Dog Boarding Chester

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Over 13
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.

1 / 1
Sitter Profile Image: Britanny B.
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Britanny B.
Star Sitter
from
$50
per night
5.0 out of 5 stars
80 reviews
23 repeat clients
20 years of experience
Madison, CT, 06443

Brittany and her family were wonderful to Enzo. It was a great vacation for him he was well supervised and had a few buddies to play with. We will be happy to leave him there again.

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Nancy S.
Sitter Profile Image: Laura G.
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Laura G.
Star Sitter
from
$45
per night
5.0 out of 5 stars
114 reviews
37 repeat clients
18 years of experience
East Haddam, CT, 06423

Laura was so wonderful! She made our family and our pup so comfortable and sent pictures and updates throughout our trip. We were so happy knowing that our dog got to be part of Laura’s family while we were away. We’d highly recommend Laura!

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Hadley K.
Sitter Profile Image: Serenity M.
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Serenity M.
Star Sitter
from
$55
per night
4.9 out of 5 stars
15 reviews
5 repeat clients
4 years of experience
Essex, CT, 06426

Serenity offered to meet our pups prior to their stay with her. She sent regular updates to let me know how they were doing. When we picked them up they seemed at ease. I will definitely reach out to her again when needed.

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Laurie B.
Sitter Profile Image: Laura C.
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Laura C.
from
$45
per night
5.0 out of 5 stars
25 reviews
8 repeat clients
15 years of experience
East Haddam, CT, 06423

Laura went above and beyond to make sure our first time leaving our puppy went smoothly. From thorough communication before the booking, to updates during our vacation, it was such a relief to know that he was in good hands (and also having fun too)! If we travel again and need dog care, I will definitely be checking Laura's availability; I'm so glad I found her!

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Laura A.
Sitter Profile Image: Julius G.
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Julius G.
from
$62
per night
4.9 out of 5 stars
36 reviews
12 repeat clients
5 years of experience
Deep river, CT, 06417

Julius and family took good care of our dog. Julius is super-responsive and sent several cute pictures of the visit. It looked like everyone got along well and were very active. Our dog came home exhausted, which is a good thing. We also needed to adjust the end time a little bit, and Julius was very accommodating of the last minute change.

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Shubert K.
Sitter Profile Image: Erica & Thomas C.
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Erica & Thomas C.
Star Sitter
from
$48
per night
5.0 out of 5 stars
218 reviews
82 repeat clients
40 years of experience
East Lyme, CT, 06333

Moby, a clinger, was in a total comfort zone amongst this loving family. Care was complete + a boot camp of healthy activity. Other 🐾 campers alongside was great for his social abilities. Now, our go-to when we have to be away!

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Beatrice W.
Sitter Profile Image: Jillison S.
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Jillison S.
from
$40
per night
5.0 out of 5 stars
13 reviews
1 repeat client
40 years of experience
Old Saybrook, CT, 06475

Jill was amazing! We met before our booking so we could make sure my dog would be comfortable and fit in at their home. She sent me pupdates throughout the weekend and did so many adventures with our dog. I'm so happy to have found her!

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Kate D.
Sitter Profile Image: Concetta & Jerome & Brett W.
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Concetta & Jerome & Brett W.
from
$75
per night
5.0 out of 5 stars
10 reviews
4 repeat clients
25 years of experience
Clinton, CT, 06413

My Golden had a great stay with Connie and family. She sent photos, gave updates, and we met before at a dog park to make sure our dogs got along. He was well cared for, and even sent him home with a goodie bad with some treats. They are much more like professional caretakers and couldn’t recommend enough.

