Dog Sitting Weston

Book a Weston dog sitter to watch your dog in your sitter’s home or yours.

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Over 16
pet parents in Weston have booked dog sitting

Weston, Find top rated dog sitting

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Matthew D.
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Matthew D.
from
$31
per visit
5.0 out of 5 stars
• 9 reviews
1 year of experience
Westport, CT, 06880

About: Growing up with cats and various household pets, and loving dogs all my life has lead me to care and appreciate pets into my adult life. Looking to take care of the ones who love us the most for you. I am currently a full time music educator during the weekdays so I am available after school to walk and pet sit on an hourly basis. On Fridays and weekends I am also available for over night care as needed. In your home I will abide by all rules and routines you may have already. I can also ensure consistent care and attention to your pet’s needs.

Sitter Profile Image: Dawn P.
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Dawn P.
from
$30
per visit
5.0 out of 5 stars
• 13 reviews
2 repeat clients
30 years of experience
Weston, CT, 06883

“Dawn was wonderful with my 3 dogs!! I really appreciated her kindness and flexibility!! Would definitely recommend her and will use her again in the future!”

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Emily D.
Sitter Profile Image: Laura P.
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Laura P.
from
$30
per visit
5.0 out of 5 stars
• 10 reviews
2 repeat clients
25 years of experience
Redding, CT, 06896

“Absolutely recommend Laura for all your pet needs! She was incredibly communicative from the very start. She was flexible and kind, always making me feel so comfortable my dogs were in great care. I will absolutely be using Laura again and you should too!”

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Sarah M.
Sitter Profile Image: Aileen C.
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Aileen C.
from
$30
per visit
5.0 out of 5 stars
• 7 reviews
35 years of experience
New Canaan, CT, 06840

“Aileen was a great communicator and very responsible. I will definitely use her again!”

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Christine W.
Sitter Profile Image: Daniel D.
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Daniel D.
from
$20
per visit
3 years of experience
Norwalk, CT, 06855

About: Hi there! I’ve mostly taken care of cats, but I’m open to taking care of dogs & god walking if they are good with people. I work from home so having a pet to play with on my breaks will for sure keep me entertained all day! I’m a young, energetic man who works a remote corporate job. Looking for a pet to love & play with during the day so I don’t stare at my screen all day. My schedule is pretty flexible since I work from home. I do usually eat dinner with my family, so it would be ideal if I could go back home for a couple hours in the evening to eat with them. I’m an affectionate person who loves to play with pets because they get exercise & I get to destress. Especially since I work from home, I definitely have the time to give your pet the care & attention that you request. Lastly, as someone who loves to talk, I talk to pets all the time, of course in a sweet tone because I truly believe that dogs & cats can understand the things we say to them!

Sitter Profile Image: Madeleine M.
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Madeleine M.
from
$17
per visit
5.0 out of 5 stars
• 1 review
14 years of experience
Fairfield, CT, 06824

About: From my experience growing up with dogs, I will adequately walk, feed, and care for medium-small dogs. I have also provided in-home catsitting services while family-friends are away for up to two weeks at a time (feeding, playing, litter). I'm currently a college student in Fairfield, Connecticut. I'm looking for a job in pet care over school breaks in the summer and between semesters in the winter. I do not take animals into my own home so I do not disturb my family or aging dog, but I will gladly care for your pet in the comfort of your home and walk your dog in your neighborhood.

Sitter Profile Image: Jael F.
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Jael F.
from
$30
per visit
5.0 out of 5 stars
• 7 reviews
2 repeat clients
7 years of experience
Stratford, CT, 06854

“Jael was great with my two boys! Very thorough, timely, and communicative & will definitely book again!”

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Yujin K.
Sitter Profile Image: Penny N.
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Penny N.
from
$40
per visit
5.0 out of 5 stars
• 13 reviews
3 repeat clients
15 years of experience
Norwalk, CT, 06851

About: Animals are my life! They literally flock to me and I've always had a way with my furry friends. In my childhood my German Shepard, Flash, was the love of my life and always loved energetic play, beach runs, and playing in the dunes. I handle dogs both big and small and my current client has a tiny teacup mix, Riley, who despite his ten years of age, will play fetch for hours on end. He does have a heart condition and problem with his trachea, so being careful during walks (not letting him pull the leash too hard) and making sure he doesn't overwork his little heart are two safety concerns to always be mindful of. I also regularly dog sit Riley for weekend stay overs and make sure to stay with him in the bed so he is comfortable. Having grown up with all kinds of pets like parakeets, dogs, and guinea pigs (just to name a few) I've literally learned to "talk to the animals" and it's easy for me to familiarize with new pets and their needs very quickly. I'm very high-energy and can take your dog for an energetic walk at a comfortable based based on their health or general needs. And If you want your pup in tip top shape I can jog with them for hours and incorporate other fun games and exercises in the mix. I'm currently a full time "Rover" so my schedule is fairly open. I'm flexible in terms of last-minute bookings as well. The same flexibility applies if you would like to book a day or overnight sitter. I live on High Ridge Rd in Stamford near the Merritt so I'm only about 10 minutes away from the Mianus River State Park and 7 minutes from the Stamford dog park

