Dog Boarding in Chester, CT
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Top rated Chester dog boarders

“We felt very comfortable leaving our Sheltie Winston with Brittney (and family!) and the daily updates and pics were great so we never worried while away. Definitely will use her service again!”


“Holly was great! As a nervous dog mom, she made me feel reassured that Hank was in capable hands from the first Facetime meet and greet to continual updates and photos throughout Hank's stay!”


“Laura was so wonderful! She made our family and our pup so comfortable and sent pictures and updates throughout our trip. We were so happy knowing that our dog got to be part of Laura’s family while we were away. We’d highly recommend Laura!”


“My dog had a great time. Because she is/was an anxiety prone rescue of 8 months, I was worried she would become very nervous again. But she was very happy. Melissa's back yard is great and I am sure that was one reason my small dog was so happy. And Melissa is very accommodating.”


“Erica, Thomas, and their family were amazing to my sweet Kona! She’s a young GSP so she’s very active and high energy. She’s a great dog but not everyone can handle her energy level. They were great and immediately knew what to do with exercising and treating her like family. It helps that they have a big front lawn and had other dogs staying with them too! Kona made great friends judging from the pics. But most importantly, they went out of their way to be her dog handler for us on our wedding day. They made our special day even more magical by letting Kona participate in the ceremony as our dog of honor. She was tired for 2 full days after we picked her up! That’s a long time for a GSP. So grateful!”


“Shannon was very considerate with our last minute request, which was appreciated. She did the meet and greet thoughtfully with her current pups, to give everyone the best chance of harmony. Bill came back from his stay with a wagging tail and was exhausted, both of which are a good sign. I wouldn't hesitate to use Shannon again!”


“Our son was getting married in upstate NY so we needed a sitter for our dog Kai while we were away. We have always left Kai with either family or friends, but since everyone we knew was attending the wedding I reached out to Laura. We set up a meet and greet -I knew from the first time I met her that she was a perfect match. She was warm and kind - obviously a dog lover - and she made a connection with our normally shy dog right away. She asked a lot of questions about Kai's habits - she wanted to make sure she followed his normal daily routine so that he would be comfortable in her home.. Her house is beautiful and she has a large, fenced in back yard that allowed Kai to run free in a safe environment. Laura took him for a 3 mile daily walk, and sent many pictures and updates the whole 6 days she had him. He became a part of her family❤️ I cannot say enough about how happy we were to have found her. She gave us peace of mind that Kai was well loved and cared for so we were able to enjoy the wedding without any worries. I would HIGHLY recommend Laura to anyone looking for a sitter!!”


“Julius and family took good care of our dog. Julius is super-responsive and sent several cute pictures of the visit. It looked like everyone got along well and were very active. Our dog came home exhausted, which is a good thing. We also needed to adjust the end time a little bit, and Julius was very accommodating of the last minute change.”


“Absolutely perfect at every turn. Francis was great with our Goldendoodle. She sent pictures and looked after her with great care. We can’t recommend her enough. The home was perfect for dogs with a fenced in backyard and comfortable places for her to sit/sleep/relax.”


“I highly recommended Sherry, she’s an angel! She had our Finn finn for 6 days and it was our first time to get a dog sitter. We are a bit uneasy at first coz our dog still needs training. (Not friendly with other humans and dogs he just met) also there’s the barking situation. She’s an angel bcos she was able to gain our dog’s trust at a very short period of time and our dog didn’t give any problem at all. A Complete turnaround to what we were expecting. (Big Sigh of relief ?) We enjoyed our vacation and didn’t even worried about our dog bcos she never fails to update us. Highly recommended and we’ll definitely book her again. P.S we came back to get his crate and our dog was sooo happy to see her and he let her pet him, no sweat. We never saw our dog that happy whenever we go to our sis in law’s house and every time they tried to pet him, he will dodge. ? It’s just amazing experience overall.”


“Our puppy had a great time staying at Brittany’s house for the day. I felt he was in good hands while we were gone for the day. We will definitely use her services again. Thank you Brittany!”


