Dog Boarding Cheshire
Find a loving dog sitter to watch your dog overnight at your sitter's home.
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%.
“Brooke took excellent care of my dog. When I picked her up from Brooke's house, she was relaxed and calm, not anxious and pulling like she usually is when I return from a trip. Leah really enjoyed her stay with Brooke and she came home tired and happy. I appreciated Brooke's notes and pictures while we were away. I would not hesitate to recommend her and would love to use her services again.”
“Irene is the best! She is very responsive and caring with our slightly neurotic dog. 🐶 He always comes home happy and calm. Irene has a great setup for playtime (fenced yard, screened porch).”
“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.”
“Mary and Todd were amazing! Sent us pics of Oakley having fun on her walks and other pups Communication was terrific and Oakley seemed so happy being there! We can’t wait until her next visit with them! Plus, she made friends with the chickens!!”
“Chelsea was really great! This was the first time I had left Ruby with someone while being out of the country, and I thought I would be anxious about it, but Chelsea made me feel at ease. She gave lots of updates and let me see how Ruby was settling in. Ruby clearly got a lot of exercise and play with Chelsea's dog Zeus, and I am so happy we found someone so close where Ruby really seems to enjoy staying!”
“Omg, we’re so thankful for Geena! Story time, so our previous sitter was unavailable but the app said she was available (technology lol). So we were worried because we didn’t have a backup plan and we needed a sitter for my grandma’s funeral. Geena was so helpful with last minute arrangements and made us feel so comfortable with leaving our fur babies for the day. She responded to all my messages, questions and even sent pictures. We were able to attend the funeral with no worries and even booked her again for our vacation. I would definitely recommend using her and we will continue to book with her. Thank you again 💜🫶🏾💜”
About: Dogs and I understand each other. I've always gotten them and they've always gotten me. Maybe because I grew up with three mammoth Samoyeds and Malamutes, and shared my life with Max, my sweet Cavalier, until he passed. Beyond love and care, I'm good at training and socializing, and dogs respond to my calm, confident leadership. I once cared for a reactive dog who barked at everyone who came near her, and I was the only one who could get her to settle and listen. After a month with a young Portuguese Water Dog, her owners told me she moped after I left. But mostly I think dogs feel good around me because they sense I genuinely care about them. I believe dogs are here to teach us to love and I want every dog to experience great care. For me, good dog care starts with getting to know the dog and the people who love them. I think dogs feel safest when their sitter truly knows them. Before any stay, I like to meet you and your dog, take a short walk together, and learn the little things that make your dog feel at home. That's why every stay begins with a meet and greet. What I offer that's different: - Pick-up and drop-off for longer stays: For stays of a week or more, I'll pick up and drop off your dog anywhere within a 30 minute drive of Dalton, including Lenox, Stockbridge, and Great Barrington. One less thing to manage before your trip. My home is calm and quiet, with a large, fully fenced backyard on a peaceful street in Dalton. I work from home, so your dog has company through the day, plus walks, play, and plenty of affection. I follow your instructions to the letter so your dog's routine stays as close to home as possible, and you'll get photos and a quick update every day so you can relax and enjoy your trip. Also happy to reinforce any training your dog is working on like leash manners. How I work: Every new client starts with a meet and greet, about 30 minutes with a short walk together, so your dog and I can meet before the stay. It helps make sure we're a great match, and your dog arrives already knowing a friendly face. Boarding in my home is a great fit if your dog: Settles comfortably for stretches after the initial sniffing and cuddles to get used to a new space. Is house-trained and walks well on a leash Is not a heavy shedder or super vocal Services Boarding: 2-night minimum House sitting: 2- night minimum, 2 night maximum for first sit I'd love to hear about your dog! I work from home so your dog will have plenty of companionship and attention from morning to evening. I usually walk dogs according to the schedule they are used to. In between, they can hang with me. IFeeding times will also coincide with your instructions. I'm an early riser so you are welcome to drop your dog off (with notice) as early as 7:30 am. I have a large three bedroom home with an huge fenced back yard on a quiet street near trails. It's single floor so no stairs for older dogs to contend with.
“Davey had a lovely stay with Kathleen! It was very clear when I picked him up that she took great care of him - he had a lot of affection for her! Kathleen sent regular updates and pictures, which set my mind at ease. I would be happy for Davey to stay with Kathleen again!”
“Vera was the perfect dog sitter for our Pixel. She sent great updates and pictures throughout our trip to make us feel comfortable and show us that Pixel was having a great time. She is very thorough and asks all the right questions (even the ones that we forgot). Highly recommend Vera for all your doggy needs!”
“Both of our dogs were calm and relaxed after a 4-day stay. James was attentive to all of their needs and was very kind. His roomates were a bonus, because someone was almost always around to hang out with our dogs! Thanks James, we will be back!”
