Pet-friendly vacation rentals in Madison

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Popular amenities for Madison pet-friendly home rentals

Pet-friendly house rentals

Guest favorite

Home in Sag Harbor

4.85 out of 5 average rating, 160 reviews

Sag Harbor House for rent.

MichaelRating, 5 stars4 months ago
Ed was great at communicating, house was everything we could have asked for. Would definitely book again!
Superhost

Home in Coventry

4.72 out of 5 average rating, 39 reviews

Cabin Love at the Lake

JaneRating, 5 stars3 months ago
This cottage was perfect for our family. The side yard was just what the toddlers needed to get some fresh air and exercise. The beds were comfortable and the kitchen was well stocked to prepare a big family meal.
Guest favorite

Home in Black Rock

4.96 out of 5 average rating, 84 reviews

Cape on the Water

AlexaRating, 5 stars1 week ago
This beautiful cape on the water in Black Rock is perfect. Jim is an excellent host, responding right away when we had a couple of questions. We lived in the area all our lives and after retiring out of state we returned for the holidays this year. The house is in an excellent location, close to everything, and the house itself was just beautiful. It looks recently remodeled with a well equipped kitchen and 2 full baths. The downstairs was open, but cozy, and the bedrooms were really comfy. The view of Ash Creek is just beautiful. The house also had everything you would need in the kitchen, bathrooms, and bedrooms. Wifi and smart TVs completed any need you would want in a rental. It is walking distance to a lot of restaurants and a short walk to St. Mary's by the Sea which is a beautiful walk by the water. We were so glad we found this gem!
Superhost

Home in New London

4.82 out of 5 average rating, 39 reviews

Ocean Beach Family Fun near Mystic!

KatiaRating, 5 stars2 months ago
The place was perfect for our getaway weekend! The house is super spacious, very clean and has everything one may need to enjoy your stay. The host was friendly, accommodating and always available to answer any questions we may had. Will absolutely recommend this place
Guest favorite

Home in Westport

5 out of 5 average rating, 17 reviews

Cozy Retreat - Near Shops & Beaches, Pet Friendly!

MelanieRating, 5 stars1 month ago
Great find in Westport! Walking distance to main street with shops & restaurants. Didn't realize that someone lived in the unit below until we saw the check-in instructions but it was totally fine/you didn't even notice it during the stay.
Guest favorite

Home in North Fork

4.91 out of 5 average rating, 101 reviews

North Fork Escape - Walk To Village, Beach, Parks

JacquieRating, 5 stars2 months ago
Very nice setup for two couples, a baby, and a dog - could spread out with bedrooms and full bathrooms on each floor. Comfortable space with amenities you'd want while traveling with a dog and a baby (fenced in yard, laundry, etc). Very walkable to all the shops & restaurants in town, and easy drives to wineries & breweries. The only drawback was that it was close to a fire station and the sirens woke the baby from a nap.
Guest favorite

Home in Mystic

4.99 out of 5 average rating, 84 reviews

The Magnolia House, a Magical Vacation Rental in Mystic CT

KarinRating, 5 stars2 months ago
We had a fantastic stay at Ellen’s beautiful home. The description is spot on and the house really delivers. It was the perfect choice for our family of 4 when we were visiting our daughter for family weekend at Conn College. We could all spread out and relax in the open concept main areas. The bedrooms and bathrooms are good sized, spotless and whimsically appointed. The kitchen is perfect and has everything one needs to cook (which I did a fair amount of while there). We all felt welcomed and relaxed and also enjoyed walking into the town of Mystic. A superb stay all around. I highly recommend!
Superhost

Home in Clinton

4.68 out of 5 average rating, 81 reviews

Year-Round Waterview 4 Bds/2Bths, Sleeps 13 Linens

KylieRating, 5 stars1 month ago
We loved our stay! It was so cozy and the short 1 minute walk to two different beaches made it so worth it! There were a lot of houses close by, but it still felt to private. And when I messed up my reservation and needed an extra day, Laura was so accommodating and quick to respond to help us! Would love to come back and stay again.

Pet-friendly home rentals with a pool

Guest favorite

Home in East Hampton

4.93 out of 5 average rating, 108 reviews

Private & Pristine with Pool and Kid’s Playard

StephenRating, 5 stars1 month 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 favorite

Bungalow in East Hampton

4.93 out of 5 average rating, 107 reviews

East Hampton Ranch with Access to Clearwater Private Beach

KateRating, 5 stars2 months ago
We had a wonderful stay at Peter's home. It was beautifully decorated, very comfortable and a quick drive to Springs. Access to the private clearwater beach was a plus! Thank you for sharing your beautiful home with us.
Guest favorite

Home in East Hampton

4.87 out of 5 average rating, 100 reviews

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

GioiaRating, 5 stars1 day ago
Thank you so much Ashton. Your place was great, the chimney gave our stay over Christmas that extra warmth and coziness. We will rent it from you during summer in the future also, the pool looked very inviting.
Superhost

Home in Litchfield

4.82 out of 5 average rating, 105 reviews

The Getaway-HOST & Co.