“This couple are the sweetest people you will ever meet and they love dogs so much you can really tell they care for every dog they sit for Will most definitely be going to them again my puppy got to play with other dogs and have fun thank you guys for taking such good care for our puppy”



“I can’t recommend Maria enough! She provided exceptional and extremely compassionate care for our dog, Pluto, who boarded with Maria and her family for almost 3 weeks. I was very anxious about leaving Pluto with a stranger because he has some complicated health issues. However, before Pluto boarded with Maria and her family, she came to our place to meet us and discuss Pluto’s needs. She reassured us that she knew how to deal with seizures and could administer Pluto’s pills. Maria was great about reaching out when Pluto was experiencing stomach problems and was very responsive whenever I reached out for updates. She regularly sent us photos of Pluto enjoying his time with other dogs. The fact that Maria also has her own dogs and boards other dogs was a huge plus since Pluto is always with our family at home or at doggy daycare, so he hates being alone. In addition to being highly experienced in pet care, Maria is also extremely compassionate. I always felt that Pluto was in the best hands possible. Maria made a very difficult situation for my family easier since we knew he was getting the best care possible. Thank you so much, Maria! We will definitely be requesting your help again in the future and recommending you to anyone looking for a reliable and caring pet sitter!”


“We couldn’t have asked for a better experience for Piper’s overnight stay with a sitter! Karen did a fantastic job keeping us updated throughout the five days, sending daily photos and messages that gave us peace of mind. It was clear that Piper was well taken care of, happy, and even got to enjoy many trips to the park! Knowing she was in such great hands made our time away so much easier. We highly recommend Karen and would absolutely book with her again in the future!”


“I couldn't have asked for a better experience with Nadjeska as my pet sitter for my Ruby! Nadjeska's warmth and genuine love for animals are evident. Over the week and a half that she cared for Ruby, she provided not only exceptional attention but also sent regular updates and adorable pictures, which put my mind at ease. It was clear that Ruby was thriving in her care, and I loved seeing her happy and playful in the photos. Nadjeska's hospitality and dedication truly exceeded my expectations. I highly recommend her to any pet owner seeking a reliable and loving caretaker!”


“I recently had Jieun look after my dog and I couldn’t be happier with the experience. From start to finish, she went above and beyond to ensure Skippy was well cared for and comfortable. Skippy can be reserved with new people, but he quickly warmed up to Jieun. Communication was another standout aspect of the stay. I received regular updates and great photos of Skippy having a good time, which put my mind at ease. It was clear that Jieun genuinely cared about Skippy’s well-being. The level of attention and care Skippy received was outstanding. I highly recommend Jieun if you need someone to care for your pet. Skippy and I are both incredibly grateful for the exceptional stay!”


“We have a 10 month old rescue and were looking for a family with multiple dogs to keep our pup entertained and engaged for our first time leaving him for over a week. Kristin is the perfect fit! She is patient and accommodating and very communicative. Our dog thrived in her care and yours will too. We hope she is available next time we go out of town.”



“Mary Jo was great! She was available during a major holiday which was so amazing for us. She is very quick to respond before the booking starts, during, and at pick up. She kept us updated on how our dog was doing & was very friendly. Her young children love dogs and I’m sure made our old guy feel right at home. He was happy and not anxious at all when we picked him up. Thank you so much!!”


“Samantha was such a wonderful friend to our baby Clover while we were on vacation. She sent lots of pics and updates and it was clear they both really enjoyed each other's company. She was also extremely flexible and accommodating when we needed to extend Clover's stay a few days, and we really appreciated that! Samantha will definitely be our go-to when we need a sitter in Westbrook!”


“Ariel has watched Max a few times now and each time has been a great experience. Ariel keeps me updated with photos, has a giant fenced in yard for Max to roam, and accommodates any special care needs! Max always comes home happy! Would definitely recommend Ariel to others!”

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1. Britanny B.


“We felt very comfortable leaving our Sheltie Winston with Brittney (and family!) and the daily updates and pics were great so we never worried while away. Definitely will use her service again!”


2. Holly M.

“Holly was great! As a nervous dog mom, she made me feel reassured that Hank was in capable hands from the first Facetime meet and greet to continual updates and photos throughout Hank's stay!”


