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: Amy C.
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Amy C.
from
$20
per visit
5.0 out of 5 stars
7 reviews
1 repeat client
40 years of experience
Westport, CT, 06880

Can’t wait to have her back again! She sent me photos, filled me in on my nervous dog and was so concerned for his safety. Grateful to find someone near me. Thank you!

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Christina M.
Sitter Profile Image: Pam C.
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Pam C.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
8 reviews
4 repeat clients
20 years of experience
Norwalk, CT, 06854

Pam was so great with our two kitties while we were away. She was on time every day and we truly appreciated the extra steps she took like vacuuming and offering to take out the trash. Would definitely book again. Thanks!

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Rabecca P.
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: Christina M.
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Christina M.
Star Sitter
from
$45
per visit
5.0 out of 5 stars
7 reviews
5 repeat clients
30 years of experience
Weston, CT, 06883

The pets were well taken care of and loved. Christina did a wonderful job.

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Jo Ann M.
Sitter Profile Image: Isabelle G.
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Isabelle G.
from
$25
per visit
5.0 out of 5 stars
2 reviews
1 repeat client
17 years of experience
Wilton, CT, 06897

Isabelle has taken great care of my cats. She is very responsible and has a great personality.

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Catherine M.
Sitter Profile Image: Mia K.
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Mia K.
from
$18
per visit
2 years of experience
Ridgefield, CT, 06810

About: I've grown up with a variety of animals my whole life, including dogs, cats, and farm animals. Although I've only pet sit a little, I'm very comfortable with all kinds of dogs and cats. I'm currently working 2 part-time jobs as a barista, however I'm super flexible as my work schedule changes from week to week. Besides that I like to go to the gym and spend time with my chickens as much as I can. Around that I still have plenty of free time to start pet sitting. I love spending time and playing with pets, so a lot of what I would do is keep your pet company and engage with them as much as I can. With dogs I would play fetch outside if possible and with cats I would run them around with whatever toys they have. As well as, making sure the animals have enough food / water and keeping their home as clean as possible.

Sitter Profile Image: Ginger R.
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Ginger R.
from
$20
per visit
5.0 out of 5 stars
10 reviews
2 repeat clients
13 years of experience
Norwalk, CT, 06850

Ginger was great! She bonded quickly with both dogs. The visit went smoothly and I really appreciated the pictures. Will definitely book again!

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Kc H.
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: Alexandra S.
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Alexandra S.
from
$25
per visit
5.0 out of 5 stars
18 reviews
6 repeat clients
12 years of experience
Fairfield, CT, 06825

Very nice girl.

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Marie B.
Sitter Profile Image: Taylor L.
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Taylor L.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
10 reviews
7 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: 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: Sophie H.
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Sophie H.
from
$22
per visit
5 years of experience
Westport, CT, 06880

About: I've grown up with dogs my whole life, I've had a dog for 11 years, so I understand firsthand what it means to care for a pet like family. I have hands-on experience with dog sitting and walking, and I'm comfortable with daily routines, exercise needs, and making sure dogs feel safe and comfortable in any environment. Your dog will always be in caring, attentive hands! I work part-time, which means I have plenty of flexibility throughout the week to give dogs the time and attention they deserve. Whether it's weekday walks or weekend sitting, I'm available, your pet always comes first. When caring for pets in your home, my top priority is keeping things consistent and stress-free for your dog. I follow your established routines: feeding schedules, walk times, and any house rules, so your pet feels comfortable and secure in their own space. I treat every client's home with respect, ensure doors and gates are always secure, and provide updates and photos so you always know your pup is happy and safe.

Sitter Profile Image: Dominique P.
Verified Enhanced Background Check
Dominique P.
from
$15
per visit
6 years of experience
Norwalk, CT, 06850

About: Whether you need a simple walk, overnight care, or more specialized services (like drop-in visits for feeding and playtime), I offer a variety of flexible options to fit your dog’s routine and your schedule. I know how important it is to stay connected while you’re away, so I send regular updates, photos, and videos so you can see your dog enjoying their time, knowing they're in great hands. I currently have a rather flexible schedule because I only work freelance so I can make plenty of time for your pets and their needs. When I care for pets at your home, I make sure to stick to your pet's usual schedule—whether that’s feeding, walking, or playtime. This routine consistency helps reduce stress and keeps them comfortable in their familiar environment.

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: Jodie O.
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Jodie O.
from
$30
per visit
5.0 out of 5 stars
40 reviews
29 repeat clients
30 years of experience
Southport, CT, 06890

It is the first time that Jodie did drop-in-visit for Oskar, my 10-year-old Cairn Terrier. She seems dependable and caring. I will use her services again when needed.

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Asish G.
Sitter Profile Image: Shannia C.
Verified Enhanced Background Check
Shannia C.
from
$20
per visit
4.3 out of 5 stars
6 reviews
2 repeat clients
1 year of experience
Norwalk, CT, 06855

I was a bit hesitant leaving her with anyone, BUT SHANNIA is fantastic with my English Bulldog! She has a right shoulder injury and Shannia picks my dog up (weighing 54 lbs) up and downstairs! She wipes her 🐾 really good! She is amazing

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Linda L.
Sitter Profile Image: Hillary B.
Verified Enhanced Background Check
Hillary B.
from
$20
per visit
5.0 out of 5 stars
21 reviews
6 repeat clients
6 years of experience
Westport, CT, 06880

Hillary was great at handling all my questions since the day I was leaving my cat started having issues with his eye. She followed my snack and medicine request perfectly and made sure everything in the house was secure before she left. Both cats were happy and well taken care of.

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Vanessa B.
Sitter Profile Image: Maria & Jake S.
Verified Enhanced Background Check
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: Erin & Caitlin M.
Verified Enhanced Background Check
Erin & Caitlin M.
from
$20
per visit
5.0 out of 5 stars
23 reviews
11 repeat clients
10 years of experience
Ridgefield, CT, 06877

Erin was simply amazing! She committed perfectly! Sent me plenty of pictures of my dog and gave him all the love in the world. I highly recommend her and we will be using her again. Gunner can’t wait to hangout with you again! Thank you?

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Alyssa T.
Sitter Profile Image: Lydia B.
Verified Enhanced Background Check
Lydia B.
from
$15
per visit
5.0 out of 5 stars
2 reviews
20 years of experience
Norwalk, CT, 06850

Lydia was great caring for my cat, Elsie, while we were away for a long weekend. She is very responsive and we would definitely book her in the future!

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Hannah A.
1 / 1
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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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Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

    It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Meet local sitters who will treat your dogs like family

  1. 1. Search

    Browse profiles of sitters near you who offer dog sitting
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

Sitters in Weston average 5
repeat dog sitting clients

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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