Dog Boarding Leonardtown

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Over 176
pet parents in Leonardtown have booked dog boarding

Leonardtown, Find top rated dog boarding

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Denise R.
Verified Background Check
Denise R.
Star Sitter
from
$35
per night
5.0 out of 5 stars
• 150 reviews
59 repeat clients
5 years of experience
hollywood, MD, 20636

“My dogs had a great stay! Denise even got my picky dog to eat from a dish. I have a very hard time with. Her eating. The pictures of my dogs relaxing with the family gave me peace of mind so that I could enjoy my vacation. I would highly recommend Denise.”

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Mary A.
Sitter Profile Image: Sarah F.
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Sarah F.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 58 reviews
12 repeat clients
30 years of experience
Leonardtown, MD, 20650

“Sarah was so easy to work with, responsive, and friendly. She has a lovely home with a great yard. I appreciated her checking in with updates and pics, and could enjoy my trip knowing my pup was in such great care. Will definitely book again and highly recommended!”

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Amy L.
Sitter Profile Image: Jaliah D.
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Jaliah D.
from
$60
per night
5.0 out of 5 stars
• 18 reviews
5 repeat clients
5 years of experience
Lexington park, MD, 20653

“Thank you so much for taking such wonderful care of my dog while I was away. It gave me real peace of mind knowing they were in such loving and capable hands. Your patience, kindness, and attention truly mean a lot, and I could tell my dog felt comfortable and happy with you. I really appreciate the time, effort, and love you put into caring for them. Thank you again for everything!”

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Kathi B.
Sitter Profile Image: Haley W.
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Haley W.
from
$55
per night
5.0 out of 5 stars
• 45 reviews
8 repeat clients
10 years of experience
Lusby, MD, 20657

“Haley is the best! She accommodated my schedule & went above and beyond for my fur baby, Charlie. I was able to go on an overnight trip with no stress about how Charlie was doing.”

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Sierra R.
Sitter Profile Image: Anika C.
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Anika C.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 47 reviews
14 repeat clients
45 years of experience
Mechanicsville, MD, 20659

“Anika did an excellent job with my baby, October. She communicated with me throughout his stay with texts, photos, videos. October wasn’t quite ready to leave her, which makes me feel the love and care she has for my furbaby. I will definitely be using her in the future.”

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Ron M.
Sitter Profile Image: Kathryn A.
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Kathryn A.
from
$55
per night
5.0 out of 5 stars
• 14 reviews
2 repeat clients
30 years of experience
Leonardtown, MD, 20650

“When I picked up Jackson, I was not sure he wanted to leave his vacation with Kathryn and her wonderful family! Sure he was excited to see us, but, then he laid down next to Kathryn as if he was feeling pretty comfortable at her home! She sent photos and write ups daily and this made me feel so much better about leaving him in her care. It was like he knew the family forever! This was the first time we went away without him in 8 years so I was a bit anxious about leaving. I would have no problems leaving him again if I have another opportunity to do so. I highly recommend Kathryn and I know he was very happy being there and well cared for. He enjoyed his daily walks and never missed a meal and perhaps, Me!!!! If there were 10 stars I would click everyone of them!”

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Carol N.
Sitter Profile Image: Daniela H.
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Daniela H.
from
$40
per night
5 years of experience
Prince Frederick, MD, 20678

About: I’ve been taking care of dogs and cats for friends and neighbors for the past 5 years. I absolutely love animals and treat every pet like they’re my own! 🐾❤️ Our family homeschools, so there’s almost always someone home. Your dog will be welcomed as part of our family, with plenty of attention, love, and companionship. They’ll rarely have to be home alone 😊 We have a Boston Terrier who is used to having other dogs around and does well sharing her space with them. I keep dogs on a leash when we go outside since we don’t have a fenced-in yard, and I take them out multiple times throughout the day for potty breaks and fresh air. When I need to leave the house, I crate the dogs for their safety and peace of mind. I want every pet staying with us to feel comfortable, cared for, and part of the family!

Sitter Profile Image: Lori W.
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Lori W.
from
$45
per night
5.0 out of 5 stars
• 80 reviews
31 repeat clients
20 years of experience
Chesapeake Beach, MD, 20732

“Lori, is wonderful! She cared for my little Sienna as if she were her own. She provided several updates daily including photos. I was always informed of Sienna’s activities. I’ll absolutely book Lori again!”

