Dog Sitting Winchester

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

End Date
Search

Over 34
pet parents in Winchester have booked dog sitting

Winchester, Find top rated dog sitting

Prices are estimates per visit for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.

1 / 1
Sitter Profile Image: Kerri S.
Verified Enhanced Background Check
Kerri S.
Star Sitter
$28
total per visit
5.0 out of 5 stars
30 reviews
20 repeat clients
15 years of experience
Reading, MA, 01867

Kerri is extremely flexible and wonderful with our pup. She is patient and kind. Our pup is the happiest to see her! She is definitely our go-to person to entrust our pup’s care !

Profile image
Divya A.
Sitter Profile Image: Sabrina C.
Verified Enhanced Background Check
Sabrina C.
Star Sitter
$28
total per visit
5.0 out of 5 stars
9 reviews
3 repeat clients
10 years of experience
Watertown, MA, 02472

Sabrina was a fantastic caretaker for my pup during his lunch time walks! She was responsive, gave great updates and I could tell my dog was in a great hands!

Profile image
Liz T.
Sitter Profile Image: Maia M.
Verified Enhanced Background Check
Maia M.
$19
total per visit
5.0 out of 5 stars
4 reviews
1 repeat client
6 years of experience
Medford, MA, 02155

Maia was wonderful with our beagles. She was very responsive and sent lots of photos.

Profile image
Nicholas W.
Sitter Profile Image: Katiana M.
Verified Enhanced Background Check
Katiana M.
$28
total per visit
5.0 out of 5 stars
9 reviews
1 repeat client
10 years of experience
Winchester, MA, 01890

Katiana did a fabulous job and went above and beyond during a week of drop-in visits including taking care of a fire alarm situation. Took great care of the cat too.

Profile image
David D.
Sitter Profile Image: Justin H.
Verified Enhanced Background Check
Justin H.
$15
total per visit
5.0 out of 5 stars
12 reviews
10 repeat clients
4 years of experience
Stoneham, MA, 02180

About: For the past few years now I’ve been a dog sitter for my family and friends, walking, playing, feeding, and cleaning up after them I can house sit, dog walk, and do drop in visits, Any time of the day Mondays to Fridays, And weekends if needed anything works. I get to learn pets usually routine. How many times a day to walk them, when and how to feed them, and their bed time.

Sitter Profile Image: Stacey S.
Verified Enhanced Background Check
Stacey S.
$34
total per visit
5.0 out of 5 stars
4 reviews
3 repeat clients
5 years of experience
Lexington, MA, 02420

About: I’m reliable, flexible and a good communicator, who loves to spend time with your fur babies, whether it’s cuddles, play or a long walk in the woods. I’m a teacher who has lots of flexibility this summer! I have my own strong and active 45 pound rescue, Sox, and have walked many neighbors’ dogs and helped my kids with their own dog walking businesses. I’d love to meet your pup! I’m a teacher, currently off for summer vacation, so I have a lot of flexibility June, July and August. I may often be available last minute, as well. I have a car, and am comfortable entering and exiting your home. (My own dog greets people with a whole lot of barking, so I’m used to that!)

Sitter Profile Image: Rebecca S.
Verified Background Check
Rebecca S.
Star Sitter
$39
total per visit
4.9 out of 5 stars
123 reviews
59 repeat clients
30 years of experience
Woburn, MA, 01801

Rebecca was great with our bloodhound Abby even with the last minute addition of having to give her medications. We would definitely recommend her to anyone needing dog sitting services!

Profile image
Heather H.
Sitter Profile Image: Abigail Z.
Verified Enhanced Background Check
Abigail Z.
$19
total per visit
5.0 out of 5 stars
6 reviews
1 repeat client
10 years of experience
Wakefield, MA, 01880

Abby is amazing! Friendly and reliable!

Profile image
Liz B.
Sitter Profile Image: Fernanda G.
Verified Enhanced Background Check
Fernanda G.
$20
total per visit
5.0 out of 5 stars
9 reviews
2 repeat clients
15 years of experience
Bedford, MA, 01730

Fernanda was great! Responsible, responsive, and attentive to the specific needs of my little love bug. I highly recommend her and will request her for future needs. Thank you for providing such thoughtful and informed care!

Profile image
Mary Beth K.
Sitter Profile Image: Sasha P.
Verified Enhanced Background Check
Sasha P.
Star Sitter
$28
total per visit
5.0 out of 5 stars
33 reviews
12 repeat clients
25 years of experience
Cambridge, MA, 02140

Sasha was a diligent and kind sitter for our cat. He’s an energetic cat but Sasha kept him entertained, loved, and most importantly safe during the holiday season. I highly recommend you retain her services.

