Dog Boarding in Chesapeake
Find a loving dog sitter to watch your dog overnight at your sitter's home.
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Top rated Chesapeake dog boarders
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“My pup has stayed with Megan twice now and she loves it! I’m so glad I decided to use Rover instead of a boarding place. Megan took really good care of her and sends constant updates! 5 stars!!!”
“Kathleen was amazing. I have used plenty of sitters with Theo since I’m out of town often. Unfortunately, my usual boarding sitter was no longer providing services so I have been on the hunt for a reliable sitter that actually follows the instructions I leave. I was definitely nervous using a new sitter but Kathleen quickly put me to ease within the first few hours. She updated me several times each day, checked before giving him treats, and gave him lots of cuddles and attention. Overall, I was able to enjoy my trip knowing my baby was in good hands. Thanks so much Kathleen!”
“I have boarded Cookies more than a dozen times over the past 12 years and Julie will be my go to dog boarder! She asked great questions before drop off and communicated the schedule at pick up so we could stay on schedule at home. She sent me several pictures while I was away so that I could see my fur baby. She let me know how she was adjusting to her environment from the moment she arrived. She shared that my senior dog wasn’t ready to get up when the rest of the family was ready, so they let her sleep in❤️. When my fur baby was leaving, she looked back at the door to see if Julie was coming with us. I look forward to my next trip because I know I can relax and not worry about my dogs’ care.”
“Ellen is wonderful and took excellent care of my dog! Her fenced back yard was great for him! Ellen was awesome about communicating with me during the boarding and she texted some adorable pictures! Highly recommended!”
“NOVA had a Wonderful time with Jen. Nova is sweet and can be shy but has a lot of energy. Jen’s big fenced back yard is ideal for Nova who is a teenage dog to romp and play. This was Nova’s second time staying with Jen. Nova stayed (9) days and Jen communicated well, sent lots of pictures and gave updates on Nova’s routine while staying with her. I highly recommend Jen to watch Nova again. Any dog staying with Jen is in good hands.”
“Such a great sitter! She made me so comfortable leaving my babies with her and she checked in with me everyday with texts and photos. My dogs felt right at home and were treated like family. Highly recommend Gail for anyone looking for a reliable, caring dog sitter!”
“My dogs seemed to have a great time with Orly. They were very tired when they got home. My experience with Orly was wonderful and I hope to have Baxter and Harper stay with her again.”
“Tanaya was great! She was very welcoming to my Coco, and she kept me updated throughout the stay. Her other dogs were also very sweet and nice to Coco, and I believe Coco has new friends 🥰. Thank you so much for everything Tanaya! We will definitely return.”
“Was amazing all around. I know my dog enjoyed himself and her communication and picture updates were always fast and well needed given my 2 week separation from my fur baby. Will be reaching out again if I ever need a sitter!”
“MaryAnn did an awesome job watching my dog. She took her in on short notice over the holidays and sent me great pictures every day. She even gave her a small birthday party with extra turkey for dinner! Highly recommend!”
“Beth and her family were so great with our dog! They were reliable, caring, and kept us updated with photos and messages throughout the stay. Picked up a happy, and well cared for pup and will definitely book with them again!”
“Michelle was great, she sent me photos and promptly responded to messages. Most of all Zu adjusted very well to her and her pups. I would definitely book with her again!”
“Dane and Amber are incredible hosts! Our dogs had an amazing time with them — it’s clear they were well cared for and had lots of fun. They’re professional, reliable, and truly passionate about what they do. You can absolutely trust them with your pets. We’re so grateful to have found such a great Rover family!”
“Sean is a great sitter to nurture your puppy while you're away from home. Sean sent daily photos and videos, gave our puppy multiple baths and encouraged her to have TONS of playtime with his very friendly pups. Sean is an excellent pet professional that you can trust. Highly recommend and we'll definitely be reaching out for his services again!”
“We love Maria and Matt! Our dog, Max has stayed with them twice and it is always great! Max comes home very happy and there is always lots of communication.”
“Chris and his fiancée were kind and loving to Lola from the start. They were communicative throughout her stay. Sending texts and pics of the fun she had in their fenced in backyard. Thanks for taking care of my fur baby!”
“It's no question if we are in the area again we would choose Stephen. Even though he had multiple dogs he made sure Car dog had the personal 1 on 1 attension she needed. He sent text and photos every day. New from our first meeting greet that he totally understands dogs they're habits and their signals. Thank you Stephen”
“Stacy was very communicative and helpful with our cat. She gave photo and video updates every night and let us know how she was adjusting to her new environment. She was caring by playing and holding her since our cat needs lots of activity.”
Loving dog boarding sitters in your neighborhood
Search Results
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
Megan L.Star Sitter
“My pup has stayed with Megan twice now and she loves it! I’m so glad I decided to use Rover instead of a boarding place. Megan took really good care of her and sends constant updates! 5 stars!!!”
Kathleen S.Star Sitter
“Kathleen was amazing. I have used plenty of sitters with Theo since I’m out of town often. Unfortunately, my usual boarding sitter was no longer providing services so I have been on the hunt for a reliable sitter that actually follows the instructions I leave. I was definitely nervous using a new sitter but Kathleen quickly put me to ease within the first few hours. She updated me several times each day, checked before giving him treats, and gave him lots of cuddles and attention. Overall, I was able to enjoy my trip knowing my baby was in good hands. Thanks so much Kathleen!”
Julie & Kenneth N.
