Dog Boarding in Chester, MA
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Top rated Chester dog boarders
“I would highly recommend Allison to take care of your dogs! She is so caring and definitely communicates with you to let you know what's going on! Her dog, Mollie is so sweet too! She has 2 fenced in areas- a front yard and back yard with a pool! There is definitely plenty of places for your dogs to roam and play outside. She also has a nice area inside for them to play and where she gives tons of cuddles! She honors whatever your routine is, as I wanted my dog to sleep in her soft crate and be fed twice a day with pottie breaks every 4hrs. She is very reliable, dependable, efficient and a total sweetheart! She knows how to slowly introduce dogs and makes sure everyone is safe and comfortable besides having fun! I was so calm knowing that my Lola was in good hands and given so much attention by her, her family, and the other dogs! A definite 5 star rating in my book!”
“Aisha was great with my two dogs, who liked her on sight! She communicated and sent photos and I could tell, when I picked them up, that they'd been safe and happy.”
“Jessica and Josie were wonderful with Miss Ruby. Even understanding her occasional accident in the house as coming from anxiety. Possibly due to construction noises which were expected to be gone before Miss Ruby’s visit. It changed my perspective from paying for Dogcare to paying to have Miss Ruby share her joy with Josie and Jessica and their family. ???”
“Amanda and her family took care of Butters very well. the family is welcoming and caring. Butters had a wonderful time. definitely recommend. Thank you so much for taking care of Butters.”
“Cannot thank them enough. It was my first time using Rover and on a short notice request- no problem. I got pictures of Alfie playing and cuddling throughout his stay which set me at ease. He also came back smelling nicer and was freshly brushed, he was so happy! I 100% recommend Heather and Norman”
“Our dog just stayed with Patti and family and had an amazing time! Patti’s daily messages and photos were great, and reassuring. It was clear to us that she was being well cared for and that our dog was in a knowledgeable, experienced and caring home. We’ve already booked again and will continue to do so! Thank you, Patti!”
“Sandra was very accommodating and welcoming. This was our first experience with having someone other than family care for Chase. He seemed at ease and well cared for. We will definitely rebook with Sandra and cannot thank her enough for making this process easy.”
“Our two dogs stayed with Brooke and her family for the weekend and had a great time!! They came back very happy. Brooke provided updates and pictures throughout the weekend which we appreciated. We would absolutely book with her again! Thanks again 😊”
“Theresa was an excellent communicator & sent pictures, video & regular updates, which was super reassuring since we had only had this puppy for 2 weeks. I have already recommended her to family members in the area.”
“Tetiana was amazing with our two older Tibetan spaniels. She sent us tons of photos and kept us updated on their care. She was very accommodating and took care of our dogs like her own. Would 100% recommend!”
“We love knowing Clover has such a loving place to stay with such terrific people, and appreciate the high level of communication and care. Can’t say enough good things.”
“Kim was great with our beloved pup! She kept in contact with us and sent us pictures to update us on his wonderful vacation away from home! We would definitely recommend!”
“Karl was an amazing dog sitter! He was punctual with returning my messages, kind, caring, and provided great service for my two big Doodles! Doodles! Karl sent images which were so great to get since we love our babies like their are our dogs ❤️ I highly recommend Karl for all your dog care needs.”
“Caitlin was an amazing sitter for our dog Steve! During our pup’s 10-day stay, Caitlin provided picture and video updates to help us know he was safe and happy. When we picked him up, Steve was so relaxed and happy (way more so than when we used to keep him at the kennel). It was clear that Caitlin truly cared about making sure Steve's stay was comfortable and close to his normal routine. Her young kids were so gentle and kind with the dog, and we never had any concerns. I definitely recommend Caitlin!”
“Heidi was awesome! We chose her to give my little westie the most homelike environment while we traveled. At home he is allowed on furniture and to sleep in the bed so we loved that Heidi allowed the same. He’s also an old guy so we loved that she takes only 1 dog at a time. She was super communicative/responsive and sent lots of photo updates. Thanks for loving on our fur baby, Heidi!!”
“Chris was amazing with our Scruffy! We appreciated her photos and messages…and Scruffy appreciated the walks and the love! We highly recommend booking with her! Thank you, Chris ?❤️”
“Shelby treated my dog like her own. Daisy was loved and so happy while staying with her. Shelby’s communication was great and she sent me frequent pictures of Daisy while we were away. We will definitely be using Shelby again.”
“Kathleen was very easy to deal with. I had to arrange my drop off for Christmas weekend from another state. She responded quickly to emails. She seemed very sensitive to my dog’s needs, and accommodated all my requests. I wouldn’t hesitate to use her again.”
Loving dog boarding sitters in your neighborhood
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Allison Nicole M.Star Sitter
“I would highly recommend Allison to take care of your dogs! She is so caring and definitely communicates with you to let you know what's going on! Her dog, Mollie is so sweet too! She has 2 fenced in areas- a front yard and back yard with a pool! There is definitely plenty of places for your dogs to roam and play outside. She also has a nice area inside for them to play and where she gives tons of cuddles! She honors whatever your routine is, as I wanted my dog to sleep in her soft crate and be fed twice a day with pottie breaks every 4hrs. She is very reliable, dependable, efficient and a total sweetheart! She knows how to slowly introduce dogs and makes sure everyone is safe and comfortable besides having fun! I was so calm knowing that my Lola was in good hands and given so much attention by her, her family, and the other dogs! A definite 5 star rating in my book!”
Aishea A.Star Sitter
“Aisha was great with my two dogs, who liked her on sight! She communicated and sent photos and I could tell, when I picked them up, that they'd been safe and happy.”
