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Pet-friendly vacation 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 favorite
The large two-tiered deck is illuminated with soft lighting, creating a cozy atmosphere. A staircase leads to the upper level, where seating and decor are visible. An above-ground pool is situated beside the deck, surrounded by greenery and evening skies.
Home in Montville
4.92 out of 5 average rating, 272 reviews

Casino Wine Down House

EsperanzaRating, 5 stars5 days ago
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
Top guest favorite
Home in North Haven
5 out of 5 average rating, 144 reviews

Luxury Stay in Expansive Historical Home

Rebecca Rating, 5 stars1 week ago
The house was wonderful! We stayed for my daughter’s graduation and it couldn’t have been more perfect. The special touches like having the kitchen so well stocked and toiletries in all of the rooms was especially nice, and the house had plenty of room for everyone to relax and spread out. We thoroughly enjoyed our stay!
Top guest favorite
A two-story oceanfront home features a light gray exterior with large windows and a turquoise front door. A spacious ground level is accessible via white railings, leading to an outdoor sitting area. The serene beach and water views are visible in the background.
Home in Woodmont
5 out of 5 average rating, 96 reviews

Oceanfront Retreat: Modern Beach House

ShannonRating, 5 stars1 week ago
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!!
Superhost
The exterior of a quaint cape-style home is surrounded by a carpet of autumn leaves. A dark-colored vehicle is parked in the driveway, which is lined with gravel. The house features a welcoming entrance and a neatly maintained lawn, framed by trees shedding their leaves.
Home in Clinton
4.94 out of 5 average rating, 65 reviews

“11:11” 🙏 Updated Stylish Retreat 🌊 2 Mi To Beach

BrendaRating, 5 stars1 week ago
This Abnb is absolutely adorable!! Loved every single thing about it. We stayed for my nieces wedding. Her rehearsal was at Chamard Vineyard which was only minutes away. The wedding was at Madison Beach Hotel quick easy 15 minute drive! I Highly highly recommend staying at this Abnb …Super clean, very spacious, tranquil sunroom, 4 bedrooms and 2 full bath! Anna was so nice and super helpful. Definitely would stay again ☺️
Top guest favorite
A cozy bedroom featuring a spacious bed dressed in soft linens is positioned against a light-colored wall. Natural light filters through two windows, casting gentle shadows on the warm wooden floor. A ceiling fan hangs overhead, and a mirror and chair add functional elements to the space.
Home in North Fork
4.97 out of 5 average rating, 154 reviews

Secluded Farmhouse - Studio Apartment Style Unit

JosephRating, 5 stars5 days ago
Great location, private and comfortable. Close to wineries and breweries. Very clean and convenient. I highly recommend.
Guest favorite
A serene view of calm water featuring kayakers enjoying a sunny day. The distant shoreline is dotted with houses, creating a relaxed coastal atmosphere. Clear blue skies reflect on the water, enhancing the peaceful scene.
Home in Southampton
4.96 out of 5 average rating, 170 reviews

Waterview+Pool, FreeForDogs! Kayaks/PingPong/Bikes

ChristiRating, 5 stars1 month ago
We had a wonderful two day stay at Roger and Amy’s place. It was fantastic- such a beautiful, inviting home. Our kids had a blast in the heated pool- we could barely get them to come out despite it being under 60 degrees out! The kitchen was stocked with more than just kitchen basics- the spice cabinet had soo many different choices ! It was probably the most perfect AirBnb experience I’ve had and we travel plenty.
Top guest favorite
A serene view of the Long Island Sound showcases several sailboats gently drifting on the blue water. The scene is framed by a simple fence and grassy area, with a clear blue sky above, creating a peaceful coastal atmosphere.
Home in New Haven
4.98 out of 5 average rating, 174 reviews

WaterviewsTakeWedding pics,CollegeTours Yale&Beach

LaurrenRating, 5 stars1 week ago
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!
Guest favorite
A two-story farmhouse presents a blend of modern and vintage elements, accented by a red front door. The surrounding landscape features a large tree and a grassy area, with additional outbuildings visible in the background, contributing to a serene rural setting.
Home in Haddam
4.93 out of 5 average rating, 143 reviews

Charming 1806 farm house close to the CT River.

DavidRating, 5 stars2 weeks ago
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.

Pet-friendly home rentals with a pool

Top guest favorite
A stone pathway leads to a sparkling pool surrounded by lush greenery. Flowering plants in pots frame the pool area, while lounge chairs and a shaded umbrella provide seating options. Tall trees offer privacy, creating a serene outdoor retreat.
Guesthouse in Southbury
4.93 out of 5 average rating, 322 reviews

Charming Guest Cottage with Modern Amenities

YelizaRating, 5 stars1 week ago
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.
Superhost
A modern home is set in a lush green environment, showcasing a spacious heated saltwater pool surrounded by a stone patio. Relaxing lounge chairs are placed alongside the pool, and the house features large windows that reflect the tranquility of the yard.
Home in East Hampton
4.88 out of 5 average rating, 111 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

MariaRating, 5 stars3 weeks ago
Beautiful home, very clean, spacious and comfortable to stay with the family. We used the grill on multiple occasions and it was easy to use. The fire pitt was also enjoyable. The kitchen was well stocked, would bring own source of caffeine if you’re picky with your coffee though. Stephen, the host was very responsive and easy to reach when asked questions. The one thing I would recommend is to check in with the host if the pool is available to use prior to booking. Overall a great experience, would stay with them again.
Top guest favorite
An inviting outdoor area features a heated pool surrounded by a spacious patio. Comfortable lounge chairs are neatly arranged on the side, with umbrellas providing shade. Lush greenery and trees create a serene backdrop, enhancing the tranquil setting of the Pool House.
Home in Cheshire
5 out of 5 average rating, 135 reviews

