Dog Boarding Chester

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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

Another great stay Piper had with Alexis. First sleepover and did great. Alexis is amazing with my dog in all aspects. Thank you , we appreciate you 🙏🏻

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

Sandra and her husband took great care of my little girl. Her communication is excellent and she sent me pictures to keep me updated on my little girl's stay. She was very flexible with me due to my crazy schedule. I will absolutely be using her and her husband again in the future!

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Alisia W.
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 great! I’ve never left my dogs with anyone other than family, so I was honestly really nervous. Now that I have Daisy, my 2.5-year-old rescue, I needed to find someone I could trust. My vet recommended Rover, which helped, and after reading Carla’s reviews I felt much better. She was super communicative before the booking, and when I dropped Daisy off and saw the fenced-in yard (something she doesn’t get at home), I knew she’d love it. Carla also had a separate room set up for her to sleep in, which I really appreciated. When I picked Daisy up, she was happy and relaxed—it was obvious she had a great time. I’ll definitely be booking with Carla again. So glad I found someone I can trust. Thanks, Carla!

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Meg U.
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

John and his family took care of my two pups and did an awesome job. They sent updates and pictures everyday. Seeing how fast my pups took to his family says everything. I will definitely be using them again for all my boarding needs.

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Steven E.
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 great care of Tully and she came home happy and tuckered out from her weekend vacation. He was very responsive with communication and took her on short notice after my previously booked sitter canceled.

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Patrick L.
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

This is my 3rd time leaving our precious pup with Daniel & his wife. They are such kind people and I always feel comfortable with leaving my pup with them. They are very professional and have great communication.

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Rosalie S.
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

Awesome experience! This was our first time ever leaving our dog with someone and it was a great experience for us and our dog!! Great pictures also that kept us updated to how he was, since we were missing him. Without a doubt would have them watch him anytime.

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Kathlin I.
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

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: 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’s son took personal care of our Blondie. She came back tired and exhausted from all the fun fetch and swim play she had. If your dog loves playing in the pool this is definitely a great option. The owner’s dog Jaguar is well trained and has such calm temperament that even surprised me. Lieb took us in a last minute situation which was great all around.

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Ko S.
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: 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 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: 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

110% recommend! Maria was excellent. We are new to NY and were in a rush to find someone to watch our pup. We got very lucky to have found Maria! She showed true passion and love for our pup just with one visit! She also noticed that he had an ear infection and took it upon herself to do something about it- can you say amazing? She ALSO gave him a bath— literally doesn’t get any better! We will certainly be using Maria again! Can’t thank her enough! ??

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Paige H.
Sitter Profile Image: Arsenii S.
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Arsenii S.
from
$72
per night
5.0 out of 5 stars
11 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: 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

Couldn’t have asked for a better dog sitter. Morgan was so attentive and responsive ! Would highly recommend her to anyone looking for a fur baby sitter.

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Marjorie M.
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 and Hamir took wonderful care of our beagle mix. They sent updates and photos daily. He was very comfortable with them which made our trip more enjoyable to know he was in such great care.

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Lisa K.
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.
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: Sujanna K.
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Sujanna K.
from
$65
per night
4.9 out of 5 stars
19 reviews
7 repeat clients
30 years of experience
Bloomingdale, NJ, 07403

Sujanna was WONDERFUL! She took thoughtful care of our Toby and went above and beyond. Toby got lots of love and attention the entire time he was there. Toby will definitely be back. We highly recommend Sujanna!!!

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Marybeth W.
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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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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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