Dog Boarding in Chester, VT
Find a loving dog sitter to watch your dog overnight at your sitter's home.
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Loving dog sitters in your neighborhood
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1. Ashley M.
“Yogi enjoyed his stay with Ashley’s family. He has a bit of separation anxiety yet was relaxed and calm there. Thank you Ashley and your adorable family❣️”
2. Joseph B.
“Toffee, my 3-year old golden retriever, had a good time staying at Joe’s place. She looks happy and healthy when we picked her up and she almost did not want to leave! 😅 It was wonderful to see Toffee made some friends while staying with Joe (16 days!). It is not easy to find a good pet sitter or a boarding service provider here around Upper Valley. We really appreciate the services Joe and his partner provided.”
3. Hope R.
“Hope was great for our 5-month old Aussie puppy. She had a number of other dogs there to play and had a great time. She was very responsive during her stay and asked a lot of questions prior to agreeing to watch her. Hope has a lot of experience with dogs and loves dogs. Will definitely have our pup stay with her again if we are in the area.”
4. Tom D.
“Tom has watched him for a day and boarded my Doodle twice now and always takes amazing care of him. He comes back happy and tired each time and I get updates while we are away to show he is adjusting fine. He gets excited for each return.”
5. Kaitilin G.
“Kaitlin is an incredibly accommodating, attentive, and professional caretaker. She sent pictures to us throughout our dog's stay with her which made us feel a lot better about leaving our baby behind. Highly recommend!”
6. Kevin & Inez W.
“Finn was very happy to have other dogs to play with! Kevin and Inez sent us a photo or video most days and that was great! Highly recommend these sitters for your fur babies!”
7. 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!”
8. Samantha L.
“Samantha was a hero! She provided a warm welcome for our dog, was flexible with all requests, and communicated with us throughout our pet’s stay (including some adorable photos). Highly recommend!!”
9. Jessica P.
“Jessica did a superb job! Can't recommend her highly enough. She was fantastic with our dog, taking her on lots of hikes and other adventures. And she was a very thoughtful and responsive communicator. It was a pleasure working with her from start to finish. We're lucky to have such a wonderful dog sitter in our area!”
10. Briana L.
“I highly recommend Briana as a pet caregiver! She’s responsible, highly attentive, and genuinely loves animals. My babies are always in great hands with her!”
11. Kaitlin O.
“Awesome host! Caitlin did a very good job sending me updates and pictures of my pup. Lailah seemed to be in very good spirits when I picked her up.”
12. Laura P.
“Pepper stayed with Laura for 3 nights while we went away. We felt at ease leaving her, knowing she would be well taken care of. We were not wrong. When we went to pick her up I could tell she had made a new friend and was comfortable with Laura. I am so thankful we picked Laura to take care of Pepper.❤️”
13. Sean D.
“My dogs didn't want to leave! They loved Sean and Lisa, and especially Pluto and Cosmo, their dogs. Big fenced yard. Nice area. Dogs slept in their bed.”
14. Christine C.
“It appeared that Darley loved her stay with Christine. Christine sent us pictures and commentary every day while we were away. We really appreciated that. We were a little concerned that Darley and Christine's cat, Gonzo would not get along but I think all went very well. The yard around the house was good for letting Darley out and Christine took Darley to places where she could really get some exercise. We will want to return to Christine's in the future and definitely recommend her.”
15. 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.”
16. Richard & Hope R.
“Richard has been renting from me for about six months and helping with the dogs I have here when I get busy. He has helped in the past when I have needed an extra helper with some of the dogs I have. He helps me to organize the feeding and sometimes brings them out for walks so we can get them out in a timely manner. He is a loving and responsible person who can be trusted with your dog as he has always had dogs in his life, getting his first dog (a Great Dane mix) when he was ten years old. He has cared for my dog Maebe numerous times and she loves him dearly.”
17. Jaimi L.
“Jaimi was very welcoming and flexible with our schedule. Simba enjoyed his visit. We will rebook next year on our return to ski at Okemo.”
18. Casandra B.
“Cassandra was great with my golden puppy Chance! She kept me informed throughout his stay and sent pics. If I had questions I would reach out to her and she responded quickly. Chance has a great time playing in the yard with Cassandra’s dog. He got all the exercise he needed to drain his puppy energy. I would definitely book Cassandra again.”
19. 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.”
20. Letícia B.
“Leticia is not only a stellar human being with a kind and patient soul, but she LOVES dogs. She never hesitates to care for my little dog—who is not the easiest pup to care for! She gives her a loving environment, exercise, play time, and even got her to try some new adventures like swimming. Do not hesitate to trust Leticia with your pet. I promise you will be worry free for your time away from your pup, who will feel right at home, happy, and loved!”
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1. Search
Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs
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Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs while you’re away
3. Book & Pay
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Why Choose Rover?
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It doesn’t happen often, but if your dog sitter has to cancel, we’ll work with you to find a new sitter.
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Dog Boarding FAQs
Frequently asked questions about Rover
As of Mar 2025, the median cost of dog boarding in Chester is $62 per night, including service fees. Boarding your dog for one week typically costs $434. 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 $42 to as high as $97 per night.
As of Mar 2025, 38 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, 93% of Chester dog boarding sitters respond in under an hour.
Dog boarding sitters with repeat customers have an average of 10 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 38 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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