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Jonathan M.
Sitter Profile Image: Carolina O.
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Carolina O.
from
$45
per night
5.0 out of 5 stars
108 reviews
35 repeat clients
10 years of experience
Groton, CT, 06340

Thank you so much for taking such wonderful care of Forest this weekend. It means the world to us knowing he was safe, happy, and loved while we were away. Your kindness, reliability, and genuine care gave us complete peace of mind, and we’re so grateful for the time and attention you gave him. We truly appreciate you and feel lucky to have someone we can trust with our furry family member. With heartfelt thanks, Dave and Ana

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David B.
Sitter Profile Image: Ariel T.
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Ariel T.
from
$63
per night
5.0 out of 5 stars
97 reviews
42 repeat clients
10 years of experience
Guilford, CT, 06437

Gigi had a fabulous time staying with Ariel, as evidenced by the photos of her racing around with a few of her new best dog friends that Ariel sent us each day of our six-day trip. From her description of her property, Ariel's accommodations stood out, with its big, fenced backyard and in-the-house living for dog guests. Although leash walks were an additional option, we knew Gigi would want to run and play. She came fitter, sleeker, and a happy dog. We will definitely book with her again.

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Lea S.
Sitter Profile Image: Nadjeska R.
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Nadjeska R.
from
$65
per night
5.0 out of 5 stars
67 reviews
27 repeat clients
18 years of experience
Guilford, CT, 06437

Nadjeska provided such excellent care for our rescue dog! She sent multiple pictures each day and was very conscientious. We definitely plan to schedule with her again!

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Katie S.
Sitter Profile Image: Mary Jo M.
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Mary Jo M.
Star Sitter
from
$60
per night
4.9 out of 5 stars
157 reviews
64 repeat clients
30 years of experience
Old Lyme, CT, 06371

Mary Jo was great taking care of my senior dog. She was happy when picking her up and it was easy to see she was well cared for. Thank you Mary Jo!

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Ann B.
Sitter Profile Image: Danielle G.
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Danielle G.
from
$55
per night
5.0 out of 5 stars
19 reviews
1 repeat client
12 years of experience
Cheshire, CT, 06410

Danielle and her family are absolutely wonderful. I continue to recommend them, so great and attentive. Always provide updates and just so sweet.

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Camila B.
Sitter Profile Image: Karen F.
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Karen F.
Star Sitter
from
$31
per night
5.0 out of 5 stars
60 reviews
19 repeat clients
11 years of experience
New London, CT, 06320

Karen took our Poodle puppy on a last minute request and we’re so happy she did! She stayed in contact throughout, sent tons of photos and videos and was very flexible with pickup and drop off time. She even gave us a little parting gift! Would definitely recommend Karen if you are in the New London/Mystic area!

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Annie K.
Sitter Profile Image: Elisa N.
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Elisa N.
Star Sitter
from
$65
per night
5.0 out of 5 stars
20 reviews
2 repeat clients
30 years of experience
WATERFORD, CT, 06385

Elisa was wonderful with communication and updates for my Bru, as well as very responsive. Very easy and professional to book with and very trustworthy. Would absolutely use her services again in the future. 🐾

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Alicia D.
Sitter Profile Image: Sherry B.
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Sherry B.
Star Sitter
from
$45
per night
5.0 out of 5 stars
213 reviews
49 repeat clients
10 years of experience
Cromwell, CT, 06416

You know you have a great sitter when you dogs are just as excited to see you as they are them! Sherry was great when them and we are so grateful to have found her.

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Colleen M.
Sitter Profile Image: Brittany W.
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Brittany W.
Star Sitter
from
$45
per night
5.0 out of 5 stars
63 reviews
16 repeat clients
25 years of experience
Lebanon, CT, 06249

Brittany was AMAZING! Our dog, Bailey was only 18 weeks old and she knew all the right things to do with a puppy. We never worried once about his care. She sent pictures every day of his antics which made us laugh but also convinced us that he was happy and loved. She was in tune with his quirky personality, from his removal of ALL the toys from the toy box before deciding what to play with, to helping with the laundry by stealing the socks, to proudly carrying things around that he “found” . AND Brittany was reasonably priced. We will use her again in a heartbeat. We felt so incredibly blessed to have found her. We can’t thank her enough for making our vacation stress free.

