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Pet-friendly holiday rentals in Madison

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Madison pet-friendly home rentals

Pet-friendly house rentals

Guest favourite
Home in Fairfield
4.95 out of 5 average rating, 19 reviews

Once a Pond - time and stress slow down.

KerrinRating, 5 stars3 weeks ago
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!
Guest favourite
Home in North Branford
5 out of 5 average rating, 5 reviews

The Gait House at High Gait Farm

ChesterRating, 5 stars4 months ago
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.
Superhost
Home in Milford
4.84 out of 5 average rating, 55 reviews

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

LindaRating, 5 stars2 months ago
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!!
Guest favourite
Home in Black Rock
4.96 out of 5 average rating, 85 reviews

Cape on the Water

BethRating, 5 stars2 months ago
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 !!
Guest favourite
Home in Westport
5 out of 5 average rating, 18 reviews

Westport Gem - walk to shops, dining, town center

LeahRating, 5 stars4 months ago
Conveniently located and perfectly comfortable for our family of four visiting our extended family around the corner. Would stay again!
Guest favourite
Home in North Fork
4.91 out of 5 average rating, 103 reviews

Cozy Farmhouse Retreat in North Fork, NY

AndrewRating, 5 stars3 weeks ago
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!
Guest favourite
Home in East Hampton
5 out of 5 average rating, 15 reviews

Captains Quarters | Avail for July 2025 Still

KristaRating, 5 stars5 months ago
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!
Top guest favourite
Home in Mystic
4.99 out of 5 average rating, 87 reviews

The Magnolia House, a Magical Vacation Rental in Mystic CT

HeatherRating, 5 stars3 days ago
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

Guest favourite
Home in East Hampton
4.93 out of 5 average rating, 109 reviews

Private & Pristine with Pool and Kid’s Playard

StephenRating, 5 stars4 months ago
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!
Guest favourite
Home in East Hampton
4.88 out of 5 average rating, 106 reviews

4 BD w/ Heated Pool in E Hampton, Fully Furnished

IanRating, 5 stars2 days ago
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.
Guest favourite
Home in North Fork
4.94 out of 5 average rating, 33 reviews

Bailey House

ZarinaRating, 5 stars6 months ago
It was a lovely stay. Great location. House felt like a home and had great vibes.
Superhost
Home in East Hampton
4.88 out of 5 average rating, 110 reviews

Gorgeous East Hampton Getaway

LisaRating, 5 stars7 months ago
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.
Top guest favourite
Home in Cheshire
5 out of 5 average rating, 131 reviews

Pool House

MelissaRating, 5 stars3 months ago
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.
Guest favourite
Cottage in Montauk
4.92 out of 5 average rating, 261 reviews

Montauk Oceanview Studio 6

Janie,LynnRating, 5 stars1 month ago
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!
Top guest favourite
Home in East Hampton
4.98 out of 5 average rating, 128 reviews

Explore the Water & Woods at a Relaxing Retreat

JulianaRating, 5 stars6 months ago
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!
Guest favourite
Home in Litchfield
4.93 out of 5 average rating, 184 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

AndreaRating, 5 stars2 months ago
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

Superhost
Flat in East Hampton
4.75 out of 5 average rating, 20 reviews

Total Privacy in Springs.

SylviavRating, 5 stars5 months ago
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.
Guest favourite
Guest suite in Wolcott
4.92 out of 5 average rating, 52 reviews

Modern cozy, pet friendly

HasanRating, 5 stars1 month ago
Great place, super nice people to help and assistance. I loved the ping-pong table!!!
Superhost
Flat in Montauk
4.76 out of 5 average rating, 21 reviews

Twin Pond Ocean View 2 Bedroom #4

CatherineRating, 5 stars10 months ago
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!
Guest favourite
Farm stay in Middlebury
4.92 out of 5 average rating, 251 reviews

Almosta Vineyard Farm Getaway

LibertyRating, 5 stars4 months ago
Lovely old farmhouse with beautiful fields, easy access to Middlebury, Southbury, Woodbury town centers. Animals are adorable.
Guest favourite
Cottage in Newtown
4.92 out of 5 average rating, 239 reviews

Private and Serene home close to I-84 and shopping

SarahRating, 5 stars4 days ago
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!
Guest favourite
Flat in Wallingford
5 out of 5 average rating, 22 reviews

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

GiovanniRating, 5 stars1 month ago
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!
Guest favourite
Cottage in Deep River
4.91 out of 5 average rating, 22 reviews

Serene Waterfront Cottage

RobertRating, 5 stars4 months ago
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.
Top guest favourite
Home in North Fork
4.97 out of 5 average rating, 142 reviews

Secluded Farmhouse - Studio Apartment Style Unit

JorgeRating, 5 stars2 weeks ago
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

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