Doggy Day Care in Chester

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Top rated Chester doggy day care sitters

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

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Sitter Profile Image: Kathleen M.
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Kathleen M.
Star Sitter
$50
total per day
5.0 out of 5 stars
153 reviews
42 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: 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: Tricia G.
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Tricia G.
Star Sitter
$45
total per day
5.0 out of 5 stars
12 reviews
3 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: megan b.
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megan b.
$39
total per day
4.9 out of 5 stars
128 reviews
37 repeat clients
20 years of experience
South Hadley, MA, 01075

Miss Megan is great! JJ loves going to visit whenever we’re in town and I feel so confident that he is safe and happy with her. She does a great job keeping him quiet and calm until I come back. Thank you, Miss Megan ♥️

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Diane M.
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: Yenifer V.
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Yenifer V.
$67
total per day
5.0 out of 5 stars
23 reviews
4 repeat clients
3 years of experience
Pittsfield, MA, 01201

Yenifer was a rare gem!! I was in town last minute with my dog, and she was amazing to accommodate Pancake for doggy day care with no notice. She kept me up to date and Pancake was so excited to see her the second day!

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Julie C.
Sitter Profile Image: Saige G.
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Saige G.
$39
total per day
4.8 out of 5 stars
33 reviews
13 repeat clients
11 years of experience
Easthampton, MA, 01027

Ziggy was great with our dog Jet! Jet is a high energy Springer Spaniel and she went above and beyond with taking him for hikes and making sure he got enough exercise. She took care of Jet at our home and was respectful of the space and was able to keep Jet’s routine as normal as possible which made us comfortable leaving him with her. We would definitely book with Ziggy again in the future!

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

About: I’ve taken care of dogs and cats since I was 5. I love them all! I have a horse named Olay that I board not at my house!) And dogs and a cat! I’m a first grade teacher so I have summer off starting 6/5! So will be able to do anytime at that point! For now I can do weekdays after 3pm and anytime weekends! I have a fenced in yard with lots of fun smells and my dog likes everyone and every dog he’s ever met! He’ll play all day but can als take a hint! Then we can hang out inside too!

Sitter Profile Image: Sarah G.
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Sarah G.
Star Sitter
$56
total per day
5.0 out of 5 stars
10 reviews
4 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: Irene T.
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Irene T.
Star Sitter
$45
total per day
5.0 out of 5 stars
17 reviews
6 repeat clients
20 years of experience
Pittsfield, MA, 01201

Irene was great with Sadie. Sadie loved playing with Goldie and loved the friendly and warm reception she got. Sadie was given both play and rest time and really looked really comfortable with Irene when I picked her up.

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

Emma was great!! She took my two puppies, one being only 3 months old and they look like they had the best time. She kept me updated throughout the day with pictures and videos and how they were doing. 10/10 would recommend!

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Megan M.
Sitter Profile Image: Caitlin J.
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Caitlin J.
$37
total per day
5.0 out of 5 stars
4 reviews
20 years of experience
Windsor, MA, 01270

About: I've loved animals forever and have cared for everything from a cockatiel to a chameleon, Great Pyrenees to Pekapoo. I currently have 1 Goldendoodle and 1 chocolate tabby cat in my home with fenced area and walking trails. I'm currently homeschooling my children at our 10+ acre home with fenced area and walking trails. We have a light schedule and are home more often than away. We currently walk our Goldendoodle daily and pet care is our love, in addition to our responsibility. I have a fenced area and multiple indoor secure areas where animals can get healthy time in a safe home without overstimulation. I have 1 Goldendoodle and 1 chocolate tabby cat who are the best of friends and are supportive to newcomers.

Sitter Profile Image: Lataya I.
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Lataya I.
$34
total per day
4.6 out of 5 stars
15 reviews
2 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: Tetiana M.
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Tetiana M.
Star Sitter
$67
total per day
5.0 out of 5 stars
59 reviews
13 repeat clients
2 years of experience
Pittsfield, MA, 01201

Tetiana was marvelous! She was able to take us rather last minute and provided very attentive care to our extremely playful but also a bit nervous dog. She greeted us outside and immediately got to work making our dog feel comfortable. She invited us into her home to help acclimate our dog. And then sent a number of updates with pictures confirming all was well. We are so grateful for the care she provided.