About: My family has always had dogs, and I feel that they enhance the family unit. No discrimination against certain breeds. German Shepherd, Rottweiler, American Staffordshire, Boxer, makes no difference to me. I adore all the four-legged kids! I have my own four-legged kid, and truly appreciate the help I’ve received through Rover.com, while being at work or out of town. It’s such a relief to know that the he is taken care of, so I can continue working to provide for him. Updating you on the visit with pictures and/or videos, so you can see your four-legged kid(s) have been cared for, would be my pleasure. Dogs are family, and I would gladly treat yours as part of my pack. I would be happy to perform drop-in visits or walk your dog(s) during the day, or into the night hours, as my schedule allows. Currently, I am unavailable for midday drop-ins and walks Mondays through Thursdays. Updating you on the visit with pictures and/or videos, so you can see your four-legged kid(s) have been cared for, would be my pleasure. I happily treat your fur kids as lovingly as my own. Always checking that food and water bowls filled as needed. Utilizing the crate should they need it upon my leaving.
About: I have pet/house sat multiple times over the past several years for friends and family, and have worked with several types of animals from small critters like guinea pigs and ferrets, cats, and even large dog breeds. I also have 2 years experience volunteering for a local shelter in socialization and vet transport, 3 years experience working for a doggy daycare and boarding facility, and I currently work part time for another local animal shelter. I am an experienced owner of dogs, cats, ferrets, chickens, guinea pigs, and more. I also have experience as a wedding dog handler, and would be happy to offer this service if requested so your furry companion can accompany you or someone you know on yours or their special day without any added stress, please let me know if this is something you'd be interested in! I currently work part time so I have lots of time to play with your pup, and hopefully can build savings towards a larger space to meet more people's needs! I am always looking to learn, grow, and provide better care for animals. Animal welfare is very important to me. At this point in time, due to the space I'm only able to accommodate smaller breeds that generally can get along with others. I do have a small fenced in yard, but I also have the bike trail and nearby hiking trails readily available, your dog will need to be on leash at all times when outside on walks/hikes, I do not provide "off-leash" trail experience as a safety precaution, thank you for your understanding! I am happy to provide pictures and updates of your pup whenever requested, please never be afraid to reach out!
“Cong was amazing!! We had to leave town with one day's notice for a death in the family, and were frantic with worry about who would take care of our boys for us. Cong came through in a *big* way. She let us drop our boys off at 3am, on our way to the airport! We got frequent and regular updates from her, most with photos, and knowing that our boys were getting love and care removed a giant source of worry from us at a difficult time. Cong's doggie is a sweetheart, and she had fun playing our boys. I will 100% be contacting Cong in the future to keep our boys safe and happy! Thank you!!”
“Tenzin and her husband did a great job taking care of my almost 6 month old puppy who was away from me overnight for the first time. She sent pictures and sent updates that really helped ease my mind.”
“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!”
“Christian responded quickly to our initial request & because we had a long drive he agreed to accommodate a 2 hour drop off window (we texted updates). He was friendly at drop off, happily engaged the dogs, asked good questions about their needs & sent photos as requested. At pick-up he offered details about their stay. Both dogs were happy to see us but seemed to have enjoyed their night with Christian. Would book again”
“Lydia was absolutely wonderful with my dog Paddy, I couldn’t have asked for a better Rover sitter. She went above and beyond to make sure my pup was happy and comfortable the entire time. She sent multiple pictures and updates every day, which gave me a lot of peace of mind, it was clear they were truly spending quality time together. They even did activities like yoga and went on multiple car rides, which I loved seeing. When I came to pick Paddy up after a few days, she didn’t even want to leave Lydia, which says everything about how well she was cared for and how much attention and affection she received. I would highly recommend Lydia to anyone looking for a reliable, thoughtful, and caring pet sitter. I will absolutely book with her again!”
“My pups had another great stay with Emma - happy, healthy and excited to see her again for a night! Emma takes great care of them, and she's both super-friendly and accommodating schedule-wise. Thanks!”
“I only have great things to say about our experiences with Shawna! She's great at communicating - she was always quick to respond to qurstions and sent daily updates and pictures. She is also just a very nice person who immediately puts you at ease when leaving your pup in her care. She took great care of our guy and we will definitely use her again!”
The median cost per night for dog boarding in Cheshire is $55
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- 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?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
How to book dog boarding
1. Search
Browse profiles of sitters near you who offer dog boarding.
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit.
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform.
Popular requests for dog boarding - Cheshire
Select a filter and find qualifying sitters offering dog boarding.Sitters in Cheshire average 12 repeat dog boarding clients
FAQs for Dog Boarding - Cheshire
Frequently asked questions about Rover
As of November 2026, there are 233 sitters on Rover offering Dog Boarding across Cheshire. Enter your ZIP code to see which available sitters are closest to your home.
If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.
The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.
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.
96% of sitters in Cheshire can provide daily exercise during dog boarding stays. Depending on the sitter, their home environment, and your dog’s needs, this 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, we recommend 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.
Tip: You can upload your dog’s routine and medical info directly onto their profile so your sitter always has the details at their fingertips.
Yes, you can find sitters who have experience with handling special pet needs in Cheshire. On Rover:
- 86% of sitters can help with special care needs
- 97% can help with giving oral medications or injections
- 96% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.
Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.
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 Rover Guarantee, 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 Rover's Trust & Safety page.
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.
Adding another pup to the pack? Most sitters and walkers offer a reduced rate for additional dogs. You’ll find these exact rates listed under the "Services" tab on any sitter's profile. Since every dog is unique, final pricing may vary depending on the level of care required.
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