Dog Boarding Chesapeake Ranch Estates-Drum Point

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

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Sitter Profile Image: Nikki G.
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Nikki G.
from
$32
per night
5.0 out of 5 stars
• 88 reviews
19 repeat clients
13 years of experience
Saint Leonard, MD, 20685

“Nikki is absolutely amazing. My dog is very nervous around people, she did not rush him. Initially, I reached out to have her handle some dinners a couple of times a year but then I had an unexpected death in the family that required me to go out of town for seven days. She was wonderful working around my schedule. We received multiple updates showing how happy he is hanging with her family and dogs. This meant the world to us knowing he was is such good hands.”

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Bonnie H.
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: Kerri L.
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Kerri L.
from
$50
per night
5.0 out of 5 stars
• 13 reviews
6 repeat clients
20 years of experience
Lusby, MD, 20657

“Kerry and her family took amazing care of my dog Briggs while I was out of town. I got loads of adorable pictures, and he was returned groomed and fluffy with a new bandana. I highly recommend them and will be reaching out again when I travel.”

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Angela K.
Sitter Profile Image: Linda W.
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Linda W.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 132 reviews
47 repeat clients
20 years of experience
Lexington-Park, MD, 20653

“Linda is a kind, reliable, and a wonderful pet sitter. Both my experiences have been totally positive, and I will continue to choose Linda as my preferred pet sitter!”

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Crystal W.
Sitter Profile Image: Alexandra B.
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Alexandra B.
from
$45
per night
5.0 out of 5 stars
• 3 reviews
2 repeat clients
20 years of experience
Lusby, MD, 20657

About: My name is Alexandra. I have 3 Chihuahuas. I also have a 17 year old dachshund. My pups are my world! My little fur babies as I like to call them. I absolutely love dogs. My whole life I have been an animal lover. I have 20 years plus years experience with dogs. I've never met a dog that didn't like me. My Schedule is very flexible. I am available is for walks and in home sitting/day visits. I can not do overnight visits. Please don't haste to contact me if you have any questions and concerns. Thank you for you time and I look forward to hearing from you and meeting your little fur babies! Have a wonderful day! Alexandra My schedule is open. Depending on when care is needed depends on how often I will come and how long I can stay. 24 / 7 I provide a safe, loving environment for pets to enjoy and feel comfortable in. Lots of pets and companionship will be provided for your loved one.

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

“Lori was amazing with our Elmer! She was attentive to his needs and kept us informed along the way. I loved that she provided us with daily photos. I highly recommend her care and Elmer can’t wait to visit again!”

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Melissa G.
Sitter Profile Image: Christine S.
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Christine S.
Star Sitter
from
$55
per night
5.0 out of 5 stars
• 55 reviews
17 repeat clients
20 years of experience
CALIFORNIA, MD, 20619

“Christine is wonderful. Laika was very happy staying with Christine. Christine took care of my dog Laika above and beyond expectation. I highly recommend Christine. Thank you .”

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Bella Y.
Sitter Profile Image: Michelle M.
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Michelle M.
from
$55
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: Brooke H.
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Brooke H.
from
$35
per night
5.0 out of 5 stars
• 43 reviews
17 repeat clients
26 years of experience
Leonardtown, MD, 20650

“Brooke is excellent with Jasper her reports are very detailed and she is proactive in trying to help Jasper with his training accomplishments. Also a very good individual for boarding.”

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Mike R.
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 was awesome, very responsive and took great care of our dog. It was our first time boarding our 9 month old puppy but he adjusted well and seemed to have a good time playing with the other dogs either at day care or boarding with Kelly too. Thaanks and definitely recommend!”

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June-Wei S.
Sitter Profile Image: Bianca M.
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Bianca M.
from
$40
per night
5.0 out of 5 stars
• 5 reviews
2 repeat clients
15 years of experience
Owings, MD, 20736

“Bianca was fantastic!! From the get go she made Bailey feel welcome, comfortable and loved! She is a genuine pet lover! Bianca was accommodating to our asks re Baileys rules, super communicative kept us updated during his stay and we could tell he was happy. Bianca has a great space and set up for the doggies. I would totally recommend and would def book again. Thank you Bianca and Family!”

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Romina A.
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: Bianca T.
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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 took such wonderful care of our dog! This was our first time having a sitter and she was very reassuring and responsive. She's very communicative and made sure to plenty of take photos, which I appreciated. Her whole family made Kiki feel at home, with lots cuddles!”

