Pet Sitting in Winchester

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

Search Results

Confirmed availability: Memorial Day
Charlene S.
Trustworthy and reliable pet lover.Wakefield, MA, 01880
Dog Boarding, Drop-In Visits, Dog Walking
2 repeat clients
10 years of experience

About: I’ve had dogs and cats my whole life. I currently have a spry 11 year old rescue dog. She’s a Boston Terrier mix and she’s protective, playful, and s… (more)

from
$22
per visit
Confirmed availability: Memorial Day
Amy K.
2.
Amy 
Verified Enhanced Background Check
Vet Tech/Dog Foster, Come Play!Malden, MA, 02148
Dog Boarding, Drop-In Visits, Doggy Day Care

I can’t say too many good things about Amy. She’s obviously an animal lover, and quickly bonded with my cats. She is also flexible and went above and beyond the… (more)

from
$30
per visit
Confirmed availability: Memorial Day
Jun O.
3.
Jun 
Verified Background Check
Dog lover and college professor!Medford, MA, 02155
Drop-In Visits, Dog Walking

Jun is amazing with dogs. She is like a dog whisperer. When my dog first met her, before she even stopped her car or stepped out of her car, my dog started to g… (more)

from
$18
per visit
Calendar Recently Updated
Erin B.
4.
Feline & Canine Companion PetsitterWinchester, MA, 01890
House Sitting, Drop-In Visits

I have known Erin for almost 10 years and she is one of the most caring, patient, responsible and compassionate people I know. She loves my dogs and alw'ays ask… (more)

from
$20
per visit
Confirmed availability: Memorial Day
Cheyenne S.
Pet care with love and experience.Winchester, MA, 01890
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Cheyenne was wonderful! I felt such peace of mind while traveling, knowing she was looking after my fur baby. I got updates and pictures every time she dropped … (more)

from
$28
per visit
Confirmed availability: Memorial Day
Kitty Care Arlington and LexingtonArlington, MA, 02476
Drop-In Visits, Dog Walking

Dave took such great care of our cats! They are typically upset with us upon our return, but are totally well adjusted. They had plenty of food, water, and atte… (more)

from
$23
per visit
Calendar Recently Updated
Very active, have fenced in yardMedford, MA, 02155
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Wes and Amber, our doggie and kitty, loved being cared for by Kristen! Kristen was amazing, she took great care of our critters while we were away. She was car… (more)

from
$20
per visit
Calendar Recently Updated
Walks & Wags with TMelrose, MA, 02176
Drop-In Visits, Dog Walking

Tainara was great! She gave our cats lots of attention during her drop in visits. She was professional and great at communicating. I would definitely hire her … (more)

from
$16
per visit
Calendar Recently Updated
All about belly scratches &snugglesArlington, MA, 02474
Drop-In Visits, Dog Walking

Aysegul was very friendly, communicative and overall a great sitter! She was very patient with my cat, who is quite shy. I really enjoyed that she sent lots of … (more)

from
$22
per visit
Calendar Recently Updated
10.
Puppy Paradise!Arlington, MA, 02474
Dog Boarding, Drop-In Visits, Doggy Day Care

Paul took care of my dog for an entire. She was very well treated and loved her time there. She got plenty of attention and exercise. I would recommend Paul to … (more)

from
$28
per visit
Confirmed availability: Memorial Day
11.
Former Vet Student & Shelter WorkerArlington, MA, 02476
Drop-In Visits, Dog Walking

Amber helped look after our two cats on short notice when our other sitter told us that she wasn't available for one of our vacation days. Amber was friendly, e… (more)

from
$38
per visit
Calendar Recently Updated
12.
East Arlington Dog MomArlington, MA, 02474
House Sitting, Drop-In Visits, Dog Walking

All of my pets absolutely love Cali. I trust them to take care of my two cats and dog and would highly reccomend them for walking and house/pet sitting. I tru… (more)

from
$17
per visit
Calendar Recently Updated
13.
Liz 
Verified Background Check
Lifelong animal lover!Winchester, MA, 01890
House Sitting, Drop-In Visits, Dog Walking

Liz was great with our cat and gave him some much needed attention while we were away. I would definitely use Liz's services again and would recommend her to an… (more)

from
$18
per visit
Calendar Recently Updated
14.
Experienced cat loving coupleArlington, MA, 02474
Drop-In Visits, Dog Walking

Colleen was great for us! We contacted her on short notice to take care of our elderly cat for approximately a week. She was very responsive, and was very commu… (more)

from
$30
per visit
Calendar Recently Updated
15.
Your dogs home away from home!Arlington, MA, 02476
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Alysha is phenomenal! I typically hesitate to have other people watch my German Shepherd because she has a specialized pain management plan for her hips. Alysha… (more)

from
$15
per visit
Confirmed availability: Memorial Day
16.
I have over 35 years of animal careMedford, MA, 02155
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: I live in West Medford. ❤️ 🐶 🙀 This is a total dream space for any animal. I am so lucky to live where I live. ♥ You should choose me because I love … (more)

from
$25
per visit
Confirmed availability: Memorial Day
17.
Dog and animal lover extrodinaireWoburn, MA, 01801
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Rebecca is a very gentle and caring person. She has been wonderful with our 17wk old frenchie (Ollie). She is loving and extremely flexible. She sends pics and … (more)

from
$30
per visit
Confirmed availability: Memorial Day
I'm honored to care for your bestieWinchester, MA, 01890
House Sitting, Drop-In Visits, Dog Walking

Sally was so attentive and gave us such a detailed review of her check in!! We enjoyed all the photos of our little guy and felt like he was in great hands. Wou… (more)

from
$30
per visit
Confirmed availability: Memorial Day
19.
A loving experience for your pet!Winchester, MA, 01890
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: I grew up caring for dogs of various sizes and breeds. My children and I cherish the love and joy of having a pet to care for and play with. I no lo… (more)

from
$25
per visit
Confirmed availability: Memorial Day
Best walk your dog will ever have!Winchester, MA, 01890
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
10 years of experience

About: I owned two dogs for 10 years and loved taking care of them, taking them on walks and playing with them at any chance. I have watched my neighbors ve… (more)

from
$17
per visit

As pet lovers, we understand how difficult it can be to leave your pet when you have to head out of town. Luckily, you can find the perfect pet sitter in seconds on Rover.com. If you're looking for trusted pet sitters while you're away, whether it's for one night or a whole month, you can find a sitter who meets your - and your pet's - needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your pet - including background checks, sitter testimonials, community reviews. We also offer training and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of pet lovers for hire.