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 5.0 stars
32 reviews
9 repeat clients
25 years of experience
Middletown, NY, 10940

First time using Rover and super apprehensive… but Alexis made the experience of leaving my puppy behind super comforting. I was kept updated on Khloe and what she was doing. Comments throughout the day which I appreciated. I definitely recommend Alexis and will use her again and again.

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Krishna M.
Sitter Profile Image: Jadyn G.
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Jadyn G.
Star Sitter
from
$55
per night
5.0 out of 5.0 stars
50 reviews
10 repeat clients
2 years of experience
Highland Mills, NY, 10930

Jadyn does it again🫶🏽! Our #1 sitter to contact whenever we need a loving, caring, knowledgeable place for our fur baby Beau. Thank you Jadyn for being such a wonderful, accessible, loving, and understanding person. To see Beau, get so excited from the time we turn onto your block, shows the Love he has for you. Our family appreciates you and your time.♥️

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Kenneth G.
Sitter Profile Image: Sandra E.
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Sandra E.
Star Sitter
from
$55
per night
5.0 out of 5.0 stars
133 reviews
51 repeat clients
10 years of experience
Middletown, NY, 10940

Sandy, was absolutely amazing and patient. My fur baby is very needy and gets seizures and high anxiety she was attentive and caring. I would 100% without a doubt recommend her. Thank you for being so kind.

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Madeline R.
Sitter Profile Image: Rachel K.
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Rachel K.
from
$60
per night
5.0 out of 5.0 stars
28 reviews
8 repeat clients
10 years of experience
New Windsor, NY, 12553

Rachel is the best! My pup loves her so much!

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Alletta E. C.
Sitter Profile Image: Lyanne S.
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Lyanne S.
Star Sitter
from
$55
per night
4.9 out of 5.0 stars
90 reviews
28 repeat clients
11 years of experience
Newburgh, NY, 12550

Lyanne and her husband were taking care of our dog Bruce who is 6 months old. We had last minute booking and thing worked out for us. Lyanne responded us quick. Her boarding location is clean and spacious. She updated photo and info while Bruce was there. I will continue to book her when we are away.

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Panwarat Ginger D.
Sitter Profile Image: Carla C.
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Carla C.
Star Sitter
from
$45
per night
4.9 out of 5.0 stars
90 reviews
18 repeat clients
15 years of experience
Highland Lakes, NJ, 07422

Carla was very accommodating to both me and my dog. She took great care of him and was able to work around my schedule for pick up and drop off.

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Liam A.
Sitter Profile Image: Isabell S.
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Isabell S.
from
$40
per night
5.0 out of 5.0 stars
9 reviews
1 repeat client
15 years of experience
Monroe, NY, 10950

Isabell was amazing with our two dogs. She made sure to send us pictures and videos of the dogs everyday. Seemed like they were having too much fun in the yard. One of our dog is a bit of challenge and she made sure to take care of him. We will be definitely using her services again.

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Tyler H.
Sitter Profile Image: Alana M.
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Alana M.
from
$55
per night
5.0 out of 5.0 stars
14 reviews
4 repeat clients
20 years of experience
Rock Tavern, NY, 12575

My Dog Buttons had an awesome stay with Alana. He seemed happy to be there and was well taken care of. Thank you so much for taking care of Buttons.

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Gus J.
Sitter Profile Image: Pam V.
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Pam V.
from
$55
per night
5.0 out of 5.0 stars
14 reviews
3 repeat clients
15 years of experience
Montgomery, NY, 12549

Pam and her husband Jason were amazing. They took great care of our pup Teddy and even sent us pictures of him each day he was with them. They communicated with us

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David R.
Sitter Profile Image: Jonathon M.
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Jonathon M.
Star Sitter
from
$45
per night
5.0 out of 5.0 stars
12 reviews
2 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: Sonia G.
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Sonia G.
Star Sitter
from
$50
per night
5.0 out of 5.0 stars
26 reviews
6 repeat clients
10 years of experience
Peekskill, NY, 10566

Sonia is amazing!! She LOVES dogs and took great care of Moonie. She shares photos and videos for everyday updates. our dog had wonderful time with Misty (Sonia’s dog) and other dogs for day care and boarding. Will certainly back to Sonia for day care or boarding again in the future.

