Dog Sitting Weston

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

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Over 14
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.

1 / 1
Sitter Profile Image: Taylor L.
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Taylor L.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
12 reviews
9 repeat clients
10 years of experience
Trumbull, CT, 06611

Taylor is fantastic with our dog! She takes great care of her, is on time and communicates clearly about her visits! Cheez is always happy and calm when we come home from her time with Taylor and we love that we have someone we can trust to care for her while we’re away!

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Jessica G.
Sitter Profile Image: Samantha D.
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Samantha D.
from
$25
per visit
5.0 out of 5 stars
4 reviews
1 repeat client
25 years of experience
Bridgeport, CT, 06605

About: Hi! My name is Sam and I'm here to help ease your anxiety 🩷 I'm all too familiar with the constant cloud of worry that can follow you around when you're not with your dog, so I will do anything I can to help alleviate any anxiety you have about leaving your best friend at home for the day (or while you go on that much-needed vacation)! I've loved dogs for as long as I can remember and have been taking care of them since I was in high school. From raising a puppy to caring for a senior, I've been there through every stage of life. I have experience managing chronic conditions that require medication multiple times a day, dietary restrictions, and administering sub-q fluids. I understand what it means to care for a dog both physically and emotionally - dogs are family, end of story. What to expect when you book with me: ✔️ solid communication: I love to send photo updates and will respond to any texts as soon as possible ✔️ undivided attention: your dog is my #1 priority, always ✔️ reliability: I will arrive on time and follow any directions you leave to a T ✔️ endless patience: your dog and your worries are never an inconvenience Thank you so much for taking the time to read this and I can't wait to meet your fuzzy family members! I work from home full-time on my small, handmade business, so I'm almost always able to rearrange my schedule to fit in your dog's needs! I'm extremely attentive to your dog to make sure they are always safe and well-cared for. I listen to their needs and follow any schedule you leave for me.

Sitter Profile Image: Erin C.
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Erin C.
from
$38
per visit
10 years of experience
Westport, CT, 06880

About: I began pet sitting for neighbors in Boston and continued building my network after moving back to Connecticut. I now care for dogs throughout the year for friends and their families, usually four to five weeks annually. I work fully remote, so pets get steady company and attention throughout the day. I enjoy having animals around and treat them like part of the routine, not an interruption. I have an indoor cat who is fully vaccinated, so dogs are still welcome. If your pet needs a calm home, a reliable schedule, and someone who is present, I am a strong fit. I work fully remote, so pets are with me throughout the day. I start early, which leaves time for morning routines before work, and I take regular breaks for walks and check ins. Evenings are for longer walks, feeding, and downtime. If a pet has specific needs, I adjust my routine to match them. Pets stay in a calm, tidy home where I am present throughout the day. I work fully remote, so dogs get steady company, regular walk breaks, playtime, and a consistent routine. I follow each pet’s feeding schedule, medication needs, and any rules you share. My indoor cat is fully vaccinated and comfortable with visiting dogs. I introduce pets slowly and make sure everyone has their own space. If your dog has specific routines or preferences, I adjust to match them.

Sitter Profile Image: John H.
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John H.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
10 reviews
4 repeat clients
10 years of experience
Downtown, Ridgefield, CT, 06877

John did a great job taking care of our pets. He was responsive, easy to talk to and genuinely cared for our crew of 2 cats and an energetic dog. We will utilize his services again soon.

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Trish P.
Sitter Profile Image: Samantha D.
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Samantha D.
from
$25
per visit
5.0 out of 5 stars
10 reviews
3 repeat clients
30 years of experience
New Canaan, CT, 06840

Samantha provided drop in visits for our 3 cats while we were away on vacation. She was super friendly, reliable and an excellent communicator. She was also accommodating to our specific requests and we were able to relax knowing that our cats and house were in amazing hands while we were away. We will not hesitate to book Samantha again in the future.

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Elena T.
Sitter Profile Image: Amy C.
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Amy C.
from
$20
per visit
5.0 out of 5 stars
8 reviews
1 repeat client
40 years of experience
Westport, CT, 06880

Amy has been so great with my little Archie. She is so very reliable and kind. Trust is so important and I can confidently say you can trust Amy with your pet!

