
Pet-friendly holiday rentals in Weston
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Top-rated pet-friendly home rentals in Weston
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Popular amenities for Weston pet-friendly home rentals
Pet-friendly house rentals

Once a Pond - time and stress slow down.
Spacious home with a nice outside area. Enjoyed coffee with birds and bunnies. Will stay here again.

Private WHOLE HOUSE + Fenced Backyard+ Parking 4br
Andrea’s place is very clean, has everything we need. Beds are comfortable, kitchen and dining room are very nice. Our kids enjoyed the playground in the backyard so much. Andrea is always responsive. Thank you!

Steps2Beach, Fish Pond w/Tropical Backyard Oasis!
We loved Laura and Dana’s Big Easy home by the beach. It was big and comfortable and every detail had been thought about to maximize our enjoyment. Drawers and closets and cabinets were all labeled so we didn’t have to search for anything or guess where anything was. Literally every need had been anticipated! Amazing. The beds and bedding and linens and towels were abundant and soft and comfortable. The kitchen amenities were awesome, from an air fryer, to a full set of bar tools and blender, to great appliances. The decor was happy and cheerful and creative and fun. There were so many places to sit and enjoy, both inside and out. Do not hesitate to choose this wonderful place for a visit of any length. You will love it!

Bright Stylish Chic 4BR 4BA Home
The home had so much room which was great since we were 6 adults and 4 children. We were able to spend time together yet had spots for some quiet time. The backyard was wonderful for the children and the playroom was a life saver on a rainy day. The house is very close to activities in Stamford and Norwalk which we took advantage of each day.

Fairfield 2nd Fl–2 Rms | Exclusive Entry & Parking
John and Crystal's place is in a safe and comfortable part of town. The space was well kept and well described. The bathroom and bedroom(s) were comfortable and definitely worth my time in Fairfield!

Quiet and Cozy Cottage near NYC with a Pond
We loved Erin’s style, her beautiful cottage was comfortable and welcoming from the first. We found all we needed in the kitchen and everything worked well. The home was light and bright and well thought out. The grounds around the house were heavenly, with grassy dappled pathways through the woods and a gorgeous pond beyond the garden, with a river running through. Endless bird song and deer passing by, it was charming and peaceful. I highly recommend it.

Nature Retreat Airbnb
This ouse is a beautiful home in a beautiful setting. Peaceful and private. Well maintained. Spacious and very clean. Comfortable beds and very cozy bedrooms. We loved our stay in Redding. Thank you for being such wonderful hosts.

Westport Retreat/5 min to Town/10 min to Beach
Adam’s place is truly exceptional. I love the attention to the little details, everything from the design to the choice of colors, to the artworks, furniture and much more. There is sunlight in the unit throughout the day from the beautiful skylight above.The place is located in a leafy and quiet neighborhood. Adam and his co hosts were very kind and responded fast to our requests. The restaurants, stores and beaches are also located close to the accommodation. At the end of the days my kids looked forward to going back to Adam’s place and I highly recommend this place for anyone with kids and dogs.
Pet-friendly home rentals with a pool

Spacious Studio Apartment- near SBU
Gabby’s apartment is exactly as described. It is in a great location. Very close to Stoney Brook Village. We enjoyed walking to get our morning coffee. The apartment was very well stocked and spotless. Gabby thought of everything we could have possibly needed. We hope to be back next year!

Pool House
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!

E and T Getaway LLC
I would highly recommend this place, Tracy was very helpful. She gave us clear instructions. She had the place prepared for us. She even customized for us a card and guiding us to where everything is, the place was very clean, very well taken care of, and a lot of thoughts went into designing this place with all the amenities and comfortabilities

Cozy studio unit
We had a lovely stay! The home was exactly as pictured — beautifully maintained with charming indoor and outdoor spaces. The pool was great, though unfortunately the weather didn’t quite cooperate during our visit. The location was also a big plus — close to so many great restaurants and shopping options. The Karleen and Kim were wonderful — kind, responsive, and clearly a lovely family. We felt very welcome and would absolutely recommend this spot to anyone looking for a relaxing and convenient getaway.

Prvt pool Huge, Eclectic space… 1.5 hr to NYC!
Blake is a kind and attentive host. The house is fun and eclectic. Many interesting things to look at, art books to leaf through and she has a great record album collection. It has all the necessities you would hope to see in an airbandb. I like the location. We enjoyed taking a hike in Mount Beacon park to see the remnants of an old casino and great views of the Hudson Valley.

