Dog Boarding in Cheshire, MA
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Top rated Cheshire dog boarders
“Brooke immediately set our minds at ease by texting us just several hours after dropping our dog off, telling us that Ella had eaten and was getting along with everybody. We were then able to relax and begin to enjoy our trip. She kept the messages and photos coming which was so nice! If we every go away again we will definitely leave Ella with Brooke.”
“Tetiana is an amazing petsitter! She is communicative, attentive to details and, most importantly, has a loving and giving heart. She and her lovely mom Maria treated my Edna like their own, with play and cuddles and outdoor adventures — many pictures clearly showing to me Edna’s enjoyment. I hope Edna can return to Tetiana’s and I highly recommend her.”
“Elli was awesome with our dog, Matilda. She sent us pictures and kept us updated on her well-being. I felt very comfortable leaving our pup with Elli as I knew she was getting excellent care and lots of love. Five stars!”
“I was very happy with this service. Mahayla was able to take Dougal onshort notice and was very accommodating to my schedule. I got daily videos that were much appreciated!!”
“Jess was good. We booked her while we were in Berkshires for our weekend ski/snowboard trip. It was a basically a 2 day noticed thankfully she was available. We enjoyed ourselves knowing that our Shiba girl Yumi was taken care of. Twice a day updates as requested. Whenever were in the area again, will rebook. Thanks Jess!”
“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.”
About: I’ve owned and taken care of dogs more than half my life. They are family and should be treated as such. I use a gentle approach and we will make sure we are the right fit before committing to a stay. I currently work from home with our fur baby Goldie. We go for walks or hang out in the AC, or by the warm fire. Offering play and enrichment throughout the day. I have a fenced in yard, plenty of doggie beds, treats and tons of affection. A super friendly medium sized dog named Goldie and a fast moving 8 year old daughter. Must be dog and kid friendly. No cats in home.
“Ericca took very good care of my dog while I was gone for three days. She sent updates and photos without me even asking, and he was in great spirits when I picked him up. Highly recommend!”
“Kate is a wonderful host. Our blue heeler mix is high energy and Kate really impressed us with care and attention she showed. Kate was very attentive and sent us pics and updates of our dog. I give her the best rating. A pleasure to work with.”
“Jenn was a magnificent sitter for our pup, Mac. She made our trip much more enjoyable by constantly communicating with us and sending us pictures and videos. I could not recommend her enough for your pet needs!”
“Cheryle is a great dog-sitter. Her house is well set-up for a little dog, with low couches, ramps and lots of cozy spots. Her dachsund was a great companion for my dog, Roscoe. Roscoe came home calm and happy after 5 days at Cherlye's. He was on a variety of meds for a sore back and she managed all those well and took great care of him.”
About: Retired Military Veteran, 12 years of service. Very reliable and love animals. I love all breeds of dogs regardless of the stereotypes. Can’t wait to start watching your dogs. I have a vast background, military and emergency services. I’m in the process of becoming a nys emt and then will go on for my paramedic hopefully my flight medic. I’ve grown up with dogs and haven’t had a dog in a year. Feel free to look up my information in the military to know that I’m a veteran. I am always available even for a last minute vacation. My husband and I would love to help who ever needs that extra tlc while their owners go away. I’m home all day every day. I work overnights so my hubby could let your little or big pups out to go potty before work. They will have free range of the house unless they are specifically crated then I can put them in the crate and take them out when needed.
“Karl and his dogs are very welcoming. Karl’s yard is well suited for the dogs with a large space and a fence. Karl communicates timely and goes out of his way to ensure all goes well. All the dogs got along well and our dogs adjusted well on both sends of their stay.”
“Sandra is super professional and took great care of our dog. She sent lots of great pictures and communicated really well. Sandra is clearly both a real dog lover and terrific caregiver.”
“Mikayla was super accommodating to our hectic schedule and helped work around some funny times that we had. She sent picture updates of my dog and her response time was fast whenever I had questions or was just checking in. We did a meet and greet before boarding to make sure she was a perfect fit for my crazy goofy dog and it was a sure hit! I felt safe and comfortable leaving my dog with Mikayla and I will definitely be using her services again for future boarding. 10/10 recommend!”
“Robin & John were fantastic. They (and their doggos) helped Patch feel right at home. He got lots of love and exercise in the yard. We would definitely leave Patch with them again.”
“We cannot say enough nice things about Laura. She took our two medium sized dogs in for over a week when we were in a pinch. She took all of our instructions to make sure our dogs were well taken care of and kept us updated with pictures the entire time…which helped us enjoy our vacation free of worry!”
Loving dog boarding sitters in your neighborhood
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Brooke B.
Star Sitter
“Brooke immediately set our minds at ease by texting us just several hours after dropping our dog off, telling us that Ella had eaten and was getting along with everybody. We were then able to relax and begin to enjoy our trip. She kept the messages and photos coming which was so nice! If we every go away again we will definitely leave Ella with Brooke.”