3. Laura G.

“Laura was so wonderful! She made our family and our pup so comfortable and sent pictures and updates throughout our trip. We were so happy knowing that our dog got to be part of Laura’s family while we were away. We’d highly recommend Laura!”


4. Melisa M.

“My dog had a great time. Because she is/was an anxiety prone rescue of 8 months, I was worried she would become very nervous again. But she was very happy. Melissa's back yard is great and I am sure that was one reason my small dog was so happy. And Melissa is very accommodating.”


5. Erica & Thomas C.

“Erica, Thomas, and their family were amazing to my sweet Kona! She’s a young GSP so she’s very active and high energy. She’s a great dog but not everyone can handle her energy level. They were great and immediately knew what to do with exercising and treating her like family. It helps that they have a big front lawn and had other dogs staying with them too! Kona made great friends judging from the pics. But most importantly, they went out of their way to be her dog handler for us on our wedding day. They made our special day even more magical by letting Kona participate in the ceremony as our dog of honor. She was tired for 2 full days after we picked her up! That’s a long time for a GSP. So grateful!”


6. Shannon C.

“Shannon was very considerate with our last minute request, which was appreciated. She did the meet and greet thoughtfully with her current pups, to give everyone the best chance of harmony. Bill came back from his stay with a wagging tail and was exhausted, both of which are a good sign. I wouldn't hesitate to use Shannon again!”


7. Laura C.

“Our son was getting married in upstate NY so we needed a sitter for our dog Kai while we were away. We have always left Kai with either family or friends, but since everyone we knew was attending the wedding I reached out to Laura. We set up a meet and greet -I knew from the first time I met her that she was a perfect match. She was warm and kind - obviously a dog lover - and she made a connection with our normally shy dog right away. She asked a lot of questions about Kai's habits - she wanted to make sure she followed his normal daily routine so that he would be comfortable in her home.. Her house is beautiful and she has a large, fenced in back yard that allowed Kai to run free in a safe environment. Laura took him for a 3 mile daily walk, and sent many pictures and updates the whole 6 days she had him. He became a part of her family❤️ I cannot say enough about how happy we were to have found her. She gave us peace of mind that Kai was well loved and cared for so we were able to enjoy the wedding without any worries. I would HIGHLY recommend Laura to anyone looking for a sitter!!”


8. Julius G.

“Julius and family took good care of our dog. Julius is super-responsive and sent several cute pictures of the visit. It looked like everyone got along well and were very active. Our dog came home exhausted, which is a good thing. We also needed to adjust the end time a little bit, and Julius was very accommodating of the last minute change.”


9. Francis E.

“Absolutely perfect at every turn. Francis was great with our Goldendoodle. She sent pictures and looked after her with great care. We can’t recommend her enough. The home was perfect for dogs with a fenced in backyard and comfortable places for her to sit/sleep/relax.”


10. Sherry B.

“I highly recommended Sherry, she’s an angel! She had our Finn finn for 6 days and it was our first time to get a dog sitter. We are a bit uneasy at first coz our dog still needs training. (Not friendly with other humans and dogs he just met) also there’s the barking situation. She’s an angel bcos she was able to gain our dog’s trust at a very short period of time and our dog didn’t give any problem at all. A Complete turnaround to what we were expecting. (Big Sigh of relief ?) We enjoyed our vacation and didn’t even worried about our dog bcos she never fails to update us. Highly recommended and we’ll definitely book her again. P.S we came back to get his crate and our dog was sooo happy to see her and he let her pet him, no sweat. We never saw our dog that happy whenever we go to our sis in law’s house and every time they tried to pet him, he will dodge. ? It’s just amazing experience overall.”


11. Brittany W.

“Our puppy had a great time staying at Brittany’s house for the day. I felt he was in good hands while we were gone for the day. We will definitely use her services again. Thank you Brittany!”