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Karen N.
Sitter Profile Image: Kayla D.
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Kayla D.
from
$22
per visit
5.0 out of 5 stars
2 reviews
1 repeat client
7 years of experience
Westport, CT, 06880

About: I love dogs and cats! I’ve had many pets in my life and I currently have two dogs and one cat at home. One of my dogs Rusty is a senior and I help waking and taking care of him as well as my other pets. I’m currently taking a semester at home before applying for college for the fall. I have lots of time to play and walk you’re pets! I have three pets at home so I know how hard it is to leave them. I hope you’ll trust me to walk and take care of your pets.

Sitter Profile Image: Matthew D.
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Matthew D.
from
$30
per visit
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: Maria F.
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Maria F.
from
$30
per visit
4 years of experience
Wilton, CT, 06897

About: I’m patient, reliable, and truly care about every dog I walk. I pay attention to their behavior, energy, and comfort so they feel safe and happy. I follow instructions closely and treat every dog like my own. I’m available for pet care in the afternoons after 3pm on weekdays, as well as all day on weekends. I offer walks, drop-ins, and boarding when you’re away on vacation. I always prioritize safety, trust, and comfort. In my care, pets are supervised, kept on their routine, and treated gently and patiently. In a client’s home, I respect their space and follow all instructions carefully to make sure the pet feels secure and comfortable.

Sitter Profile Image: Catherine O.
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Catherine O.
from
$18
per visit
15 years of experience
Norwalk, CT, 06850

About: Fair warning: Pets are a little spoiled in my house! 😊 I've cared for animals my entire life and have experience with pets of all ages, sizes, and personalities. I've cared for my own senior dog throughout her final years, large and small breed dogs, rescue kittens, and adult cats, including raising my own two cats since they were kittens. I've trained all of my own pets and understand the importance of consistency. If your pet has specific routines, commands, or training practices you'd like maintained, I'm happy to follow them closely so their progress and structure continue seamlessly while they're in my care. I have a genuine soft spot for animals, and every pet in my care receives the highest quality treatment. Whether your furry friend enjoys treats, walks, playtime, or cuddles, they'll receive plenty of love, attention, and personalized care and are sure to have a great time while you're away. The day is dedicated to taking care of the fur babies. I'm available 7 days for check-ins, walks, home visits, and boarding. Let's connect and set up a time! My home is a relaxed space for cats or dogs to roam freely. My community offers a fenced in dog park and in my unit I have plenty of vertical space for your cat to rule over, including 2 cat towers and plenty of enrichment toys. I also have a catio on my balcony for some fresh air. If needed, I will separate my cats from more reactive animals while in my care.

Sitter Profile Image: Patrícia C.
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Patrícia C.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
85 reviews
33 repeat clients
4 years of experience
Norwalk, CT, 06854

Our cats were very happy when we came back, we got consistent updates and photos, she was communicative and she did what we had asked regarding the care of our kitties as well as keeping our home secure. We recommend booking Patricia, and will use her in the future! Thank you! 😻😻

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Jacqueline G.
Sitter Profile Image: fabi b.
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fabi b.
from
$19
per visit
2 years of experience
Wilton, CT, 06897

About: I’ve grown up around animals and currently have a cat of my own, so I truly understand how important it is to find someone you trust with your pet. On the other hand my partner is a preferred sitter on here , and through him I’ve learned so much about providing attentive, reliable, and compassionate care!! I am a student so I will try to fit pet caring as best as possible, by providing as much time as possible to each pet. And multiple visits a day if needed. Taking care of your pet as if it were my own is my main goal, and I want to respect your home as it were mine.

Sitter Profile Image: Maria & Jake S.
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Maria & Jake S.
from
$25
per visit
5.0 out of 5 stars
5 reviews
20 years of experience
Wilton, CT, 06897

Thanks for being awesome and responsive! Jake is a calm experienced dog handler that was able to handle Phoenix and Sundae’s energy!

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Josh S.
Sitter Profile Image: Lilliana S.
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Lilliana S.
from
$25
per visit
5.0 out of 5 stars
2 reviews
10 years of experience
Weston, CT, 06883

About: I’ve spent years caring for pets of all kinds, from energetic puppies to shy cats and everything in between. I’m comfortable with any schedule your pet needs and I always treat every pet like they’re my own. I am currently a student so all of my days are flexible. The semester is almost over but next semester I only have class on Tuesdays and Thursdays. I’m available for boarding during the week and weekends and everything else is flexible and able to fit into my schedule. There’s plenty of places for them to walk and play. They can easily be crated as well. Anything can be accommodated and done as needed.

