Pet Sitting Winchester

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Winchester, Find top rated pet 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: Amadie C.
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Amadie C.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
23 reviews
5 repeat clients
2 years of experience
Swanzey, NH, 03446

Amie was a rockstar! She was very thorough and asked appropriate questions to ensure the best possible care for my cat. She is knowledgeable, has excellent communication, and provided detailed updates. She was incredibly kind and patient with my anxious kitty, and I am so grateful to her!

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Victoria C.
Sitter Profile Image: Susan S.
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Susan S.
from
$17
per visit
5.0 out of 5 stars
6 reviews
2 repeat clients
20 years of experience
Swanzey, NH, 03446

Susan did a great job taking care of our 100 lb Maremma. She was on time for all the sessions, and spent plenty of time with our dog. Our dog really liked seeing her. We will definitely be using her again.

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Doug H.
Sitter Profile Image: Amanda P.
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Amanda P.
Star Sitter
from
$20
per visit
4.9 out of 5 stars
35 reviews
9 repeat clients
20 years of experience
Winchendon, MA, 01475

Amanda was great! She responded quickly when I had questions, and was careful to keep me updated while I was on vacation. Highly recommended!

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Coreen D.
Sitter Profile Image: Scarlett F.
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Scarlett F.
from
$14
per visit
5.0 out of 5 stars
3 reviews
2 repeat clients
3 years of experience
Keene, NH, 03431

About: I used to babysit for my friends, family membersand & neighbors. As well as I've had many pets of my own; cats, dogs guinea pigs, hamsters, you name it. I'm very good at handling bigger dogs. I'm very flexible when it comes to time and will work around your schedule. I'm currently home from college for spring break and my time is very open for both weekends and weekdays. My working hours start at 7am and go till 11pm. (But I can fluctuate with your schedule) I have a fenced backyard. And one very friendly small/medium dog, he's a little shy, but he gets along with everyone. I believe that our pet should be treated like family members. Walks, treats, attention and lots of love.

Sitter Profile Image: Kiersten S.
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Kiersten S.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
58 reviews
16 repeat clients
6 years of experience
Orange, MA, 01364

Kiersten did a wonderful job caring for our cats while we were away. She followed our instructions, and our cats were relaxed and well fed. One of our cats has been sick and she gave him his medicines, and he is looking even healthier than when we left!

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Mashubi R.
Sitter Profile Image: Haley C.
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Haley C.
from
$30
per visit
5.0 out of 5 stars
96 reviews
36 repeat clients
17 years of experience
Hinsdale, NH, 03451

Haley was a wonderful caretaker for our two cats! We got plenty of updates and pictures. Both cats took to her immediately and soon they were playing and making biscuits 🥰. We appreciate the time she spent getting to know them and would definitely book again!

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Leigh Y.
Sitter Profile Image: Ayden H.
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Ayden H.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
18 reviews
5 repeat clients
15 years of experience
Hinsdale, NH, 03451

Ayden was a fantastic house sitter. He took incredible care of our numerous animals, and even noticed that our pellet stove had malfunctioned and let us know! We highly recommend him.

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Emma C.
Sitter Profile Image: Jorden A.
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Jorden A.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
83 reviews
15 repeat clients
15 years of experience
Rindge, NH, 03461

Thank you Jordan for your visit with Bailey today. I know that he is so happy during your time with him. You’re a true pleasure and keep up the good work.

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A P.
Sitter Profile Image: Elias V.
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Elias V.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
25 reviews
13 repeat clients
19 years of experience
Putney, VT, 05346

Elias took fantastic care of my tricky kitty, including administering meds in food and dealing with frozen wet food (Smalls) which is trickier than scooping dry food or opening a can. They were very responsive communication-wise and enthusiastic. I will definitely turn to them again for kitty care when I next leave town.

