Pet Sitting Winchester

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Over 2
pet parents in Winchester have booked pet sitting

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.

1 / 1
Sitter Profile Image: Marisa M.
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Marisa M.
from
$25
per visit
5.0 out of 5 stars
• 33 reviews
11 repeat clients
16 years of experience
Torrington, CT, 06790

“Marisa is very attentive and reliable. She sent regular updates.”

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Sonja B.
Sitter Profile Image: gina k.
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gina k.
from
$30
per visit
5.0 out of 5 stars
• 34 reviews
16 repeat clients
13 years of experience
North Canaan, CT, 06024

“Gina was wonderful to work with. She was super responsive while setting up visits, and gave lots of love to our kitties while we were away. Would highly recommend!”

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Christi S.
Sitter Profile Image: Alexandrine W.
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Alexandrine W.
from
$25
per visit
5.0 out of 5 stars
• 3 reviews
1 repeat client
18 years of experience
Winchester, CT, 06098

About: I have grown up with pets in my house all my life! Whether it be cats, dogs, chickens, goats, you name it! We rescued all of our fur babies so I have seen and experienced a lot in the animal world. I am currently a full time college student and I work part time. I can drop in before school, before I go to work, and when I am out of work! I can also do other times as long as we stay in communication. As I will be doing drop in and walks I will keep your animals leashed at all times unless specified differently so there are no escapees. I love giving my fur babies treats so if you provide me with the certain kind your babies can have I will gladly give them a treat for being adorable!

Sitter Profile Image: Lynsey M.
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Lynsey M.
from
$30
per visit
5.0 out of 5 stars
• 29 reviews
11 repeat clients
8 years of experience
Torrington, CT, 06790

“Lynsey is the best! She took great care of my pups and I would definitely use her again in the future! Some nice pictures of them during the visit, a detailed report, and message. It's hard leaving your fur family at home but it was made easier knowing they were in great hands with Lynsey!”

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Kristin P.
Sitter Profile Image: Priscilla E.
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Priscilla E.
from
$20
per visit
5.0 out of 5 stars
• 14 reviews
2 repeat clients
20 years of experience
New Hartford, CT, 06057

About: I’ve been around animals my entire life and have hands-on experience caring for a variety of pets, including dogs, bunnies, and birds. Growing up with different types of animals taught me how to adapt to each pet’s unique personality, needs, and routines. I’m comfortable with everything from energetic dogs who need structured walks and play, to smaller animals that require gentle handling and consistency. I pay close attention to behavior, appetite, and mood to make sure every pet is happy, healthy, and comfortable. I currently have open availability, which allows me to be flexible and fully accommodate your pet’s routine. Whether your pet needs early morning visits, midday check-ins, or evening care, I can adjust my schedule to fit their needs. Because I’m not rushing between commitments, I’m able to give each pet focused, unhurried attention during every visit. I care for pets in their own home, where they feel most safe and comfortable. My approach is always needs-based, meaning I follow your pet’s routine closely and adjust to their personality. whether they need lots of interaction or a calm, low-key presence.

Sitter Profile Image: Katie O.
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Katie O.
from
$40
per visit
5.0 out of 5 stars
• 23 reviews
4 repeat clients
20 years of experience
Torrington, CT, 06790

About: I have been around dogs my whole life, I took animal science in High school and worked in dog related jobs for about 5 years. I currently have five of my own fur babies. 3 pups and 2 cats I currently am out of work for the summer and I have open availability. Late August I will return to work as a preschool teacher and will be available evenings and weekends. I will take care of your dog as if they were my own, following all the requirements that you set up before hand. Giving your dog all my attention and love.

Sitter Profile Image: Meaghan G.
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Meaghan G.
from
$25
per visit
5.0 out of 5 stars
• 20 reviews
8 repeat clients
10 years of experience
Harwinton, CT, 06791

“She did a wonderful job eith my cats. They did hide on her but if I had her a few more days I am sure they would have liked her. If there is ever a time when I need a cat sitter again, I will hire her again”

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Thomas B.
Sitter Profile Image: James E.
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James E.
Star Sitter
from
$35
per visit
5.0 out of 5 stars
• 45 reviews
10 repeat clients
40 years of experience
Bristol, CT, 06010

About: Welcome, y'all! I love watching dogs. We watch kitty cats too 😁. Cheapest rates around! Let me make it easier for you to celebrate your vacation and holidays! Let me sit for your pup. I...love... dogs! My parents were dog breeders for years. As a youngster, I was responsible for many of the chores. As an adult, I have always had pets. I know how important your dog is to you. Your dog is your 'baby'. We are definitely dog lovers in this house! Big dog specialist. I love the little dogs too, though! ☺️💪🎄🎁❤️‍🩹 I will treat your pup like my own. I am a teacher during the day. I'm usually home by 3. I'm home every afternoon and every night and every weekend. I do have flexibility in my work schedule should they need arise. I have a dog lead hooked up to the house and it goes all the way back to the maple tree on the back of the property. 20 ft in either direction gives Fido plenty of room to go to the bathroom. Otherwise, your pup is in the house with me and my family. I am offering dog boarding services. This is a friendly Christian home. Lots of love to share.