Sitter Profile Image: Caitlin O.
Verified Enhanced Background Check
Caitlin O.
from
$20
per visit
15 years of experience
Wilton, CT, 06897

About: I've taken care of, owned, and loved dogs and cats my entire life. My friends and family often rely on me to care for their pets. I have volunteered at a local pet shelter, cleaning, playing with, and feeding dogs of a wide range of ages and with various medical needs. I can provide excellent care for all kinds of pets, including senior animals. I'm active, organized, and ready to adapt to any pet need! I currently work part-time, so I have flexibility and time to care for pets! I'm available weekdays or weekends from 9am-8pm. I can adjust my schedule either ahead of time or on a touch-and-go basis to fit what works best for you. I can tailor my approach based on your pet's specific needs and your personal preferences. I have a large, grassy yard for pets to play in; I keep an extremely close watch on them when they are outside; I play with them too and make sure they have fun! I usually let them out multiple times a day for however long I can be out there with them. Indoors, I have cozy couches, bean bags, and dog beds for all pets. I have a variety of food and healthy/dental treats. I know of plenty of walking trails and dog parks near me.

Sitter Profile Image: Katlyn T.
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Katlyn T.
from
$20
per visit
5.0 out of 5 stars
3 reviews
10 years of experience
Norwalk, CT, 06855

About: I started dog sitting when I was in 6th grade and have been taking care of pets since then. I grew up with 3 dogs and 2 cats and have tons of experience with walking, training, and other pet care! I work full time and get off around 5 p.m. Monday - Thursday and can assist with early morning walks/care or evening to late evening. I am limited on caring for dogs in my apartment due to apartment policies. However, short stays can be arranged! I live with just myself in a community and no longer have pets in my care.

Sitter Profile Image: Alysa V.
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Alysa V.
from
$20
per visit
5.0 out of 5 stars
6 reviews
1 repeat client
10 years of experience
Norwalk, CT, 06851

Alysa was one of the best pet-sitters we have ever had! I would most definitely recommend her. She was communicative, timely, asked questions to confirm, and paid attention to details. Thanks for taking care for our Bailey!

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Deirdre D.
Sitter Profile Image: Farva S.
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Farva S.
from
$30
per visit
4.9 out of 5 stars
115 reviews
77 repeat clients
17 years of experience
Pound Ridge, NY, 10576

Farva was available last minute and really helped us out when we booked a last minute trip! She was very responsive, prompt and professional. We’d definitely use her again!

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Amanda L.
Sitter Profile Image: Theresa K.
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Theresa K.
from
$18
per visit
20 years of experience
Norwalk, CT, 06851

About: I truly understand dogs- their behavior, body language, and needs. I treat every dog based on what it is that they need and truly have a genuine love for all animals I currently work during the day but I get out early most days with a flexible schedule. I am very active and love going to new places I make sure that they are comfortable, and that I familiarize myself . I am Punctual, responsible, and considerate in other peoples homes. I make sure the home and the dog are taken care of

Sitter Profile Image: Kathy G.
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Kathy G.
from
$30
per visit
5.0 out of 5 stars
25 reviews
6 repeat clients
30 years of experience
Norwalk, CT, 06854

I felt very comfortable going out of town and leaving my new cat in Kathy's care. He's very shy but she managed to see him. There was good communication and I found her to be very caring.

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Sally S.
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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
5.0 out of 5 stars

Dana was awesome! She came by took care of my pup and cleaned up a potty mistake by my pup. I’m thankful for her and I highly recommend her!

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Norville Y.
Drop-In Visits
1 / 1
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  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
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Popular requests for dog sitting - Weston

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Sitters in Weston average 5
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FAQs for Drop-In Visits - Weston

Frequently asked questions about Rover

The average cost for Dog Sitting in Weston on Rover is $27.75 per visit (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Sitting. For more information on service fees, click here .

As of July 2026, there are 4,419 sitters on Rover offering Dog Sitting across Weston. Enter your ZIP code to see which available sitters are closest to your home.

A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.

Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Weston stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.

Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.

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 Rover's Trust & Safety page .

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 Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.

A Meet & Greet is a short introductory meeting between you, your dog, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter 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. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

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:

  • 92% of sitters can help with special care needs
  • 96% can help with giving oral medications or injections
  • 95% 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 cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

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

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