Profile image
John M.
Sitter Profile Image: Maria J.
Verified Enhanced Background Check
Maria J.
$12
total per visit
5.0 out of 5 stars
22 reviews
11 repeat clients
5 years of experience
Medford, MA, 02155

Maria and her partner happily accepted a quick meet up before meeting Mochi and I. They were eager, friendly, and very respectful. They spent and hour each day playing, petting, chasing, and cuddling with Mochi. My little Mochi was ecstatic to see them and play with them. Knowing that she was in great, eager, and safe company and while providing her nonstop attention for the hour was the best I could ask for. Would love to have Maria and her partner hang with Mochi again soon!

Profile image
Christian S.
Sitter Profile Image: Emily S.
Verified Background Check
Emily S.
Star Sitter
$28
total per visit
5.0 out of 5 stars
38 reviews
20 repeat clients
14 years of experience
Charlestown, Charlestown, MA, 02129

Emily is very responsive and was super helpful in taking take of my young pup on short notice! She followed instructions perfectly and I came home to a very happy puppy. I highly recommend booking with Emily!

Profile image
Danielle D.
Sitter Profile Image: Sophia M.
Verified Enhanced Background Check
Sophia M.
$28
total per visit
5.0 out of 5 stars
37 reviews
13 repeat clients
8 years of experience
Winchester, MA, 01890

Sophia was amazing throughout the whole time! she went above and beyond and made sure she spent time playing with all three cats every day! she scooped the litter without being asked & we will definitely be hiring her again!

Profile image
Ashley B.
Sitter Profile Image: Annabelle K.
Verified Enhanced Background Check
Annabelle K.
$27
total per visit
5.0 out of 5 stars
18 reviews
4 repeat clients
18 years of experience
Arlington, MA, 02474

Annabelle was amazing! She made everything super easy for us. Super reliable. She sent us the cutest photos after every visit. We are so grateful for her!

Profile image
Angelica R.
Sitter Profile Image: Cierra K.
Verified Enhanced Background Check
Cierra K.
Star Sitter
$26
total per visit
4.9 out of 5 stars
16 reviews
8 repeat clients
17 years of experience
Medford, MA, 02155

Cierra took great care of my cat while I was away. Thank you!

Profile image
Will B.
Sitter Profile Image: Andrew T.
Verified Enhanced Background Check
Andrew T.
Star Sitter
$45
total per visit
5.0 out of 5 stars
172 reviews
57 repeat clients
15 years of experience
Medford, MA, 02155

Andrew did drop in visits for our cat Louie while we were out of town and was great. Louie is usually pretty independent but loved the daily visits.

Profile image
Luke M.
Sitter Profile Image: Kayla B.
Verified Enhanced Background Check
Kayla B.
Star Sitter
$56
total per visit
5.0 out of 5 stars
134 reviews
44 repeat clients
17 years of experience
Woburn, MA, 01801

