Dog Boarding in Chester

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Top rated Chester dog boarders

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

Alexis was great with our Archie! She was attentive to his needs, gave him lots of love and nice long walks, which he loves! She also sent us pictures throughout the day.We’ll ,without a doubt, book with her again in the future!

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Larissa R.
Sitter Profile Image: Jadyn G.
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Jadyn G.
Star Sitter
from
$55
per night
5.0 out of 5 stars
52 reviews
11 repeat clients
5 years of experience
Highland Mills, NY, 10930

Jadyn was EXCELLENT with my dog Sam while I went away. She sent me pictures and updates through out the whole stay. I would high recommend her, and will definitely continue to use her for dog sitting services. Thank you so much Jadyn :) we love you 🩷

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

Sandra was extremely nice and Nala seemed to lovely her time there. I would definitely use Sandra again in the future, she sent a picture of Nala while in her care. Thank you again

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James B.
Sitter Profile Image: Carla C.
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Carla C.
Star Sitter
from
$45
per night
4.9 out of 5 stars
115 reviews
28 repeat clients
15 years of experience
Highland Lakes, NJ, 07422

Carla was absolutely amazing with Maple. She treated her like she was her own, and that meant everything to me. I felt completely comfortable and relaxed knowing Maple was in such loving, capable hands. You can truly tell how much she cares. I honestly think Maple would have happily stayed with her! I’m so grateful to have found someone I trust this much and would highly recommend Carla to anyone looking for exceptional care.

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Jennifer P.
Sitter Profile Image: Vicky A.
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Vicky A.
from
$60
per night
5.0 out of 5 stars
14 reviews
6 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: Jonathon M.
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Jonathon M.
Star Sitter
from
$45
per night
5.0 out of 5 stars
14 reviews
4 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: 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 took very good care of my boy. He was not used to being away from me, but I feel like he felt like home. Daniel sent me photos and daily updates. I do not live in the area, but I definitely recommend Daniel.

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Alexandra M.
Sitter Profile Image: Lieb B.
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Lieb B.
from
$70
per night
5.0 out of 5 stars
71 reviews
35 repeat clients
5 years of experience
Suffern, NY, 10901

Lieb did an amazing job taking care of our Sky! He kept in constant communication, sending us pictures and videos, which gave us so much peace of mind. It was clear that he truly cared for Sky like she was part of the family. We highly recommend him—absolutely wonderful and trustworthy!

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Jeudy R.
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: 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 and his wonderful family are the definition of “above and beyond” when watching our pup Eleanor! He took very special care to provide enrichment, exercise, and to make sure all of her needs were met. He kept diligent notes for us, was an excellent communicator, and was clearly so invested in the health and happiness of our pup. He even sent us home with a couple of treats he’d found out she liked! He’s absolutely wonderful and I cannot recommend him enough.

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Rikki S.
Sitter Profile Image: Terrance R.
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Terrance R.
Star Sitter
from
$45
per night
5.0 out of 5 stars
23 reviews
8 repeat clients
12 years of experience
Newburgh, NY, 12550

Was able to enjoy my time away knowing she was in great care. Got updates and pictures. Will reach out again to Terrence anytime I'm going anywhere!

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Nicole G.
Sitter Profile Image: Maria V.
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Maria V.
Star Sitter
from
$45
per night
5.0 out of 5 stars
59 reviews
24 repeat clients
20 years of experience
Milton, NY, 12547

she was an excellent nanny for Pluto .. she was always in contact with me, she sent me photos and videos, she looked after Pluto for 5 days ... 100% recommended, she has a lot of love and responsibility for pets

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Sol N.
Sitter Profile Image: Arsenii S.
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Arsenii S.
from
$75
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: Natasha & Hamir D.
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Natasha & Hamir D.
Star Sitter
from
$80
per night
5.0 out of 5 stars
25 reviews
3 repeat clients
14 years of experience
Cortlandt Manor, NY, 10567

Natasha took amazing care of our senior Saint Bernard! Great communication, sent lots of photos, and we knew Ophelia was in the best of hands

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Susanne F.
Sitter Profile Image: Craig M.
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Craig M.
from
$65
per night
5.0 out of 5 stars
18 reviews
5 repeat clients
1 year of experience
Croton on hudson, NY, 10520

Once again my dog Tucker had a wonder day with Craig. Tucker looks forward to going there. Craig even sent pictures of Tucker enjoying himself. My first choice dog sitter.

