Dog Boarding in Chester, VT
Find a loving dog sitter to watch your dog overnight at your sitter's home.
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Top rated Chester dog boarders
“Hope is excellent and our first experience on Rover, she exceeded our expectations and gave our dog a loving and caring experience. Our dog stayed with her overnight the week after Christmas. She was very responsive and easy to communicate with. I made a last minute request for care and Hope made the entire process simple. We were from out of town skiing at a nearby resort. Hope was generous with her time and care for our treasured Potato. We will use Hope again when we return for another ski week. I was very happy with our experience and our dog Potato had a great time playing at Hope’s house. We were lucky to find her!”
“Romeo seemed to have a good stay overnight with Elijah, Carson and their dogs and cats. I received photos and updates and Romeo seemed very tuckered out when he got home so I think he probably had lots of stimulation and fun. Thank you! We will be back!”
“Kevin & Inez took such good care of our girl last minute when our care plan fell though. She had so much fun playing with their dogs, and came back very happy. Highly recommended!”
“Callie had a wonderful time and their dog Amber is her new best friend! Tom kept us up to date with plenty of pictures and we could see she was being well-cared for. She was "doggone" tired when she got home, which we appreciated!”
“We are pleased with the care that Tara provided for our dog. She reassured us that she was going to be attentive and gentle while introducing her dog with ours. Texts and pictures to keep us informed also meant a lot to us. Board your dog with confidence.”
“Richard and Hope took great care of Betty; lots of outdoor time and playing with children. They obviously LOVE dogs and make them part of their family! If I’m back in their ar3a, Betty is definitely staying with them again!”
“Kaitlin is absolutely amazing! I've been using her for the last couple of months and my pup Lailah really has taken to her. Lailah experiences some separation anxiety so its a good feeling to not hear her screaming down the hall after I drop her off :) Kaitlin also does a very good job keeping in the loop while I'm away, and provides Lailah with plenty of entertainment including taking her to Central Park and Randall's Island. Always an adventure. Not to mention, she takes the best pics lol.”
“Min Joo is a very thoughtful and accommodating dog sitter. We had a wonderful experience and felt reassured that our dog was well taken care of with the frequent communication and photo/video updates.”
“Laura was great, she took my pup on long walks every day and sent photos and check in points. Exactly what I would hope for when leaving my furbaby. I was very nervous leaving him but she helped ease that and truly showed care and love for him. Thank you!”
“Christine was absolutely wonderful with Bean! Bean is a very shy and anxious pup and I've never left her with a stranger before. Christine made sure to have a few meet and greets to ease Bean's anxiety and get to know her prior to my weekend away. She has wonderful calming energy and was very patient and caring with Bean. I was completely comfortable leaving Bean in Christine and Lilly's hands. While away, I got regular photos and updates. Overall it was a great experience with Christine and I would highly recommend her!”
“Appreciate the care given to Daisy for 6 days when out of town.. Received daily photos of Daisy having fun with their dog Bean. She is high energy and having a yard and playmate is the best. Many thanks.”
About: I have taken care of cats and dogs for as long as I can remember. Looking to get my own, but in the meantime, would be excited to watch yours. I have plenty of toys and treats and I’m happy to do anything that makes you feel comfortable to keep your furry friend happy! I currently work at Dartmouth Hitchcock full-time which is why I typically can only watch during the weekend. My flexibility means I can also sometimes work remote. Depending on your preference, I’m sure we can work out something great. I am happy to do anything that makes you feel comfortable. I love to go for a walk, so I’m happy to take them down to the small park that we have. Or if they’re not much of a walker, I’m happy to sit and relax as long as they know how to pick a TV show.
“Danielle looked after our dog for a few days while we travelled. Without hesitation, I would recommend her and gladly use her services again. Danielle has a kind, positive nature. She was accommodating and our dog took to her immediately. She kept us updated, gave him lots of exercise and attention, and has a lovely location for a dog to have a holiday of their own. 5+ stars! Thanks Danielle.”
“Jill was great! She sent pictures everyday and let me know how Daisy was doing. Daisy looked like she was having a great time with Jill’s pups and romping in the yard. Highly recommend!”
Loving dog boarding sitters in your neighborhood
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Hope R.Star Sitter
“Hope is excellent and our first experience on Rover, she exceeded our expectations and gave our dog a loving and caring experience. Our dog stayed with her overnight the week after Christmas. She was very responsive and easy to communicate with. I made a last minute request for care and Hope made the entire process simple. We were from out of town skiing at a nearby resort. Hope was generous with her time and care for our treasured Potato. We will use Hope again when we return for another ski week. I was very happy with our experience and our dog Potato had a great time playing at Hope’s house. We were lucky to find her!”
Elijah & Carson H.
