Dog Boarding Chesterland

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Over 6
pet parents in Chesterland have booked dog boarding

Chesterland, 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: Kelsey L.
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Kelsey L.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 37 reviews
19 repeat clients
15 years of experience
Willowick, OH, 44095

“Thanks to Kelsey and her husband for watching our dog on somewhat short notice. First time use of the Rover app and felt completely comfortable with a multiple day boarding with them. I could tell by the texts and pictures we received that she was well taken care of and got plenty of attention and exercise while in their care. Would definitely book with Kelsey again!”

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John E.
Sitter Profile Image: Kathy K.
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Kathy K.
Star Sitter
from
$36
per night
5.0 out of 5 stars
• 74 reviews
26 repeat clients
40 years of experience
Cleveland Heights, OH, 44121

“My dog Jojo and her cousin Ruby spent 6 nights with Kathy while my family was on vacation with my sister’s family. I was very nervous to leave Jojo, because she had never been left with anyone else before since getting her as a puppy in 2020. Kathy was wonderful! She was so kind and caring towards the dogs. It was so great to get her daily texts and pictures! I could tell both Jojo and Ruby were so well taken care of, and I was able to relax and enjoy my vacation. I would most definitely have Kathy take care of Jojo again. ;)”

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Shereen S.
Sitter Profile Image: Daniel P.
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Daniel P.
from
$40
per night
5.0 out of 5 stars
• 10 reviews
1 repeat client
10 years of experience
Cleveland, OH, 44124

“Wonderful to work with and available with very short notice. Our pup seemed to be very well loved while we were away. We look forward to boarding with Daniel again!”

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Katherine M.
Sitter Profile Image: Tara & Peter O.
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Tara & Peter O.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 133 reviews
53 repeat clients
40 years of experience
Lyndhurst, OH, 44124

“ABSOLUTELY AMAZING experience!!!! Tara & Peter sent pictures the entire weekend along with updates on our dog. Their fence in back yard was perfect for our energetic husky to get lots of energy out. We picked her up on Sunday and she was exhausted! We will definitely book every time with Tara & Peter!!!!”

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Amanda T.
Sitter Profile Image: Beth & Edward B.
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Beth & Edward B.
from
$30
per night
5.0 out of 5 stars
• 296 reviews
90 repeat clients
25 years of experience
Novelty, OH, 44072

“Beth is wonderful! She was patient with my pup and instead of refusing her services to me she was willing to give him a try. Turned out to be a success! Thank you so much for putting my mind at ease and allowing my puppy a chance to develop his confidence.”

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Daria P.
Sitter Profile Image: Patricia & Paul S.
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Patricia & Paul S.
from
$50
per night
5.0 out of 5 stars
• 35 reviews
11 repeat clients
40 years of experience
Willoughby, OH, 44094

“Patti and Paul were absolutely amazing with Stanley!! They took care of and treated him like their own, we will definitely be bringing Stanley back to them, he already misses them!”

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Jeremy H.
Sitter Profile Image: Mike T.
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Mike T.
Star Sitter
from
$65
per night
5.0 out of 5 stars
• 69 reviews
18 repeat clients
10 years of experience
Mayfield Village, OH, 44143

“Mike did a great job watching my dogs. He sent pics, communicated often and took really great care of both of them. we were so pleased!!! I highly recommend him as a trusted person to take care of your dog family!!”

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Katherine J.
Sitter Profile Image: Kaitlynn M.
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Kaitlynn M.
Star Sitter
from
$42
per night
5.0 out of 5 stars
• 76 reviews
29 repeat clients
27 years of experience
Euclid, OH, 44117

“Kaitlyn took wonderful care of Kaya while we were away on a weekend trip. She sent lots of pictures and updates and we were so glad to have the peace of mind that she was safe and happy while we were away. :) Thanks again, Kaitlynn!”

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Alaina & Brett T.
Sitter Profile Image: Melissa & Mathew G.
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Melissa & Mathew G.
from
$50
per night
4.9 out of 5 stars
• 8 reviews
2 repeat clients
37 years of experience
Mentor, OH, 44060

“Great experience overall. This was my first time leaving my dogs with anyone. Melissa and Matt were very good with them and kept in contact with me for updates and photos. Will definitely book again!”

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Joe B.
Sitter Profile Image: Angela W.
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Angela W.
Star Sitter
from
$27
per night
5.0 out of 5 stars
• 20 reviews
5 repeat clients
25 years of experience
Old Brooklyn, Cleveland, OH, 44109

“Angela was once again fantastic with Abel! I received multiple updates and photos throughout his stay. She followed his medication schedule and her and Jack made accommodations for his mobility with the stairs. I can’t recommend Angela enough!”

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Cory W.
Sitter Profile Image: Amanda W.
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Amanda W.
from
$38
per night
5.0 out of 5 stars
• 25 reviews
7 repeat clients
15 years of experience
Mayfield Heights, OH, 44124

“Amanda and her family were just fantastic with our dog, Nala. They were super considerate on letting Nala get used to their own dogs, giving her plenty of time to adapt. They had her during two rainy days and they kept her inside, pampering her so much that I was worried Nala wouldn’t want to come back with us! They are just terrific people who really love dogs. They will be our first choice next time we travel with her to Cleveland!”

