Doggy Day Care Chester

Drop off your dog at your sitter's home in the morning, and pick them up in the evening.

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Over 23
pet parents in Chester have booked doggy day care

Chester, Find top rated doggy day care

Prices are estimates per day for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.

1 / 1
Sitter Profile Image: Kathleen M.
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Kathleen M.
Star Sitter
$50
total per day
5.0 out of 5 stars
159 reviews
45 repeat clients
12 years of experience
Becket, MA, 01223

She did such a great job! Nozzle came home so tired and I was a happy dog Mom bShe was able to take him at such a short notice and was a life saver for us. I would recommend her to anyone. She’s very flexible with schedules too!

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Laura H.
Sitter Profile Image: Katelyn S.
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Katelyn S.
Star Sitter
$34
total per day
5.0 out of 5 stars
7 reviews
4 repeat clients
25 years of experience
Westfield, MA, 01085

Katie and her family were an absolute dream! I couldn’t be more pleased with how attentive and caring they were towards our puppy. I highly recommend Katie! I wish we lived closer to use her again! Thank you, Katie!

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Regina T.
Sitter Profile Image: Yenifer V.
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Yenifer V.
$67
total per day
5.0 out of 5 stars
29 reviews
5 repeat clients
3 years of experience
Pittsfield, MA, 01201

Yenifer and her family did an excellent job! PeeWee got lots of attention and he seemed so happy at the end of the day. We will definitely use Yenifer again on our next visit.

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Victoria M.
Sitter Profile Image: Jesse L.
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Jesse L.
$32
total per day
5.0 out of 5 stars
2 reviews
9 years of experience
Northampton, MA, 01062

I’m so glad to have connected with Jesse (and so is my pup)! I could tell right away that he loves and genuinely cares about any dogs who are lucky enough to hang out with him. And Sadie, my slightly nervous/sometimes hyper rescue settled right in with him and his family. Thanks again Jesse! We’ll be back!

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Alie S.
Sitter Profile Image: Sarah G.
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Sarah G.
Star Sitter
$56
total per day
5.0 out of 5 stars
18 reviews
6 repeat clients
25 years of experience
West Springfield, MA, 01089

Sarah is very attentive to my dog! She has made her very welcome and my dog has adjusted very well. I am very glad to have a safe and comfortable place to leave my dog while I am at work. Sarah is wonderful!

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Lisa M.
Sitter Profile Image: Shawna B.
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Shawna B.
$69
total per day
5.0 out of 5 stars
9 reviews
4 repeat clients
15 years of experience
Westhampton, MA, 01027

Shawna was a great sitter. My dogs are never tired. But they were worn out when I picked them up so I know they got plenty of exercise and attention. I highly recommend Shawna!!

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Amanda G.
Sitter Profile Image: Tetiana M.
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Tetiana M.
Star Sitter
$67
total per day
5.0 out of 5 stars
61 reviews
14 repeat clients
2 years of experience
Pittsfield, MA, 01201

I’m so thankful I found Tetiana. I left my 5-month puppy for the first time with her and I could not be happier. She took care of her with love and so much warmth. I received many pictures thought the day. Thank you Tetiana!!!

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Marta H.
Sitter Profile Image: Lisa A.
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Lisa A.
$67
total per day
5.0 out of 5 stars
6 reviews
2 repeat clients
20 years of experience
Florence, MA, 01062

Lisa took great care of Benny and provided many updates during his visit!

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Jesse G.
Sitter Profile Image: Emma G.
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Emma G.
Star Sitter
$56
total per day
5.0 out of 5 stars
52 reviews
13 repeat clients
15 years of experience
Northampton, MA, 01060

I am so happy to have found Emma. My two sweet but somewhat anxious dogs were immediately at ease in her lovely space. Her calm, confident energy is just what we were all looking for in a caregiver. Emma was easy to communicate with and very professional. I look forward to working with her again!

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Jill F.
Sitter Profile Image: Lataya I.
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Lataya I.
$34
total per day
4.6 out of 5 stars
16 reviews
3 repeat clients
10 years of experience
holyoke, MA, 01040

About: i’ve taken care of dogs/animals mostly all my life ,im 21 and owned a dog half my life also but sadly i had to put him down so now i would love to dog sit to still show my love , interest and care into dogs without owning my own again yet i’m home all day unless i make plans and adding pet care into my day would allow me to be more active and it just gives me something do to during the day i have a fended in yard and a good sized back yard for pets to play and roam freely , no other pets in the house hold at the moment,

Sitter Profile Image: Tricia G.
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Tricia G.
Star Sitter
$45
total per day
5.0 out of 5 stars
20 reviews
6 repeat clients
20 years of experience
Chicopee, MA, 01020

We have loved working with Tricia! Very flexible, understanding, and affordable. She went the extra mile for our senior dog. Can’t wait to book the next visit for our dog!