Sitter Profile Image: Kelly H.
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Kelly H.
from
$50
per visit
5.0 out of 5 stars
• 66 reviews
31 repeat clients
14 years of experience
Otis, MA, 01253

“As always, our dogs were SUPER excited to see Kelly!”

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Eric L.
Sitter Profile Image: Jennifer H.
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Jennifer H.
from
$30
per visit
5.0 out of 5 stars
• 2 reviews
30 years of experience
Thomaston, CT, 06787

About: I’ve always been comfortable with dogs of all types. I grew up with dogs and have spent my whole life around animals, so caring for them feels natural to me. I’m calm, confident, and make sure to adjust to each dog’s individual needs so they feel safe, understood, and well cared for. I work full‑time during the day, but I’m available in the early mornings and evenings to take care of your pet. That gives me plenty of time for feeding, walks, playtime, or whatever they need before and after work. Mondays are my completely open day, so I’m available all day then for longer visits or extra care. My goal is to ensure your pet feels genuinely cared for. I pay close attention to their routine and what they need, and I make sure they stay comfortable, happy, and relaxed the whole time they’re with me.

Sitter Profile Image: Ashley S.
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Ashley S.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
• 7 reviews
2 repeat clients
15 years of experience
Behind The Rocks, Hartford, CT, 06106

About: I provide loving, attentive pet care, ensuring pets feel safe, comfortable, and happy while maintaining routines, exercise, feeding schedules, individualized attention, and clear owner communication. (Bilingual) Habló español Pet care fits into my routine part-time and per diem, allowing me to dedicate quality time, flexibility, and focused attention to each pet without feeling rushed. I follow each pet’s routine closely, including feeding, walks, playtime, and rest. I keep environments clean, safe, calm, and provide regular updates to owners for peace of mind.

Sitter Profile Image: Kadriya B.
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Kadriya B.
from
$30
per visit
5.0 out of 5 stars
• 5 reviews
1 repeat client
8 years of experience
Oakville, CT, 06779

About: I have owned a cat for seven years, and I enjoy brushing him, feeding him, giving him treats, cleaning the litter box, and cuddling. Sometimes he comes into my room, jumps on my bed, and sleeps with me. I also walk a puppy, a bulldog, named Buckiss. I clean up after him, and enjoy spending time rubbing his belly, and playing catch. At the end of our walk, I bring him back to his house, feed him, and give him water. I follow strict feeding instructions on how much food to give, and what kind of food he's allowed to have (no more than 2 treats a day). When walking in the winter, I make sure Buckiss has dog booties so his feet don't get hurt. I’m currently working part time so I have plenty of time in my schedule to care for your pet! I have a pretty flexible schedule. When I come to take care of a pet in my client’s home, I make sure that they are cared for with love and I do everything I can to make them feel safe, happy, and comfortable with me. I also make sure that when I end the stay, the client’s home is in the same or better condition than when I first came. I will make sure to clean after myself and leave the place looking as spotless as I can. I try to be a considerate and clean house guest.

Sitter Profile Image: Kyara F.
Verified Background Check
Kyara F.
from
$25
per visit
5.0 out of 5 stars
• 1 review
3 years of experience
Waterbury, CT, 06704

About: As someone who knows that your pet is a part of your family, you can trust that I will do my absolute best to take care of them. I have been a pet sitter for 4 years, providing exceptional care to the pets of neighbors, family, friends and clients. I have experience caring for pets with special needs, dietary restrictions, and medication. I’m currently working full time, but I’m available for overnights with any pet! I’m okay with traveling the distance to your house to watch your pet as well as house sit if needed! I understand that animals feel most comfortable around familiar surroundings, and wouldn’t want to displace them. I’m very flexible, just let me know when I’d be needed. The environment will be your own home. Your pet will not feel displaced, and will remain comfortable in his or her own bed. I understand that familiarity is key when owners are away.

