Pet-friendly holiday rentals in Madison

Claudia is a wonderful and responsive host, who sent us helpful information and recommendations of area restaurants. Her home is so cozy and immaculate, with special touches throughout. It’s also in the heart of Fairfield, within minutes of anywhere in town. We’ll certainly 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!

Laurie was an amazing host, very responsive! We wanted to bring our dog with us for the weekend and the fenced in yard added to the great experience! The place is much larger than the photos with plenty of living room space for the family. The kitchen was well equipped, with everything needed! We appreciated her hospitality and friendliness and would definitely stay again!

My family and I had such a wonderful stay at this house. The house was immaculate and well stocked for our stay. Matthew and Celia are great hosts. We really appreciated the basket of snacks and dog cookies that were left for us and our fur babies (Thank you!). They truly thought of everything and it felt like “home” the entire time we were there. The views from the back deck are truly spectacular. We spent many hours sitting in the sunroom and out on the deck enjoying the sights. My pups enjoyed daily walks at the sea wall park that was steps from the house. I can’t say enough great things about our stay. Thanks to our hosts for sharing their beautiful home with me and my family.

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

Cannot say enough good things about this charming home! The house had beautiful bay windows with a spectacular view, large bedrooms with plenty of room, and was very clean. Directly across the street was a waterfront park with trails along the coastline that were a blast to explore. And it was close to everything. Highly recommend!

Charming house in a nice neighborhood. We didn’t have a car rented but could walk to some restaurants (about a mile or so away). Hot tub and outdoor area was nice. Attended a graduation at Yale University and could easily Uber there.

Vinnie was very responsive to all our questions. The house was clean, well stocked, and very roomy. Everything in the bathrooms worked well for an older house. The downstairs is well decorated and has lots of interesting furniture! There are a lot of table lamps so you'd want to be careful staying there with smaller children. Very comfortable family room with large TV. The location is picturesque and very private. We enjoyed our stay.

This place is absolutely gorgeous. I spent quite a bit of time just exploring the grounds with my dog. It was too cold to use the pool but it was still beautiful to look at and a nice view while I was cooking/washing dishes. I appreciate the tour I received when I arrived to show me around. I would definitely recommend this place and hope to book again in the future.

Beautiful, relaxing, clean Airbnb. Had an issue with the shower, which can happen anywhere, Mk was super responsive and came over quickly. Loved loved loved our stay here. Didn’t use the swimming pool due to weather but the screened deck with the Fire Pit and the superb game room saved the day. Thank you for hosting us will be back

We had an excellent stay while attending our son's graduation at UCONN. The place was clean and homey, perfect when traveling back and forth. Our plans changed and we did not bring our dog, and Ashley was kind enough to refund us. My son goes back to UConn in the fall for his master's, and we know where we will stay again next May.

Highly recommend Patrick and Monica’s location. You feel right at home when you walk! The pool and patio views are breathtaking. The beds are very comfortable. Patrick was super responsive to my messages regarding restaurants.

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!!

Loved the stay! Exactly what we thought it was - extremely convenient and cozy. Plenty of beaches to walk to and the food options were plentiful. Would definitely stay again.

Absolutely beautiful home and wonderful experience!! The host was quick to respond and the amenities were excellent. There was zero lack! Would definitely return for another stay!

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

What a beautiful place! We needed accommodations for our family as we attended our daughter’s graduation. This place was perfect . Plenty of space and we had everything we needed . We didn’t want to leave .

Tracy's spot was as advertised . . . great location, walkable to restaurants, and well appointed. Definitely worth a stay!

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!!

We absolutely loved this little bungalow and can’t wait to come back! It is so close to the beach and there are a couple restaurants and bars within walking distance. A ton of other restaurants and bars less than a 10 minute drive away. And Trish is one of the nicest people I’ve ever met! We chose this Airbnb specifically because it was dog friendly and really wanted to give our oldest girl (13) at least one more beach vacation. Trish was super accommodating with the dogs and the beach was calm and perfect for them.

Wonder cottage in a fabulous town. Stacey is responsive and charming hostess and her snack basket is 5 star. Lovely stay

We were in town for a family Christmas party and were very happy staying at The Page Guest House. It was the perfect choice, especially since my 91-year-old mother was with me. The walk-in shower and the small step to get in made it easy. As former residents of Guilford, I highly recommend this centrally located, cozy guest house to anyone visiting the area.

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!

Alex’s home was a vintage design beauty! You could tell how much thought and detail he put into his home. The amenities were wonderful, including a gorgeous living room, great sound system, well-stocked kitchen, outdoor wood burning chimney, BBQ, and bucolic tree-surrounded hot tub (which we loved). But the best part was Alex himself. What a nice guy! He welcomed us at check-in with delicious freshly baked sourdough bread and homemade ginger cookies later in our stay. He also gave us fantastic advice on things to do in the area. Overall, you’ll love this home nestled in the CT woods!