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Jill A.
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: Jeffrey S.
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Jeffrey S.
$32
total per day
5.0 out of 5 stars
1 review
25 years of experience
Russell, MA, 01071

About: I am a loving and attentive dog owner. I love nothing more than to take care of my K9 friends. I have always had a dog and currently one. I understand that all dogs have a big personality with a lot of understanding required. I am just as happy running with a dog as I am a quiet day of relaxation indoors. Whatever your pet needs I provide. I take pride in understanding my pets needs. It can be hard when their owner is always gone at work but I can help relieve some of that anxiety. I’ll work within your pets restrictions and needs to better suit them and to make sure they feel at home! Give me a call if you need! I’m a professional artist and I work from home so dog care needs fit well into my life. I have a dog of my own and a cat as well that are both well loved. My environment is very well suited for pet care. I have a social elderly dog and a sweet kitty who’s very friendly. We have a big yard, spacious house and pet friendly environment. Pups always get two walks a day and plenty of attention:

Sitter Profile Image: Jess L.
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Jess L.
$34
total per day
5.0 out of 5 stars
86 reviews
21 repeat clients
5 years of experience
Pittsfield, MA, 01201

Jess took great care of my pup and sent me lots of pics and updates throughout the day! She has a sweet dog, and her dog and mine played together all day. Uva came home fed, healthy and tired! Thank you Jess!

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Janice G.
Sitter Profile Image: Amad E.
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Amad E.
$50
total per day
5.0 out of 5 stars
32 reviews
7 repeat clients
15 years of experience
Northampton, MA, 01060

Amed was prompt with communication, and was sweet with our dog. He took her for a walk and the dog park, and she was tuckered out after. It worked out well to have Ahmed watch our dog while we were visiting from out of town to see a concert. Thank you Amed!

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Mary Beth B.
Sitter Profile Image: Kelley W.
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Kelley W.
$39
total per day
5.0 out of 5 stars
7 reviews
2 repeat clients
15 years of experience
Holyoke, MA, 01040

Felt very comfortable leaving the pups and her care. Lots of pics throughout the day to reassure they were doing well. Will definitely reach out to again.

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Christina J.
Sitter Profile Image: Jessica C.
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Jessica C.
$32
total per day
5.0 out of 5 stars
54 reviews
18 repeat clients
35 years of experience
Sunderland, MA, 01375

About: Parents Jessica and Philip are the responsible adults guaranteeing that your dog will get everything they need, but 13-year-old Josie is the primary caretaker of our dog guests. She is a very attentive, loving and engaged pet pal! Since we started on Rover as a summer job for Josie in 2023, we have hosted dogs of all sizes, energy levels and needs and she loved every single one of them. She gets up early every day (whether or not she is caring for a dog) so she often gives the pups their first walk of the day before anyone else has gotten out of bed. In spring of 2023 Josie rescued an Eastern Phoebe (songbird) that was pushed out of its nest and injured; she fed it dry cat food soaked in sugar water and set it free a week later as a robust young fledgling (see pictures). On weekends and school vacations, Josie has little to do other than care for your dog! We are early risers. Our calendar has school days blocked off, but we would consider boarding a dog during the school week if its needs match Josie's availability so please inquire. Both parents work mostly or fully from home and could manage a midday walk for a quiet dog. Jessica is an elementary teacher and education administrator who is accustomed to carrying great responsibility for the safety of precious smaller beings. She closely supervises Josie as the primary caregiver. Our home is in the woods with access to Mt. Toby trails so your pup will get to enjoy the outdoors several times a day. Sometimes dogs who are anxious in the busy neighborhoods of their homes are much calmer when they come to our quiet, wooded setting. We have a flock of chickens in an enclosed outdoor area.

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Over 2
pet parents in Chester have booked doggy day care

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

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    It doesn’t happen often, but if your dog sitter has to cancel, we’ll work with you to find a new sitter.

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    We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.

Sitters in Chester 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 Chester on Rover as of Jun 2026 was about $40 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.

If you’re searching for a Chester doggy day care sitter for the first time, visit the sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, 96 sitters provided doggy day care in Chester. 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, 82% of Chester sitters offering doggy day care respond in under an hour.

Sitters who provide doggy day care in Chester have an average of 20 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 Chester.

Chester 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 Chester 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 96 sitters offering doggy day care in Chester on Rover, so you’re sure to find the perfect match for your dog! In Chester, 100% of sitters offer daily exercise, 92% offer medication administration, and 92% 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.

Note: If your doggy day care sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your doggy day care service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.