Dog Boarding Cheshire

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Cheshire, Find top rated dog boarding

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

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Sitter Profile Image: Brooke B.
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Brooke B.
Star Sitter
$50
total per night
5.0 out of 5 stars
• 139 reviews
36 repeat clients
25 years of experience
Pittsfield, MA, 01201

“Brooke and her family were kind and loving to Millie! She hasn’t been with anyone but us and she isn’t a very easygoing pup so we were so relieved when Millie was so relaxed and happy in Brooke’s home. Brooke kept us updated and sent many adorable photos! I would absolutely book with Brooke again and will recommend her to anyone needing care for their fur children.”

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Kisti O.
Sitter Profile Image: Yenifer V.
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Yenifer V.
$73
total per night
5.0 out of 5 stars
• 35 reviews
7 repeat clients
3 years of experience
Pittsfield, MA, 01201

“Yenifer took excellent care of my dog. He was so happy with her! She made sure she communicated everyday with us during the stay, sent us pictures and updates. We are very happy with her services and would strongly recommend her. Thank you, Yenifer.”

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Divya C.
Sitter Profile Image: Ericca B.
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Ericca B.
$70
total per night
5.0 out of 5 stars
• 58 reviews
18 repeat clients
36 years of experience
Bennington, VT, 05201

“Ericca was great, coming through for us on really short notice! Our dog seemed totally comfortable and happy with her. We definitely recommend Ericca!”

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Martha H.
Sitter Profile Image: Kellie H.
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Kellie H.
$107
total per night
5.0 out of 5 stars
• 15 reviews
6 repeat clients
10 years of experience
Dalton, MA, 01226

About: I love a challenge and a new four legged friend! Puppy biting, pulling on walks, endless energy? Let me know and we can come up with a good plan to meet your pups needs. I’m happy to hike with dogs, water activities, or other outdoor outings if it is what your pup needs to be their best at home. I also have a large fenced in yard to play fetch as opposed to a walk if that helps your dog get their energy out better! (6ft tall wood privacy) I learn quickly and care about how you want your pet care of above all else. I’ve owned, cared for, and fostered many animals across numerous ages and breeds. I have availability on weekends and after 4pm most weekdays. I am flexible and don’t mind last minute requests as my job allows for a good amount of flexibility I can adjust for a specific situation. I reinforce good behaviors or redirect bad behaviors with positive methods. I will not place any animal in an overly stressful environment and will meet them where they are at.

Sitter Profile Image: Chelsea H.
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Chelsea H.
$62
total per night
5.0 out of 5 stars
• 10 reviews
1 repeat client
22 years of experience
Nassau, NY, 12123

“Chelsea offered her home to our pup, Sansa, and treated her like family while we traveled. She is an excellent communicator and sent plenty of updates and photos of our girl enjoying her visit. I highly recommend Chelsea for your dog boarding needs!”

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JJ B.
Sitter Profile Image: danielle p.
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danielle p.
$56
total per night
4.8 out of 5 stars
• 4 reviews
10 years of experience
Pittsfield, MA, 01201

About: I have owned a dog ever since I was about 4 or 5 years old. I’ve had anywhere from poodles, to a Maltese to a Malinois, & Pitbull :) I am currently working from home, making me available almost 24/7. My partner and I currently raising our puppy, Nemo. He is an adorable 3 month old puppy we adopted from the local Berkshire Humane Society. My partner and I love dogs, so if you are in need of some you time, please feel safe and comfortable leaving them with us :) Up as early as 5am Twenty - four seven availability Work from home Active lifestyle Am able to play, watch, manage, walk at any time I care for pets in my home by allowing for walks/car rides as needed for potty breaks. I do close off my bedroom, & bathroom to animals; free roam of a long hallway and kitchen/living room. Food/treats are given or left out at the owners request.