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

I cannot recommend Melissa and her family enough. From the moment we had a meet and greet with her, I knew Watson would be in amazing hands! After dropping him off, I was updated multiple times a day with pictures, videos, and updates of him living his absolute best life. There was also so much care taken to accommodate him since he had a recent injury that he’s just out of recovery for. They took care of him as if he was their own, even going for walks in the rain! I’m so grateful to have found people so truly caring and who love animals to take care of my little guy! He is currently sound asleep after an adventure filled few nights! I’ll absolutely be booking again in the future! Thank you all again for being incredible ☺️

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Allison B.
Sitter Profile Image: Francesca & John B.
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Francesca & John B.
from
$75
per night
5.0 out of 5 stars
5 reviews
1 repeat client
10 years of experience
Walden, NY, 12586

About: As lifelong dog owners who love to travel, we know how nerve racking it can be to leave your beloved pets in the care of strangers. We have 2 acres of property, of which a significant portion is fully fenced to let your dogs run and play with the security of knowing they are safe. We have three fenced in areas to separate dogs that might prefer to play on their own. Our resident dogs are Emma, who's never met a dog she didn't consider her best friend, and Honey, our bossy Pomeranian. We own an on-property outbuilding behind our home that is insulated, heated, and has water and electric. We are also very flexible for special needs guests--just tell us about your dog and what he or she needs to feel comfortable away from you. We will also provide pictures during your dog's stay if that is desired. Even if you have a unique situation, please inquire, we're happy to work with you! We are currently working from home and have plenty of time and space to provide your pup with the care and attention he or she needs! We have three fenced in dog areas along with a heated, insulated outbuilding with water and electric. Depending on how many dogs we are hosting, your pup will sleep comfortably in a crate with soft bedding with other dogs secured nearby. We are very flexible and happy to provide tailored service depending on your pup's needs.

Sitter Profile Image: Tina T.
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Tina T.
from
$45
per night
5.0 out of 5 stars
6 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: Julia R.
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Julia R.
Star Sitter
from
$75
per night
5.0 out of 5 stars
39 reviews
10 repeat clients
20 years of experience
Warwick, NY, 10990

Julia is great! Maggie loved being there. She took great care of her. I was very comfortable leaving her. I knew she was in good hands!! She sent me updates and pictures. 100% satisfied!

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Maureen K.
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 such a positive experience! First time leaving our pup for multiple days outside of close family and friends, and Jane made us feel great about it. Not only did she send pictures and updates, it was evident that she and her family really accepted Elwood into their lives and made him feel welcome. I think he was even a little sad to leave them behind when it came time to come home! Jane was also very accommodating with drop off and pick up times, which made the experience that much easier.

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Corrie W.
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Over 147
pet parents in Chester have booked dog boarding

Chester dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

This was the first time leaving my dogs with "strangers". My dogs were taken care of like family and seeing all the photos/updates it was definitely a dog vacation. I would highly recommend this great family. 🙂

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Chris M.
Boarding
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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How Rover works

  1. 1. Search

    Read verified reviews by dog parents like you and choose a boarder who’s a great match for you and your dogs
  2. 2. Meet & Greet

    Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

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

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 dog boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.

  • World-class support

    We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.

Sitters in Chester average 10
repeat dog boarding clients

Dog Boarding FAQs

Frequently asked questions about Rover

As of Jun 2026, the median cost of dog boarding in Chester is $60 per night, including service fees. Boarding your dog for one week typically costs $420. Sitters on Rover set their own rates based on their qualifications, your dog's needs, and their space's amenities. As a result, most Chester dog boarding rates can be found as low as $36 to as high as $66 per night.

If you’re searching for a Chester dog boarding sitter for the first time, visit the sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, 521 sitters provided dog boarding in Chester. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, dog boarding sitters joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple sitters about your booking. Typically, 90% of Chester dog boarding sitters respond in under an hour.

Sitters who provide dog boarding in Chester have an average of 19 years of experience. Dog boarding sitters with repeat customers have an average of 10 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters in Chester.

Rover makes it easy to find Chester dog boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog boarding is great for:

  • Dogs of all ages and abilities, including puppies
  • Pet parents looking for a safe, loving alternative to a kennel
  • Dogs who’d love to socialize with their sitter’s pets

There are 521 dog boarding sitters in Chester on Rover, so you’re sure to find the perfect match for your dog! In Chester, 94% of sitters offer daily exercise, 98% offer medication administration, and 95% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog boarding sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog boarding sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your dog boarding sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your dog boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.