House Sitting Winchester

Find a loving house sitter to watch over your pets and your home.

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Winchester, Find top rated house sitting

Prices are estimates per night. 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
$60
per night
5.0 out of 5 stars
• 42 reviews
13 repeat clients
2 years of experience
Swanzey, NH, 03446

“Fabulous experience! Our Fig loves Amy!! Excellent communication and attention to detail. We have already scheduled two more overnight sits.”

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Laura C.
Sitter Profile Image: Christian M.
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Christian M.
Star Sitter
from
$55
per night
5.0 out of 5 stars
• 37 reviews
13 repeat clients
10 years of experience
Greenfield, MA, 01301

“No problems whatsoever and Christian responded to my messages promptly. He also left the house just as he found it. Thanks Christian!”

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Kevin T.
Sitter Profile Image: Grace C.
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Grace C.
from
$70
per night
5.0 out of 5 stars
• 4 reviews
5 years of experience
Keene, NH, 03431

“Grace was terrific! On time, sweet with our dogs, took some amazing photos she shared with us, and best of all the little guys were calm and happy when we got home. Would absolutely hire her again!”

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Alison D.
Sitter Profile Image: Kathleen M.
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Kathleen M.
from
$75
per night
5.0 out of 5 stars
• 4 reviews
20 years of experience
Roxbury, NH, 03431

“I 100% recommend Kathleen! She really saved us! Our pet sitter canceled the morning we were supposed to leave for a seven-day vacation. I posted a job on Rover and she responded immediately, and very kindly stepped in to help, even though she had just finished another pet sitting gig. She took care of our beloved older dog, Dewey and our nine chickens. She was thoughtful, loving, reliable, and responsible. She texted with us almost daily, which we had asked her to do, and which set our minds at ease. She went above and beyond by giving our chickens daily treats and giving our dog LOTS of love. She is warm, respectful, and a good communicator. She also left the house in immaculate condition--in some ways cleaner than we left it. An ideal house and pet sitter in every way!!”

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Shaylyn Romney G.
Sitter Profile Image: Elana K.
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Elana K.
from
$60
per night
30 years of experience
Greenfield, MA, 01301

About: I’ve loved animals all my life and felt a deep connection with them. They have been some of my greatest teachers. I’ve provided loving care for cats, dogs, and rabbits throughout my adult years, and each one has been an important part of my world. I’ve cared for other people’s dogs, both taking them for walks and boarding them in my home while their people were away. I operated a private rabbit sanctuary for many years, giving rabbits a life where they could do the things they love—dig, groom one another, explore, forage, and simply be rabbits. I have experience caring for senior dogs and cats, as well as rabbits at all stages of life. I’m comfortable administering vitamins and medications to dogs, cats, and rabbits, including pills, liquids, and injections, and providing the extra care sick animals may need. I enjoy all aspects of caring for animals, from feeding and attending to their everyday needs to walking and hiking with dogs, playing with them, brushing them, and simply spending time together. I take the time to get to know each animal’s personality, routines, and individual needs. My goal is to make them feel safe, comfortable, happy, and genuinely cared for while their person is away. Having hired caregivers for my own animals, I understand how important it is to truly trust the person caring for your beloved companion. I’m dependable and take commitments seriously. If I say I’ll be there for a certain amount of time or take your dog for a particular length of walk, I follow through. I want you to feel confident that your animal is receiving the same attentive, thoughtful care I would want for my own. Caring for your companions fits naturally into my daily routine. I have flexibility during the day and enjoy building my schedule around the animals I’m caring for. I’m able to make time for walks, feeding, play, companionship, and other care throughout the day, and I take commitments seriously. When I agree to care for an animal, I make sure they receive the time, attention, and consistency they need.rently working part time and am available to care for your companion animals I care for pets in their own home, where they can stay in a familiar, comfortable environment and maintain their normal routines. I follow their feeding, medication, exercise, and care instructions carefully, while also making time for play, companionship, walks, brushing, and plenty of attention. I take the time to get to know each animal and adapt my care to their individual personality and needs.

Sitter Profile Image: Tessa H.
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Tessa H.
Star Sitter
from
$70
per night
5.0 out of 5 stars
• 10 reviews
3 repeat clients
8 years of experience
Springfield, VT, 05156

“Tessa was great! The pets loved her and got lots of picturs. She followed all the directions to the T, and left the place cleane than she found it! I have rebooked her already!”