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Shawn Alexandra G.
Sitter Profile Image: Drew R.
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Drew R.
from
$45
per night
5.0 out of 5 stars
• 7 reviews
3 repeat clients
2 years of experience
Leonardtown, MD, 20650

“Amazing communication; super friendly 😊”

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Nikie W.
Sitter Profile Image: Tara L.
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Tara L.
from
$48
per night
5.0 out of 5 stars
• 1 review
20 years of experience
Montross, VA, 22520

“The boarding of my dog was fabulous. I got regular updates and photos to see how he was getting along with the other dog. when I picked him up He was nice and happy-naturally glad to see me- but still very happy with Tara. Their attention to detail was wonderful and I know he was taken care of with love. There was so much room for him to play and run and so many things to explore I know we had a terrific vacation with them. I am definitely going back.”

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Denise S.
Sitter Profile Image: Kelly G.
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Kelly G.
Star Sitter
from
$44
per night
5.0 out of 5 stars
• 341 reviews
157 repeat clients
25 years of experience
Hughesville, MD, 20637

“Kelly has watched Piper a few times for us now and we couldn’t be happier. She regularly sends updates, takes such amazing care of Piper, and adds little special touches during the stay. Kelly was flexible with us when we had a flight delay. Most importantly, Piper is so excited every time we pull up to Kelly’s house and hardly wants to leave because she has such a good time. We highly recommend Kelly to care for your babies!”

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Ray M.
Sitter Profile Image: Donna A.
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Donna A.
from
$40
per night
5.0 out of 5 stars
• 4 reviews
1 repeat client
10 years of experience
Leonardtown, MD, 20650

“Was very appreciative that Donna took Kodi at the last minute when her usual border wasn't available. She seems so pleasant. Kodi was fine. I will definitely use her again if necessary. I gave her a cash tip which I always do so that they can get full benefit of it.”

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Jayne S.
Sitter Profile Image: Lilian u.
Verified Enhanced Background Check
Lilian u.
Star Sitter
from
$60
per night
5.0 out of 5 stars
• 167 reviews
69 repeat clients
6 years of experience
Waldorf, MD, 20602

“This was our first time booking with Lilian & she was wonderful! She took the time to do a meet & greet to make sure Lucy got along well with her own dogs and she made sure to inquire about any special needs Lucy might have. During Lucy’s stay for 10 days she checked in regularly with updates and sent photos of Lucy playing. She had good communication during the entire stay, as well as leading up to it, and she took great care of Lucy! We would definitely book again!”

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Bonnie S.
Sitter Profile Image: Matthew Y.
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Matthew Y.
from
$50
per night
10 years of experience
Mechanicsville, MD, 20659