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Sebastian G.
Sitter Profile Image: Everett A.
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Everett A.
from
$25
per visit
6 years of experience
Northfield, MA, 01360

About: Experienced in caring for puppies, kittens, and senior pets. I provide walks, playtime, and can manage medications or special diets. I treat every pet like a cherished member of the family, ensuring they feel happy, safe, and loved while you’re away. My schedule is flexible during weekdays, which allows me to provide reliable walks, drop-ins, and pet care throughout the day. I work part time, so I’m able to accommodate many daytime and evening requests with advance notice. I make sure pets feel safe, comfortable, and cared for while keeping their normal routine consistent. I provide feeding, walks, playtime, fresh water, and lots of attention, while also keeping owners updated with pictures and messages. I’m respectful of clients’ homes and always make sure pets are happy and well cared for.

Sitter Profile Image: Maggie R.
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Maggie R.
from
$20
per visit
5.0 out of 5 stars
32 reviews
14 repeat clients
15 years of experience
Gill, MA, 01354

Maggie provided excellent cat care and house sitting. I appreciated that she fit us in last minute and accommodated our schedule around some other commitments she had. I would definitely book her again!

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Sarah P.
Sitter Profile Image: Lori L.
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Lori L.
Star Sitter
from
$35
per visit
5.0 out of 5 stars
101 reviews
40 repeat clients
15 years of experience
Greenfield, MA, 01301

Lori was great with our boys and communicated with us the entire time, sending us pictures that made us very comfortable. I would highly recommend Lori.

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Joe
Sitter Profile Image: Rachel L.
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Rachel L.
from
$15
per visit
10 years of experience
Brattleboro, VT, 05301

About: I have over 10 years of pet care experience including walks, overnight stays, and short visits. I also grew up with dogs and have lived with a few different cats in my adult life. I am new to the Rover app but am happy to provide references upon request. I work Monday-Friday 11-5 in Brattleboro. I can do overnights any day of the week, but just know that on these days I will be away for 6-7 hours depending on distance from your house. I love taking dogs on long walks and can do so 2-3 times a day. I am super communicative and experienced at house sitting while pet sitting. I am very respectful of people's homes and pets' routines. I will make sure to keep your house as clean - and your pet as happy - as you left them.

Sitter Profile Image: Amber D.
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Amber D.
from
$22
per visit
5.0 out of 5 stars
39 reviews
10 repeat clients
20 years of experience
Hinsdale, NH, 03451

We’ve had Amber drop in on a few separate occasions now and have had a great experience each time. She’s been attentive to both dogs behaviors and makes sure to check in with questions or concerns. I have a peace of mind when Amber visits if I’ll be away from home for an extended time during the day. Based on the photos, the dogs definitely have a great time with her too!

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Briana G.
Sitter Profile Image: Nadine N.
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Nadine N.
Star Sitter
from
$32
per visit
5.0 out of 5 stars
12 reviews
4 repeat clients
20 years of experience
Keene, NH, 03431

Nadine was Fantastic, it took a few visits for our Cats to warm up to her, she kept the kids Litter box’s clean, and food bowls Filled, also Vacuum around their Litter Boxes, so their area was always Clean, the Bangel Brothers love her time spent playing with them! We are Extremely happy with Nadine, and will Definitely use her Services again when we travel out of town!

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Myron G.
Sitter Profile Image: Taylor F.
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Taylor F.
from
$30
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
6 years of experience
Hinsdale, NH, 03451

About: Hi there! My name is Taylor. I absolutely love dogs and believe that most times they are better than people. I will take care of your dog(s) as if they are my own. I am available all day every day except between the hours of 3-6 pm. I love running and playing with dogs and do not mind cleaning up messes. I have two dogs of my own, a black lab and a hound mix that I absolutely adore. I love taking them for hikes and just spending as much time with them as I can. If you choose me to help take care of your dog(s), I promise you will not regret it. Thank you for taking the time to look at my profile! I work as a school teacher right now so am only available after 5 during the week and anytime during the weekends. After June 17th, I will be on summer vacation and will be available all day every day. I have a fenced in yard and a black lab that loves other dogs to play with if you'd like for me to bring them to my home to get some energy out.