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Katy N.
Sitter Profile Image: Alison D.
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Alison D.
$45
total per day
15 years of experience
Northampton, MA, 01053

About: I have been the go to dog sitter for family, friends and coworkers for the last 15 years. I was finally able to adopt my very own pup a little over a year ago and have been obsessed with him ever since. We have a small fenced in backyard and live extremely close to the bike path and park! Lots of walks and exploring. I am looking to make pet care my full time career. I am aiming to be available daily for all types of care. Walking, daycare as well as overnight sleepovers! I have a small fenced in back yard and a cozy ranch style home. No stairs, for those pups who have a hard time getting around. I take daily morning walks with my guy around the park and have many other spots we visit on the weekends. Couches, beds, chairs, none of those are off limits. Your pet can be comfortable! If you want your pup to be spoiled, loved, and entertained while you are busy, look no further!

Sitter Profile Image: Josselin M.
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Josselin M.
$32
total per day
5 years of experience
Pittsfield, MA, 01201

About: Hi! My name is Joss, and I’m a passionate animal lover with years of experience caring for pets. I’ve had dogs and other pets throughout my life, so I understand how important they are as members of the family. I’m responsible, patient, trustworthy, and caring, and I always make sure every pet feels safe, comfortable, and loved while they’re in my care. Whether it’s walks, playtime, feeding, administering basic care, or simply keeping them company, I’ll treat your furry friend as if they were my own. I know how much trust it takes to leave your pet with someone else, and my goal is to give you peace of mind while providing your pet with the attention, affection, and care they deserve. If you have any questions or would like to schedule pet care, please don’t hesitate to call or text me . I’d love the opportunity to meet you and your furry friend! I provide loving, attentive, and reliable care for every dog as if they were my own. I take dogs out for potty breaks at least three times a day and make sure they get plenty of exercise, playtime, and attention. I love taking dogs on long walks, visiting dog parks, going on hikes, and enjoying outdoor adventures whenever possible. Since I work part-time, I have a flexible schedule that allows me to spend quality time with your pet instead of rushing through visits. My goal is to make sure your dog stays happy, active, safe, and well cared for while you’re away. I can also keep you updated with messages and photos, so you always know how your furry friend is doing! Your dog’s safety and comfort are my top priorities. I live in a safe, clean, and pet-friendly home where dogs can relax and feel comfortable. I always keep a close eye on the pets in my care and make sure they’re supervised, happy, and well cared for at all times. I understand that every dog has different needs and routines, and I’m happy to follow your instructions to help them feel right at home. My goal is to provide a loving, stress-free environment where your furry friend feels safe, comfortable, and treated like family.

Sitter Profile Image: Talula T.
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Talula T.
$50
total per day
5.0 out of 5 stars
15 reviews
4 repeat clients
14 years of experience
Southampton, MA, 01073

Talula took such good care of our pup! She was responsive, flexible with timing, and generally a great human being. Thanks Talula!

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Anastasia D.
Sitter Profile Image: Gabriela K.
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Gabriela K.
$50
total per day
5.0 out of 5 stars
6 reviews
3 repeat clients
5 years of experience
Northampton, MA, 01060

I’m so glad to have connected with Gabi (and so is my pup)! I could tell right away that she loves and genuinely cares about any dogs who are lucky enough to hang out with her. And Sadie, my slightly nervous/sometimes hyper girl settled right in. Thanks Gabi, we’ll see you soon!

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Alie S.
Sitter Profile Image: AMY L.
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AMY L.
$67
total per day
5.0 out of 5 stars
11 reviews
1 repeat client
8 years of experience
Easthampton, MA, 01020

About: I sincerely LOVE getting to know each individual dog's personality (quirks and all!) and learning about what makes them happiest. I have many years of experience: walking dogs in NYC & in Western Mass; pet-sitting for my friends', neighbors' and partner's dogs (as well as for other types of pets). I create a warm, nurturing and happy environment for my precious furry friends to thrive. (Please note: on Tuesdays, Thursdays & Fridays, I am usually available from 11 AM-5:30 PM; on Mondays & Wednesdays, I am usually available from 11 AM -12 PM) I'm currently working part-time as a educator (tutor) so I have ample time to provide dog care (walking, drop-in day care and occasional boarding) during the week, Mon-Wed and Thurs-Friday. On occasion, I may be able to board dogs during the weekend. I live in an extremely peaceful, quiet, dog-friendly neighborhood (the Plains of Easthampton) toward the end of a cul-de-sac. So there is almost no cars or traffic here. I do have a front & back yard. Although it is not fenced, it is backed by trees and, as mentioned, almost zero traffic

Sitter Profile Image: megan b.
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megan b.
$39
total per day
4.9 out of 5 stars
134 reviews
39 repeat clients
20 years of experience
South Hadley, MA, 01075

Megan was great with JJ, he fit right in with her doggie family! Her location is great, close to my folks’ place so I’ll def be booking with her again. Wonderful day!