Pool House

CindyRating, 5 stars3 weeks ago
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!
Guest favorite
An above-ground swimming pool is featured in a spacious outdoor area, surrounded by a wooden deck adorned with colorful lounge furniture. Lush greenery provides a tranquil backdrop, enhancing the peaceful rural setting. A paved patio offers additional outdoor space for relaxation.
Guest suite in Brooklyn
4.93 out of 5 average rating, 189 reviews

Affordable In-Law Apartment in Brooklyn, CT

KathyRating, 5 stars1 month ago
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.
Guest favorite
A clear blue pool is surrounded by a stone patio, featuring colorful floatation devices in the water. A diving board extends over the edge, while lounge seating and cabana beds are visible in the background. The pool area is enclosed by a white fence.
Apartment in Burlington
4.85 out of 5 average rating, 110 reviews

Charming apartment with breathtaking view!

AshleyRating, 5 stars2 weeks ago
Patrick and Monica were incredibly welcoming, making us feel right at home. They were communicative, helpful, and especially great with our dogs. We loved the property and left feeling fully rested. We would love to come back!
Superhost
An outdoor area features a rectangular pool surrounded by a wooden deck. Lounge chairs are positioned along the pool's edge, and a shaded seating area is located nearby under an umbrella. Lush trees provide privacy and a natural backdrop.
Home in East Hampton
4.84 out of 5 average rating, 99 reviews

East Hampton Oasis - Pool and Hot Tub

MaryRating, 5 stars1 week ago
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!!
Guest favorite
Home in Litchfield
4.93 out of 5 average rating, 189 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

ThomasRating, 5 stars2 weeks ago
Only complaint would be the noise from road during the morning commute
Guest favorite
A spacious pool area features a crystal-clear swimming pool surrounded by a wooden deck. Colorful sun loungers are arranged neatly, accompanied by large umbrellas offering shade. Lush greenery is visible in the background, enhancing the tranquil outdoor setting.
Home in East Hampton
4.93 out of 5 average rating, 153 reviews

Large heated pool, games room, near private beach

KarlaRating, 5 stars2 weeks ago
A beautiful house to always spend time with important people.

Private, pet-friendly home rentals

Guest favorite
An aerial view of the farm showcases expansive green grounds interspersed with tree cover and pathways. Several fenced areas and horse barns are visible, along with well-maintained fields. The surrounding nature creates a serene environment, inviting a sense of peace and relaxation.
Apartment in Killingworth
4.9 out of 5 average rating, 48 reviews

Life on the Farm

BrooklynRating, 5 stars2 weeks ago
We loved our stay here for when we visited New Haven! The place was clean and worked perfect for our dog! We loved the farm outside and the peaceful and private area outside. Would stay here again!
Guest favorite
A spacious living area features a light-colored sectional sofa with various decorative pillows. A circular coffee table sits on a patterned area rug, accompanied by a small potted plant. The sloped ceiling adds to the room's unique character, with soft lighting creating a warm environment.
Apartment in East Rock
4.97 out of 5 average rating, 29 reviews

Cozy East Rock apartment

JanetRating, 5 stars3 weeks ago
Immaculate space. Comfy couch and bed. Soft linens. Easy check in. Nice, historic neighborhood. Highly recommend!
Top guest favorite
A traditional two-story home features white siding and a purple front door. Large windows on the first floor allow natural light into the spaces. The front steps are flanked by potted plants, and a stone pathway leads to the entrance, surrounded by well-maintained greenery.
Apartment in Guilford
4.96 out of 5 average rating, 50 reviews

Enjoy a taste of New England Charm

BryanRating, 5 stars1 month ago
Tracy's spot was as advertised . . . great location, walkable to restaurants, and well appointed. Definitely worth a stay!
Guest favorite
The image presents a serene beach scene, featuring a sandy pathway leading to a calm water body. A safety barrier is visible in the water, marking designated swimming areas. Lush green grass borders the beach, enhancing the tranquil coastal environment.
Home in Westbrook
4.96 out of 5 average rating, 48 reviews

Zion's Light Beach Cottage

JimRating, 5 stars5 months ago
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.
Superhost
A bright kitchen space is highlighted by pale blue cabinetry and rich wooden countertops. A wooden table with chairs sits at the center, adorned with a vase of flowers. Large windows allow natural light to illuminate the area, enhancing its inviting feel.
Home in Guilford
4.72 out of 5 average rating, 140 reviews

Purple Button Factory Sleeps 6 Walk to Town Green

JulieRating, 5 stars4 weeks ago
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.
Guest favorite
A charming bungalow is visible in the foreground, featuring wooden shingle siding and a welcoming entrance. Two lounge chairs are positioned on the well-maintained lawn. A large willow tree and a fenced area provide a serene backdrop, enhancing the outdoor space's tranquil atmosphere.
Bungalow in Clinton
4.94 out of 5 average rating, 17 reviews

Clinton Beach Bungalow #4 Waterside Landing

JaimieRating, 5 stars9 months ago
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.
Top guest favorite
The exterior of a private guest house is depicted, showcasing a blue facade complemented by multiple windows. A spacious stone patio features outdoor seating surrounded by lush greenery and garden flowers. The roof is sloped, and trees provide a natural canopy overhead.
Guesthouse in Guilford
4.99 out of 5 average rating, 89 reviews

Page Guest House

ReneeRating, 5 stars6 months ago
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.
Superhost
Cabin in Northford
4.93 out of 5 average rating, 42 reviews

Yamagoya House

KatieRating, 5 stars2 weeks ago
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!

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

  • Total rentals

    40 properties

  • Nightly prices starting at

    G$16,719 GYD before taxes and fees

  • Total number of reviews

    1.3K 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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