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Amy F.
Sitter Profile Image: Sofie A.
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Sofie A.
from
$95
per night
5.0 out of 5 stars
• 16 reviews
4 repeat clients
10 years of experience
Orange, MA, 01364

“Sofie was great - saved us last minute when our previous sitter cancelled and was super communicative. Our pup was happy and spoiled by the time we got home! ?”

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Jessica M.
Sitter Profile Image: Kae L.
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Kae L.
from
$65
per night
1 repeat client
15 years of experience
Fitchburg, MA, 01420

About: Let me bring your dog on an adventure - my dog walks start at $20 but I do hikes on a sliding scale. I have group play experience, I can bring your dog to a dog park without any fear that your dog will get into any sort of trouble. I'm a quiet, clean, petsitter, I will likely leave your house cleaner than it was when you let me in. "I have worked with Kae, of Little Lyons, for about a year. He is contentious, dedicated, and loving to all the people and pets he comes into contact with. I highly recommend his services and happily look forward to working with him again in the future." - Nicole E. "Kae dogsits for me when I go away on business trips or go into Boston for the weekend, and I could not recommend him more highly! He is caring and attentive to my dog; my dog gets so excited to see him. My dog is medium to high energy and Kae always tires her out. He is extremely knowledgable about dogs and dog behavior and has given me several tools to help keep my dog more mentally engaged and less stressed. Kae is punctual, he remembers all sorts of details about every dog, and he is my go-to whenever I need someone. Best dog sitter/walker in the Providence area!" - Kate R. I have worked with a doggy daycare, where I learnt dog behavior, and positive reinforcement training. I have worked in home pet sitting for dogs, cats, rabbits, snakes, tortoises, geckos, bearded lizards, salt and fresh water fish, for over a decade. Schedule a meet and greet with your pets! LGBTQIA+ friendly, Disability and Sensory Friendly I have kept strange hours for a very long time. I can fit your furry (or scaly or feathered) family into my schedule without issue. As a pet service professional, I like to make sure your pet is well attended to, and you feel as safe and comfortable as they do. I enjoy waking up to walk a client's dog, or making sure your cat feels safe before it's time to turn the lights off. You can rest assured while I am with your pets that they will be well attended to. A typical visit includes 15-20 minutes of play with your pet depending on energy levels, lots of positive attention and love, feeding and making sure they have access to water and making sure any business is done. As an overnight visitor, often for pets with anxiety or special needs/senior pets, I am with your pet in your home from 10pm-8am, plus visits during any of their usual scheduled feedings. As a dog walker, you can expect me to arrive and provide a full 30 minute walk to your pet. If you book through rover, you can also get a map of the walk we did, how long it took, and I provide pictures along the way. When it's time to go home, I make sure they and your home are safe and secure.

Sitter Profile Image: Brandy V.
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Brandy V.
from
$80
per night
5.0 out of 5 stars
• 12 reviews
3 repeat clients
18 years of experience
Newfane, VT, 05345

“Brandy was fantastic! My dog is not easy due to anxiety and fear (she is a rescue). Elly didn't take that long to warm up and once she did they were able to stick to her regular schedule. Brandy was understanding and compassionate to where Elly was emotionally. She took her for great walks and played with her. Brandy sent pictures and lots of updates. Also Brandy was respectful of our house and left it as she found it. I would highly recommend her to anyone and will definitely ask her back. Thank you!”

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Rachel S.
Sitter Profile Image: Brianyn M.
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Brianyn M.
from
$125
per night
5.0 out of 5 stars
• 5 reviews
1 repeat client
15 years of experience
Amherst, MA, 01002

“Bri was the perfect fit for our energetic dog. She provided updates and pictures while we were away. It put our minds at ease knowing she was taking such great care of our dog. I would definitely book with her again!”