Jessica C.Star Sitter
“Jessica and Josie were wonderful with Miss Ruby. Even understanding her occasional accident in the house as coming from anxiety. Possibly due to construction noises which were expected to be gone before Miss Ruby’s visit. It changed my perspective from paying for Dogcare to paying to have Miss Ruby share her joy with Josie and Jessica and their family. ???”
Amanda & Stewart J.Star Sitter
“Amanda and her family took care of Butters very well. the family is welcoming and caring. Butters had a wonderful time. definitely recommend. Thank you so much for taking care of Butters.”
Heather R.Star Sitter
“Cannot thank them enough. It was my first time using Rover and on a short notice request- no problem. I got pictures of Alfie playing and cuddling throughout his stay which set me at ease. He also came back smelling nicer and was freshly brushed, he was so happy! I 100% recommend Heather and Norman”
Patti B.
Star Sitter
“Our dog just stayed with Patti and family and had an amazing time! Patti’s daily messages and photos were great, and reassuring. It was clear to us that she was being well cared for and that our dog was in a knowledgeable, experienced and caring home. We’ve already booked again and will continue to do so! Thank you, Patti!”
Sandra C.Star Sitter
“Sandra was very accommodating and welcoming. This was our first experience with having someone other than family care for Chase. He seemed at ease and well cared for. We will definitely rebook with Sandra and cannot thank her enough for making this process easy.”
Brooke B.Star Sitter
“Our two dogs stayed with Brooke and her family for the weekend and had a great time!! They came back very happy. Brooke provided updates and pictures throughout the weekend which we appreciated. We would absolutely book with her again! Thanks again 😊”
Teresa D.Star Sitter
“Theresa was an excellent communicator & sent pictures, video & regular updates, which was super reassuring since we had only had this puppy for 2 weeks. I have already recommended her to family members in the area.”
megan b.
“Excellent overnight for 2 nights. Very accommodating. Great communication, provided updates and pictures. Bloom was very relaxed and adjusted quickly into a new environment.”
Tetiana M.Star Sitter
“Tetiana was amazing with our two older Tibetan spaniels. She sent us tons of photos and kept us updated on their care. She was very accommodating and took care of our dogs like her own. Would 100% recommend!”
John S.Star Sitter
“We love knowing Clover has such a loving place to stay with such terrific people, and appreciate the high level of communication and care. Can’t say enough good things.”
Kim M.Star Sitter
“Kim was great with our beloved pup! She kept in contact with us and sent us pictures to update us on his wonderful vacation away from home! We would definitely recommend!”
Yvette T.
“She is excellent, we had communication all the time and my daughter 🐾She was delighted with her. For this reason I recommend it and give it 5 stars.”
Karl K.
“Karl was an amazing dog sitter! He was punctual with returning my messages, kind, caring, and provided great service for my two big Doodles! Doodles! Karl sent images which were so great to get since we love our babies like their are our dogs ❤️ I highly recommend Karl for all your dog care needs.”
Caitlin C.Star Sitter
“Caitlin was an amazing sitter for our dog Steve! During our pup’s 10-day stay, Caitlin provided picture and video updates to help us know he was safe and happy. When we picked him up, Steve was so relaxed and happy (way more so than when we used to keep him at the kennel). It was clear that Caitlin truly cared about making sure Steve's stay was comfortable and close to his normal routine. Her young kids were so gentle and kind with the dog, and we never had any concerns. I definitely recommend Caitlin!”
Heidi H.
“Heidi was awesome! We chose her to give my little westie the most homelike environment while we traveled. At home he is allowed on furniture and to sleep in the bed so we loved that Heidi allowed the same. He’s also an old guy so we loved that she takes only 1 dog at a time. She was super communicative/responsive and sent lots of photo updates. Thanks for loving on our fur baby, Heidi!!”
Chris S.
“Chris was amazing with our Scruffy! We appreciated her photos and messages…and Scruffy appreciated the walks and the love! We highly recommend booking with her! Thank you, Chris ?❤️”
Shelby L.Star Sitter
“Shelby treated my dog like her own. Daisy was loved and so happy while staying with her. Shelby’s communication was great and she sent me frequent pictures of Daisy while we were away. We will definitely be using Shelby again.”
Kathleen M.Star Sitter
“Kathleen was very easy to deal with. I had to arrange my drop off for Christmas weekend from another state. She responded quickly to emails. She seemed very sensitive to my dog’s needs, and accommodated all my requests. I wouldn’t hesitate to use her again.”
Over 5 pet parents in Chester have booked dog boarding
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1. Search
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2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs while you’re away
3. Book & Pay
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The median cost per night for dog boarding in Chester is $50
Why Choose Rover?
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Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your dog boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Sitters in Chester average 9 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Aug 2025, the median cost of dog boarding in Chester is $50 per night, including service fees. Boarding your dog for one week typically costs $350. Sitters on Rover set their own rates based on their qualifications, your dog's needs, and their space's amenities. As a result, most Chester dog boarding rates can be found as low as $33 to as high as $89 per night.
As of Aug 2025, 139 sitters provided dog boarding in Chester. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, dog boarding sitters 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, 88% of Chester dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Chester have an average of 21 years of experience. Dog boarding sitters with repeat customers have an average of 9 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.
Rover makes it easy to find Chester dog boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog boarding is great for:
- Dogs of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their sitter’s pets
There are 139 dog boarding sitters in Chester on Rover, so you’re sure to find the perfect match for your dog! In Chester, 95% of sitters offer daily exercise, 95% offer medication administration, and 95% 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 dog boarding 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 dog boarding 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 dog boarding 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 dog boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
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