Sitter Profile Image: Gabriel S.
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Gabriel S.
from
$25
per visit
2 years of experience
Bridgeport, CT, 06606

About: I have hands-on experience caring for dogs of all sizes, ages, and temperaments. I provide safe walks, feeding, bathing, and playtime. I am reliable, caring, and attentive to each pet’s unique needs. With my background as a biologist and my love for animals, I ensure your dog feels happy, healthy, and loved while in my care I currently work independently, which allows me to keep a flexible schedule and adjust according to each client’s needs. Whether weekdays or weekends, I can adapt my time to ensure your pets receive the best possible care, attention, and companionship. Safety and trust are my top priorities when caring for pets. I provide a calm, clean, and safe environment, whether in my client’s home or during walks. I always pay close attention to each dog’s behavior and comfort, making sure they feel secure and loved. With my background as a biologist and dog walker, I’m experienced in handling pets of all sizes and temperaments. Pet parents can rely on me to treat their furry friends like family, ensuring they receive the care, patience, and affection they deserve.

Sitter Profile Image: Cassidy M.
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Cassidy M.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
• 118 reviews
42 repeat clients
6 years of experience
Downtown, Stamford, CT, 06905

“Cassidy was a stellar sitter for my two cats! We were gone for 10 days which was the longest in a while that they’d been on their own and we came back to very happy, well-taken-care-of buddies, even our stand-offish diva cat who only came out a few times for her. Cassidy’s daily updates were sweet and thorough and she even let us know about a small issue with the house. Absolutely wonderful experience!”

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Olivia T.
Sitter Profile Image: Carolina B.
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Carolina B.
from
$20
per visit
5 years of experience
Norwalk, CT, 06854

About: I will take care of your dogs as if they were mine. I will become your doggos bff until your back home! I will also make sure to send lots of pictures :) I will be available on weekends and week nights. It would be very important to me to meet your dog before sitting so they know me before sitting. I do not have any pets. I recently lost my beautiful Choco to cancer. He was a beautiful brown golden doodle but looked more like a brown golden retriever. I have a small fenced yard and the neighborhood I am in is very quiet and pet friendly.

Sitter Profile Image: Molly N.
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Molly N.
from
$30
per visit
5.0 out of 5 stars
• 13 reviews
5 repeat clients
17 years of experience
Bethel, CT, 06801

About: Throughout my entire life I have grown up with dogs and the longest the household went without one was about 3 months. I also have been pet-sitting since I was about 10 years old - from fish to dogs I've done it all. I have done extended house-sitting and also just stopped by for a half hour to feed and spend time with someone's dog. I am easy to get ahold of through text. I am responsible, reliable, and most importantly, I love animals, especially dogs, and want them to feel happy and comfortable when in my care. I like pets to feel completely at ease around me. I treat them as I would my own pets and make sure to give them all the love, as well as space, that they need to be happy and cared for. Pet sitting is a part time career for me. I prioritize it and make sure I am available and have a flexible schedule. I am always easy to get ahold of and have great communication skills to make sure we are on the same page when it comes to caring for your pet. I will always send pictures when pet sitting too so that you feel more at ease and know I’m with your pet and can see how they’re doing! I make sure to be extra safe when at your house or on walks. I make sure I’m aware of how the pet is doing and the surrounding environment. I follow directions and rules to make sure the pet is getting consistent care. I also leave a house in the same condition I found it when house-sitting.

Sitter Profile Image: Clarissa G.
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Clarissa G.
from
$23
per visit
5.0 out of 5 stars
• 3 reviews
8 years of experience
Glenbrook, Stamford, CT, 06906

“We needed a new dog walker and Clarissa has been great with our puppies- they love her.”

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Jonathan B.
Sitter Profile Image: Leigh K.
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Leigh K.
from
$15
per visit
5.0 out of 5 stars
• 4 reviews
3 years of experience
Ridgefield, CT, 06877

“Leigh was amazing!!! I have a grumpy old lady Lab who she took excellent care of.”

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Michelle M.
Sitter Profile Image: Julia B.
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Julia B.
from
$20
per visit
10 years of experience
Norwalk, CT, 06854

About: I have taken care of dogs ever since I was ten. I love being around them too. My family had relied on me throughout the years to be sure to be responsible. I currently own a fitness business, so my schedule is pretty lenient. I live alone so I can take care of a lot during my day. I have a park outside my apartment along with a rooftop and I live alone so the door will always be locked when needed :)

Sitter Profile Image: Kayla P.
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Kayla P.
from
$30
per visit
5.0 out of 5 stars
• 11 reviews
2 repeat clients
6 years of experience
Ridgefield, CT, 06877

“Kayla is warm, responsible, and reliable. She took care of our dogs with love and attention. :) When we got back, the dogs were happy, and it seemed that they hardly knew we were gone!! We will be relying on Kayla for all of our future pet needs. :)”

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Teresa S.
Sitter Profile Image: Katharina D.
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Katharina D.
from
$25
per visit
5.0 out of 5 stars
• 2 reviews
10 years of experience
South Salem, NY, 10590