About: Your pet's safety, comfort, and well-being are my top priorities. I have professional experience working as a dog handler with detection canines, which has given me hands-on experience with canine behavior, handling, safety, and maintaining a structured environment. I understand that every pet has a different personality, comfort level, and set of needs, and I take the time to provide appropriate care for each pet entrusted to me. Safety is always the priority for your pet, my family, other animals, and anyone interacting with your pet. I believe good boarding should provide owners with peace of mind knowing their pet is being cared for by someone who is attentive, responsible, and experienced around animals. Pets are housed in a secure, indoor, climate-controlled kennel area where they can remain comfortable regardless of the weather. They also have access to a fenced outdoor kennel area that provides additional space, fresh air, and shelter from the elements. I provide a clean, structured, and secure environment and will follow your pet's normal feeding schedule, medications, routines, and other care instructions as closely as possible. Whether you're away for a night, a weekend, or a longer trip, my goal is simple: keep your pet safe, comfortable, well cared for, and give you confidence that they're in capable hands while you're away. I work offsite during the day, but I have a strong and dependable family support system at home to ensure pets receive appropriate oversight and care throughout the day. I personally handle morning and evening care, including feeding, exercise, kennel care, and ensuring each pet’s individual needs and routine are being met. Our boarding kennel is separate from our family home, providing pets with their own dedicated, quiet, and controlled space. The indoor kennel area is climate controlled and provides access to a secure, fenced outdoor kennel area with shelter, allowing dogs to safely spend time outside when appropriate. While I am at work, trusted family members are available to provide supervision, potty breaks, feeding, exercise, or other care according to each pet’s needs. I remain responsible for their overall care and delegate daytime responsibilities with clear instructions. I also maintain video surveillance of the kennel areas, allowing me to monitor pets throughout the day even while I am offsite. My professional experience handling detection canines has made safety, structure, and responsible handling especially important to me. My goal is to provide a secure environment with consistent care while minimizing unnecessary interactions between boarded pets, our household, and other animals. Safety is the foundation of how I care for animals. My professional experience handling detection canines has taught me the importance of understanding canine behavior, maintaining secure environments, following established routines, and never taking unnecessary risks with an animal in my care. Our boarding kennel is separate from our family home, providing a dedicated and controlled environment for our guests. Dogs stay in a clean, climate-controlled indoor kennel with access to a secure, fenced outdoor kennel area with shelter. This setup allows me to control interactions and provide each dog with appropriate space rather than requiring unfamiliar pets to immediately integrate into a household environment. The kennel areas are also under video surveillance, allowing me to monitor pets when I am not physically present. My family provides additional daytime oversight and supervision while I personally remain responsible for each pet’s overall care. I take owner instructions seriously and want to know about your pet’s temperament, routines, triggers, medical needs, and any behavioral concerns before their stay. Honest communication helps me keep your pet, my family, and other animals safe. We are an animal-loving family with our own very well-loved barn cats, so responsible animal care is already part of our everyday life. My goal is to provide owners with peace of mind knowing their pet is staying in a safe, secure, structured, and caring environment.

Sitter Profile Image: Schuyler C.
Verified Enhanced Background Check
Schuyler C.
from
$35
per night
5.0 out of 5 stars
• 38 reviews
9 repeat clients
15 years of experience
La Plata, MD, 20646

“Schuyler was flexible and helped navigate a change of plans. She and her husband came over twice a day and spent time with our pups, played with them, and gave them much needed attention while I was away.”

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Kristen Q.
Sitter Profile Image: Anna L.
Verified Background Check
Anna L.
from
$50
per night
4.9 out of 5 stars
• 71 reviews
23 repeat clients
12 years of experience
La Plata, MD, 20646

“Anna was fantastic with my old dog! This was our first time using Rover and Anna made our first experience very pleasant. From the moment of request she was quick to communicate and ask questions to make sure she was the right fit for my 13 year old Labrador. My wife and I had a late notice trip we needed to take with odd flight times and tight layovers, that being said Anna was able to be flexible if our flights got delayed and even made sure that if anything unexpected helped with out return flight, my dog was going to be taken care of. She also was thorough of letting me know what information she needed for caring for my dog and what items we needed to send with her to better settle my dog into a new environment. Anna checked in daily with a quick message and photo of my dog’s stay which really helped us put our minds at ease. Thank you, Anna! You’re a lifesaver and Olive came home in great spirits!”

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Thomas B.
Sitter Profile Image: Michelle M.
Verified Background Check
Michelle M.
from
$45
per night
5.0 out of 5 stars
• 19 reviews
7 repeat clients
25 years of experience
Chesapeake Beach, MD, 20732

“Michelle was fantastic with our pup! He had so much fun playing with her sweet dog and friends, and she sent us pictures throughout his stay so we could see how happy he was! She was great at arranging pickup and drop off, to make sure it worked with our schedule too. Will definitely be rebooking when we need.”

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Stephanie L.
Sitter Profile Image: Stephanie M.
Verified Enhanced Background Check
Stephanie M.
from
$35
per night
5.0 out of 5 stars
• 54 reviews
19 repeat clients
10 years of experience
Huntingtown, MD, 20639

“Stephanie is amazing! Absolutely will use her again. Albus had such a great time with her family and with Blaze! She sent photos and updates often. I love how organized her routine is and fit well with our lifestyle. She is the best!!!”