Spacious Cottage Loft
Jim’s place was an absolute gem for my inaugural trip to Black Rock! The Loft is incredibly spacious and equipped with everything you could possibly need for a perfect stay. From the moment I arrived, I was impressed by the meticulous cleanliness, attention to detail, and beautiful furnishings. Jim's communication was top-notch, making the entire experience seamless. One of the highlights was the extensive music collection, perfect for setting the mood during my downtime. The bed and furniture provided a level of comfort that made it hard to leave. Nestled on a serene, tree-lined street, the location couldn’t be better; it’s just a leisurely stroll away from delightful restaurants, charming shops, food markets, and more. I can’t wait to return for another stay whenever I’m in the area!

Riverfront Cottage Retreat & Pool 35 mins from NYC
Fabulous getaway, beautiful surroundings, hard to believe we were just a few minutes from highways and downtown and civilization! Responsive host, many amenities -- pool, bbq, outdoor dining, waterfall, river view, soaking tub, sun loungers, spacious kitchen, dreamy sofa.

Port Jefferson Convenient, Cozy and Chic!
We we’re going to Port Jefferson for a family wedding. Our Airbnb was perfectly situated. There is a pool area that we never used because we just didn’t have time. But it looked very inviting. The town of Port Jefferson had plenty of nice restaurants and shops. This house was perfect for our situation. We had six adults, all family members.
Private, pet-friendly home rentals

Streamside Cottage @ Sticks & Stones Farm
Hands-down one of the most beautiful airbnb I’ve ever had the fortune of staying at! Every detail - from the floor mat to the picnic basket to the window placement - was perfection. The little creek and vegetal labyrinth nearby was also such a treat. Heather and Chip were very responsive and flexible. The place is pretty conveniently located, with grocery shops and restaurants within a ten-minute drive, though I would recommend checking in before it gets too dark since the house is a little hard to find.

Westport CT, Hide-away!
Loved my stay. Great location, very clean and quiet, and within easy distances to where I was in Westport. Really appreciate John’s quick responses to my questions and am looking forward to staying here on future visits to Westport!

Enjoy our Connecticut Carriage House
The Carriage House is beautiful and Meredith and Mike are great hosts. The kitchen has everything you could ever need (not to mention arriving to a fridge with local milk and fresh eggs). The bedrooms and bathrooms are pristine. Mike even offered to help our son collect the eggs from the coop. All round exceptional stay.

Stylish Sheek Loft Ricport Studio 2, Downtown
This was the perfect spot for an overnight trip! The apartment was clean & stocked with everything you might need during the stay. Parking was available right down the street & it was within walking distance to the Hartford Healthcare Amphitheater!

Nature Retreat on 2.5 Acres
Just as described. Peaceful and private setting. Only 15 minutes from downtown Wilton but a very rural setting in nice neighborhood.

Polita’s Place # 2
Polita is very friendly and inviting host. The place and location are as described, spacious with no clutter. Polita is a Superhost. The beds were very comfortable, which is very important. Polita takes pride in her decoration and make you feel at home. An added bonus, there is a washer and dryer. The property is well maintained, with beautiful flowers. The entry and access are easy and secure. She allowed me to park in her driveway which was very important to me, I did not need to park on the street. The apartment is on the third floor, and she has a neat and welcoming balcony with a table and chairs. Polita, we will love to come again and visit.

The Cottage in Redding
Cozy guest cottage in a gorgeous New England setting. The perfect launch-point for exploring the historic towns and rolling hills and mountains of western Connecticut / eastern New York. The chickens were a charming addition. ;) Would be happy to stay again! The fall colors were stunning.

Redding Getaway
I had such a wonderful, welcoming stay here. Robert was extremely responsive and helpful. The studio was exactly as described, clean, and had everything I needed. The property was gorgeous and fun to explore with my dog while we were in the area for a dog show. I would definitely recommend Robert's place and plan to return next time I'm brought to the area!
Quick stats about holiday rentals that are pet-friendly in Weston
Total rentals
20 properties
Nightly prices starting at
₹5,138 before taxes and fees
Total number of reviews
490 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
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- Times Square
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Barclays Center
- Jones Beach
- Fairfield Beach
- Yale University
- Rye Beach
- Citi Field
- MetLife Stadium
- Yankee Stadium
- Gilgo Beach
- United Nations Headquarters
- Rye Playland Beach
- Statue of Liberty
- USTA Billie Jean King National Tennis Center
- Rockefeller Center
- Bronx Zoo
- Central Park Zoo
- Radio City Music Hall
- The Metropolitan Museum of Art