- there aren't any window shades in the bedroom.

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

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.