About: Animals have been part of my entire life, and I bring 17 years of hands-on animal-care experience along with professional experience as an Animal Care Technician and Laboratory Technician. My experience spans companion animals, small animals, exotics, reptiles, birds and poultry, farm animals, and pets requiring senior, medical or specialized care. Professionally, my Animal Care Technician experience has given me hands-on experience with animal husbandry, daily care, observation, sanitation and maintaining structured care routines. My laboratory experience strengthened the detail-oriented side of my work as well—following established protocols, maintaining accurate documentation and understanding that small changes in an animal’s condition or behavior can matter. My experience isn’t limited to professional settings. I’ve spent my entire life around animals and have personally owned and cared for many different species. That includes dogs, cats, my own horse, chickens and other poultry, small mammals, reptiles and exotics. Having responsibility for animals with very different needs has taught me that quality animal care is never one-size-fits-all. Feeding, handling, housing, sanitation, enrichment, exercise, environmental needs and safety can look completely different from one species—or one individual—to another. With dogs and cats, I have experience across different breeds, sizes, ages, personalities and levels of care—from puppies and kittens through adulthood and senior years. I’m also comfortable caring for multi-pet and multi-species households where several feeding schedules, medications, exercise needs, separation requirements and daily routines may need to be managed at once. My special-care experience includes administering oral and topical medications, injections and insulin, subcutaneous fluids, following detailed feeding and medication schedules, mobility assistance, senior care and caring for animals requiring additional observation or support. I follow established owner- and veterinarian-directed instructions within my experience and scope of care. With dogs specifically, I’ve cared for a wide range of sizes, energy levels, play styles and temperaments. This includes puppies and adolescent dogs requiring additional supervision and structure, adults with established routines, seniors who may need a slower pace, and dogs who benefit from a more individualized approach because of anxiety, reactivity, separation concerns or other behavioral considerations. Years of caring for different animals have also taught me to notice the little things: body language, appetite, water intake, bathroom habits, mobility, energy, behavior and changes from an animal’s normal baseline. Those observations help me adapt care to the individual rather than expecting every animal to behave, socialize or settle in the same way. For dogs staying in my home, introductions are handled individually and gradually. Temperament, body language, play style, energy level and comfort are considered before group participation. Not every dog is expected to participate in every activity, and individualized care is always more important than forcing a pet into a particular routine. My goal is to combine professional animal-care experience with a lifetime of hands-on animal ownership and care—providing thoughtful, structured and attentive service while still giving pets the affection and comfort of a real home environment. Fantastic Friends — Home + Pet Solutions | Luxury with Love Pet care is part of my everyday routine, but I intentionally don’t operate on a rigid, one-size-fits-all schedule. Each day is planned around the individual animals in my care, their normal routines, feeding and medication schedules, age, temperament, energy level, weather, group dynamics and planned activities. A typical day may include potty opportunities, supervised indoor and outdoor play, fenced-yard time, walks, enrichment, individual attention, appropriate social interaction, meals, fresh water and plenty of opportunities for rest and decompression. Feeding, medications and other time-sensitive care instructions are prioritized according to each pet’s individual needs. Activities and schedules may change from day to day based on weather, safety and the needs of the animals in my care. The structure stays consistent; the exact itinerary stays flexible. My goal is to provide a safe, comfortable home environment rather than a traditional kennel-style experience. Pets have access to supervised indoor and outdoor areas, including our fenced yard. Multiple triple-filtered pet water fountain dispensers are available indoors and outdoors. They are checked throughout the day and cleaned, refreshed and refilled 1–2 times daily, or more often as needed. Pets receive opportunities for activity as well as downtime and individual attention. Feeding, rest, medications, crate or separate-space use when appropriate, and other routines are managed according to the individual pet. SAFETY + INTRODUCTIONS: Safety and compatibility come first. New dogs are introduced thoughtfully and one-on-one rather than being placed immediately into an established group. I consider temperament, play style, energy level, body language and individual comfort when determining appropriate social activities. Not every dog needs to participate in group play to have a great stay. Please disclose relevant behavioral history—including bite history, resource guarding, dog or human reactivity, leash reactivity, separation anxiety, escape behavior, handling sensitivities or significant fears—before care begins. These behaviors do not automatically make a pet unwelcome. Honest information allows me to determine whether my home and care setup are an appropriate and safe match and how your pet’s care should be structured. CRATES + SEPARATE SPACES: Crates and separate spaces may be used appropriately for feeding, rest, decompression, overnight routines, controlled introductions and safe household management. They are tools for appropriate care and management—not a substitute for activity or attention. Please let me know before booking if your dog cannot safely or comfortably use a crate or separate space so I can determine the best care arrangement.

Sitter Profile Image: Anna L.
Verified Enhanced Background Check
Anna L.
$34
total per visit
5.0 out of 5 stars
53 reviews
21 repeat clients
12 years of experience
Arlington, MA, 02474

Anna did a great job for us. Very reassuring, and in contact with me during her visits. My flight home was canceled, and she went the extra mile for me and the cats!

Profile image
Martha Ann S.
Sitter Profile Image: Noila A.
Verified Enhanced Background Check
Noila A.
Star Sitter
$27
total per visit
5.0 out of 5 stars
14 reviews
3 repeat clients
20 years of experience
Stoneham, MA, 02180

Noila was great at taking care of our 2 cats! Very considerate about a few things that I had left out and asking questions about how to best take care of both them and our house. Very recommended.

Profile image
Rashid Y.
Sitter Profile Image: Sanela F.
Verified Enhanced Background Check
Sanela F.
Star Sitter
$34
total per visit
5.0 out of 5 stars
29 reviews
8 repeat clients
30 years of experience
Stoneham, MA, 02180

Sanela did an amazing job caring for our two boy cats! She provided many photos and videos during her visits with them and that was so nice to see while we were away. She was very communicative throughout the entire process and also let me set up a FaceTime call with her prior to the visits to show her around our home. Right off the bat I could tell that she loves caring for animals, and that our boys would be in great hands. We came home to a clean apartment and happy and healthy kitties, and we are excited to use Sanela again for future visits!

Profile image
Mikaila S.
1 / 1
View more

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

Dog parents share their Rover experiences - Winchester

1 / 1
5.0 out of 5 stars

Sophia was great with both Kaito (dog) and Edgar (cat), giving them plenty of attention and being very attentive and responsive. Also, her photos are incredible, and we always looked forward to them while on our trip.

Profile image
Mark K.
Drop-In Visits
5.0 out of 5 stars

Nina was great. She cared for him while we were away. She sent updates, photos and videos. Thank you!!

