Dog Boarding Chesterville

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Chesterville, 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: Mike B.
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Mike B.
Star Sitter
from
$29
per night
5.0 out of 5 stars
• 164 reviews
66 repeat clients
35 years of experience
Townsend, DE, 19734

“Mike is very patient and absolutely took great care of my dog. He was very communicative, sent pictures and updates about my dog during the stay. I was happy to know my dog was happy and relaxed during the stay. Highly recommended!”

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Kranthi V.
Sitter Profile Image: Kari & Jospeh M.
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Kari & Jospeh M.
Star Sitter
from
$35
per night
5.0 out of 5 stars
• 44 reviews
21 repeat clients
30 years of experience
Townsend, DE, 19734

“Such a great experience. We had 3 dogs stay with them. Our dogs were treated great and with love. We definitely recommend using Kari & Joseph”

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Kevin C.
Sitter Profile Image: Brittany F.
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Brittany F.
from
$55
per night
5.0 out of 5 stars
• 19 reviews
3 repeat clients
20 years of experience
Warwick, MD, 21912

“Brittany’s home is an oasis for dogs. Our girls loved chilling out in their big fenced in yard which they could sunbath or hide out under the shade trees especially the beautifully willow. Brittany is very responsive and without a doubt a true dog and animal lover. Trust that this would be a great place for your furry friends.”

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Mary K.
Sitter Profile Image: Jen C.
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Jen C.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 186 reviews
66 repeat clients
20 years of experience
SMYRNA, DE, 19977

“Jen took very good care of my dog and I will definitely use her again to sit. She was very nice and communicated with me from the 1st meet-up and up until I picked Kobe up. Thanks again Jen”

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Gregory W.
Sitter Profile Image: Jenny M.
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Jenny M.
from
$41
per night
5.0 out of 5 stars
• 206 reviews
85 repeat clients
9 years of experience
Dover, DE, 19901

“Jenny was extremely friendly and took excellent care of our cat. I can tell that her experience with pets is a great asset. Highly recommend!”

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Rachel T.
Sitter Profile Image: Karen D.
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Karen D.
from
$38
per night
4.9 out of 5 stars
• 178 reviews
81 repeat clients
30 years of experience
North East, MD, 21901

“Chance was comfortable and happy in her care. I love that she sends photos. He was in great spirits when I came to pick him up. Will use her services again in the future”

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LaShaun C.
Sitter Profile Image: Charles & Heather F.
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Charles & Heather F.
Star Sitter
from
$28
per night
5.0 out of 5 stars
• 8 reviews
4 repeat clients
30 years of experience
Smyrna, DE, 19977

“Gully had a wonderful stay with Charles & Heather and their 2 pooches! They made him feel right at home with lots of cuddles & attention. Thank you!”

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Sandy B.
Sitter Profile Image: Paris V S.
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Paris V S.
Star Sitter
from
$58
per night
5.0 out of 5 stars
• 268 reviews
61 repeat clients
17 years of experience
Edgewood, MD, 21040

“Paris was so good to my sweet little princess. Blu just loves her. I highly recommend this dog sitter and will definitely utilize her services again.”

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Heather H.
Sitter Profile Image: Justin & Stephanie W.
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Justin & Stephanie W.
from
$50
per night
5.0 out of 5 stars
• 191 reviews
69 repeat clients
15 years of experience
Elkton, MD, 21921

“Justin was great with Tucker I definitely recommend if you want you a safe boarder , I was updated with lots pictures and felt comfortable leaving Tucker with Justin”

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Tina W.
Sitter Profile Image: Thomas H.
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Thomas H.
Star Sitter
from
$35
per night
5.0 out of 5 stars
• 20 reviews
10 repeat clients
30 years of experience
Aberdeen, MD, 21001

“Thomas and his sons took great care of Tucker while I was away. He responded quickly every time I reached out and Tucker seemed right at home when I picked him up at the end of his stay!”

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Irene M.
Sitter Profile Image: Jill & Thomas K.
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Jill & Thomas K.
Star Sitter
from
$60
per night
5.0 out of 5 stars
• 162 reviews
77 repeat clients
15 years of experience
Middletown, DE, 19709

“We were extremely nervous with having our dog stay with strangers but meeting Jill and Thomas quickly changed our hesitation. As soon as you meet then you can tell they are dog lovers. We recieved photos all weekend and our dog was having a great time. We will definitely be returning as a client.”

