House holiday rentals in Madison

This was the perfect spot for what we were looking for as my son graduated from Conn College. The host was very responsive to my questions and flexible with check in times which we needed. House was exactly what was described and we had a wonderful time. Thank you!!

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 thoroughly enjoyed our short stay in Mystic at this great home. The pool was the biggest hit, but the kitchen/living room area was an amazing place for our group to gather for meals and games. Location is spectacular as you can just park at the house and walk to all the great restaurants the area has to offer and if you have kids, there’s a great playground just a short walk away. We would definitely stay here again!

We had the most beautiful weekend stay at Tim’s home! Everything is accurately described and the pool and hot tub were amazing!! All the beds were very comfortable. Was perfect for a 5 girl weekend getaway!! Tim was incredibly communicative and checking in was a breeze. The location is PERFECT in East Hampton!! So many amazing restaurants and bars nearby. 100% will stay here again for my next Hamptons trip. Thank you so much Tim!!

We had a great time at AJ's place! The space is very spacious and comfortable, everything was clean, and the backyard was PERFECT for our group. Close to casinos and restaurants. Highly recommend for groups and families!

Great location, private and comfortable. Close to wineries and breweries. Very clean and convenient. I highly recommend.

Ben is a super host. His home is absolutely beautiful and well managed. His thoughtful recommendations and well timed check ins and reminders were the height of polished professionalism. We felt right at home, down to the bins of toys in the living room that our toddler and baby played with every day.

Only complaint would be the noise from road during the morning commute

we have stayed at this place multiple times. It is very conveniently located near our kids and also very easy to get to. It is spacious and comfortable and clean. The house is a bit on the “vintage” side, but that shouldn’t matter, and it contains pretty much everything you could want as a guest in a house. It is a little on the pricy side, but if you need three bedrooms and three bathrooms, it is a good value. And Sharon is very responsive. She does have particular rules and expectations, but nothing more than should be expected of a good guest in someone’s house. (as opposed to being a hotel guest where you don’t need to clean up after yourself) we strongly recommend this place.

Mario’s place was beautifully renovated and outfitted perfectly making us feel right at home. Actually the home was furnished, cleaned and stocked better than most peoples primary homes! We’re ocd clean people and travel with our own cleaning products but that was completely not needed in Mario’s place. It was spotless! Even the washer/dryer were like new which we took advantage of during our stay. Traveling with seniors, infant and young toddler, we appreciated the home was baby safe and had kids games and toys. Love that the home was well thought out for guests and included plenty of paper products, plush linens, soaps, towel racks in every bedroom. etc. beds and furniture were both very comfy. This location is perfect and serene. We honestly would have been very comfortable staying for a much longer trip. Close to town with delicious food and lovely shops. Easy access to the highway too. We were all around impressed with this rental..One of our favorite airbnbs to date!

We had a wonderful weekend stay at Eileen's beautiful waterfront home. The view from the living room and primary bedroom of the water was so peaceful. The kitchen was well appointed and the cozy living room made for a wonderful family gathering spot when we weren't dining out at the fabulous nearby restaurants, visiting wineries, or viewing local scenery. Eileen was incredibly responsive to small questions we had. We would definitely book again!!

We are a group of 5 women who have been getting together for long weekends once or twice a year for many years. Brenda and Dean’s place is one of the most wonderful homes we have stayed in. They are terrific hosts — communicate quickly, answer all questions and are very generous in the treats provided. The house is perfect - exceptionally clean, comfortable beds, lots of seating and a lovely view. We can’t say enough about how much we enjoyed our stay!

Our family had a beautiful stay at the Purple Button Factory. Charming and comfortable, this historic house was perfect for exploring Guilford. A special nostalgic trip for us as my children grew up here. Short walk to wonderful cafes and shops on The Green. We loved the birdlife and views from the back patio and absolutely fell in love with the picturesque sunny kitchen. Spent a lot of time gathered together there around the wooden table. Than you for sharing your home.

We had a great stay! Very charming house with peaceful backyard. There are restaurants within walking distance. If we’re ever back in the area, I will definitely book again!

Suzanne’s home is beautiful and felt like being in our own home. The property is serene and very private. The house and kitchen were well equipped for cooking. Suzanne was so easy to communicate with pre during and post stay. We have family in the area so I hope to be back again.

We had an amazing stay at Peter’s home by Saint Clement’s Castle for our wedding weekend! From start to finish, Peter was an exceptional host—friendly, responsive, and incredibly flexible with the details of our stay, which helped make a busy and emotional weekend so much smoother. The home itself was spotless, modern, and thoughtfully maintained. Every room felt comfortable and inviting, and the clean, updated aesthetic made it the perfect place to relax between events and get ready for our big day. It truly felt like a peaceful retreat during a very special time in our lives. We couldn’t have asked for a better experience and would absolutely recommend Peter’s place to anyone visiting the area—especially for events at Saint Clement’s. Thank you again, Peter!

We would stay again. The cottage is well maintained. It was nice to have some basic cleaning supplies so you can touch up if needed. Toiletries, laundry supplies, coffee pods, nice touches, felt like home.

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.

We had a relaxing overnight with our two pups! The bay/sound area is so peaceful. Our dogs enjoyed swimming before the tide came in and we kayaked along the shoreline. The inside was stunning and had everything you needed and more! We door dashed lobster rolls from the Bonfire Grille nearby (10/10) and ended the night in the hot tub! Coffee on the sunny patio was a great perk, too! Thanks again!!

Chelsea was communicative and helpful about her beautiful house. It had all we needed, was well appointed, beautifully decorated and in a gorgeous natural setting. We spent time lounging in the living room as a family and it was so comfortable. Top notch! Grab this place now!

Mariza's house was not only beautiful on the inside, but on the outside aswell. We felt very welcome from the moment we stepped foot into her home. We had lots of room for everyone, which was nice. I would highly recommend it!

Jessica's home has a great location on Middle Beach Rd, perfect for walks and bike rides. Walking distance to East Wharf Beach. The home is older and beautifully appointed. The bedrooms/bathrooms/kitchen are all clean and in good shape. Jessica responded to questions promptly. We had a wonderful time!

Jeremy’s “Doll House” was a charming little place on lovely peaceful grounds. The location was very convenient for visiting our Connecticut relatives and attending our granddaughter’s graduation. His kitchen is well stocked with all the essentials and then some. Everything was very clean and the bed was very comfortable. There is a huge walk in closet in the bedroom and great laundry area in the bathroom. I would recommend Jeremy’s place and would stay there again.

Beautiful and peaceful rural setting, yet just minutes from shopping, dining, and anything else you might need. We stayed here while attending a graduation ceremony in New Haven and really appreciated the calm surroundings—perfect for relaxing after busy days. The drive into the city was quick and easy. The house itself was spotless and thoughtfully equipped with every amenity you could need—and then some.