Tetiana M.Star Sitter
“Tetiana is an amazing petsitter! She is communicative, attentive to details and, most importantly, has a loving and giving heart. She and her lovely mom Maria treated my Edna like their own, with play and cuddles and outdoor adventures — many pictures clearly showing to me Edna’s enjoyment. I hope Edna can return to Tetiana’s and I highly recommend her.”
Elli S.
“Elli was awesome with our dog, Matilda. She sent us pictures and kept us updated on her well-being. I felt very comfortable leaving our pup with Elli as I knew she was getting excellent care and lots of love. Five stars!”
Mahayla G.
“I was very happy with this service. Mahayla was able to take Dougal onshort notice and was very accommodating to my schedule. I got daily videos that were much appreciated!!”
Jess L.
“Jess was good. We booked her while we were in Berkshires for our weekend ski/snowboard trip. It was a basically a 2 day noticed thankfully she was available. We enjoyed ourselves knowing that our Shiba girl Yumi was taken care of. Twice a day updates as requested. Whenever were in the area again, will rebook. Thanks Jess!”
Yenifer V.
“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.”
Irene T.
About: I’ve owned and taken care of dogs more than half my life. They are family and should be treated as such. I use a gentle approach and we will make sure we are the right fit before committing to a stay. I currently work from home with our fur baby Goldie. We go for walks or hang out in the AC, or by the warm fire. Offering play and enrichment throughout the day. I have a fenced in yard, plenty of doggie beds, treats and tons of affection. A super friendly medium sized dog named Goldie and a fast moving 8 year old daughter. Must be dog and kid friendly. No cats in home.
Aura G.
“Our puppy had a fabulous experience I. Aura’a household care. We will use her service again!”
Ericca B.Star Sitter
“Ericca took very good care of my dog while I was gone for three days. She sent updates and photos without me even asking, and he was in great spirits when I picked him up. Highly recommend!”
Kate B.
“Kate is a wonderful host. Our blue heeler mix is high energy and Kate really impressed us with care and attention she showed. Kate was very attentive and sent us pics and updates of our dog. I give her the best rating. A pleasure to work with.”
Jennifer C.Star Sitter
“Jenn was a magnificent sitter for our pup, Mac. She made our trip much more enjoyable by constantly communicating with us and sending us pictures and videos. I could not recommend her enough for your pet needs!”
Cheryle W.Star Sitter
“Cheryle is a great dog-sitter. Her house is well set-up for a little dog, with low couches, ramps and lots of cozy spots. Her dachsund was a great companion for my dog, Roscoe. Roscoe came home calm and happy after 5 days at Cherlye's. He was on a variety of meds for a sore back and she managed all those well and took great care of him.”
Ivan O.
“Ivan was a great host for Sadie. He sent photos and updates during her stay. He was also understanding and accommodating to my travel arrangements.”
Nikki R.
“What I know about Nikki is that she's a kind and caring person and has been around dogs most of her life. When she has been around any of my dogs she has always been attentive.”
Sylva & Mark M.Star Sitter
“Silva and Mark took fabulous care of my senior dachshund. She is a bit “special needs” and they were happy to accommodate her💖. I will gladly bring her again !”
Karl K.
“Karl and his dogs are very welcoming. Karl’s yard is well suited for the dogs with a large space and a fence. Karl communicates timely and goes out of his way to ensure all goes well. All the dogs got along well and our dogs adjusted well on both sends of their stay.”
Sandra W.
“Sandra is super professional and took great care of our dog. She sent lots of great pictures and communicated really well. Sandra is clearly both a real dog lover and terrific caregiver.”
Mikayla H.Star Sitter
“Mikayla was super accommodating to our hectic schedule and helped work around some funny times that we had. She sent picture updates of my dog and her response time was fast whenever I had questions or was just checking in. We did a meet and greet before boarding to make sure she was a perfect fit for my crazy goofy dog and it was a sure hit! I felt safe and comfortable leaving my dog with Mikayla and I will definitely be using her services again for future boarding. 10/10 recommend!”
Robin & John P.Star Sitter
“Robin & John were fantastic. They (and their doggos) helped Patch feel right at home. He got lots of love and exercise in the yard. We would definitely leave Patch with them again.”
Laura P.Star Sitter
“We cannot say enough nice things about Laura. She took our two medium sized dogs in for over a week when we were in a pinch. She took all of our instructions to make sure our dogs were well taken care of and kept us updated with pictures the entire time…which helped us enjoy our vacation free of worry!”
Over 15 pet parents in Cheshire have booked dog boarding
Popular requests near you
Select a filter and find qualifying Cheshire sitters!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 dogs
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
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per night for dog boarding in Cheshire is $60
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 Cheshire average 10 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Aug 2025, the median cost of dog boarding in Cheshire 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 Cheshire dog boarding rates can be found as low as $26 to as high as $32 per night.
As of Aug 2025, 46 sitters provided dog boarding in Cheshire. 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 Cheshire dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Cheshire have an average of 15 years of experience. 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 Cheshire.
Rover makes it easy to find Cheshire 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 46 dog boarding sitters in Cheshire on Rover, so you’re sure to find the perfect match for your dog! In Cheshire, 100% of sitters offer daily exercise, 100% offer medication administration, and 100% 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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