Doggy Day Care Cherry Plain

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

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Cherry Plain, Find top rated doggy day care

Prices are estimates per day. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: James S.
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James S.
from
$50
per day
5.0 out of 5 stars
8 reviews
10 years of experience
Williamstown, MA, 01267

About: I bring a unique level of structure, energy, and reliability to pet care through my experience as a college coach. My daily work revolves around building routines, paying attention to small details, and making sure individuals are supported and performing at their best — and I carry that same approach into caring for dogs. I am highly dependable and organized, so you can trust that your dog’s schedule, feeding routine, and exercise needs will be handled consistently. I also bring an active lifestyle, which is great for dogs that need engaging walks, playtime, and attention. What sets me apart is the level of care and awareness I provide. I pay close attention to behavior, energy levels, and any changes, and I prioritize clear communication so you always feel confident while you are away. My goal is to make sure your dog feels comfortable, safe, and well cared for at all times My schedule is currently wide open following the end of the swim season, which gives me plenty of flexibility for walks, drop-ins, and overnight care throughout the week and weekends. I understand how important it is to trust someone with your dog. I create a safe, comfortable environment where your pet feels secure and cared for at all times. I pay close attention to their needs, keep a watchful eye during walks, and always make sure you are updated so you can relax knowing they are in good hands.

Sitter Profile Image: Yenifer V.
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Yenifer V.
from
$60
per day
5.0 out of 5 stars
27 reviews
5 repeat clients
3 years of experience
Pittsfield, MA, 01201

Huckleberry had a great time staying with you. Thanks so much for keeping such a close eye on our little guy. It was clear he was in great hands!

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Erick N.
Sitter Profile Image: Irene T.
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Irene T.
Star Sitter
from
$40
per day
5.0 out of 5 stars
20 reviews
7 repeat clients
20 years of experience
Pittsfield, MA, 01201

Irene was an excellent sitter for our boy Aslan. He got along great with her dog, and she sent many photos of how well the two puppies got along! Our boy came back to us happy and a little tired from so much play, we highly recommend Irene and will be excited to have her watch our boy in the future!

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Yue W.
Sitter Profile Image: Tetiana M.
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Tetiana M.
Star Sitter
from
$60
per day
5.0 out of 5 stars
60 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: Iris F.
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Iris F.
from
$28
per day
4.9 out of 5 stars
55 reviews
13 repeat clients
10 years of experience
North Adams, MA, 01247

Iris was the perfect sitter for Livvy. I could not have asked for anyone better.

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Paul C.
Sitter Profile Image: Jess L.
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Jess L.
from
$30
per day
5.0 out of 5 stars
88 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: Maura A.
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Maura A.
from
$50
per day
5.0 out of 5 stars
3 reviews
30 years of experience
Adams, MA, 01220

About: Hi! I’m Maura, a high school English teacher who has lived and worked in the Berkshires for 19 years. I’ve spent my entire life caring for animals of all kinds, and my goal is simple: to provide safe, personalized care so you can enjoy your time away without worrying about your pets. Now accepting bookings for my private pet guest house, Booked and Boarded! Unlike a traditional kennel, I board only one pet family at a time, allowing your pets to enjoy a calm, low-stress stay with individualized attention. The guest house opens directly into a fully fenced backyard, giving dogs plenty of opportunities for safe outdoor play while enjoying a cozy, home-like environment. The space is also designed with (indoor) cats in mind! Booked and Boarded is a perfect space for pets (and owners!) who want a quieter, more personal boarding experience. In addition to private boarding, I offer dog walking, drop-in visits, and small farm sitting throughout the Berkshires. Whether you need someone to check on a new puppy, care for a senior pet, or manage a small farm while you’re away, I’d love to help. I have experience caring for dogs, cats, rabbits, ferrets, hamsters, gerbils, rats, large aquariums, horses, cows, goats, and pigs. In addition to caring for my own animals, I have experience managing an equine boarding facility with 19 horses on the property and am comfortable handling a wide variety of animal personalities, energy levels, and care needs. I am experienced with: • Puppies and kittens • Senior pets • Oral medication administration • Basic trick training and potty training • High-energy dogs • Shy or anxious animals • Horses and livestock requiring daily care routines I also offer red light therapy sessions for pets, both small and large, upon request. When your pet stays with me at Booked and Boarded, you can expect plenty of communication. I send regular photos, videos, and updates throughout their chapter with me, and every boarding guest goes home with a personalized treat bag and a fun “report card” highlighting their time at Booked and Boarded. I know firsthand how stressful it can be to leave beloved pets behind when traveling. That’s why I prioritize communication, reliability, and individualized care so you can feel confident your pets are safe, comfortable, and genuinely enjoying themselves while you’re away. Whether you’re visiting the Berkshires for a weekend, heading out for a day of boating, skiing, or sightseeing, or leaving town for a longer trip, I’d love the opportunity to care for your pets as if they were my own. Please feel free to reach out with any questions about services, availability, or your pet’s specific needs. I look forward to meeting you and your animals! Find Booked & Boarded on Facebook! I’m always running errands for my pets, spending time with my pets, or I’m at the barn with my horse. Taking care of the needs of my own pets is one of my top priorities, and I can easily work your furry friend into my schedule! It’s important that we discuss your specific expectations and needs as a pet owner/parent to ensure that you get the best care! Every pet owner and pet is different and I want to tailor my approach to what your pet is used to and comfortable with.