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Teng Y.
Sitter Profile Image: David G.
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David G.
Star Sitter
from
$60
per night
5.0 out of 5.0 stars
73 reviews
20 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: Ilona P.
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Ilona P.
from
$50
per night
4.9 out of 5.0 stars
34 reviews
8 repeat clients
30 years of experience
Harriman, NY, 10926

Ilona was great. She accepted a very last minute request and made it easy to meet and get Athena dropped off. She immediately confirmed when she was settled and sent updates. Our pup came back tired and happy. We could tell she had a fun active weekend.

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Arlene S.
Sitter Profile Image: Vicky A.
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Vicky A.
from
$60
per night
5.0 out of 5.0 stars
7 reviews
2 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: Navile V.
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Navile V.
from
$60
per night
5.0 out of 5.0 stars
17 reviews
2 repeat clients
5 years of experience
Florida, NY, 10921

Navile took in our dog for the weekend and she had an amazing time! She was super accommodating and communicative and would recommend her to anyone.

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Max R.
Sitter Profile Image: Daniel R.
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Daniel R.
Star Sitter
from
$50
per night
5.0 out of 5.0 stars
50 reviews
15 repeat clients
25 years of experience
Middletown, NY, 10940

This is the second time we leave our pup with Daniel and he's officially our go-to sitter. He and his wife give and show much care and the communication/business side of things always runs smooth. Thanks again Daniel! Till the next time 👋

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Rosalie S.
Sitter Profile Image: Morgan F.
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Morgan F.
Star Sitter
from
$64
per night
4.9 out of 5.0 stars
176 reviews
107 repeat clients
17 years of experience
West Milford, NJ, 07480

We are first time dog owners and we brought our 11 month old German Shepherd to Morgan after seeing her rave reviews. We can verify she deserves all five stars - she was able to quickly interpret our puppy’s behavior and gave us tips for after the boarding experience. We were nervous as well since this was the first time our dog would be away from us for an extended amount of time but Morgan made us feel at ease with her professional veterinary experience and ability to help along our puppy’s socialization. We boarded our dog for 6 days and Morgan was very communicative during the stay, with quick response to our messages. We highly recommend her and plan to use her again.

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Sabrina A.
Sitter Profile Image: Amy D.
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Amy D.
from
$65
per night
4.8 out of 5.0 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: Leticia C.
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Leticia C.
Star Sitter
from
$60
per night
5.0 out of 5.0 stars
87 reviews
24 repeat clients
10 years of experience
New Windsor, NY, 12553

Letitia was so welcoming and caring with our two dogs. She sent us lots of photos, was quick with communication and her home was lovely and had a spacious backyard. Our dogs were picked up after 3 days, healthy, happy; and rested. Highly recommended!

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Joel B.
Sitter Profile Image: Melissa C.
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Melissa C.
Star Sitter
from
$65
per night
5.0 out of 5.0 stars
21 reviews
4 repeat clients
35 years of experience
Chestnut Ridge, NY, 10977

Melissa and family gave Ranger the best weekend while I was out of town. She kept me in the loop with respect to his sleeping and eating habits, familiarization with other pets in the home, and shared many photos along the way. I would absolutely book with Melissa again. Thanks so much, Melissa!

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Frank 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 5.0 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
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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 9
repeat dog boarding clients

Dog Boarding FAQs

Frequently asked questions about Rover

As of Jan 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 Jan 2026, 558 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, 92% 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 9 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 558 dog boarding sitters in Chester on Rover, so you’re sure to find the perfect match for your dog! In Chester, 97% 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.