Dog Boarding Chester

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Over 47
pet parents in Chester have booked dog boarding

Chester, 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: Jadyn G.
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Jadyn G.
Star Sitter
from
$55
per night
5.0 out of 5 stars
53 reviews
12 repeat clients
5 years of experience
Highland Mills, NY, 10930

Jadyn is a terrific and loving sitter. Our fur baby Beau was definitely loved and well cared for, Jadyn even gave him a bath before we picked him up. She is our No. 1 choice whenever we need someone to care for Beau and we'll be referring her to our friends and family in the area. Thank you so much Jadyn.🫶🏽😊

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Kenneth G.
Sitter Profile Image: Alexis A.
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Alexis A.
Star Sitter
from
$70
per night
5.0 out of 5 stars
42 reviews
14 repeat clients
25 years of experience
Middletown, NY, 10940

Alexis took great care of our dogs and provided regular updates. She was thoughtful, accommodating, and considerate with all of our plans. Would absolutely recommend her and would definitely book with her again!

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Sarah A.
Sitter Profile Image: Sandra E.
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Sandra E.
from
$55
per night
5.0 out of 5 stars
142 reviews
56 repeat clients
10 years of experience
Middletown, NY, 10940

Sandra was perfect. My dog is a little particular and needs one on one Care and Sandra delivered her and her husband treated didi like family. Thank you.

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Anthony B.
Sitter Profile Image: Jonathon M.
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Jonathon M.
Star Sitter
from
$45
per night
5.0 out of 5 stars
15 reviews
5 repeat clients
20 years of experience
Walden, NY, 12586

Highly recommend. Johnathon has a lovely space where my pups had a blast. Loved the pictures he sent of them while I was away at my wedding. My Luna is an anxious dog and yet she did great. Definitely would rebook from here on out.

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Pavela S.
Sitter Profile Image: Carla C.
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Carla C.
Star Sitter
from
$45
per night
4.9 out of 5 stars
121 reviews
33 repeat clients
15 years of experience
Highland Lakes, NJ, 07422

Carla was a great dog sitter!!! Nugget stayed with her over the weekend. It was really short notice but she was very accommodating. I can tell my boy had fun because when it was time to go, he wanted to go back inside the house!!! Will definitely be using her services in the future 😊

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Tiffani N H.
Sitter Profile Image: Daniel R.
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Daniel R.
from
$55
per night
5.0 out of 5 stars
52 reviews
16 repeat clients
25 years of experience
Middletown, NY, 10940

Daniel & his wife were amazing! I was worried that my 15 year old Shit-Zu Yorkie mix would not adjust very well. She does not do well with new people or environments, but she felt very comfortable and at ease. She had a great stay. I highly recommend them. Thank you so much!!!

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Leidy P.
Sitter Profile Image: David G.
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David G.
Star Sitter
from
$60
per night
5.0 out of 5 stars
78 reviews
22 repeat clients
5 years of experience
New Windsor, NY, 12553

David took such good care of my boy Hades. He was exceptionally acomidating and went out of his way to make sure Hades got back home safely when I was unexpectedly waylayed at work. Good not recommend a better sitter.

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Myko H.
Sitter Profile Image: Jane H.
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Jane H.
from
$70
per night
5.0 out of 5 stars
39 reviews
23 repeat clients
20 years of experience
Chester, NY, 10918

This was our first time using Rover.com for our dog Macy. Jane was very sensitive to Macy's needs and the message updates and photos were reassuring. Jane said Macy was welcome back anytime and I look forward to booking future stays with Jane.

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Maureen L.
Sitter Profile Image: Lieb B.
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Lieb B.
from
$70
per night
5.0 out of 5 stars
74 reviews
38 repeat clients
5 years of experience
Suffern, NY, 10901

Lieb was great! He sent lots of photos and gave Cal plenty of attention and exercise. I would definitely trust him to care for Cal again ☺️

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Vivian L.
Sitter Profile Image: Arsenii S.
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Arsenii S.
from
$72
per night
5.0 out of 5 stars
10 reviews
2 repeat clients
4 years of experience
Montrose, NY, 10548

We only used Arsenii once so far but will definitely be going back. Oscar has a bit of separation anxiety but Arsenii's place provides a relaxed vibe and Oscar made himself right at home.

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Nancy K.
Sitter Profile Image: Dawn R.
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Dawn R.
from
$65
per night
5.0 out of 5 stars
33 reviews
15 repeat clients
20 years of experience
middletown, NY, 10940

Buttons loves it there with the other dogs. Buttons always comes back sad when he is back home. He always misses the other dogs. Happy to send him back there. thx

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Gus J.
Sitter Profile Image: Melissa C.
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Melissa C.
Star Sitter
from
$65
per night
5.0 out of 5 stars
36 reviews
9 repeat clients
35 years of experience
Chestnut Ridge, NY, 10977

Melissa did a great job taking care of my precious dog. She sends up pictures and videos updates more than I expected. I highly recommend her and will book again.