“I have boarded Cookies more than a dozen times over the past 12 years and Julie will be my go to dog boarder! She asked great questions before drop off and communicated the schedule at pick up so we could stay on schedule at home. She sent me several pictures while I was away so that I could see my fur baby. She let me know how she was adjusting to her environment from the moment she arrived. She shared that my senior dog wasn’t ready to get up when the rest of the family was ready, so they let her sleep in❤️. When my fur baby was leaving, she looked back at the door to see if Julie was coming with us. I look forward to my next trip because I know I can relax and not worry about my dogs’ care.”
Ellen K.Star Sitter
“Ellen is wonderful and took excellent care of my dog! Her fenced back yard was great for him! Ellen was awesome about communicating with me during the boarding and she texted some adorable pictures! Highly recommended!”
Jenn B.Star Sitter
“NOVA had a Wonderful time with Jen. Nova is sweet and can be shy but has a lot of energy. Jen’s big fenced back yard is ideal for Nova who is a teenage dog to romp and play. This was Nova’s second time staying with Jen. Nova stayed (9) days and Jen communicated well, sent lots of pictures and gave updates on Nova’s routine while staying with her. I highly recommend Jen to watch Nova again. Any dog staying with Jen is in good hands.”
Gail T.Star Sitter
“Such a great sitter! She made me so comfortable leaving my babies with her and she checked in with me everyday with texts and photos. My dogs felt right at home and were treated like family. Highly recommend Gail for anyone looking for a reliable, caring dog sitter!”
Orly O.
“My dogs seemed to have a great time with Orly. They were very tired when they got home. My experience with Orly was wonderful and I hope to have Baxter and Harper stay with her again.”
Tanaya H.
“Tanaya was great! She was very welcoming to my Coco, and she kept me updated throughout the stay. Her other dogs were also very sweet and nice to Coco, and I believe Coco has new friends 🥰. Thank you so much for everything Tanaya! We will definitely return.”
Kaitlynn H.Star Sitter
“Was amazing all around. I know my dog enjoyed himself and her communication and picture updates were always fast and well needed given my 2 week separation from my fur baby. Will be reaching out again if I ever need a sitter!”
MaryAnn S.Star Sitter
“MaryAnn did an awesome job watching my dog. She took her in on short notice over the holidays and sent me great pictures every day. She even gave her a small birthday party with extra turkey for dinner! Highly recommend!”
Beth C.Star Sitter
“Beth and her family were so great with our dog! They were reliable, caring, and kept us updated with photos and messages throughout the stay. Picked up a happy, and well cared for pup and will definitely book with them again!”
Michelle R.Star Sitter
“Michelle was great, she sent me photos and promptly responded to messages. Most of all Zu adjusted very well to her and her pups. I would definitely book with her again!”
Amber & Dane C.
“Dane and Amber are incredible hosts! Our dogs had an amazing time with them — it’s clear they were well cared for and had lots of fun. They’re professional, reliable, and truly passionate about what they do. You can absolutely trust them with your pets. We’re so grateful to have found such a great Rover family!”
Sean M.
“Sean is a great sitter to nurture your puppy while you're away from home. Sean sent daily photos and videos, gave our puppy multiple baths and encouraged her to have TONS of playtime with his very friendly pups. Sean is an excellent pet professional that you can trust. Highly recommend and we'll definitely be reaching out for his services again!”
Maria & Matthew R.Star Sitter
“We love Maria and Matt! Our dog, Max has stayed with them twice and it is always great! Max comes home very happy and there is always lots of communication.”
Chris O.Star Sitter
“Chris and his fiancée were kind and loving to Lola from the start. They were communicative throughout her stay. Sending texts and pics of the fun she had in their fenced in backyard. Thanks for taking care of my fur baby!”
Stephen s.Star Sitter
“It's no question if we are in the area again we would choose Stephen. Even though he had multiple dogs he made sure Car dog had the personal 1 on 1 attension she needed. He sent text and photos every day. New from our first meeting greet that he totally understands dogs they're habits and their signals. Thank you Stephen”
Geneive M.Star Sitter
“Geneive is awesome!! She provided frequent updates and pictures and took the dogs on a lot of walks. She treated my two dogs as her own and I’m grateful.”
Sherry H.Star Sitter
“My pupper is always excited to see Sherry! Plus, the pics received while he's there show him happy and well loved. We will definitely use her services again!”
Stacy V.Star Sitter
“Stacy was very communicative and helpful with our cat. She gave photo and video updates every night and let us know how she was adjusting to her new environment. She was caring by playing and holding her since our cat needs lots of activity.”
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!
Why Choose Rover?
Cashless payments
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.
Dog Boarding FAQs
Frequently asked questions about Rover
As of Aug 2025, the median cost of dog boarding in Chesapeake is $38 per night, including service fees. Boarding your dog for one week typically costs $266. Sitters on Rover set their own rates based on their qualifications, your dog's needs, and their space's amenities. As a result, most Chesapeake dog boarding rates can be found as low as $25 to as high as $49 per night.
As of Aug 2025, 1,015 sitters provided dog boarding in Chesapeake. 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 Chesapeake dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Chesapeake have an average of 17 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 Chesapeake.
Rover makes it easy to find Chesapeake 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 1,015 dog boarding sitters in Chesapeake on Rover, so you’re sure to find the perfect match for your dog! In Chesapeake, 98% of sitters offer daily exercise, 99% offer medication administration, and 93% 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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