Dog Boarding Chesapeake Ranch Estates-Drum Point

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Over 22
pet parents in Chesapeake Ranch Estates-Drum Point have booked dog boarding

Chesapeake Ranch Estates-Drum Point, Find top rated dog boarding

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Sitter Profile Image: Haley W.
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Haley W.
from
$55
per night
5.0 out of 5 stars
• 47 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: Linda W.
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Linda W.
from
$50
per night
5.0 out of 5 stars
• 136 reviews
48 repeat clients
20 years of experience
Lexington-Park, MD, 20653

“Linda was great with our cat Millie. She sent us updates throughout the stay, gave her medications on schedule and did everything she could to make her comfortable. She gave us peace of mind while we were out of town. We will definitely be using her services again!”

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Breana P.
Sitter Profile Image: George S.
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George S.
from
$55
per night
5.0 out of 5 stars
• 24 reviews
9 repeat clients
19 years of experience
St Leonard, MD, 20685

“My Puppy really enjoyed being spoiled by George with allowing him to lay on the bed...lol George was really great with my puppy... he provided text messages and videos of my puppy playing with his two dogs that he got along with. He was very professional and caring as well. I highly recommend him!”

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Rhonda B.
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

“Jaliyah was great and very patient with our Clyde. She communicated promptly and often. When I picked him up and she was saying bye, he actually went and licked her hand. If you know Clyde, this was very unusual. I felt this was a sign that she was kind to him.”

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Tracy E.
Sitter Profile Image: Genil W.
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Genil W.
from
$40
per night
4.3 out of 5 stars
• 32 reviews
6 repeat clients
3 years of experience
Lusby, MD, 20657

“Genil treated our dogs with such love and was even available at the last minute during the holidays! She sent photos halfway through the booking and was so sweet to work with!”

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Taylor H.
Sitter Profile Image: Daniela H.
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Daniela H.
from
$40
per night
5.0 out of 5 stars
• 5 reviews
5 years of experience
Prince Frederick, MD, 20678

“Daniela was an amazing puppy sitter! Bruno absolutely loved her and her sweet family. While we were out of town, Daniela communicated with us daily and sent us the cutest photos and videos the entire time. We are so thankful that she was able to accommodate our last-minute request. With all the belly rubs and cuddles, I’m sure our furbaby had an amazing time and we’ll definitely be rebooking with her next time!”

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Melissa G.
Sitter Profile Image: Elizabeth G.
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Elizabeth G.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 55 reviews
13 repeat clients
30 years of experience
HUNTINGTOWN, MD, 20639

“Elizabeth was an amazing sitter for my Pyrenees/Golden mix! I could tell he genuinely appreciated her company and will remember her forever now! She was very patient with him, as he struggles with stairs. Her communication was also excellent throughout. I was 1000 miles away but receiving pictures and daily updates really help assure me that Joni was having a nice time. Thanks again!!”

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

“Thank you so much to Ms. Anika! She is the best! She has been watching our furbaby for about 4 years now and I don’t know what we would do without her. Her love and care allowed us to have a 9 day worry free family vacation❤️”

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Rashida S.
Sitter Profile Image: Amelia P.
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Amelia P.
from
$45
per night
5.0 out of 5 stars
• 2 reviews
1 repeat client
8 years of experience
Chesapeake Beach, MD, 20732

“Amelia is very kind and communicative. She was able to send me updates and photos throughout the duration of my dog’s stay with her. Highly recommended and would use her services again!”

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Damon G.
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 watched my Great Pyrenees, Daisy, last minute when I really needed a provider quickly and she just happened to have a lot of experience with the breed. Daisy did really well and was taken care of like I would have, would definitely use Kelly again. Highly recommend”

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S M.
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: Onayda P.
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Onayda P.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 569 reviews
312 repeat clients
7 years of experience
Owings, MD, 20736

“Onayda provided a loving and responsible environment for my pet, and sent me a photographic update each day. I hope to be able to use her again. Thank you Onayda!”

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William R.
Sitter Profile Image: Donna B.
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Donna B.
from
$40
per night
30 years of experience
Chesapeake Beach, MD, 20732

About: I have a young, incredibly friendly, and playful Yorkshire Terrier who loves making new friends. Your dog will have a built-in playmate for gentle games and companion naps. I treat every guest dog like a member of my own family. I am happy to send you daily photo and text updates so you can enjoy your trip with total peace of mind! I am a retired pet lover with a calm, safe, and happy home dedicated to pampering small dogs. Because I am retired, your dog will never be left alone and will receive constant, one-on-one love, supervision, and attention throughout their entire stay. About My Home & Setup: • Fully Fenced Yard: Plenty of space for safe, secure outdoor sniffing and playtime. • No Stairs: Perfect for senior dogs, puppies, or breeds prone to back issues. • Cozy Sleeping: Your pup is welcome to sleep right in bed with me, or wherever they feel most comfortable! • Constant Companionship: I am home full-time, meaning potty breaks and cuddles are available on demand.