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Carol T.
Sitter Profile Image: Margaret S.
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Margaret S.
from
$50
per night
25 years of experience
Middletown, CT, 06457

About: About Me Hi there! I’m a lifelong dog lover and retired Los Angeles firefighter who recently relocated to Middletown. Dogs aren't just a passion of mine—they’ve been my life’s work. Over the past 17+ years, I’ve worked as a professional Search and Rescue K9 handler, raising and working alongside three incredible SAR dogs of my own and helping train dozens more toward official certification. Now in my retirement, my days revolve around outdoor adventures, active play, and giving dogs the best possible care while their owners are away. My trusty companion Mojo, a friendly rescue pup, loves meeting new playmates and welcoming guests! What Sets My Care Apart * Safe, Active, and Enriched: I walk or hike almost daily and love taking guest dogs along for the journey! Whether your pup enjoys a leisurely neighborhood stroll, learning to hike safely, or exploring new surroundings, they’ll get plenty of physical exercise and fun. * Positive, Brain-Boosting Fun: My training philosophy is rooted in positive reinforcement and reward-based training. I love watching what behaviors dogs naturally offer and shaping them into fun new "tricks." It’s an incredible bonding experience that gives dogs great mental stimulation and keeps them happily engaged. * Spacious Acreage: I have a wonderful local property with tons of room for dogs to run, play, and burn off energy in a calm, safe environment (fully fenced as of late September!). * Unmatched Peace of Mind: Being fully retired means I am almost always home! I never host or board dogs on days when I need to be away for more than a couple of hours, ensuring your pet gets round-the-clock attention, safety, and companionship. Guests and Compatibility I am completely comfortable with dogs of all sizes, breeds, and life stages—from energetic puppies to senior companions. I also occasionally foster rescue dogs, so Mojo and I are well-versed in hosting social pups who enjoy extra canine company. Need help fine-tuning your dog’s leash manners during their stay? Just ask—we can easily discuss building positive leash habits while they’re here! Reach out today to schedule a meet-and-greet. Mojo and I can’t wait to welcome your pup to their home away from home! Being retired means my entire day is built around quality pet care! Our mornings always start with a good outdoor workout, followed by short, engaging training and exercise sessions spread throughout the day. Because I am home full-time, your pup will enjoy a structured routine packed with continuous companionship, mental enrichment, and plenty of activity. Your dog’s safety and peace of mind are my top priorities. My home is nestled in a quiet, low-traffic rural area, offering a calm and peaceful setting away from busy streets. Outdoor playtime happens in a spacious, full-acre yard—completely fenced as of September 21st—giving pets a secure, massive space to run and play freely. To ensure constant security and supervision, my property is also equipped with indoor and outdoor smart cameras, so I always have an eye on my guests whether we're inside or out in the yard.

Sitter Profile Image: Stephen S.
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Stephen S.
Star Sitter
from
$50
per night
5.0 out of 5 stars
87 reviews
29 repeat clients
40 years of experience
Hebron, CT, 06231

They did amazing with my semi rowdy Luna. I was updated everyday with lovely photos of her and her adventures! They accepted my last minute booking along with a meet and greet. It went as good as I could have expected plus more! I highly recommend and I will be booking in the future.

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Lizah H.
Sitter Profile Image: Cassandra F.
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Cassandra F.
from
$50
per night
5.0 out of 5 stars
23 reviews
8 repeat clients
10 years of experience
Hamden, CT, 06518

Cassandra & Nolan took excellent care of my Rosie girl while I was on a day trip to NYC. Frequent walks, cuddles, playtime, and plenty of photo updates. She enjoyed taking part in their holiday celebration! I will definitely book them again next time I'm in CT.

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Amy V.
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The median cost per night for dog boarding in Chester is $55

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Popular requests for dog boarding - Chester

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Sitters in Chester average 12
repeat dog boarding clients

FAQs for Boarding - Chester

Frequently asked questions about Rover

The average cost for Dog Boarding in Chester on Rover is $48.84 per night (as of September 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 September 2026, there are 822 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 CT 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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