Profile image
Allison D.
Drop-In Visits
5.0 out of 5 stars

Monica has been so terrific watching Willow while we are at work. Willow was recovering from an Injury and Monica adapted wonderfully to assist her as needed. and Monica’s positive attitude, flexibility, and frequent updates make her one of our favorite pet-sitters ever! Strongly recommend!

Profile image
Brenden O.
Drop-In Visits
5.0 out of 5 stars

Our anxious pup is always so calm and chill with Matilde thanks to her gentle energy! Will definitely ask for help again :)

Profile image
Kelly B.
Drop-In Visits
5.0 out of 5 stars

Sasha is an incredible sitter! She took such good care of our dog and was very communicative with us. We completely trusted her in our house and with our dog.

Profile image
Sammy A.
Drop-In Visits
5.0 out of 5 stars

I had a great experience with Bonnie! She checked in on my dog and two cats and made sure they were given love and attention during the day. She consistently kept me updated and sent great pics at the end of every visit!

Profile image
Mackenzie K.
Drop-In Visits
5.0 out of 5 stars

Alissa was great! Clio has a lot of special care needs from behavior to meds and Alissa was attentive to everything.

Profile image
Ashley M.
Drop-In Visits
5.0 out of 5 stars

Sarah was wonderful with my old dog. She was affectionate and thoughtful. I would love to have Sarah come again for dogsitting or dogwalking! Thank you Sarah!

Profile image
Barbara C.
Drop-In Visits
5.0 out of 5 stars

Anna is wonderful and she always takes great care of our dog! Thank you for all of your help! We will book again!

Profile image
Ciara F.
Drop-In Visits
5.0 out of 5 stars

Sharon came to meet Marzipan a few days before sitting for him which we appreciated. All went well smoothly and she sent a report card and cozy pic of herself with Marz. I was pleased with the experience and would definitely ask Sharon to pet visit again!

Profile image
Julia B.
Drop-In Visits
5.0 out of 5 stars

chance has been working with our Doggy for more than a year now and he’s one of the best best dog walkers we ever had to be truly loves dogs and I couldn’t imagine anyone better to take care of our little pup suck my suck suck my who are you talking t

Profile image
Erik B.
Drop-In Visits
5.0 out of 5 stars

Daphne was great! She was super responsive, on time and reliable. She took really good care of Harley and Harley had so much fun getting a nice walk and extra attention. Would definitely book with Daphne again!

Profile image
Jacqueline M.
Drop-In Visits
5.0 out of 5 stars

Andrew was great. He was able to take care of my pet needs without a lot of notice. He was communicative and professional.

Profile image
Bradley H.
Drop-In Visits
5.0 out of 5 stars

Very friendly, great communication, and good with pets! Thanks Charlotte for helping out with my big baby<3

Profile image
Madison C.
Drop-In Visits
5.0 out of 5 stars

Great communication! Cheryl was delightful, fabulous with my two giant breeds, and sent photos! We will certainly use her again.

Profile image
Debra H.
Drop-In Visits
5.0 out of 5 stars

Andrea took great care of our 2 beagles! She sent pictures of them snuggling on the couch and wondering the yard.

Profile image
Nicholas W.
Drop-In Visits
5.0 out of 5 stars

Justin was great with my dog while I was out of town. Very reliable and communicated updates frequently

Profile image
Keith D.
Drop-In Visits
5.0 out of 5 stars

Angela always does an incredible job, went above and beyond with Carter! Allowed us to fully relax knowing we they were in amazing hands!

Profile image
David & Eric M.
Drop-In Visits
5.0 out of 5 stars

Brooke was so responsive and professional. She took great care of my pup and I enjoyed her thoughtful report. I came home to a happy puppy! I would definitely book with Brooke again!

Profile image
Danielle D.
Drop-In Visits
5.0 out of 5 stars

Olivia was great with my dogs! We did a meet and greet (which I like to do with all potential dog walkers/sitters) and it was great! I look forward to using Olivia’s services again.

Profile image
Molly B.
Drop-In Visits
1 / 1
Find pet care near you

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

Popular requests for dog sitting - Winchester

Select a filter and find qualifying sitters offering dog sitting.

Sitters in Winchester average 6
repeat dog sitting clients

FAQs for Drop-In Visits - Winchester

Frequently asked questions about Rover

The average cost for Dog Sitting in Winchester on Rover is $27.75 per visit (as of August 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 August 2026, there are 10,235 sitters on Rover offering Dog Sitting across Winchester. 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 Winchester 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 Winchester 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 Winchester 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 Winchester. On Rover:

  • 90% of sitters can help with special care needs
  • 95% 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.

Connect anywhere with the Rover app

Download on the App Store BadgeGet it on Google Play Badge