CrystalRating, 5 stars4 months ago
I absolutely enjoyed my weekend here. The home is beautiful. Everything you could possibly need was provided In the home. Everything was clean, and neat. House is filled with light. The pool and hot tub were enjoyable. The host were amazing and had great communication, assisted us when needed right away. I would highly recommend staying here, and they are pet friendly which is always a plus for me. The yard is fenced in. Which made it easy to let the dog out, and great for the dog to explore. A++++ Will probably be back sometime In the future.
Guest favorite

Home in North Fork

4.94 out of 5 average rating, 33 reviews

Bailey House

ZarinaRating, 5 stars3 months ago
It was a lovely stay. Great location. House felt like a home and had great vibes.
Guest favorite

Home in Litchfield

4.99 out of 5 average rating, 80 reviews

Hilltop House w/POOL/SPA- HOST & Co.

KathrynRating, 5 stars2 months ago
Elizabeth has impeccable taste- her place is thoughtfully designed and tastefully decorated. This is the perfect location for a group trip, lots of spaces to sit and gather, or relax. Elizabeth has thought of everything, from linens to kitchen gadgets to cleaning supplies. The pictures are accurate, but the home is even more impressive in person. This is our second stay with Elizabeth, and we would absolutely continue to book again with her.
Superhost

Home in Sag Harbor

4.86 out of 5 average rating, 100 reviews

Sag Harbor Wonder, 3 bedroom 2 Bath & Heated Pool

IrisRating, 5 stars2 weeks ago
We had a wonderful time staying at this wonderful little hideaway in the Hamptons. We stood here earlier this year and loved it so much we had to return to closed out the year. Happy Holidays!!!
Superhost

Home in East Hampton

4.94 out of 5 average rating, 16 reviews

Walk to Water. Stunning Home with Gorgeous Pool & Grounds.

LarryRating, 5 stars43 months ago
House is well represented. Spacious, very clean, and great location. Good for families or groups of friends.

Private, pet-friendly home rentals

Superhost

Apartment in East Hampton

4.75 out of 5 average rating, 20 reviews

Total Privacy in Springs.

SylviavRating, 5 stars2 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 favorite

Home in Southbury

4.9 out of 5 average rating, 21 reviews

Cozy Family and Pet friendly 3 br Home

JennaRating, 5 stars1 month ago
We stayed at Ryan's place while visiting family in the area over the holiday weekend. The place was comfortable and clean and the bonus of being able to bring our pups was the best part. The dog park down the road was amazing and the locals were very friendly. The location was great, very convenient to shops, grocery store, gas etc. Overall we had a great time. Thanks again, Ryan!
Superhost

Apartment in Montauk

4.75 out of 5 average rating, 20 reviews

Twin Pond Ocean View 2 Bedroom #4

CatherineRating, 5 stars7 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 favorite

Cottage in Newtown

4.92 out of 5 average rating, 233 reviews

Private and Serene home close to I-84 and shopping

MiaRating, 5 stars2 days ago
We enjoyed our quick and cozy stay at Rio's cottage. Walking the trails and visiting the waterfall on the property was the highlight of the trip. Rio was very responsive and provided some great suggestions on things to do and see in the area.
Guest favorite

Guest suite in Groton

4.92 out of 5 average rating, 78 reviews

Heart of Mystic's Historic District

GaryRating, 5 stars3 weeks ago
Theresa's place exceeded our expectations. The rooms were spacious, bright, clean, and very well equipped to travellers' comforts. There were complimentary snacks, and even a few beer in the refigerator. The property was dog friendly, and there was a big, private back yard, with interesting trees and habitat for our dog to sniff. Teresa made sure out dog felt most welcome during our stay. The property's location was ideal; private, on a quite street, yet only an 8 minute walk to the beautiful, numerous shops and restaurants of Mystic. Theresa's communications, and the instructions inside, were simple, clear, and concise. Easy and stress free. You will be extremely happy staying at Theresa's.
Guest favorite

Home in North Fork

4.98 out of 5 average rating, 138 reviews

Secluded Farmhouse - Studio Apartment Style Unit

steveRating, 5 stars3 weeks ago
Jess and Zack have a first rate place here. They clearly care a lot about their home and the comfort of their guest. The room was very clean, the bath was spotless, and the decoration was tastefully done. They provide high quality soaps, linens, and the food they had prepped for breakfast was delicious. This place is a quiet gem and I greatly appreciate your attention to detail.
Guest favorite

Cottage in Amagansett

4.93 out of 5 average rating, 89 reviews

Amagansett Dunes Gem

SeanRating, 5 stars1 month ago
Judy and Joe’s home was the ideal getaway for our family’s extended Thanksgiving break. It had all the comforts to make us feel right at home, with a perfect location for exploring everything from South Hampton to Montauk. The private beach access was the cherry on top, offering the perfect spot to soak up the sun and enjoy the ocean waves. We can’t wait to return!
Guest favorite

Guest suite in Newtown

4.95 out of 5 average rating, 82 reviews

Light and airy, pet friendly rental in Newtown

LeesaRating, 5 stars4 days ago
This was our first AirBnB experience and it did not disappoint. Very thoughtful amenities.

Quick stats about vacation rentals that are pet-friendly in Madison

  • Total rentals

    40 properties

  • Nightly prices starting at

    $80 before taxes and fees

  • Total number of reviews

    1.1K reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    40 properties include access to wifi

Destinations to explore