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Diane M.
Sitter Profile Image: Glorymar O.
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Glorymar O.
$50
total per day
5.0 out of 5 stars
47 reviews
17 repeat clients
6 years of experience
Memorial Square, SPRINGFIELD, MA, 01107

Thank you so much for your understanding and care. She had such a great time and slept all the way home. Wish you lived closer because I know Mei would love to visit again. She is so shy and you really became friends fast. You are the best!

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Helen I.
Sitter Profile Image: Evan A.
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Evan A.
$111
total per day
5.0 out of 5 stars
7 reviews
10 years of experience
Florence, MA, 01062

Evan was amazing!! He was so communicative and was so sweet with our dogs. He also took us on an insanely last minute request. He was the best!! Thank you Evan ☺️

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Alexandra L.
Sitter Profile Image: Desiree S.
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Desiree S.
$54
total per day
20 years of experience
Westfield, MA, 01085

About: I have always been drawn to animals and loved to be around them and care for them. I have owned a variety of pets over the years and would love to grow and learn with your pets. I have experience working in a kennel that boarded dogs. I have bathed and done basic grooming. I am home with children during the week days and regularly have weekend spots available. I have plenty of time to care for furry friends in my home or yours. I am flexible during the day and able to walk and play with your furry friends. I have a fenced in yard. I have a dog and cat in the home. My children are animal lovers just like myself and we try to have a safe and comfortable home environment.

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The median cost per day for doggy day care in Chester is $40

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Popular requests for doggy day care - Chester

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Sitters in Chester average 4
repeat doggy day care clients

FAQs for Doggy Day Care - Chester

Frequently asked questions about Rover

The average cost for Doggy Day Care in Chester on Rover is $42.8 per day (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Doggy Day Care easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Doggy Day Care. For more information on service fees, click here .

As of August 2026, there are 227 sitters on Rover offering Doggy Day Care across Chester. Enter your ZIP code to see which available sitters are closest to your home.

Sitters on Rover can offer flexible scheduling, so you can coordinate times that work best for you and your pet—whether that’s early drop-off or later pick-up to match your Chester commute.

If your schedule changes, it’s best to let your sitter know through the app as early as possible. Many sitters can adjust pick-up and drop-off times when needed.

Think of doggy day care as your dog’s fun, supervised play date that happens to fit into your workday. Day care through Rover takes place in a real home. This offers a calmer and more personalized environment for your pup.

A typical day can include companionship, one-on-one attention, and same day pick-up and drop-off. Many sitters can also offer structured routines and exercise throughout the day. For recurring, weekly day care, sitters will include photo updates so you can see your dog in their element.

Here are tips for finding the ideal day care fit for your dog:

  • For some small dogs: In-home day care can be the perfect fit. Look for sitters whose "can host" section only lists dogs weighing 0–7 kilograms and/or 7–18 kilograms. During your Meet & Greet, ask about play areas based on dog size and energy level.
  • For high-energy dogs: The ideal doggy day care can offer scheduled breaks and outdoor spaces or activities. You can also find sitters who host multiple dogs to satisfy your pup’s socializing needs.
  • For dogs who prefer human-only companionship: Use the filters "Doesn't own a dog" and "Only accepts one pet at a time" to find the right care.

Play groups can be an option when you book with a day care sitter through Rover. Many sitters do host a small number of dogs at the same time. Smaller dog packs are generally safer, more fun, and ideal for dogs who enjoy playtime but also want to relax throughout the day. When looking for your dog’s pack, check the sitter’s profile to see if they "Accept multiple clients" or have their own dogs. Then during the Meet & Greet, you can see whether your dog is a good fit for their social circle!

While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.

Many sitters in MA ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies.

By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.

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.

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

Yes, Rover is well-suited for finding sitters who can care for your pet within 24 hours. With 227 sitters in Chester, 91% respond to messages in under an hour.

You can message multiple sitters simultaneously to find the fastest available match. If you need care today or tomorrow, you can look for sitters with a "calendar last updated" notice on their profiles.

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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