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
56 reviews
14 repeat clients
5 years of experience
Highland Mills, NY, 10930

Jadyn was excellent with Max. He was so happy with her. She is awesome and loving with Max. She took pictures and kept us updated. She takes great care of our dog. She is a definitely someone that you can trust with your pets. We will definitely be use her services for the future. I was thrilled with the care she provided for Max.

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Melissa E.
Sitter Profile Image: Fiona R.
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Fiona R.
Star Sitter
from
$65
per night
5.0 out of 5 stars
17 reviews
5 repeat clients
9 years of experience
Highland Lakes, NJ, 07422

This was my first time using rover and I could not have been happier. Fiona was so sweet and treated my Lucy like her own! I felt at ease knowing she was in good hands while we were out of town. I’ll definitely be using her again!!

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Pamela T.
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

Jane and her family were wonderful! Roxy & Scout were very comfortable and well loved! Would recommend Jane to everyone. Will definitely use Jane when we come back to NY.

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Christina L.
Sitter Profile Image: Daniel R.
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Daniel R.
Star Sitter
from
$55
per night
5.0 out of 5 stars
52 reviews
17 repeat clients
25 years of experience
Middletown, NY, 10940

Daniel watched our one and a half year old cockapoo for a long weekend. Our pup had a great time. Daniel sent daily updates and took him for walks. There is a fenced in yard which was great too! We will definitely book again for future trips.

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Nora C.
Sitter Profile Image: Sandra E.
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Sandra E.
from
$55
per night
5.0 out of 5 stars
147 reviews
61 repeat clients
10 years of experience
Middletown, NY, 10940

Sandra took great care of my dog. She made sure to stick to his usual routines and habits while keeping me updated the whole time and even sent me pictures so I could see him while I was away. I highly recommend her services:)

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Brandon R.
Sitter Profile Image: Carla C.
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Carla C.
from
$50
per night
4.9 out of 5 stars
129 reviews
37 repeat clients
15 years of experience
Highland Lakes, NJ, 07422

Carla was super pleasant to deal with and took excellent care of our fur babies. Would highly recommend and hope to do business again in the future.

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Kyle A.
Sitter Profile Image: Sonia G.
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Sonia G.
Star Sitter
from
$60
per night
5.0 out of 5 stars
56 reviews
16 repeat clients
10 years of experience
Peekskill, NY, 10566

Sonia is an amazing dog sitter! Very kind, caring and responsible. Treated my dog like her own. Lives in a beautiful neighborhood to walk dogs. Very easy to talk to and arrange dates and times. Sent pictures every day. My dog made new friends and had a nice vacation with Sonia and her family.

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Jill S.
Sitter Profile Image: Tina T.
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Tina T.
from
$45
per night
5.0 out of 5 stars
9 reviews
2 repeat clients
20 years of experience
Monroe, NY, 10950

We are SO thankful that Tina was available to watch our Ranger. She was so patient with his needs and gave us updates all the time while he was there. She is truly loving and we were able to enjoy our vacation time because of her. It’s very obvious how much she loves animals. We know our Ranger had a good time because he was very relaxed during pick up and Tina was able to provide him with a safe and relaxing environment. I would absolutely recommend her to anyone!

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Cassandra D.
Sitter Profile Image: Melissa C.
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Melissa C.
Star Sitter
from
$70
per night
5.0 out of 5 stars
39 reviews
9 repeat clients
35 years of experience
Chestnut Ridge, NY, 10977

Melissa did such an amazing job taking care of my dog Melo. I went away for the weekend and was able to book with her a week before. She introduced my dog to her other animals for the first time and I think he was so happy to have other furry friends for the weekend. Melissa was super clear and communicative throughout. I loved seeing the photos and videos every few hours so I always felt like melo was in good hands. She also had a print out award and treat for Melo after his stay which was so sweet. Thanks again Melissa for watching Melo :)

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Ashley K.
Sitter Profile Image: Patricia R.
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Patricia R.
Star Sitter
from
$40
per night
5.0 out of 5 stars
128 reviews
39 repeat clients
12 years of experience
New Windsor, NY, 12553

Pat is amazing! Treated my Harli like her own. Sent me pictures throughout her stay which always came at the perfect time. I knew Harli was in good hands and received all the love and care she would normally get at home. :) My spoiled princess was well taken care of!

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

Alexis was so great! My Rosie absolutely loves her! Alexis sent me pictures every day with updates on her. When I picked her up after 4 days she wasn’t trying to pull me out of Alexis’ home which she usually does when I’ve picked her up from other places she’s stayed. Rosie was very well cared for and I highly recommend Alexis! Thank you for the love and care you gave her!