“Romeo seemed to have a good stay overnight with Elijah, Carson and their dogs and cats. I received photos and updates and Romeo seemed very tuckered out when he got home so I think he probably had lots of stimulation and fun. Thank you! We will be back!”
Kevin & Inez W.Star Sitter
“Kevin & Inez took such good care of our girl last minute when our care plan fell though. She had so much fun playing with their dogs, and came back very happy. Highly recommended!”
Joseph B.Star Sitter
“Joseph was a wonderful pet sitter! He was great at communicating and even sent me a pet picture every day. I will definitely use Joseph in the future!”
Tom D.
“Callie had a wonderful time and their dog Amber is her new best friend! Tom kept us up to date with plenty of pictures and we could see she was being well-cared for. She was "doggone" tired when she got home, which we appreciated!”
Briana L.Star Sitter
“Briana was great to work with. She was very flexible and communicative, and my pup had a great time with her. I strongly recommend her services!”
Tara R.Star Sitter
“We are pleased with the care that Tara provided for our dog. She reassured us that she was going to be attentive and gentle while introducing her dog with ours. Texts and pictures to keep us informed also meant a lot to us. Board your dog with confidence.”
Richard & Hope R.
“Richard and Hope took great care of Betty; lots of outdoor time and playing with children. They obviously LOVE dogs and make them part of their family! If I’m back in their ar3a, Betty is definitely staying with them again!”
Kaitlin O.
“Kaitlin is absolutely amazing! I've been using her for the last couple of months and my pup Lailah really has taken to her. Lailah experiences some separation anxiety so its a good feeling to not hear her screaming down the hall after I drop her off :) Kaitlin also does a very good job keeping in the loop while I'm away, and provides Lailah with plenty of entertainment including taking her to Central Park and Randall's Island. Always an adventure. Not to mention, she takes the best pics lol.”
Nancy H.
“Shifu did very well with Nancy and we will be going back!”
Min Joo L.
“Min Joo is a very thoughtful and accommodating dog sitter. We had a wonderful experience and felt reassured that our dog was well taken care of with the frequent communication and photo/video updates.”
Laura P.Star Sitter
“Laura was great, she took my pup on long walks every day and sent photos and check in points. Exactly what I would hope for when leaving my furbaby. I was very nervous leaving him but she helped ease that and truly showed care and love for him. Thank you!”
Mike & Laura O.
“Mike and Laura took exceptional care of our 17-year old Jack Russell. Mike was extremely communicative during the entire process and helped make our trip to Ludlow happen!”
Christine C.
“Christine was absolutely wonderful with Bean! Bean is a very shy and anxious pup and I've never left her with a stranger before. Christine made sure to have a few meet and greets to ease Bean's anxiety and get to know her prior to my weekend away. She has wonderful calming energy and was very patient and caring with Bean. I was completely comfortable leaving Bean in Christine and Lilly's hands. While away, I got regular photos and updates. Overall it was a great experience with Christine and I would highly recommend her!”
Sarah & Ben A.
“Appreciate the care given to Daisy for 6 days when out of town.. Received daily photos of Daisy having fun with their dog Bean. She is high energy and having a yard and playmate is the best. Many thanks.”
Jessica P.
“Our pup had a fantastic time with Jessica! She kept us updated with lots of photos and even took her to her favorite hiking spots. Highly recommended!!”
Maxamus S.
“I cannot recommend Maxamus highly enough! He took exceptional care of our dogs and cats making sure our pets were not only safe but happy and well-loved in our absence. Max is trustworthy, dependable, and has a wonderful, calming nature. Our pets loved him. We will absolutely be using Max again!”
Danielle L.
“Danielle looked after our dog for a few days while we travelled. Without hesitation, I would recommend her and gladly use her services again. Danielle has a kind, positive nature. She was accommodating and our dog took to her immediately. She kept us updated, gave him lots of exercise and attention, and has a lovely location for a dog to have a holiday of their own. 5+ stars! Thanks Danielle.”
Letícia B.
“My dog had a great time with Leticia! She sent us pictures during the day which were much appreciated! We look forward to booking with her again soon!”
Jill F.
“Jill was great! She sent pictures everyday and let me know how Daisy was doing. Daisy looked like she was having a great time with Jill’s pups and romping in the yard. Highly recommend!”
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1. Search
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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.
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Dog Boarding FAQs
Frequently asked questions about Rover
As of Aug 2025, the median cost of dog boarding in Chester is $60 per night, including service fees. Boarding your dog for one week typically costs $420. 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 $35 to as high as $96 per night.
As of Aug 2025, 40 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, 96% of Chester dog boarding sitters respond in under an hour.
Dog boarding sitters with repeat customers have an average of 11 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 40 dog boarding sitters in Chester on Rover, so you’re sure to find the perfect match for your dog! We understand that each dog is unique and may require specific 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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