Family-friendly holiday rentals in Trumbull

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

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

We had an event nearby and Brian’s place was a great base for us. Lovely and peaceful neighborhood. Brian was super responsive and reached out to us when the house was ready(before the official check-in time). Would def recommend to anyone!

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!

Abigail is an incredible host. She is super accommodating and communicative. She is the sweetest and her home is incredible. This place is definitely worth it. Beautiful space and a wonderful experience.

We loved Jane's cozy home. The hot tub is perfect and has the best view.

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!

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.

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.

Emily and Carol were wonderful hosts. They were responsive to our questions and provided great recommendations. Sitting on the balcony with the view of the trees and the lake beyond was tranquil. The living area is cozily furnished and both the fireplace and tv were easy to use. The nearby community beach was fun to visit and an added benefit of the stay. Great location with plenty of good food and small town charm!

A lovely home with beautiful views of the surrounding woods from each room. Very clean, modern, and comfortable with a well stocked kitchen. Mark provided detailed and useful info on the place and the surrounding area. A great spot if you’re looking for some peace and quiet close to all the local attractions of the Hudson Valley.

Cute and cozy home with lovely outdoor sitting area. Woke up to the sounds of the breeze and chirping birds! You can see the water from out the kitchen windows!

We stayed at Monica's place multiple times when visiting my son at Wesleyan. We loved it! We appreciated the convenience of the location and ease of parking. We wish we had found it sooner because we had been staying at hotels 15-30 minuets away. The apartment is as shown and has always been clean. Its comfortable, has everything needed and is no fuss. We enjoyed inviting people over between activities on campus. Monica is very responsive and helpful and kind. She has a beautiful garden and a sweet sitting area outside for when the weather is nice!

Dan & Jill’s home was beyond beautiful and comfy. It was very easy to find, private and felt safe. The inside of the home was more spacious than expected and extremely clean. The panoramic views from all windows was truly a treat. The hosts were very thoughtful and sweet. If you forgot to pack something, they most likely had it. Check in was smooth, stores/supermarket was a 3 min drive. 0 complaints and cannot wait to stay again!

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 enjoyed our stay! Such easy access to the beach was so convenient. You’re definitely better off venturing out after high tide to enjoy the most amount of beach and there are a lot of shells that make being barefoot challenging. We did arrive after major storms which could have contributed to that. The house was spotless with everything you need to be comfortable! We did not utilize the outdoor space but definitely would have if the weather was drier! Definitely would stay here again.

We had a wonderful stay at Todd's place! Todd greeted us warmly and was very responsive. The pool was fantastic and surrounded by beautiful nature, making it a serene spot to relax. We stayed in the pool apartment, which looked out at the pool and stunning backyard. It was well-equipped with a kitchen, pool towels, a TV, couches, and a dining table. Wendy, Todd's wife, welcomed us with cookies, and they provided milk, orange juice, eggs, yogurt, and fruits. There was also a grill available. We stayed for three nights and enjoyed the pool a lot. Despite being a shared pool, there was plenty of space and time for everyone. We also used the tennis court and played some basketball at the basketball rink there. Todd and Wendy made our stay very comfortable and enjoyable. We highly recommend their place!

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!

This place really is a gem. The bedroom and bathroom and spacious and have everything you need. The kitchen is small and can be challenging to work in, but the outdoor grill and dining space make up for that. We spent most of our time outside by the private pool relaxing. James and Margie were great hosts. They greeted us upon arrival and were so friendly and warm. They even brought fresh-bakes cookies. We had a great time!

Jeff's place has a lot of character and is spacious. The setting is excellent, near the water, with Satterly Landing right down the road. We enjoyed our stay.

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.

Kathleens place was perfect for our friends and family weekend vacation upstate. The house and property was absolutely stunning and fit our group of 10 so comfortably. We were talking about our next stay there before we even left. Highly recommend!