Sitter Profile Image: Josselin M.
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Josselin M.
from
$28
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: Mariana F.
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Mariana F.
from
$19
per day
5.0 out of 5 stars
2 reviews
10 years of experience
North adams, MA, 01247

Mariana was an absolute life savior and our dog had the time of his life with them. Very responsive, helpful and attentive to your doggos needs. We even got some cutest Polaroids back :)

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Artem P.
Sitter Profile Image: Ivan O.
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Ivan O.
from
$30
per day
5.0 out of 5 stars
6 reviews
20 years of experience
New Lebanon, NY, 12125

Thank you for keeping Scout safe and happy:)!

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Julia M.
Sitter Profile Image: Sylva & Mark M.
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Sylva & Mark M.
Star Sitter
from
$35
per day
5.0 out of 5 stars
65 reviews
19 repeat clients
9 years of experience
Troy, NY, 12180

Mark & Sylva were great hosts for my dog when we needed a few hours of care while my son toured a nearby college. They were welcoming and kind and did a great job with her. I'd happily book again if we're in Troy in the future. Thank you!

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Liz M.
Sitter Profile Image: Ericca B.
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Ericca B.
Star Sitter
from
$50
per day
5.0 out of 5 stars
52 reviews
17 repeat clients
36 years of experience
Bennington, VT, 05201

Ericca was extremely communicative and flexible when it came to getting my dog dropped off and picked up! Highly recommend, especially if you’re looking for someone with experience with GSDs!

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Jackson C.
Sitter Profile Image: Davis B.
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Davis B.
Star Sitter
from
$50
per day
5.0 out of 5 stars
36 reviews
10 repeat clients
10 years of experience
BENNINGTON, VT, 05201

Davis was a wonderful sitter for our pup, Beau. We left Beau with Davis, her partner, and her pups for a few hours while we went to a museum and Beau seemed perfectly content when we picked him up. Thanks, Davis!

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Jacqueline N.
Sitter Profile Image: Kenia K.
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Kenia K.
from
$35
per day
5.0 out of 5 stars
4 reviews
10 years of experience
Rensselaer, NY, 12144

Kenia is kind, flexible and communicative. The second day I brought my anxious rescue poodle to her, she sprinted up the steps and could NOT wait to get inside! Her warmth is unmatched and she brought me great comfort knowing my pup was in a safe, loving environment while I tended to family needs. Will definitely use Kenia again if I’m in the area, and highly recommend anyone in need use her too!!

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Ashley B.
Sitter Profile Image: MaryEllen M.
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MaryEllen M.
from
$40
per day
5.0 out of 5 stars
5 reviews
2 repeat clients
25 years of experience
Menands, NY, 12204

MaryEllen was all I could have asked for and more to watch my little girl Nala! She was kind, easy to work with, responsive, and thoughtful! She went above and beyond to make Nala feel at home and welcome! I will absolutely ask her to watch Nala again!

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Genevieve G.
Sitter Profile Image: Logan S.
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Logan S.
Star Sitter
from
$40
per day
5.0 out of 5 stars
30 reviews
11 repeat clients
25 years of experience
Castleton, NY, 12033

Marcie's stay with Logan went very well, he sent us updates with photos and videos. Logan really knows and loves dogs! We will be happy to bring Marcie back.

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Katie V.
Sitter Profile Image: Lindsay L.
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Lindsay L.
from
$50
per day
5.0 out of 5 stars
5 reviews
20 years of experience
Canaan, NY, 12029

Our pup had a great day with Lindsay. Definitely will book again in the future when we are back in the area!

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Christine N.
Sitter Profile Image: Kimberly E.
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Kimberly E.
from
$32
per day
5.0 out of 5 stars
141 reviews
50 repeat clients
25 years of experience
Troy, NY, 12180

Xena had a great time at doggy daycare with Kimberly. I’d highly recommend her. She kept in contact all day and sent photos and videos. Which is what any crazy dog mom needs! ??

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Victoria K.
Sitter Profile Image: Awoo H.
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Awoo H.
from
$27
per day
5.0 out of 5 stars
171 reviews
72 repeat clients
20 years of experience
Johnsonville, NY, 12094

Devin was super cool and caring. He made me very comfortable by taking care of my 14 month old high energy German Shepherd. He was always available for a call or text and kept me informed about my pups activities during the day care. Will definitely use again, he has the love towards pets, also has a great fenced yard and good facilities to get the energy out from the pups. I am happy and pleased to have used his services.

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Raj K.
Sitter Profile Image: Katherine H.
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Katherine H.
from
$40
per day
5.0 out of 5 stars
20 reviews
8 repeat clients
12 years of experience
East greenbush, NY, 12061

Katherine is an excellent dog rover. She is a strong communicator, caretaker, and most importantly a good hearted dog person. Your dog is in great hands with her. When I’m in the area she will be my go-to person.

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Paul M.
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The median cost per day for doggy day care in Cherry Plain is $40

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  • 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?

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  • Reservation protection

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

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

Meet local sitters who will treat your dogs like family

  1. 1. Search

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Popular requests for doggy day care - Cherry Plain

Select a filter and find qualifying sitters offering doggy day care.

Sitters in Cherry Plain average 4
repeat doggy day care clients

FAQs for Doggy Day Care - Cherry Plain

Frequently asked questions about Rover

As of July 2026, there are 235 sitters on Rover offering Doggy Day Care across Cherry Plain. 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 Cherry Plain 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 NY 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 235 sitters in Cherry Plain, 87% 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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