About: Hi there! My name is Kat, and I have a deep, well-rounded background in animal care. With 3+ years of hands-on experience in animal rescue and 10 years of personal pet sitting (and 22+ years of animal-loving!), I bring calm expertise, safety awareness, and specialized care that goes far beyond standard pet sitting. I'm also a certified Wilderness First Responder and American Red Cross CPR Certified. Rescue Training: My time in animal rescue taught me to read subtle animal body language, prevent stressful situations, and keep pets safe and relaxed in any environment, while also serving as a friend and comfort to animals in need! Medication Administration: I have experience giving oral, topical, and routine medications to a wide variety of animals, ranging from kittens to senior dogs. Experience in All Sizes & Energy Levels: From toy breeds to giant dogs, I understand how to handle different temperaments and physical needs. I love taking high-energy dogs on extensive, engaging walks (especially on our local hiking trails!) to keep them physically exercised and mentally happy. I am a full-time student supporting myself while working toward my paralegal certification. I take my courses online from 9 a.m. to 1 p.m. (Monday-Thursday), so I am available for in-home sitting, drop-in visits, or whatever your pet may need! Since I offer only In-House Sitting, Drop-In Visits, and walk services, your pets will receive 1-on-1 attention without leaving the comfort of their familiar surroundings. My priority is maintaining their daily routine while keeping your home secure and your pets safe. With every visit, I will provide consistent photo updates and detailed reports after each drop-in/day! Flexible, personalized pet care (drop-ins & sitting): Regardless of whether it's a quick 30-minute stop-in for food, meds, play, and potty breaks, or an overnight stay, I adapt entirely to your pet’s individual needs and routine. I strive to keep homes tidy, secure, and maintained, reducing travel stress for everyone and helping pets feel their best! Outdoor Safety: During walks and outdoor breaks, safety is paramount- I practice attentive situational awareness and strive to maintain large distances from any off-leash dogs, as well as ensuring your pet is safely and securely harnessed/leashed. Overall Safety Precautions: From my rescue experience, animals are curious!- In this, I ensure all doors, gates, and deadbolts are latched securely during every entry and exit, double-check that food and medications are sealed out of reach, as well as keeping a watchful eye out for subtle changes in pet health or behavior. Home Maintenance/Overall Peace of Mind: During house sits and drop-ins, I am happy to bring in mail, water plants, keep your living spaces spotless, or help with any other tasks.

Sitter Profile Image: Jay L.
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Jay L.
Star Sitter
from
$39
per visit
5.0 out of 5 stars
• 288 reviews
143 repeat clients
6 years of experience
Downtown, Bridgeport, CT, 06604

“Jay was great with my dogs who together are the ultimate challenge - big, strong and like two brothers that have to wrestle constantly. He took great care of them and instinctively knew how to handle them. I will be using him again.”

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Chris P.
Sitter Profile Image: Rachel O.
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Rachel O.
Star Sitter
from
$40
per visit
5.0 out of 5 stars
• 59 reviews
26 repeat clients
20 years of experience
Bethel, CT, 06801

“Rachel is the best! Took such good care of our girls when we were away and they seemed very happy with her, I loved all the photos updates. She’s the best!!!”

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Jennifer M.
Sitter Profile Image: Ella S.
Verified Enhanced Background Check
Ella S.
from
$20
per visit
15 years of experience
Fairfield, CT, 06824

About: Grown up with multiple dogs my whole life! Self trained them all and love taking long walks and giving pets! Love hanging around dogs and caring for them. I am currently a student at Fairfield University but can be flexible outside of class time! I have a car so I am also able to drive myself wherever needed. I have a dog which we walk with a leash. I can handle dogs very easily as I’m used to it from growing up with them!

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The median cost per visit for dog sitting in Weston is $25

Dog parents share their Rover experiences - Weston

1 / 1
5.0 out of 5 stars

Dana is amazing! Super responsive and was able to help me out in a pinch when a cancelled flight caused travel plans to be delayed.

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Jeff H.
Drop-In Visits
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How to book dog sitting

  1. 1. Search

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Popular requests for dog sitting - Weston

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Sitters in Weston average 5
repeat dog sitting clients

FAQs for Dog Sitting - Weston

Frequently asked questions about Rover

The average cost of Dog Sitting in Weston is $28 per visit as of October 2026. Most bookings cost between $28 and $50 per visit. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of October 2026, there are 4,320 sitters on Rover offering Dog Sitting across Weston. Enter your ZIP code to see which available sitters are closest to your home.

You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.

Before booking, confirm:

  • the timing, length, and frequency of visits;
  • the care instructions the sitter should follow;
  • which parts of your pet’s usual routine should be prioritized;
  • how often you would like to receive messages, photos, or other updates.

Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Weston choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit .

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the , which provides up to $25,000 in eligible veterinary care reimbursement.

A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet or the new environment.

During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first .

While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.

To find sitters in Weston with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.

Yes, you can find sitters who have experience with handling special pet needs in Weston. On Rover:

  • 89% of sitters can help with special care needs
  • 92% can help with giving oral medications or injections
  • 96% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

sitters on Rover set their own , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.

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