Sitter Profile Image: Jialin & John Y.
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Jialin & John Y.
Star Sitter
$50
total per night
5.0 out of 5 stars
• 29 reviews
11 repeat clients
4 years of experience
East Greenbush, NY, 12061

“Jialin and John watched my new senior rescue Bianca for a long weekend and were so good to her! I was a little nervous since I had her less than a month and was still figuring out her unique behaviors and preferences but she was in great hands. We did a meet and greet beforehand and Boo-boo was a great host, sharing his home and parents. Jialin even taught Bianca a new trick that we have been working on back home. Bianca was sent home with a plastic baggie of some treats she liked to keep the good times going back home. I look forward to the next time Bianca can stay with them!”

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Kerry T.
Sitter Profile Image: Josselin M.
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Josselin M.
$73
total per night
5.0 out of 5 stars
• 3 reviews
5 years of experience
Pittsfield, MA, 01201

“Josselin did a nice job with our two little dogs. We would use her again.”

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Paul R.
Sitter Profile Image: Christopher H.
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Christopher H.
Star Sitter
$49
total per night
5.0 out of 5 stars
• 32 reviews
6 repeat clients
16 years of experience
Menands, NY, 12204

“They were great with Bailey, communicated just the right amount of times to help us feel at ease while far away, that he was doing okay. When he arrived home, he was calm and relaxed, and that's a sure sign for us that he was well cared for and felt comfortable. Would highly recommend and definitely will use them again. Thank you for letting us enjoy our time with our family without worrying about Bailey. :-)”

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Debbie H.
Sitter Profile Image: Sylva & Mark M.
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Sylva & Mark M.
Star Sitter
$62
total per night
5.0 out of 5 stars
• 67 reviews
19 repeat clients
9 years of experience
Troy, NY, 12180

“Couldn’t ask for a better and more reassuring experience!! Sylva and Mark are a great couple and went out of their way not only making Oliver comfortable but also understanding our concern for this first time boarding. They sent us several pictures and Oliver obviously had no problem making himself at home. He’ll be spending a weekend with them later this month.”

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Michael B.
Sitter Profile Image: Diana G.
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Diana G.
$67
total per night
5.0 out of 5 stars
• 7 reviews
2 repeat clients
5 years of experience
Valatie, NY, 12184

“Diana was amazing and we felt at ease leaving our two pups with her. When picking them up after our quick trip it was very clear that she had already bonded with them.”

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Sophie G.
Sitter Profile Image: Kierra H.
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Kierra H.
$56
total per night
5.0 out of 5 stars
• 47 reviews
15 repeat clients
10 years of experience
Troy, NY, 12180

“Kierra was great! Jarvis loved staying with her and her pup. She provided pictures of them playing and getting lots of attention. He can't wait to go back and visit.”

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Michael M.
Sitter Profile Image: Darcy J.
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Darcy J.
$56
total per night
5.0 out of 5 stars
• 9 reviews
1 repeat client
36 years of experience
Castleton-on-Hudson, NY, 12033

“Darcy was wonderful and we felt very comfortable leaving our pup with her family. Our dog was well cared for and came home happy. We will highly recommend Darcy to friends and family who also need dog sitting services. Thank you Darcy!”

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Jessica J.
Sitter Profile Image: Tenzin W.
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Tenzin W.
$73
total per night
5.0 out of 5 stars
• 10 reviews
2 repeat clients
8 years of experience
Troy, NY, 12180

“Tenzin was amazing! She took great care of my nigh energy puppy and was super communicative throughout the stay. I really appreciated her help. My puppy came home relax, tired, and happy. Thanks Tenzin!!”

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Camille D.
Sitter Profile Image: Maritza O.
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Maritza O.
$35
total per night
4.6 out of 5 stars
• 13 reviews
3 repeat clients
1 year of experience
North Adams, MA, 01247

“Maritza did an awesome job taking care of Lola. She sent me frequent updates on how things were going while I was away that put me at ease. I would definitely use her again she’s highly recommended.”

