
Pet-friendly holiday rentals in Madison
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Top-rated pet-friendly home rentals in Madison
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Pet-friendly house rentals

Once a Pond - time and stress slow down.
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!

The Gait House at High Gait Farm
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.

Relaxing 2BR Stay | Fast Wi-Fi & Full Kitchen
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!!

Cape on the Water
Jim’s home is lovely and tranquil. To look at the beautiful ash creek every day with the wonderful wildlife was amazing. The inside of the home was very well appointed … excellent attention to detail in the kitchen and bathrooms. Very comfortable and cozy !!

Westport Gem - walk to shops, dining, town center
Conveniently located and perfectly comfortable for our family of four visiting our extended family around the corner. Would stay again!

Cozy Farmhouse Retreat in North Fork, NY
We came back to stay for a second time and hope to be back for many more! The place is exactly as advertised, beautiful, and an easy walk into town. Marianne and Stephen were super flexible with a few requests we had around the stay and so easy to communicate with. Greenport is the best and this home is amazing - you won’t regret booking here!

Captains Quarters | Avail for July 2025 Still
Petra is an incredibly responsive host, always available and ready to answer questions. The house is quirky (and I’ll say not maybe the best if you have mobility issues), but very cute and perfectly set up for our needs. The yard is excellent for dogs, and the location is also great, with a bay beach in about a 20 minute walk and a coffee shop and a few restaurants as well. Thanks Petra!

The Magnolia House, a Magical Vacation Rental in Mystic CT
Beautiful house- even better than the pictures. We were two families with young children. We loved the open concept with plenty of space for the children. We were able to walk to town for dinner (the walk home is uphill FYI). The house was well stocked and every detail of furnishings was coastal and cute. The host is extremely responsive and helpful. We definitely will stay again when we are in town.
Pet-friendly home rentals with a pool

Private & Pristine with Pool and Kid’s Playard
Marta’s place was the perfect getaway for my family. The bedrooms were large with comfortable beds. The kitchen was huge with high end appliances, and the yard was a dream for our young dog. Lovely surroundings in the woods but close to town for shopping and restaurants. Truly an unforgettable experience!

4 BD w/ Heated Pool in E Hampton, Fully Furnished
We had a wonderful time in this beautiful home that is in an idyllic Hampton's setting. Ashton was a great host and for sure we will be back.

Bailey House
It was a lovely stay. Great location. House felt like a home and had great vibes.

Gorgeous East Hampton Getaway
Wendy’s house is immaculate, tastefully decorated, very spacious and extremely comfortable. Her instructions were clear and her responsiveness immediate. We would absolutely consider staying there again.

Pool House
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.

Montauk Oceanview Studio 6
This is our second time time staying at Ron’s airbnbs We absolutely love it there ! Ron is great! Super accommodating and easy to get a hold of. The rooms are always clean and it feels like a home away from home We will definitely be coming back!

Explore the Water & Woods at a Relaxing Retreat
We had an amazing time staying at this house! It was in a great location, well-stocked with everything we needed, and the host was incredibly responsive. The check-in process was seamless, making our stay even more enjoyable. My family and I had a wonderful experience, and we would definitely book again!

Stunning Views, Bucolic Bliss in 1790s Farmhouse
Our 2nd stay at Elizabeth’s house and it was as nice as our last visit. Our kids love exploring the home and property which has a wonderful view. The kitchen is well appointed for cooking. We especially enjoyed the stone fireplace to relax after skiing. Would highly recommend!
Private, pet-friendly home rentals

Total Privacy in Springs.
The place is roomy and clean. The bed is comfy and the shower is great. There were juices and sodas and water in the mini fridge, a coffee maker with coffee and some wrapped snacks. A comfortable place to stay in a very pricy part of Long Island if you prefer a home over a hotel. We were only there for the 2 nights of our stay since we were out all day and for that it was perfect.

Modern cozy, pet friendly
Great place, super nice people to help and assistance. I loved the ping-pong table!!!

Twin Pond Ocean View 2 Bedroom #4
We come to Montauk often & loved this spot. Walkable & convenient to town plus a beach pass. The accommodation had plenty of space for a family with convenient parking. Highly recommend!

Almosta Vineyard Farm Getaway
Lovely old farmhouse with beautiful fields, easy access to Middlebury, Southbury, Woodbury town centers. Animals are adorable.

Private and Serene home close to I-84 and shopping
Rio was a really friendly and helpful host and his cottage was very cute in a lovely area surrounded by trees and great walks and hikes. We made s'mores over the fire pit, enjoyed the quiet, and explored a few towns nearby. Great weekend!

Eclectic 2 BR, 1 Ba apt w/Free Off-Street Parking
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!

Serene Waterfront Cottage
As always, we love our stay at the cottage. It’s becoming our home away from home when visiting our son. Thanks for all our goodies! Always a great surprise! Have a wonderful Christmas. We’ll see you next year I hope.

Secluded Farmhouse - Studio Apartment Style Unit
Thanx for a great time! We're from Port Jeff area, so close by, but we love to have extended stays on the North Fork. Was central to all our favorite places: Love Lane in Southhold, Hellenic Greek Restaurant in East Marion, Magic Fountain Ice Cream and Laurel where I grew up, etc. Some places were still closed for off season, but still plenty to enjoy! Apartment was cozy, bathroom has nice shower, king sized bed was perfect. Will try to come back during summer season. Great breakfast too, thanx Jess and Zach!
Quick stats about holiday rentals that are pet-friendly in Madison
Total rentals
40 properties
Nightly prices starting at
£61 before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
30 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi
Destinations to explore
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- Beach
- Yale University
- Foxwoods Resort Casino
- Ocean Beach Park
- Quotonset Beach
- Giants Neck Beach
- Clinton Town Beach
- Shennecossett Beach
- Cooper's Beach, Southampton
- Woodmont Beach
- Marvin Beach
- Horton Lane Beach
- Mystic Seaport Museum
- South Pine Creek Beach
- Connetquot River State Park Preserve
- Wildemere Beach
- Morningside Beach
- Anchor Beach
- Sasco Hill Beach
- Steer's Beach
- Fenway Beach
- East Beach
- Sunken Meadow State Park
- Great South Beach