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Christina G.
Sitter Profile Image: Holly L.
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Holly L.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 104 reviews
24 repeat clients
14 years of experience
Owings, MD, 20736

About: I have grown up with dogs and now I have 3 of my own! I have a pug, and 2 basset hounds. I'm experienced in all size dogs. (I previously had 2 english mastiffs that crossed the rainbow bridge) I also have chickens and ducks. I worked at a retirement community for years.. so I'm understanding and kind towards our wiser elders who made need help with their furbabies. I'm a homemaker so I'm almost always available for your pet care needs. I'm available to sit and play with them to your hearts comfort. All 3 of my dogs are inside dogs who sleep in bed with me. 🤣 Furbabies are like children to me. I truly believe they have souls and they deserve all the love in the world.

Sitter Profile Image: Laura L.
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Laura L.
Star Sitter
from
$60
per night
5.0 out of 5 stars
• 21 reviews
8 repeat clients
10 years of experience
Chesapeake Beach, MD, 20732

“Laura was awesome! Chacco had a blast during his weekend sleepover and loved hanging out with the other pups. She took great care of him, and I felt totally at ease knowing he was in good hands. He came home happy and tired—always a good sign! Definitely booking with her again.”

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Chellie Pearl P.
Sitter Profile Image: Mya P.
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Mya P.
from
$65
per night
5.0 out of 5 stars
• 6 reviews
3 repeat clients
25 years of experience
Chesapeake Beach, MD, 20732

“Mya cared for our dog (Harley) like she was her own! Harley has anxiety when we leave her but she was clean, calm and relaxed when we picked her back up. Mya sent us photos and communicated with us consistently while we were away so we felt at ease that our girl was well cared for in our absence. We will be booking with Mya again soon!”

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Christina C.
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: 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: Lindsay J.
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Lindsay J.
from
$30
per night
5.0 out of 5 stars
• 23 reviews
7 repeat clients
3 years of experience
Huntingtown, MD, 20639

“Lindsay was an amazing sitter for Kilo. She was incredibly friendly, responsive, and thoughtful from the very beginning, and took the time to do a meet and greet to be sure Kilo and her pup were a good match. She followed all of our care instructions perfectly and sent consistent updates while we were away, which gave us so much peace of mind. When we picked Kilo up, he was calm, relaxed, and clearly comfortable — it was obvious he felt right at home with Lindsay. We wouldn’t hesitate to book with her again and highly recommend her.”

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Natalia P.
Sitter Profile Image: Marti B.
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Marti B.
from
$45
per night
5.0 out of 5 stars
• 12 reviews
2 repeat clients
9 years of experience
Waldorf, MD, 20601

“Marti was so sweet and nice she send alot of pictures she keep me posted on everything I will let her keep my baby anytime I know my my baby was in great hand thank you Marti see you soon”

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Tamara W.
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Dog parents share their Rover experiences - Chesapeake Ranch Estates-Drum Point

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5.0 out of 5 stars

Thank you for taking care of Franklin and dealing with his sudden sickness. He’s doing fine now and rightfully sleepy after a long day of playing!

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Kent
Boarding
5.0 out of 5 stars

Genil was great with my 4-month-old German Shepherd mix! She kept me updated with pictures while I was away, which really put my mind at ease. Super kind and took good care of my pup. Highly recommend.

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Innocent B.
Boarding
5.0 out of 5 stars

Kerri is great, made my Elvis feel right at home and treated him like her own. We'll be using her on a regular basis!!

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Bruce W.
Boarding
5.0 out of 5 stars

Kayla & Bryant we're amazing! Our Leo loved their whole family and they took such great care of him. Leo was treated just like one of theirs. He adjusted very well and seemed so happy to be there. We look forward to having him stay there again!

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Caitlyn R.
Boarding
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    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

How to book dog boarding

  1. 1. Search

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  2. 2. Meet In Person

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FAQs for Dog Boarding - Chesapeake Ranch Estates-Drum Point

Frequently asked questions about Rover

Rover is the largest marketplace for local pet care. Whether you're looking for pet sitters, dog walkers, or house sitters who specialize in pet sitting, you can narrow your search by entering your ZIP code to find sitters within walking distance in your neighborhood.

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.

Depending on the sitter, their home environment, and your dog’s needs, daily exercise 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 Chesapeake Ranch Estates-Drum Point 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 Chesapeake Ranch Estates-Drum Point.

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 Chesapeake Ranch Estates-Drum Point 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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