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Nancy S.
Sitter Profile Image: Jenna F.
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Jenna F.
from
$45
per night
4.9 out of 5 stars
• 19 reviews
5 repeat clients
16 years of experience
Tremont, Cleveland, OH, 44113

“Jenna was so awesome!! Very communicative and responsive with scheduling, sent lots of pics and updates throughout each day, had a beautiful and safe home for my dog to play and relax. He even came home with a new toy!! Absolutely would recommend.”

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Kelsey P.
Sitter Profile Image: Lattoya P.
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Lattoya P.
from
$40
per night
5.0 out of 5 stars
• 3 reviews
1 repeat client
5 years of experience
Cleveland Heights, OH, 44121

“Lattoya did a great job watching our pup. Took him on hikes, went for pup cups, and gave him baths. She sent lots of pictures of his daily activities and he looked so happy.”

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Batsheva M.
Sitter Profile Image: Pamela & Marshall E.
Verified Background Check
Pamela & Marshall E.
Star Sitter
from
$35
per night
4.9 out of 5 stars
• 310 reviews
127 repeat clients
30 years of experience
Cleveland Heights, OH, 44106

“Always a great experience with Pam and Marshall! And we always see our dog, Louie, happy in the photos and videos. Looking forward to the next time….!”

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Martin B.
Sitter Profile Image: Sarah M.
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Sarah M.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 107 reviews
47 repeat clients
25 years of experience
Kamm's Corner, Cleveland, OH, 44111

“Brendan, Sarah, Jasper, and June went above and beyond to make sure our little pupper was comfortable and sent us lots of great updates. Kip is not an easy dog (due to his breed) and the fact that he was such a good guest throughout his stay with them is a reflection of their love, patience, experience, and knowledge of dogs. I highly recommend them if you’re in search of sitters and new friends for your furry babes! They are all amazing!”

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Bhinnata P.
Sitter Profile Image: Lillian R.
Verified Background Check
Lillian R.
from
$40
per night
5.0 out of 5 stars
• 38 reviews
10 repeat clients
6 years of experience
Union Miles Park, Cleveland, OH, 44105

“Lillian is for sure a dog whisperer! She sent me a update each day with pictures. Blondie remembered her from our meet and greet! I love the experience! I will return!!”

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Deitra W.
Sitter Profile Image: Matt R.
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Matt R.
from
$35
per night
5.0 out of 5 stars
• 7 reviews
4 years of experience
Brook park, OH, 44142

“Matt was fantastic. Very communicative during the stay, sent pictures and updates throughout. Wonderful and easy to work with, and our pup had a ball playing outside with him.”

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Alexus B.
Sitter Profile Image: Patricia D.
Verified Enhanced Background Check
Patricia D.
from
$30
per night
5.0 out of 5 stars
• 3 reviews
10 years of experience
Parma, OH, 44129

“Patricia was able to take care of my dog on such short notice and kept me updated. I can tell my dog enjoyed himself. 😊🩷”

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Ash V.
Sitter Profile Image: Steven B.
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Steven B.
from
$50
per night
5.0 out of 5 stars
• 9 reviews
1 repeat client
10 years of experience
Painesville, OH, 44077

“Steven was wonderful with our 2 year old doodle mix. He is a good communicator and a thoughtful caretaker for your pet. We will be happy to have Steven watch our her any time!”

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Renee S.
Sitter Profile Image: Kelsey K.
Verified Enhanced Background Check
Kelsey K.
from
$55
per night
5.0 out of 5 stars
• 39 reviews
16 repeat clients
20 years of experience
Mentor, OH, 44060

“She was so accommodating to my doggie. Even passed his sensitive stomach I never heard her complain. (Even though it was deserved) Such a good host to my dog and so so sweet!”

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Hayley F.
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The median cost per night for dog boarding in Chesterland is $45

Dog parents share their Rover experiences - Chesterland

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5.0 out of 5 stars

I felt very comfortable leaving my dog with Hannah. She administered her medication and took very good care of my dog. She updated us with pictures and my dog looked very happy. I would recommend Hannah and would use her again!

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Michelle W.
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 - Chesterland

Select a filter and find qualifying sitters offering dog boarding.

Sitters in Chesterland average 12
repeat dog boarding clients

FAQs for Dog Boarding - Chesterland

Frequently asked questions about Rover

The average cost of Dog Boarding in Chesterland is $27 per night as of November 2026. Most bookings cost between $27 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 November 2026, there are 714 sitters on Rover offering Dog Boarding across Chesterland. 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.

95% of sitters in Chesterland 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 Chesterland 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 Chesterland.

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 Chesterland. On Rover:

  • 91% of sitters can help with special care needs
  • 95% can help with giving oral medications or injections
  • 95% 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 Chesterland 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 OH 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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