Doggy Day Care in Winchester Village

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Top rated Winchester Village doggy day care sitters

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Sitter Profile Image: Karen D.
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Karen D.
Star Sitter
from
$27
per day
4.9 out of 5 stars
157 reviews
76 repeat clients
30 years of experience
North East, MD, 21901

My pups change home happy and tired! Karen did an amazing job caring for them. She was very responsive and friendly! They will be going back soon!

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Valerie J.
Sitter Profile Image: Angela O.
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Angela O.
from
$38
per day
5.0 out of 5 stars
110 reviews
35 repeat clients
25 years of experience
havre de grace, MD, 21078

Our dog had a blast playing at Angela’s house. She took great care of him and we would highly recommend her to anyone looking for a dog sitter.

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Polly S.
Sitter Profile Image: Susan S.
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Susan S.
Star Sitter
from
$25
per day
5.0 out of 5 stars
27 reviews
4 repeat clients
30 years of experience
Havre de Grace, MD, 21078

Susan is wonderful, so kind and caring, and I can tell that Finlay loves being at her house. He goes into her home with his tail wagging and always comes home happy and tired. It’s a relief knowing he’s in a warm, loving home while I’m away. Highly recommend Susan.

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Teal C.
Sitter Profile Image: Aria F.
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Aria F.
Star Sitter
from
$40
per day
5.0 out of 5 stars
32 reviews
14 repeat clients
10 years of experience
Darlington, MD, 21034

About: My family has always had pets and I developed a huge love for them very early on! I have always had a huge passion for them and now have been fortunate enough to turn my love for animals into what I get to do for a career! I am able to care for all sorts of pets, young, old, high energy, low energy! I can administer medication and give your pet a vacation while you’re away! Prices are negotiable so please feel free to reach out! I am a full time pet care provider so my schedule is very open to be able to come hang out and love on your fur babies!! I have a big yard and live an active life, so I’m able to give your fur baby the attention they need whether that be running around or laying on the couch! I want your pets to feel comfortable and loved while you’re away so I do everything I can for them to have a great time while they’re with me! I am also privately insured in case of any accident!

Sitter Profile Image: Geosselyn D.
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Geosselyn D.
from
$30
per day
5.0 out of 5 stars
11 reviews
4 repeat clients
7 years of experience
Elkton, MD, 21901

We were very impressed with Geosselyn’s care of our dog! Her large fenced in backyard was perfect! Our dog seemed very comfortable with her! We highly recommend Geosselyn!

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Kathleen O.
Sitter Profile Image: Sharon M.
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Sharon M.
from
$42
per day
4.9 out of 5 stars
95 reviews
46 repeat clients
40 years of experience
Elkton, MD, 21921

Sharon was very good and patient with my baby pup. She took him when so many others wouldn't. Thank you Sharon for caring for my Koda. I highly recommend her.

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Cheryl A.
Sitter Profile Image: Pearl J.
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Pearl J.
Star Sitter
from
$30
per day
4.9 out of 5 stars
125 reviews
45 repeat clients
30 years of experience
Havre De Grace, MD, 21078

Pearl took great care of Angus at a last minute request and sent me pictures with updates throughout the day! I would definitely rebook with her.

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Lauren P.
Sitter Profile Image: Jacob & Megan W.
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Jacob & Megan W.
from
$35
per day
5.0 out of 5 stars
76 reviews
46 repeat clients
10 years of experience
Bel Air, MD, 21015

Gunnar had a wonderful time and Jacob and Megan were super welcoming and on top of everything. Would definitely be using again, Gunnar had a blast and was well cared for.

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Chris A.
Sitter Profile Image: Samantha B.
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Samantha B.
from
$25
per day
50 years of experience
Aberdeen, MD, 21001

About: I have taken care of animals all my life. I love dogs, they are part of the family here in my home. Fenced yard for exercise, allowed on furniture and friends to play with. Your dog will be right at home here. I am home all day to care for your fur baby. Dog door to the back yard so they can go play and potty when they need to. Exercised daily. I have a safe fun environment for your fur baby. Love and treats given freely. Pictures sent to you daily to your phone of your fur baby.