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Wanda H.
Sitter Profile Image: Christian M.
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Christian M.
Star Sitter
$62
total per night
5.0 out of 5 stars
• 37 reviews
13 repeat clients
10 years of experience
Greenfield, MA, 01301

“Christian is great! He is patient, chill, and very good with dogs! I loved that our dog wanted to go back inside with him when we had to leave; that is a great sign!”

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Gregory A.
Sitter Profile Image: Katherine M.
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Katherine M.
$56
total per night
5.0 out of 5 stars
• 22 reviews
4 repeat clients
4 years of experience
East Greenbush, NY, 12061

“I was really in a jam and needed a dog sitter and Katherine was super flexible and simply amazing! She sent pics of Jimmy and he had a blast!”

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Denisa R.
Sitter Profile Image: Mariana F.
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Mariana F.
$20
total per night
5.0 out of 5 stars
• 3 reviews
10 years of experience
North adams, MA, 01247

“I’m very happy with Mariana and the care she gave my dog! My dog seemed very happy during the stay, got to go on lots of great walks and visit some fun spots, and came home healthy and happy. I’m also especially thankful that Mariana was able to help out on such short notice. I would absolutely book with her again and would feel very comfortable having my dog stay with her in the future. Thank you so much, Mariana!”

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Richard A.
Sitter Profile Image: Phelan S.
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Phelan S.
$84
total per night
5.0 out of 5 stars
• 33 reviews
14 repeat clients
4 years of experience
Troy, NY, 12180

“Phelan took great care of Sadie and made her feel right at home! She's a great communicator and she sent us lots of updates and pictures of Sadie. We look forward to bringing Sadie over again!”

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Katie T.
Sitter Profile Image: Stephanie M.
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Stephanie M.
$84
total per night
5.0 out of 5 stars
• 5 reviews
1 repeat client
40 years of experience
Greenfield, MA, 01301

“Stephanie took great care of our two dogs - took them on long walks, treated them with love, and they had a great time. Will definitely be in touch with her again when we're back in the area!”

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David C.
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How to book dog boarding

  1. 1. Search

    Browse profiles of sitters near you who offer dog boarding.
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Popular requests for dog boarding - Cheshire

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FAQs for Dog Boarding - Cheshire

Frequently asked questions about Rover

Rover is the largest marketplace for local pet care. Whether you're looking for pet sitters, dog walkers, or house sitters who specialize in pet sitting, you can narrow your search by entering your ZIP code to find sitters within walking distance in your neighborhood.

Every sitter on Rover has their own routine. Depending on the arrangements you agree on before the stay, a sitter can follow your dog’s regular feeding schedule, provide a comfortable place to sleep, offer companionship, and support their usual exercise and play needs.

Depending on the sitter, their home environment, and your dog’s needs, daily exercise may include walks, outdoor play, indoor enrichment activities, or supervised play with compatible dogs. These activities are not automatically included with every booking, so ask the sitter what a typical day looks like.

During the Meet & Greet, discuss your dog’s usual exercise and play routine, whether they can safely interact with other dogs, and any activities or restrictions the sitter should follow. You can also ask the sitter to send photo and message updates during the stay so you can see how your dog is spending their time.

Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Cheshire home-away-from-home, packing:

  • Health and safety essentials such as their ID tags, vaccination records, medication, and emergency vet or secondary caregiver contacts.
  • Food and gear such as harnesses, collars, food (portioned by day), and an item that smells like you.
  • Special instructions such as a list of training cues, medical administration needs, or favorite hang-out spots in your Cheshire.

<b>Tip:</b> You can upload your dog’s routine and medical info directly onto their profile so your sitter always has the details at their fingertips.

You and your Cheshire sitter can schedule drop-off and pick-up in a way that works best for the both of you—and your dog. Most sitters offer flexible times for drop-off and pick-up but the easiest way to confirm those times will be through in-app messaging. Confirm your arrival time the day of pick-up and drop-off can also help keep the process smooth and organized.

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 , which provides up to 25,000 in eligible veterinary care reimbursement.

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 .

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.

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your dog to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your dog is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

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