Sitter Profile Image: Kendra K.
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Kendra K.
from
$35
per visit
5.0 out of 5 stars
67 reviews
15 repeat clients
20 years of experience
Warwick, MA, 01378

Kendra was fantastic with doing a whole weekend of drop ins for our pup, she gave great updates and tons of pictures! So happy with her, and we would definitely have her help us again!

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Kelsey K.
Sitter Profile Image: Amber P.
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Amber P.
from
$20
per visit
5.0 out of 5 stars
6 reviews
1 repeat client
8 years of experience
Athol, MA, 01331

About: I’ve always loved animals and have spent many years helping friends and family take care of their pets. It’s something that brings me a lot of joy. Over the years, I’ve looked after all kinds of pets — from energetic pit bulls and bulldogs to small dogs like Shih Tzus and even cats. Sometimes I’ve stayed in people’s homes for a week or two, and other times I’ve just stopped by for walks or check-ins. I’ve also welcomed pets into my own home when friends needed someone they could trust. I have a calm, friendly personality and get along well with animals, even if we’re meeting for the first time. I’m always careful to notice when a pet might be nervous or needs some space, and I do my best to make sure they feel safe, happy, and cared for. My schedule is very flexible since I work a per diem job and can choose when to take shifts. This gives me plenty of time for pet sitting, walks, or overnight stays. I’m usually available on short notice, too. The only thing I plan ahead for is care for my own cat while I’m away, but that’s easy for me to arrange — so it won’t affect my availability or reliability. When I’m caring for pets in their own home, I do my best to keep their routine as normal and comfortable as possible — feeding, walks, playtime, and cuddles just the way they’re used to. I make sure they feel safe and cared for while their family is away. If a pet stays in my home, I treat them like one of my own. I create a calm, cozy environment with plenty of love, attention, and playtime. I also make sure to follow any specific instructions from the owner so each pet’s needs are met. I’m gentle, patient, and understanding of different personalities — whether a pet is shy and needs space or energetic and ready to play.

Sitter Profile Image: Karen K.
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Karen K.
from
$40
per visit
5.0 out of 5 stars
7 reviews
2 repeat clients
15 years of experience
Vernon, VT, 05354

Karen stayed with luna for 4 hours, walked her and played with her. Sheis reliable, friendly to humans and dogs and is responsible. I recommend her very highlyl

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Michael J.
Sitter Profile Image: Rosalind L.
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Rosalind L.
from
$15
per visit
30 years of experience
Northfield, MA, 01360

About: I have taken care of cats, dogs, Small animals like mice, guinea pigs, fish, turtles. All way to farm animals like sheep, goats and even horses. Due to growing up in small town farming community. Currently I am supervising and helping my teenage daughter care for multiple miniature and full size horses in Leverett MA. I also have two wonderfully spoiled cats and a dog at home. Have some openings in evening and most weekends as at this time I do have a full time 9-5 job. Looking to see where this goes. I do not have fenced in yard but I keep my current dog on tie out or 50ft lead. Very quiet not normally traveled area around house with big yard to play. At clients home depends on environment there. Would prefer no off leash unless securely fenced area.

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

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 pets like family

  1. 1. Search

    Browse profiles of sitters near you who offer pet 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 pet sitting - Winchester

Select a filter and find qualifying sitters offering pet sitting.

Sitters in Winchester average 6
repeat pet sitting clients

FAQs for Drop-In Visits - Winchester

Frequently asked questions about Rover

As of August 2026, there are 448 sitters on Rover offering Pet 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.

If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.

The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.

Many pet parents provide a spare key or arrange a lockbox. You can also exchange keys during the Meet & Greet and show your walker how to use digital fobs or personalized codes. It helps to arrange access to your home, from spare keys to concierge introductions, before pet care begins.

If you live in an apartment or condo, don’t forget to discuss details like buzzer access, codes, or elevator etiquette. These details can help a pet sitter feel more comfortable going in and out of your building.

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.

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

  • 86% of sitters can help with special care needs
  • 97% can help with giving oral medications or injections
  • 94% 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.

A Meet & Greet is a short introductory meeting between you, your pet, 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.

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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