Sitter Profile Image: Tabby A.
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Tabby A.
from
$32
per day
4.9 out of 5 stars
37 reviews
21 repeat clients
7 years of experience
Elkton, MD, 21921

About: I’ve taken care of dogs my whole life. There has not been a time I have not had a dog. I help out in a dog kennel sometimes bathing and playing with the dogs. I do not have a job right now so I am home most of the time. I do leave the house in the morning and afternoon to care for my horses. I have a big back yard that is fenced in. The dogs that come to stay here are treated with as much love as I would give my own dogs.

Sitter Profile Image: Rachel B.
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Rachel B.
from
$45
per day
5.0 out of 5 stars
49 reviews
24 repeat clients
10 years of experience
Aberdeen, MD, 21001

My puppy had the best time with Rachel and her kids. She come home happy and exhausted from playing all day. Thank you for giving her so much attention and sending so many pictures- we will definitely be back!

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Taren V.
Sitter Profile Image: Paula S.
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Paula S.
from
$35
per day
15 years of experience
Aberdeen, MD, 21001

About: Welcome to my home! All dogs must be house trained, friendly, and up to date on their vaccinations, flea, and tick prevention. I also ask that pets are well-behaved and comfortable around people and other animals. I have a loving, pet-friendly home having over 15 years of experience caring for animals of all kinds from playful puppies and energetic big dogs to senior pets. For me, pets are family, and I treat every furry guest who stays as one of my own. The home is warm, clean, and welcoming, with plenty of room for play and relaxation. I have a safe outdoor space perfect for walks, potty breaks, and exercise throughout the day. Whether your pet enjoys long walks, belly rubs, or quiet cuddle time, I make sure they get the right mix of activity, affection, and space. I offer daily walks, drop-in visits, and overnight stays with plenty of love, attention, and care. I also handle feeding routines, basic training reinforcement, and medication if needed. Since I work from home, there’s always someone around to provide companionship and ensure your pet is never left alone for long. My flexible schedule allows me to accommodate weekday and weekend stays with ease. Pets who come into my home become part of the family, surrounded by kindness, attention, and a whole lot of love. I work from home so can ensure pets are fed, loved, bathed if necessary, and walked accordingly. I walk twice a day, morning and evening. Your pet’s safety and comfort are top priorities. My home is clean, calm, and pet-friendly, a safe space where every animal feels cared for and secure. I have a friendly standard poodle who roams freely on the main level and basement, providing gentle company for visiting pets. I maintain a structured environment with eyes on pets at all times to ensure their well-being. If your pet is crate trained or prefers resting in their own space, please bring their crate so they can feel comfortable and at ease during their stay. I ask that all visiting pets are house trained, friendly, and up to date on vaccinations, flea, and tick prevention. Please also bring your pet’s bed, toys, and comfort items to help them feel at home. My goal is to create a peaceful, safe environment where your pet can relax, play, and feel loved throughout their stay

Sitter Profile Image: Ann Z.
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Ann Z.
Star Sitter
from
$60
per day
5.0 out of 5 stars
25 reviews
11 repeat clients
50 years of experience
Aberdeen Proving Ground, MD, 21050

Ann was very sweet and patient to my little rescue pup who has trust issues with new people. Within a short time, he was very comfortable and happy staying with her. She took great care of him!

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Sarah M.
Sitter Profile Image: Erin R.
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Erin R.
from
$25
per day
5.0 out of 5 stars
18 reviews
7 repeat clients
10 years of experience
Bel Air, MD, 21015

About: I’m a life long pet owner and animal lover. I truly enjoy taking care of others fur babies. I have experience with all ages, sizes, needs, etc. Pet care as well as being a stay at home mom is full time for me. I want to offer the best care possible. My routine will fit around my clients routines. Whether at my home or the clients home there will be nothing but respect for the animal and the owners. All wishes will be met. All love will be given.

Sitter Profile Image: Sunaina D.
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Sunaina D.
Star Sitter
from
$29
per day
5.0 out of 5 stars
13 reviews
7 repeat clients
6 years of experience
Newark, DE, 19702

Sunaina was great with Loki! He had such a great time with her and her family. She sent us many pictures and updates periodically of him during his time with them. She listened to our instructions on his allergies and food timing, and took him out for walks. We were super happy that he was happy! Definitely will book again when we are back in the area!

