Dog Boarding Chesapeake Ranch Estates

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Chesapeake Ranch Estates, 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.

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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
• 44 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: Tina R.
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Tina R.
from
$45
per night
5.0 out of 5 stars
• 6 reviews
1 repeat client
40 years of experience
California, MD, 20619

“Tina was a fantastic sitter for our 10-year old pup! She is clearly a “dog person” at heart and set us at ease right away. Snowball settled in right away and acted confident and comfortable with Tina. She took him for walks and played with toys and sent us cute photos each day! It was evident Tina took excellent care of him! Tina was also quick to respond and communicated well throughout our booking. Will definitely book with Tina again!”

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

“Linda was great with our dog! She was very responsive and sent pictures. We could tell he had a blast with her dogs, as he napped the entire evening when we brought him home.”

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Christin R.
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: Kimberly T.
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Kimberly T.
Star Sitter
from
$80
per night
5.0 out of 5 stars
• 149 reviews
46 repeat clients
20 years of experience
Lusby, MD, 20657

“We are so thankful to have found Kimberly - she lovingly took care of our 2 dogs while we were out of town. One of our pups is almost 16 years old with mobility issues and lots of oral medications, but Kimberly took excellent care of her and all her needs. She updated us with photos multiple times each day, which we greatly appreciated. Thank you so much Kimberly - we would give you 10 stars if we could!”

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Steven N.
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 fabulous! She genuinely cares for the animals she cares for and treats them as if they were her own. I never have to worry that our dog is being well cared for. She always goes above and beyond and we are so appreciative of all that she does!”

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Hailey and Troy L.
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

“She loves dogs truly. She let our little dog to sleep on her bed first night to let him feel like home. She updated and sent photos twice a day. The little dog seems to make the furry friends and like his stay”

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jess d.
Sitter Profile Image: Cathy D.
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Cathy D.
from
$55
per night
5.0 out of 5 stars
• 43 reviews
10 repeat clients
25 years of experience
Lusby, MD, 20657

“Cathy was awesome.When we arrived Calypso ran to Cathy and greeted her all his pent up 4 month energy and you can see and feel her love for pets. I had no reservations about leaving him. I do not think Calypso was overly anxious to come back home with me. I highly recommend her.”

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Jerome W.
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: Kelly G.
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Kelly G.
Star Sitter
from
$44
per night
5.0 out of 5 stars
• 340 reviews
157 repeat clients
25 years of experience
Hughesville, MD, 20637

“Kelly was great! This was the first time I boarded my pups and they are 7 & 8, she was patient and really seemed to know all the personalities of her dogs so she could make sure it is a safe environment for everyone. Already requested a rebook ☺️”

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Alexis G.
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: Stephanie M.
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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: 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: Faith M.
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Faith M.
Star Sitter
from
$42
per night
5.0 out of 5 stars
• 22 reviews
8 repeat clients
2 years of experience
Chesapeake Beach, MD, 20732

“Faith is very prompt at responding to requests and questions. She provides photos and my dog runs right into Faith's house when we drop her off. I think Faith spoils our pup, which is great because our doggie is a senior :)”

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Meghann O.
Sitter Profile Image: Florine D.
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Florine D.
from
$50
per night
5.0 out of 5 stars
• 4 reviews
1 repeat client
10 years of experience
Aquasco, MD, 20608

“Florine is amazing. Very caring and wonderful. I'm so glad that she is available on christmas holiday. Thank you so much Florine”

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glv m.
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: Cole K.
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Cole K.
from
$40
per night
1 repeat client
4 years of experience
Callaway, MD, 20620

About: I’ve been around dogs most of my life. I currently have a Blue Great Dane named Diesel. He is great with other dogs, and we will have to do a meet and great to make sure you’re pup will get along with him also. I’m usually available unless the wife has me doing something. I spend every min I can with my dog and will show your dog the same treatment. My yard is unfenced for now, but it is 2 acres that’s at the end of a quiet neighborhood. We have plenty of room to play and go on walks.

Sitter Profile Image: Alicia S.
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Alicia S.
from
$45
per night
5.0 out of 5 stars
• 20 reviews
5 repeat clients
10 years of experience
Chance, MD, 21821

“Thank you Galicia for always taking great care of our pups! You are awesome and accommodating during our recent emergency. I would recommend you to everyone 🩷”

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Melissa B.
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: 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.
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Dog parents share their Rover experiences - Chesapeake Ranch Estates

1 / 1
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

We are so happy with the care that Lindsey gave to our pup while we were away for the holidays. We got frequent updates (with pictures) which was just what we needed to feel comfortable, as this was our first Rover experience. Will definitely be booking with her again!!

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Marissa M.
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

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FAQs for Dog Boarding - Chesapeake Ranch Estates

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 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.

<b>Tip:</b> 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 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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