Dog Boarding in Chesterville, MD
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Top rated Chesterville dog boarders
“My dog Barkley was so well cared for by Megan & Jacob! I could tell he felt comfortable right from the start, and I appreciated their great communication before and during Barkley’s time with them.”
“Paris is excellent in every way! She really helps us out on short notices.She is caring with our big boy Deuce and sends us multiple photos & videos.Paris is incredibly nice and accommodating, and communicated with us frequently. We vacation often so Paris and the fam is Deuce second family lol .Thanks so much ❤️”
“Lindsay was so great with Olivia! She was able to watch her very last minute and work with our schedule. She kept me updated with pictures. When we took Olivia and brought her back the second night Olivia ran right up to her and her daughter crying with excitement. She came home all tired out which showed how much fun she had.”
“Barb was fantastic! We chose her because of her experience with dogs of all ages, especially older pups. Although our pup was a bit nervous, she seemed to settle in well and made herself at home. Really appreciated the updates and pics to let us know all was good.”
“Another great visit at Camp Myra. Peanut played and snuggled and had a great time. Already booked for two more trips this year. Thanks Myra for taking great care of little Peanut.”
“Candice was great with Tilley. She has a beautiful & clean home. She sent me pictures daily and informed me of some activities. I feel very comfortable leaving my dog with Candice. I will definitely use Candice again. Thank you so much Candice !”
“Jen was great!! We left our two senior chihuahuas with her for an overnight, and we were a bit nervous, as they are older and very tiny (5 lbs and 6.5 lbs). She was very patient with us and was great with the dogs. She texted us to let us know that everything was fine, and kept us updated along the way. HIGHLY RECOMMEND Jen. Will definitely use her again!!”
“I’m thankful for Kari & Jospeh’s family for loving and caring my baby like their own, it was stress free time during his stay we’re I don’t have to worry about how he is doing since he is in great hands. My boy would love to come back again,”
About: I have been pet sitting for over 20 years and have experience with furry, feathery, and scaly creatures of all shapes and sizes. I have experience with puppies and kittens all the way up to senior pets, with and without special needs. I have experience with blind and deaf animals and can administer pet medications. We have a half acre that is fenced in and perfect for your pets to play. I’m a teacher, so during the summers, fall and spring break, and weekends I am home full time. During the school year, I am usually home by 3 p.m. Pets may use crates (collars off) or free-roam in the house depending upon what they are used to at home. I like to keep our rules consistent with what pets are used to at home. I allow our pets on furniture and beds.
“Rackeem was awesome with my dogs while I was on vacation! He took excellent care of my fur babies and I highly recommend him! He provides daily updates and pictures so you can be assured your pets are safe and doing well while in his care. He's also a great trainer as well! He helped my very active 14 month old pup 🐶 stop pulling so much while on our walks.”
“Recently left my puppy with Thelma. I was able to go on vacation without concerns for my pups well being. She took extra precautions to keep him safe by putting up extra barricades around her fence to prevent him from escaping. My pup loved playing with her dogs. i definitely will have her watch my dog again.”
“Outstanding with the care that was given to our dogs Tempest and Peanut. I received updates everyday with pictures! They certainly looked happy and made themselves right at home even jumping on Janice’s lap ! We will definitely use them again whenever we decide to go away for even a weekend ! Thank you for all the love and care you gave Tempest and Peanut !♥️♥️”
Loving dog boarding sitters in your neighborhood
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Gisel D.Star Sitter
“Gisel was great, Shes super nice and the communication throughout my booking was great. I received daily updates on my pup and he had a great time in her care.”
Jenny M.
“Buckley had a wonderful time during his stay. Jenny was a wonderful sitter and super accommodating when I had a delay in pickup, I’m more than happy to book with her again.”
Jacob & Megan W.
Star Sitter
“My dog Barkley was so well cared for by Megan & Jacob! I could tell he felt comfortable right from the start, and I appreciated their great communication before and during Barkley’s time with them.”
Erin I.Star Sitter
“Erin was a wonderful pet sitter. I will definitely use her again. My pup enjoyed his friends there and the big yard! He was happy and healthy when I picked him up.”
Jill & Chad H.
“Another amazing time for our Suzie! We got tons of fun videos and photos during her stay. Along with a bunch of great updates. Can’t recommend them enough!”