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Krishna P.
Sitter Profile Image: Elena C.
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Elena C.
from
$40
per day
5.0 out of 5 stars
2 reviews
7 years of experience
Belcamp, MD, 21017

Thanks for helping us out with a rushed schedule and for taking care of our little girl!

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Jackie E.
Sitter Profile Image: kylee c.
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kylee c.
from
$50
per day
10 years of experience
Rising Sun, MD, 21911

About: What sets me apart is the genuine bond I build with each animal. I don’t just “watch” pets—I spend quality time with them so they feel safe and loved. I’m comfortable with high-energy puppies who need structure and play, as well as older pets who need slower, attentive care. I follow routines exactly and make sure your pet feels at home, even when you’re not. i’m available whenever you need me! i’m a part time server at a restaurant, so we can come up with a schedule that works for us both! and of course your pet. i will follow all instructions left to me! i will put your pets needs first, and make sure they are happy and content at all times!

Sitter Profile Image: Yvonne & Joseph K.
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Yvonne & Joseph K.
Star Sitter
from
$60
per day
5.0 out of 5 stars
187 reviews
45 repeat clients
50 years of experience
Newark, DE, 19702

Mutig was so happy when we picked him up! I have been nervous about where to leave him during a vacation we have coming up, but I was put at ease after this stay. She sent so many happy pictures of Mutig and Quincy playing and sent me updates of how he was doing. Yvonne and her husband were very caring. She fed the dogs separately, took them out often, and showed a lot of care. We are so glad we found her to have piece of mind that we are leaving Mutig in good hands when we cant be there!

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Greer B.
Sitter Profile Image: Angelene H.
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Angelene H.
from
$45
per day
5.0 out of 5 stars
453 reviews
187 repeat clients
10 years of experience
Forest hill, MD, 21050

This was my first time using a sitter and Angelene was great! I really enjoyed receiving the pictures of my dog Teddy throughout the day. I could tell he had a great time with Angelene and her family. I will definitely book Angelene again!

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Jennifer J.
Sitter Profile Image: Tarina L.
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Tarina L.
Star Sitter
from
$40
per day
5.0 out of 5 stars
37 reviews
11 repeat clients
30 years of experience
Edgewood, MD, 21040

Our golden retriever puppy, Loki had the BEST time in Tarina’s care! He was extremely comfortable there and was treated like part of the family. We are excited to have Tarina watch him again soon! :)

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Maritta B.
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The median cost per day for doggy day care in Winchester Village is €36

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Sitters in Winchester Village average 3
repeat doggy day care clients

Doggy Day Care FAQs

Frequently asked questions about Rover

Sitters on Rover are free to set their rates. The median cost to hire a sitter for doggy day care in Winchester Village on Rover as of Jun 2026 was about €36 per day, after factoring in Rover’s service fees. A sitter’s rate may also change as you customize your booking to fit your and your dog’s needs.

As of Jun 2026, 279 sitters provided doggy day care in Winchester Village. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, sitters offering doggy day care joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple sitters about your booking. Typically, 89% of Winchester Village sitters offering doggy day care respond in under an hour.

Sitters who provide doggy day care in Winchester Village have an average of 18 years of experience. Sitters offering doggy day care with repeat customers have an average of 3 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters in Winchester Village.

Winchester Village doggy day care sitters are happy to take care of your dog while you’re at work or unavailable for the day. Book a one-time visit, or set up a regular rhythm with your favorite Winchester Village sitter. Drop off your dog at the sitter’s home and rest easy knowing they’ll get frequent potty breaks, plenty of playtime, and lots of love. Doggy day care is great for:

  • Puppies and high-energy dogs
  • Dogs with special needs, including seniors
  • Pet parents who work long hours
  • Dogs with separation anxiety

There are 279 sitters offering doggy day care in Winchester Village on Rover, so you’re sure to find the perfect match for your dog! In Winchester Village, 90% of sitters offer daily exercise, 94% offer medication administration, and 94% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect doggy day care sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your doggy day care sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.