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Jonathan B.
Sitter Profile Image: Maria V.
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Maria V.
Star Sitter
from
$45
per night
5.0 out of 5 stars
60 reviews
25 repeat clients
20 years of experience
Milton, NY, 12547

My dog had a great time, we were very nervous for it being our first time leaving our dog, and Maria made us feel comfortable and reassured us that our dog would be fine, he was. Thank you Maria and your mom!

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Lizzie R.
Sitter Profile Image: Natasha & Hamir D.
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Natasha & Hamir D.
Star Sitter
from
$80
per night
5.0 out of 5 stars
26 reviews
3 repeat clients
14 years of experience
Cortlandt Manor, NY, 10567

Natasha made us so at ease when watching our girl while we got married! She sent daily updates with pictures, and Scout came back like she was on vacation!

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Julia T.
Sitter Profile Image: Amy D.
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Amy D.
from
$65
per night
4.8 out of 5 stars
34 reviews
10 repeat clients
20 years of experience
Goshen, NY, 10924

Amy was amazing with Ruba. She sent plenty of pictures and videos of Ruba having a wonderful time romping around with the other dogs! Will definitely be choosing Amy for our future dogsitting needs in this area.

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Robert W.
Sitter Profile Image: Francesca & John B.
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Francesca & John B.
from
$75
per night
5.0 out of 5 stars
6 reviews
2 repeat clients
10 years of experience
Walden, NY, 12586

Francesca and John were wonderful! Buddy did very well during his stay. This was his first time ever boarding and I was nervous about how he would do since he is an older dog. They kept me updated all the time and assured me he was relaxed and not anxious. So glad we found them!

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Meaghan B.
Sitter Profile Image: Michael C.
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Michael C.
from
$35
per night
4.9 out of 5 stars
8 reviews
1 repeat client
10 years of experience
Florida, NY, 10921

About: Hello all! I’m Michael, and I looking forward to caring for your pup. I’m experienced with all ages and I treat every pup like part of the family. (Due to my current living situation, I am ONLY allowed to dog board/house-sit hypoallergenic dogs or dogs that shed minimally.) Let’s connect! My availability varies throughout the week but I can be more than flexible to accommodate your pets needs. Whether it’s taking your dog for a quick walk or boarding for a weekend, I’m your guy. I care for pets by trying to keep a clean environment at all times. Cleanliness is very important to me as I find it very important for general health.

Sitter Profile Image: Morgan F.
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Morgan F.
Star Sitter
from
$64
per night
4.9 out of 5 stars
189 reviews
109 repeat clients
17 years of experience
West Milford, NJ, 07480

Grateful to Morgan for taking Kody on such short notice when we unexpectedly needed to leave town. She was very responsive and easy to communicate with, which gave us peace of mind. Kody clearly loved his stay, was well cared for, and even made some new friends. We truly appreciate the great care and would absolutely book with Morgan again.

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yolanda d.
Sitter Profile Image: Vicky A.
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Vicky A.
from
$60
per night
5.0 out of 5 stars
15 reviews
7 repeat clients
15 years of experience
Middletown, NY, 10940

Very professional and loving I would leave my pet with Vicky anytime as well as recommend. Will see you soon Vicky. Thanks again

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Rosalind C.
Sitter Profile Image: Beckie M.
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Beckie M.
from
$45
per night
4.6 out of 5 stars
11 reviews
4 repeat clients
15 years of experience
Walden, NY, 12586

Beckie and her family were the perfect home away from home for our high-energy 2yo German Shepherd. She has a beautiful and massive back yard and provided photo updates throughout the stay. We’ll happily trust Beckie with Echo on future trips and highly recommend her!

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Chelsea M.
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The median cost per night for dog boarding in Chester is $60

Dog parents share their Rover experiences - Chester

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5.0 out of 5 stars

The BEST pugsitter in the universe. We have used them many times over the years and they always make sure our sweet Pancake is safe and warm. The only family that we trust enough to leave our precious pup with.

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Kristy M.
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

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Sitters in Chester average 10
repeat dog boarding clients

FAQs for Dog Boarding - Chester

Frequently asked questions about Rover

The average cost for Dog Boarding in Chester on Rover is $64.2 per night (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog Boarding easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Boarding. For more information on service fees, click here .

As of July 2026, there are 1,088 sitters on Rover offering Dog Boarding across Chester. Enter your ZIP code to see which available sitters are closest to your home.

Every sitter on Rover has their own rhythm and routine, but most will follow the flow that keeps your dog happiest. Sitters can give meals on your dog's regular schedule, provide a comfortable place for sleep, and plenty of one-on-one attention.

96% of Chester sitters also include daily walks in the neighborhood during dog boarding stays. You can also request photo and message updates throughout the stay so you can see which Chester landmarks or neighborhoods your dog is enjoying.

If your dog is a little shy, consider booking a one-night trial stay! This practice run can boost your and your dog’s confidence before your trip.

Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Chester 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 Chester.

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 Chester 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 NY 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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