Family-friendly holiday rentals in Milford

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

We loved this place! So peaceful and quiet. Lovely beach to walk to. Very responsive hosts- had a slight issue with hot tub and it was handled very quickly and then someone brought us a the best coffee cake. This place felt like the best of Long Island and we are thankful to have stayed!

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!

We were all immediately happy at Susan’s place! Our two year old found the toy room and played happily, our eleven year old lived in the beautiful pool and my husband and I felt like we could really relax. The location is 5 minutes from town where you can get coffee and a bite, or 8 minutes from the beach/state park. The property feels private and the house is charming and well appointed. The pictures don’t do it justice, it’s really lovely.

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.

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.

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!

Clean, spacious, private basement apartment with some natural light. Very comfortable bed. Lovely backyard. Quiet, green residential neighborhood. Within 10 minute driving distance from Port Jefferson town center.

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.

Kate and Daniel are wonderful! Their beach cottage is a must for all families. The farmers markets within 2 miles have all the produce you need, while the fish markets within 5 miles have all the fresh caught seafood you need! There are several New York vineyards nearby and I’d recommend traveling to all the local towns like Greenport, Shelter Island, West/East/South Hampton, and Montauk to see how each one has its own identity. Overall, my wife and I loved our stay at the cottage and we spent most are days laying on the back porch with the beautiful views! Also, great kitchen for cooking and backyard grill with a view.

Jonathan and Amy were the perfect hosts. Super friendly and resourcesful. The property is beautiful and so peaceful which was perfect for our down time as we were in town for a three-day wedding. We enjoyed breakfast with the family of deer that live in the back field and so many beautiful birds. The apartment is so quaint, very clean and has everything that we needed. The beds were super comfortable. It was decorated to the age of the property which we loved! It was a great find and we highly recommend the apartment and will surely book again if ever in the area.

Jeanne's place was perfect for my trip to Guilford. Excellent location, close to the Green and to the water, quiet, peaceful. The house had everything I needed and more, Jeanne was super responsive and kind, and the bed was comfortable.

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!

As described, a charming, comfortable home on a beautiful property in a convenient yet peaceful very "New Englandy" neighborhood The house is a great place to spend time arfeceive friends, really well appointed from kitchen gear to a playroom that is made for toddlers, very comfortable sitting areas with lots of light and the bedrooms that are all quite comfortable and give all a nice level of privacy. Deirdre was a top notch host, always responsive and accommodating. No hesitations in recommending her house - probably our best Airbnb experience to date. Hope it will be available for our next visit to the Stamford area.

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!

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.

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!

Christine and Ryan were extremely gracious hosts who kept their premises well maintained. Their floors stood out the most as they were squeeky clean. Their heated pool was exceptional as well as the pool was very well managed (loved the basketball net). It was a pity because we were able to only use the pool for two days as it was a bit chilly with some rain on the other two. Though the kids had a blast and they were extremely sad to leave. The basement area is awesome for the younger ones with plenty of toys and space. It's spacious enough to even run around and play and we enjoyed it a ton during the rainy days. One thing to be mindful of is the pillars as I initially thought they were wrapped with some child safety materials but were just hard metal based pillars painted in beige. So would suggest to look out for them if any families bring their little ones there and they just love to run around to get their energy out. Overall, impeccable house and will definitely come back

This was the perfect place for our family to get away from the city. It was a family friendly home that was perfect for our little one. The house was clean and came with all of the necessary essentials we needed. The location was private and serene while still accessible to lots of wonderful local restaurants and stores. The beach was easily accessible and within walking distance. Additionally, Morgan was responsive and always available to answer any questions we had. We absolutely enjoyed our stay and recommend it to any family.

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.

Thank you to Daniel and Lexie for a wonderful stay. Their home is beautifully presented and we felt right at home straight away. The street is charming and Rye has lots to offer families and couples. Daniel was super responsive and helpful with local recommendations and advice. 5 STARS!