12. Wilson & Cherryl E.

“This couple are the sweetest people you will ever meet and they love dogs so much you can really tell they care for every dog they sit for Will most definitely be going to them again my puppy got to play with other dogs and have fun thank you guys for taking such good care for our puppy”




13. Maria D.

“I can’t recommend Maria enough! She provided exceptional and extremely compassionate care for our dog, Pluto, who boarded with Maria and her family for almost 3 weeks. I was very anxious about leaving Pluto with a stranger because he has some complicated health issues. However, before Pluto boarded with Maria and her family, she came to our place to meet us and discuss Pluto’s needs. She reassured us that she knew how to deal with seizures and could administer Pluto’s pills. Maria was great about reaching out when Pluto was experiencing stomach problems and was very responsive whenever I reached out for updates. She regularly sent us photos of Pluto enjoying his time with other dogs. The fact that Maria also has her own dogs and boards other dogs was a huge plus since Pluto is always with our family at home or at doggy daycare, so he hates being alone. In addition to being highly experienced in pet care, Maria is also extremely compassionate. I always felt that Pluto was in the best hands possible. Maria made a very difficult situation for my family easier since we knew he was getting the best care possible. Thank you so much, Maria! We will definitely be requesting your help again in the future and recommending you to anyone looking for a reliable and caring pet sitter!”


14. Karen F.

“We couldn’t have asked for a better experience for Piper’s overnight stay with a sitter! Karen did a fantastic job keeping us updated throughout the five days, sending daily photos and messages that gave us peace of mind. It was clear that Piper was well taken care of, happy, and even got to enjoy many trips to the park! Knowing she was in such great hands made our time away so much easier. We highly recommend Karen and would absolutely book with her again in the future!”


15. Nadjeska R.

“I couldn't have asked for a better experience with Nadjeska as my pet sitter for my Ruby! Nadjeska's warmth and genuine love for animals are evident. Over the week and a half that she cared for Ruby, she provided not only exceptional attention but also sent regular updates and adorable pictures, which put my mind at ease. It was clear that Ruby was thriving in her care, and I loved seeing her happy and playful in the photos. Nadjeska's hospitality and dedication truly exceeded my expectations. I highly recommend her to any pet owner seeking a reliable and loving caretaker!”


16. Jieun B.

“I recently had Jieun look after my dog and I couldn’t be happier with the experience. From start to finish, she went above and beyond to ensure Skippy was well cared for and comfortable. Skippy can be reserved with new people, but he quickly warmed up to Jieun. Communication was another standout aspect of the stay. I received regular updates and great photos of Skippy having a good time, which put my mind at ease. It was clear that Jieun genuinely cared about Skippy’s well-being. The level of attention and care Skippy received was outstanding. I highly recommend Jieun if you need someone to care for your pet. Skippy and I are both incredibly grateful for the exceptional stay!”


17. Kristin T.

“We have a 10 month old rescue and were looking for a family with multiple dogs to keep our pup entertained and engaged for our first time leaving him for over a week. Kristin is the perfect fit! She is patient and accommodating and very communicative. Our dog thrived in her care and yours will too. We hope she is available next time we go out of town.”




18. Mary Jo M.


“Mary Jo was great! She was available during a major holiday which was so amazing for us. She is very quick to respond before the booking starts, during, and at pick up. She kept us updated on how our dog was doing & was very friendly. Her young children love dogs and I’m sure made our old guy feel right at home. He was happy and not anxious at all when we picked him up. Thank you so much!!”


19. Samantha O.

“Samantha was such a wonderful friend to our baby Clover while we were on vacation. She sent lots of pics and updates and it was clear they both really enjoyed each other's company. She was also extremely flexible and accommodating when we needed to extend Clover's stay a few days, and we really appreciated that! Samantha will definitely be our go-to when we need a sitter in Westbrook!”


20. Ariel T.

“Ariel has watched Max a few times now and each time has been a great experience. Ariel keeps me updated with photos, has a giant fenced in yard for Max to roam, and accommodates any special care needs! Max always comes home happy! Would definitely recommend Ariel to others!”
How Rover works
1. Search
Read verified reviews by dog parents like you and choose a boarder who’s a great match for you and your dogs2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs while you’re away3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
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.
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We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Dog Boarding FAQs
Frequently asked questions about Rover
As of May 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 $28 to as high as $63 per night.
As of May 2025, 408 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, 87% of Chester dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Chester have an average of 19 years of experience. 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 408 dog boarding sitters in Chester on Rover, so you’re sure to find the perfect match for your dog! In Chester, 98% of sitters offer daily exercise, 98% offer medication administration, and 98% 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.