Paris V S.Star Sitter
“Paris is excellent in every way! She really helps us out on short notices.She is caring with our big boy Deuce and sends us multiple photos & videos.Paris is incredibly nice and accommodating, and communicated with us frequently. We vacation often so Paris and the fam is Deuce second family lol .Thanks so much ❤️”
Lindsay G.Star Sitter
“Lindsay was so great with Olivia! She was able to watch her very last minute and work with our schedule. She kept me updated with pictures. When we took Olivia and brought her back the second night Olivia ran right up to her and her daughter crying with excitement. She came home all tired out which showed how much fun she had.”
Barbra F.Star Sitter
“Barb was fantastic! We chose her because of her experience with dogs of all ages, especially older pups. Although our pup was a bit nervous, she seemed to settle in well and made herself at home. Really appreciated the updates and pics to let us know all was good.”
Myra D.
“Another great visit at Camp Myra. Peanut played and snuggled and had a great time. Already booked for two more trips this year. Thanks Myra for taking great care of little Peanut.”
Candice M.Star Sitter
“Candice was great with Tilley. She has a beautiful & clean home. She sent me pictures daily and informed me of some activities. I feel very comfortable leaving my dog with Candice. I will definitely use Candice again. Thank you so much Candice !”
Katherine B.Star Sitter
“Katherine and her family took wonderful care of our boys. They thoroughly enjoyed their stay and were cere well cared for. The updates and action photos were great.”
Jen C.Star Sitter
“Jen was great!! We left our two senior chihuahuas with her for an overnight, and we were a bit nervous, as they are older and very tiny (5 lbs and 6.5 lbs). She was very patient with us and was great with the dogs. She texted us to let us know that everything was fine, and kept us updated along the way. HIGHLY RECOMMEND Jen. Will definitely use her again!!”
Jill & Thomas K.
“My dog had the absolute best time! I appreciated all of the picture updates and how she was treated like one of their own! Highly recommend!!”
Briana & Isaiah S.Star Sitter
“Briana and Isaiah were lovely! They welcomed my dog Steven into their home, and treated him like one of the family. I highly recommend their services 😊”
Kari & Jospeh M.
“I’m thankful for Kari & Jospeh’s family for loving and caring my baby like their own, it was stress free time during his stay we’re I don’t have to worry about how he is doing since he is in great hands. My boy would love to come back again,”
Jessica R.
“Jessica was a great dog sitter for my pit-mix Hazel. Hazel can be a little much to handle but she got along with their dog Tanner great and I nearly had to drag her home after her stay! The fenced in back yard is spacious for the dogs to run around and they were very friendly and communicative! Will definitely have Hazel over again next time we are away! Thank you Jessica!”
Rackeem R.
“Rackeem was awesome with my dogs while I was on vacation! He took excellent care of my fur babies and I highly recommend him! He provides daily updates and pictures so you can be assured your pets are safe and doing well while in his care. He's also a great trainer as well! He helped my very active 14 month old pup 🐶 stop pulling so much while on our walks.”
Emily M.
“Emily and her family were amazing! She sent tons of pictures and made my 4 month old puppy feel safe in her home. I appreciate everything she did and would use her again!”
Thelma K.
“Recently left my puppy with Thelma. I was able to go on vacation without concerns for my pups well being. She took extra precautions to keep him safe by putting up extra barricades around her fence to prevent him from escaping. My pup loved playing with her dogs. i definitely will have her watch my dog again.”
Janice & Charles B.Star Sitter
“Outstanding with the care that was given to our dogs Tempest and Peanut. I received updates everyday with pictures! They certainly looked happy and made themselves right at home even jumping on Janice’s lap ! We will definitely use them again whenever we decide to go away for even a weekend ! Thank you for all the love and care you gave Tempest and Peanut !♥️♥️”
Popular requests near you
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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 Chesterville is $45
Why Choose Rover?
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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 Chesterville average 13 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Aug 2025, 217 sitters provided dog boarding in Chesterville. 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, 92% of Chesterville dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Chesterville have an average of 21 years of experience. Dog boarding sitters with repeat customers have an average of 13 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 Chesterville.
Rover makes it easy to find Chesterville 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 217 dog boarding sitters in Chesterville on Rover, so you’re sure to find the perfect match for your dog! In Chesterville, 96% of sitters offer daily exercise, 100% offer medication administration, and 96% 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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