Sitter Profile Image: Kailah J.
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Kailah J.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
• 11 reviews
6 repeat clients
3 years of experience
Waterbury, CT, 06706

“Kailah has been great with my dogs! I have 2 rescues who are super nervous around new people. This was our 3rd time booking with Kailah, she has been super patient and they are starting to warm up to her. I would recommend Kailah and will definitely be using her services again.”

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Molly R.
Sitter Profile Image: Alyssa F.
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Alyssa F.
from
$25
per visit
7 years of experience
Hartford, CT, 06106

About: Hi all! I’ve been pet-sitting since very young (age 10), having experience with various dog breeds and sizes as well as cats. Feel free to reach out so we can connect! I currently work per diem, so I have plenty of free time to care for little ones. I tend to have open availability, even for last minute requests! I am very open and able to follow any requests concerning your little ones. I understand that every pet is different when it comes to their needs, so I am very accommodating and willing to learn how to best care for your baby!

Sitter Profile Image: Elizabeth C.
Verified Enhanced Background Check
Elizabeth C.
from
$21
per visit
5.0 out of 5 stars
• 8 reviews
3 repeat clients
5 years of experience
New Britain, CT, 06062

About: I'm passionate about animal welfare and committed to providing the highest quality care for every dog I look after. I treat each dog as an individual, understanding their unique needs and ensuring they feel safe, loved, and cared for in my presence My Availability for the morning 5am-7:00am for Dog walking, Monday through Friday 5pm-till night for all services Saturday and Sunday full Availability day and night. If we develop a great relationship we can talk about sitting during the day, I work for a adult day center (family business) , very spacious place, nice for the dog to roam around and get to know the Seniors Citizens. I do offer house sitting services and on boarding in my home, I have a 2 bed room and living room with alot of space for your pet to roam around and play!

Sitter Profile Image: Trista S.
Verified Enhanced Background Check
Trista S.
from
$25
per visit
5.0 out of 5 stars
• 24 reviews
10 repeat clients
30 years of experience
Pittsfield, MA, 01201

“Trista was wonderful! She sent great pictures of all the pets. They all look so happy and well cared for. Great communication and followed all instructions. You can tell she really cares for your pets. We would highly recommend! 😊”

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Alana L.
Sitter Profile Image: Janice A.
Verified Enhanced Background Check
Janice A.
Star Sitter
from
$42
per visit
5.0 out of 5 stars
• 287 reviews
81 repeat clients
35 years of experience
RHINEBECK, NY, 12572

“Thank you, Janice and Noah! I can see that B basked in your attention and amazing that E is overcoming her shyness to come out to see you. It’s so good to be able to rest easy while we’re away knowing that the girls are in good hands.”

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Lauren C.
Sitter Profile Image: Amad E.
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Amad E.
from
$28
per visit
5.0 out of 5 stars
• 34 reviews
7 repeat clients
15 years of experience
Northampton, MA, 01060

“This is the second time that I used Amad to care for my cats, he has been great, will stay and play with them, easy to reach and will quickly respond . Overall we highly recommended .”

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Fabiola C.
Sitter Profile Image: Amanda K.
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Amanda K.
from
$45
per visit
5.0 out of 5 stars
• 19 reviews
8 repeat clients
23 years of experience
Southbury, CT, 06488

“Amanda is a fantastic dog walker, and once again did great with our dog, including great communication. She even took our dog for a hike and gave him a bath (with our permission).”

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

Pet parents share their Rover experiences - Winchester

1 / 1
5.0 out of 5 stars

Stacey is such a trouper! She made it up to our place despite the treacherous road due to the snow storm. She took great care of our guys and even took pretty great photos of them every day. Leaving pets while we travel is stressful and Stacey was such a great sitter and took all of that worry away from us. We really appreciate her!

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Susan H.
Drop-In Visits
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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
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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    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.

How to book pet sitting

  1. 1. Search

    Browse profiles of sitters near you who offer pet sitting.
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Popular requests for pet sitting - Winchester

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Sitters in Winchester average 5
repeat pet sitting clients

FAQs for Pet Sitting - Winchester

Frequently asked questions about Rover

The average cost of Pet Sitting in Winchester is $18 per visit as of November 2026. Most bookings cost between $17 and $25 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 November 2026, there are 1,607 sitters on Rover offering Pet Sitting across Winchester. 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.

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:

  • 90% of sitters can help with special care needs
  • 92% 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.

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 Meet & Greet.

sitters on Rover set their own cancellation policy, 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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