Pet-friendly holiday rentals in Middletown

We found Dmitry's place to be just as advertised - it was warm, comfortable and well stocked for our family get together. We enjoyed the views of the water and the open common areas. We especially appreciated having a full bath and bedroom on the first floor for our elderly mother.

We stayed here for a weekend while visiting our daughter at Fairfield University. The location was perfect! The house was beautiful- it reminded me of a modernized cottage. Everything was spotless - made you feel instantly at home! We will absolutely be back! We tried for upcoming parents weekend in October 2025 and she's already sold out!! Definitely book - you won't be disappointed!

Lori was an amazing host. She coordinated with me on everything prior to checking in. I explained that I would be using her home for a small surprise birthday party and she even offered to do some decorations or help out any way she could. Way above and beyond her responsibilities as a host. On top of that she set up a fire pit with firewood and even left a s’mores kit for us. The most amazing thing was she left a birthday card and gift for my girlfriend. It was completely unexpected and we were so appreciative. The home was very clean, cozy, and had everything that we were looking for.

My stay surpassed every expectation. The house is conveniently located near the airport and less than 10 minutes from downtown. The property offers self check in with clear instructions. The host is very responsive. Thanks Premium Trips

Ritestay was a great place. We didn’t spend much time there because we were there to see our daughter. Would be perfect in the summer!!

We had a great stay. The place was as advertised and Erin was very responsive. Perfect location for a tournament at Choate with lots of restaurants close by. Thank you.

This was my second stay at Bill’s & I’d definitely will be coming back. The house was clean, comfortable bed & a beautiful peaceful neighborhood. My son came to visit for a few hours & we had a blast playing ping pong together. Two thumbs up!!

We enjoyed our stay. The house was very clean and comfortable. Easy to get to and close to UConn which is what we were looking for while we attended a women’s basketball game. I highly recommend Mariana’s place.

The place matched the description perfectly and much more spacious than what one usually finds for a single bed/bath apartment. I enjoyed the stay and would return again. For me it was a perfect place to accommodate overflow thanksgiving guests over the holiday.

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 took the house for a family getaway, and it far beyond surpassed our expectations. From the cleanliness of the home, to the beauty and utility of the pool. There was an abundance of all things you can expect to find in a home, e.g. the bathrooms were stocked with an abundance of name brand shampoos and soaps. We enjoyed the beautiful coastline that was in close proximity to house. And we spent hours at the pool on a daily basis, it was very private. Cindy was responsive to our every need and query. She even came by a couple of times to help us out with some issues, she went beyond her call of duty. All this she did graciously, as if it’s not even a bother. She is a true super host.

Great house and great host. The place was beautiful -- big kitchen, comfortable bedrooms, great bathrooms (especially in the master bedroom), nice setup outside (jacuzzi and BBQ), etc. Perfect place for a family weekend in Litchfield. Location was perfect -- a 2 minute drive to great coffee, pastries, bread, ice cream, etc. in Bantam. Liz was an excellent host -- very helpful and responsive. We'd love to visit again soon.

Stayed here for 2 nights with a couple friends. Perfect spot for a quick getaway. Backyard and pool area was exactly what we were looking for with lots of space to lounge and relax. Lots of entertainment if you wanted to just hang inside as well. As some of the other reviewers noted, you can definitely hear the hosts move around upstairs. Didn't impact us too much except for Saturday morning. Was a little difficult to sleep in b/c of the noise.

The house was in perfect area. Got to see deer, turkey and rabbits while sitting around pristine backyard and pool area. House was directly across from ferry system to Connecticut and adjacent town was perfect for restaurants and walking around. Would highly recommend this as a destination location and house. Look forward to returning

Beautiful home, exactly how it was described and looked even better in person. Incredible surrounding areas and activities. Steven was helpful throughout the stay and incredibly flexible. Wonderful host! Will definitely be planning a yearly visit.

The host Joanna was very responsive with communication. The house was big and clean (I am extremely picky with cleanliness). We stayed there for parents weekend at Fairfield University which was about a 25minute drive to the senior beach houses which wasn't terrible. For those Sacred Heart University families it is super close to their campus. The house is in a quiet, safe, family community. Overall, we were very happy!

We had a great stay at this cottage- it was a perfect size for our family and was extremely clean, warm and comfortable. We especially enjoyed the quick walk to the beach, and proximity to town. Hosts were very friendly and responsive but never intrusive. Would highly recommend.

The place was very clean and cozy and warm. We had such a lovely stay watching the snow fall outside. The kitchen was great for cooking. Saverio was so kind and helpful when our car got stuck in the snow. Would definitely come back!

Stayed here for about a month and felt right at home with spacious rooms and lots of amenities provided, being 20 degrees in winter the apartment stood very warm and clean and it was a wonderful place to call home for 30 days. Kisha was very helpful and responsive when I needed to communicate and she’s very kind. If I’m ever near the area in the near future I would definitely book here again no hesitation! Thank you!

The bungalow was a wonderful little winter retreat. The sunsets over the water were stunning, and beach access was a short walk away. The house is small and cosy but exactly what I needed, with the living/sleeping/kitchen spaces separated enough to feel comfortable. The beds were memory foam and were very comfortable. WiFi was great and I was able to get a 2 monitor WFH set up on the kitchen table. Driveway is very narrow but I could fit my large sedan down it and could fit 3-4 cars if the street parking was taken up. It snowed while I was there and a shovel + pet safe salt was provided. Dogs sadly aren’t allowed on CT beaches, but the Charles Wheeler Wildlife Area is a 15 min walk away and dog friendly and also offers gorgeous sunsets. The neighborhood is quiet and respectful, with a cosy beach town vibe. I want to come back in summer and see how gorgeous the view is in the summer!

Such a cute cozy place, and there was clear communication. felt right at home :)

Nice place located in a beautiful secluded house in a safe neighborhood. Gorgeous property. Our dogs were allowed and they were very comfortable. The amenities were exactly as described. Extremely clean and well maintained. The place was easy to locate and easy to access. It is convenient to many local stores and restaurants. Great, responsive hosts!

Loved it! Absolutely great hosts, beautiful apt over the garage. Felt right at home (I want to transport it to my garage). 10 min drive to everything I did- hiking on frozen pond, dinners with daughter at college, gift shopping! Will do it again!

Robin was an amazing host. Very responsive when we would ask a question. The place was exactly how it was pictured/described. I highly recommend this cozy place to stay if you’re in the area!