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Veanna G.
Sitter Profile Image: Bree M.
Verified Enhanced Background Check
Bree M.
from
$50
per night
5.0 out of 5 stars
• 5 reviews
3 repeat clients
12 years of experience
Leonardtown, MD, 20650

About: I’ve had dogs growing up my whole life, have two dogs, my 8 year old Pomeranian, Toby, and my 2 year old lab scout. We also have 3 cats; Finn, Sassy and sully I’m currently a stay at home mom raising my 14 month old son. He usually comes with me to do my rovers and does really well with animals as he has a bunch at home. He’s usually kept busy with toys or a movie while I do drop ins. We have house sitted before and he’s done well with that. My dogs are let out every two - four hours . My cats are fed twice daily once in the morning and again before bedtime but dry food is left out all day for grazing.

Sitter Profile Image: Bianca T.
Verified Background Check
Bianca T.
Star Sitter
from
$37
per night
4.9 out of 5 stars
• 146 reviews
85 repeat clients
15 years of experience
Sunderland, MD, 20689

“Bianca was wonderful with our fur baby. She was proactive in keeping us informed on how Heaven was doing and sent us plenty of pictures. Heaven definitely enjoyed herself. We will definitely use her again.”

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Sabrina L.
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The median cost per night for dog boarding in Leonardtown is $45

Dog parents share their Rover experiences - Leonardtown

1 / 1
5.0 out of 5 stars

When I picked up Jackson, I was not sure he wanted to leave his vacation with Kathryn and her wonderful family! Sure he was excited to see us, but, then he laid down next to Kathryn as if he was feeling pretty comfortable at her home! She sent photos and write ups daily and this made me feel so much better about leaving him in her care. It was like he knew the family forever! This was the first time we went away without him in 8 years so I was a bit anxious about leaving. I would have no problems leaving him again if I have another opportunity to do so. I highly recommend Kathryn and I know he was very happy being there and well cared for. He enjoyed his daily walks and never missed a meal and perhaps, Me!!!! If there were 10 stars I would click everyone of them!

Profile image
Carol N.
Boarding
5.0 out of 5 stars

Was very appreciative that Donna took Kodi at the last minute when her usual border wasn't available. She seems so pleasant. Kodi was fine. I will definitely use her again if necessary. I gave her a cash tip which I always do so that they can get full benefit of it.

Profile image
Jayne S.
Boarding
1 / 1
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How to book dog boarding

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Sitters in Leonardtown average 13
repeat dog boarding clients

FAQs for Dog Boarding - Leonardtown

Frequently asked questions about Rover

The average cost of Dog Boarding in Leonardtown is $39 per night as of October 2026. Most bookings cost between $28 and $49 per night. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of October 2026, there are 265 sitters on Rover offering Dog Boarding across Leonardtown. Enter your ZIP code to see which available sitters are closest to your home.

Every sitter on Rover has their own routine. Depending on the arrangements you agree on before the stay, a sitter can follow your dog’s regular feeding schedule, provide a comfortable place to sleep, offer companionship, and support their usual exercise and play needs.

95% of sitters in Leonardtown can provide daily exercise during dog boarding stays. Depending on the sitter, their home environment, and your dog’s needs, this may include walks, outdoor play, indoor enrichment activities, or supervised play with compatible dogs. These activities are not automatically included with every booking, so ask the sitter what a typical day looks like.

During the Meet & Greet, discuss your dog’s usual exercise and play routine, whether they can safely interact with other dogs, and any activities or restrictions the sitter should follow. You can also ask the sitter to send photo and message updates during the stay so you can see how your dog is spending their time.

Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Leonardtown home-away-from-home, packing:

  • Health and safety essentials such as their ID tags, vaccination records, medication, and emergency vet or secondary caregiver contacts.
  • Food and gear such as harnesses, collars, food (portioned by day), and an item that smells like you.
  • Special instructions such as a list of training cues, medical administration needs, or favorite hang-out spots in your Leonardtown.

Tip: You can upload your dog’s routine and medical info directly onto their profile so your sitter always has the details at their fingertips.

You and your Leonardtown sitter can schedule drop-off and pick-up in a way that works best for the both of you—and your dog. Most sitters offer flexible times for drop-off and pick-up but the easiest way to confirm those times will be through in-app messaging. Confirm your arrival time the day of pick-up and drop-off can also help keep the process smooth and organized.

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the , which provides up to $25,000 in eligible veterinary care reimbursement.

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit .

While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.

Many sitters in MD ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies.

By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your dog to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your dog is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

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