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Brandi S.
Sitter Profile Image: Candice M.
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Candice M.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 132 reviews
60 repeat clients
10 years of experience
South St. Georges, DE, 19709

“What can I say, Miss Candice loves what she does. And it shows, It’s like home away from for my fur baby who all but jumps out the car window when we pull up for his stay. Thank goodness my window was up. Total opposite when pull up to the groomer.”

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Jean B.
Sitter Profile Image: Kayla A.
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Kayla A.
from
$35
per night
5.0 out of 5 stars
• 6 reviews
1 repeat client
10 years of experience
Elkton, MD, 21921

“Kayla was great and was able to accommodate me and my dog on very short notice. She’s incredibly caring and was great with updating me during my boarding time. Will definitely use her services again.”

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Lance F.
Sitter Profile Image: Barbra F.
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Barbra F.
Star Sitter
from
$55
per night
5.0 out of 5 stars
• 68 reviews
26 repeat clients
20 years of experience
Middletown, DE, 19709

“Barbra took amazing care of my little senior yorkie and he had a blast staying with her. She kept me updated while I was away and sent the cutest pictures. You can tell Barbra cares about animals and wants to make sure they are comfortable during their stay. I 100% recommend her services to anyone who reads this!!”

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emma l.
Sitter Profile Image: Gisel D.
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Gisel D.
Star Sitter
from
$60
per night
5.0 out of 5 stars
• 47 reviews
21 repeat clients
7 years of experience
Edgewood, MD, 21040

“Gisel is amazing! She accommodated me with watching my beloved puppy! She’s very responsive and friendly. She also sent over a video just to show well accumulated my puppy was when he got to her residence.”

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Danielle E.
Sitter Profile Image: Rackeem R.
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Rackeem R.
from
$55
per night
5.0 out of 5 stars
• 38 reviews
20 repeat clients
7 years of experience
Middletown, DE, 19709

“Rackeem came in clutch when we needed a last-minute sitter for our little girl Piper over the Thanksgiving holiday! He took great care of her at his home, sent plenty of photos and updates daily, and was super flexible when it came to drop-off and pickup days and times. 10/10 would absolutely leave our little girl with him again!”

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Joseph T.
Sitter Profile Image: Tarina L.
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Tarina L.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 55 reviews
21 repeat clients
30 years of experience
Edgewood, MD, 21040

“These folks are amazing. They were born to board pets - my boy Marvin had the best time! You will not regret leaving your precious pooch with them!”

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Tom Z.
Sitter Profile Image: Briana & Isaiah S.
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Briana & Isaiah S.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 76 reviews
18 repeat clients
25 years of experience
Abingdon, MD, 21009

“Super amazing people .They have had Thor twice and will probably continue to they take amazing care of him and treat him like there own . We love the fenced in yard and the walks .”

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Bethany G.
Sitter Profile Image: Jacob & Megan W.
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Jacob & Megan W.
from
$42
per night
5.0 out of 5 stars
• 85 reviews
51 repeat clients
10 years of experience
Bel Air, MD, 21015

“Megan and Jacob were wonderful hosts for our rambunctious large lab pup!! He was well taken care of and played so well with their cute lab mix! They were very kind and welcoming and calm!! We will be using them again and referring our friends too. This was a trial overnight for longer stays in the future. I loved that they suggested this. Highly recommend!”

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Kitty Y.
Sitter Profile Image: Pamela C.
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Pamela C.
from
$45
per night
5.0 out of 5 stars
• 40 reviews
12 repeat clients
11 years of experience
Bel Air, MD, 21015

“Pamela was awesome. We had a meet and greet and our Nikki found a friend in Leo. Pamela sent images and updates through out the stay. I was so comfortable knowing Nikki was in good hands and having fun. We will definitely call on Pamela again.”

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Suzanne P.
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Dog parents share their Rover experiences - Chesterville

1 / 1
5.0 out of 5 stars

Dawn is great. When we arrive for drop off, Henry runs inside and doesn’t look back at us. No stress for him is good for us.

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Steve T.
Boarding
5.0 out of 5 stars

It gives me peace of mind to know that whenever I go away my fur baby will be very well cared for by Dawn.

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Samantha F.
Boarding
5.0 out of 5 stars

Tango had a wonderful time, and was very happy with her stay with Dawn and her family. She fit right in as a member of their “pack” I was very pleased with the care she received, she had plenty of fun and stimulation too.

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Margaret C.
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.

Meet local sitters who will treat your dogs like family

  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 - Chesterville

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FAQs for Dog Boarding - Chesterville

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 Chesterville 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 Chesterville.

<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 Chesterville 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.

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