Sitter Profile Image: Mackenzie C.
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Mackenzie C.
from
$50
per night
6 years of experience
California, MD, 20619

About: I have 6 years of experience caring for pets and understand how important it is to have someone you can trust with your furry family members. I provide attentive, loving, and reliable care while making sure each pet feels safe, comfortable, and cared for. I’m happy to follow your pet’s normal routine, including feeding schedules, walks, playtime, potty breaks, medications, and plenty of attention and affection. I understand that every pet has their own personality and needs, so I take the time to make sure they receive individualized care and feel as comfortable as possible while you’re away. I am currently working full-time, mostly remote with one or two days in the office each month. Working from home gives me plenty of flexibility to provide regular potty breaks, walks, playtime, feeding, and lots of attention throughout the day. I’m also happy to accommodate each pet’s normal routine as closely as possible. Your pet’s safety and comfort are always my priority. I provide a calm, attentive environment and carefully follow any instructions you provide regarding feeding, medications, walks, routines, or special needs.

Sitter Profile Image: Tara L.
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Tara L.
from
$48
per night
5.0 out of 5 stars
• 1 review
1 repeat client
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: Elissa F.
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Elissa F.
Star Sitter
from
$55
per night
5.0 out of 5 stars
• 53 reviews
24 repeat clients
11 years of experience
Brandywine, MD, 20613

“Elissa was wonderful with my dogs. She was accommodating, asked great questions, and followed my instructions for feeding and walking perfectly. I got pictures and video of my dogs every day, which made me feel like they were in great hands while I was away. Elissa is very caring and truly likes and enjoys dogs. I highly recommend Elissa to care for your dogs when you are away. Thank you Elissa!”

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Silvia T.
Sitter Profile Image: Lindsay J.
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Lindsay J.
from
$30
per night
5.0 out of 5 stars
• 24 reviews
8 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: 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: Morgan B.
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Morgan B.
from
$35
per night
6 years of experience
Ct, MD, 20714

About: I have had breeds of all shapes and sized my entire life. I care for my 2 year old border collie and I have experience handling cats as well. I want to make your pets feel at home even when you are away. I would want the best from my boy when I am away, so I want to provide that service to others! I am full-time employee so I can stop in before and after work on weekdays, and I am free weekends for endless playing ! (I can stay in the evening during the week until around 8-9) I am very respectful of other people’s spaces and would be happy to meet your animal where they are! I do NOT offer boarding currently.

Sitter Profile Image: Kendall T.
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Kendall T.
from
$40
per night
5.0 out of 5 stars
• 3 reviews
20 years of experience
Chesapeake Beach, MD, 20732

“Kendall was great! Very responsive, and kept me updated while caring for my dog. Would absolutely recommend her.”

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anthony g.
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The median cost per night for dog boarding in Chesapeake Ranch Estates-Drum Point is CA$45

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

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5.0 out of 5 stars

Kerri is amazing ! She and her 2 daughters and beagle are great with Hutch. He spans 7 nites while I worked the Annapolis Boat show- Kerri sent lots of pics and updates and I felt he was in good hands! I would totally book with Kerri again.

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Terri I.
Boarding
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

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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Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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 sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

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

How to book dog boarding

  1. 1. Search

    Browse profiles of sitters near you who offer dog boarding.
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit.
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform.

Popular requests for dog boarding - Chesapeake Ranch Estates-Drum Point

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Sitters in Chesapeake Ranch Estates-Drum Point average 8
repeat dog boarding clients

FAQs for Dog Boarding - Chesapeake Ranch Estates-Drum Point

Frequently asked questions about Rover

The average cost of Dog Boarding in Chesapeake Ranch Estates-Drum Point is $43 per night as of November 2026. Most bookings cost between $29 and $89 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 November 2026, there are 178 sitters on Rover offering Dog Boarding across Chesapeake Ranch Estates-Drum Point. Enter your ZIP code to see which available sitters are closest to your home.

If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.

The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.

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.

94% of sitters in Chesapeake Ranch Estates-Drum Point 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 Chesapeake Ranch Estates-Drum Point home-away-from-home, we recommend 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.

Yes, you can find sitters who have experience with handling special pet needs in Chesapeake Ranch Estates-Drum Point. On Rover:

  • 88% of sitters can help with special care needs
  • 97% can help with giving oral medications or injections
  • 94% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

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 Rover Guarantee, 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 Rover's Trust & Safety page.

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.

Adding another pup to the pack? Most sitters and walkers offer a reduced rate for additional dogs. You’ll find these exact rates listed under the "Services" tab on any sitter's profile. Since every dog is unique, final pricing may vary depending on the level of care required.

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