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Gayle M.
Sitter Profile Image: Cristina C.
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Cristina C.
Star Sitter
from
$50
per night
4.9 out of 5 stars
67 reviews
35 repeat clients
20 years of experience
Middletown, NY, 10940

I am very happy with the care that my Dallas received while staying with Christina. Dallas is a timid dog and I was concern that she would have problems being away from home. But she was fine, Christina took good care of her and that means a lot to me. I like to travel twice a year and I will be using Christina for all of my future travels!

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Sylvia J.
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
27 reviews
5 repeat clients
14 years of experience
Cortlandt Manor, NY, 10567

Our dog Laika had her first experience of being with a sitter for several days and we were fortunate to have met wonderful people in Natasha and Hamir. Their kindness and attentiveness are extraordinary and they ensured to make our dog as comfortable as possible giving her love and care which made her feel as if at home. Natasha and Hamir were communicating daily with brief recap of the day and Laika’s photos from her walk and during her cozy downtime. They were willing to accommodate any requests we had. Natasha and Hamir are one of a kind and we can only wholeheartedly recommend them as wonderful people and dog lovers. We surely found a place we can call a “home-way-from home” for our Laika in the future as well.

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Andrea D.
Sitter Profile Image: Amy D.
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Amy D.
from
$65
per night
4.8 out of 5 stars
37 reviews
11 repeat clients
20 years of experience
Goshen, NY, 10924

My dog Griffin has been to other Rover sitters and this was the first time he showed me that he was completely comfortable from the moment he walked in the door at our meet and greet! He walked around the place like it was his own home! Amy and her family took care of Griffin for a 2 night stay. I was so happy he would be able to play with her kids and the other dogs there, as he loves attention from all beings. I will look to see if Amy is available any time Griffin needs sitting again! Thanks again, Amy!

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Terri C.
Sitter Profile Image: Natacha T.
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Natacha T.
from
$65
per night
5.0 out of 5 stars
17 reviews
6 repeat clients
10 years of experience
Cortlandt Manor, NY, 10567

Natacha was a God-sent. She watched out 7 month old Husky, Samon for 3 days. Natacha had a gorgeous Husky herself. She sent up pic and updates daily. We felt confident that Samson would be safe in Natacha's care, and he was. We will be using her again in the future to care for Samson. Could not have asked for a better sitter!

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George R.
Sitter Profile Image: Megen H.
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Megen H.
from
$45
per night
5.0 out of 5 stars
32 reviews
13 repeat clients
20 years of experience
Wallkill, NY, 12589

Megen took great care of our dog Lotta. She has a fenced in backyard which was great so our dog was outside a lot and played with the other dogs there. Easy to communicate with. Highly recommend!

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Hazel K.
Sitter Profile Image: Hayden G.
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Hayden G.
from
$75
per night
5.0 out of 5 stars
53 reviews
14 repeat clients
10 years of experience
Lake Peekskill, NY, 10537

Great experience. Hayden responds to messages super quick, provides great pictures and updates and my pup was doing great when I picked him up. Using Hayden again for another dog sit session.

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Jessica K.
Sitter Profile Image: Tiffany M.
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Tiffany M.
from
$50
per night
5.0 out of 5 stars
205 reviews
32 repeat clients
7 years of experience
Highland Lakes, Highland Lakes, NJ, 07422

Tiffany was amazing! She sent pics everyday of our pup and we could tell she was getting a lot of love while we were away. Highly recommend Tiffany!!

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

We used Morgan, and actually Rover.com, for the first time. My husband dropped off Laska (our hound mix rescue dog), and noticed that she seemed happy to go with Morgan. For us, this is a big deal because she's been through a lot. When we used the kennel Laska would fight us going in, and would come home stressed out and completely out of it. This was not the case after picking up Laska from Morgan's. Laska was clean, happy, and not stressed out! This was a first for her! Laska did have some separation anxiety, so she chewed her bed up. That was our fault because we forgot to tell Morgan about the routine that we have when we leave the house. As a result, we thought Morgan would tell us that she wouldn't watch Laska again, but to our delight, Morgan said she will take her in the future.

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Larissa P.
Sitter Profile Image: Maria V.
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Maria V.
Star Sitter
from
$45
per night
5.0 out of 5 stars
64 reviews
26 repeat clients
20 years of experience
Milton, NY, 12547

Maria (and family) were lifesavers and saved our trip by having availability last minute when another sitter canceled on us. Our dogs looked so happy and loved while we were gone. Definetly recommend and look forward to using her again!

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Candice G.
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The median cost per night for dog boarding in Chester is $63

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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Sitters in Chester average 10
repeat dog boarding clients

FAQs for Boarding - Chester

Frequently asked questions about Rover

The average cost for Dog Boarding in Chester on Rover is $64.2 per night (as of August 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 August 2026, there are 1,085 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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