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Marissa G.
Sitter Profile Image: Linda I.
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Linda I.
from
$60
per night
5.0 out of 5 stars
• 3 reviews
20 years of experience
Hatfield, MA, 12057

“My husband and I were leaving for our 10-day honeymoon when, just a week before our trip, our dogs virus acted up and he could no longer attend daycare as we had planned. We were so relieved to find Linda! She was incredibly communicative from the start and made herself available to lock everything in quickly, which gave us so much peace of mind before we left. While we were away, Linda sent us daily updates and photos of our pup, which we looked forward to every day. It was so reassuring knowing he was able to stay in the comfort of his own home and maintain his normal routine while Linda took such great care of both him and our house. Our 2.5-year-old Golden Retriever is full of energy, and Linda did an amazing job building a relationship with him and keeping him happy, active, and comfortable while we were gone. We came home to a happy dog and a well-cared-for home. We couldn't have asked for a better experience and would highly recommend Linda to anyone looking for a trustworthy, caring, and reliable dog sitter!”

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Marissa N.
Sitter Profile Image: Zachary H.
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Zachary H.
from
$30
per night
5 years of experience
Paxton, MA, 01612

About: I have grown up around animals my entire life and know exactly what it takes to keep a home running smoothly and pets feeling completely safe and comfortable. I currently work a highly flexible local schedule in media and production, which means my calendar is wide open for dedicated drop-in visits, overnight housesitting, and checking in on your place exactly when you need me. I pride myself on being incredibly reliable, detail-oriented, and communicative. Whether it's keeping a strict feeding schedule, making sure the litter box is pristine, or just providing some great company and playtime, I treat every pet like my own. I'm always happy to send quick text and photo updates so you have total peace of mind while you're away! I work a flexible local schedule in media/radio production, which gives me excellent availability throughout the week and weekend. Because my hours are highly manageable, I can easily accommodate early morning check-ins, late afternoon or evening drop-ins, and dedicated overnight housesitting. I structure my days to ensure that your pets are always visited right on time, giving them consistent care and a regular routine while you are away. Safety and respect for your home are my highest priorities. When performing drop-in visits or overnight housesitting, I strictly follow all security entry protocols, double-check that doors and windows are locked, and keep the space completely tidy. I maintain a safe, calm environment for your pets by adhering exactly to your feeding, medication, and care guidelines. You can expect frequent photo and text updates so you know your pets and your home are in secure, responsible hands.

Sitter Profile Image: Monique S.
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Monique S.
from
$100
per night
5.0 out of 5 stars
• 5 reviews
18 years of experience
Goffstown, NH, 03045

About: I have cared for pets for more than 18 yrs in both Fla and New England. Always willing to travel with you or to your home. I am able to schedule pet sits in advance as needed. Always reliable loving and caring and aware of pets needs. I love the pets. I offer care in your home as well as water plants etc. I will do whatever is asked of me to do for the pets and the families.

Sitter Profile Image: Maksim M.
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Maksim M.
from
$20
per night
5.0 out of 5 stars
• 6 reviews
20 years of experience
Worcester, MA, 01608

About: I had a dog and a cat who lived with me for more than 17 years. Their death impacted me to become a Vet. I finished my degree in Russia. But currently I work as a musician and want to take care of pets. Skills: Professional vet experience I work as a musician and work in my home studio in my apartment. It’s a lot of routine of preparing and making music for people. And I would enjoy some fluffy company. I'm a vet. And first I will ask to provide all core vaccines. And will make a quick animal check-up including information from the Owner ( food, meds, allergies, and any chronicle sicknesses.) Also, I will ask the Owner how their baby prefers to spend the day, and based on the answer, I will take care of your pet.

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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.

How to book house sitting

  1. 1. Search

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

Select a filter and find qualifying sitters offering house sitting.

FAQs for House Sitting - Winchester

Frequently asked questions about Rover

Rover is the largest marketplace for local pet care. Whether you're looking for pet sitters, dog walkers, or house sitters who specialize in pet sitting, you can narrow your search by entering your ZIP code to find sitters within walking distance in your neighborhood.

Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:

  • Mail & deliveries: Collecting letters and packages so they don't pile up.
  • Plant care: Keeping your indoor or outdoor garden hydrated.
  • Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
  • Home security: Sitters can stay overnight to keep your home occupied.

The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Winchester walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.

It’s helpful to think of house sitting as a "home base" service. Most sitters in Winchester maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:

  • Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
  • Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
  • Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.

<b>Tip:</b> Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!

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!

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

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 .

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

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 .

sitters on Rover set their own , 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.

Yes, you can find sitters who have experience administering medication or managing dietary requirements. You can also find pet sitters who accept only one pet at a time, which is ideal for anxious puppies 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 request a Meet & Greet to walk your sitter through your expectations.

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