Dog Boarding Chesterfield

Find a loving dog sitter to watch your dog overnight at your sitter's home.

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Chesterfield, Find top rated dog boarding

Prices are estimates per night for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.

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Sitter Profile Image: Brooke B.
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Brooke B.
Star Sitter
$50
total per night
5.0 out of 5 stars
• 140 reviews
36 repeat clients
25 years of experience
Pittsfield, MA, 01201

“Brooke took great care of Poppy. The pickup and drop-off process was quick and easy and Brooke was great with communication. Poppy also loved played with their dog Suki”

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Ben H.
Sitter Profile Image: Sarah & Noah P.
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Sarah & Noah P.
$45
total per night
5.0 out of 5 stars
• 6 reviews
1 repeat client
10 years of experience
Pittsfield, MA, 01201

“Noah and Sarah were wonderful! They were reliable, communicative, and took great care of Tahoe. I felt completely comfortable leaving him in their hands and would absolutely recommend them to other pet parents. I’d happily book with them again!”

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David W.
Sitter Profile Image: Jess L.
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Jess L.
$47
total per night
5.0 out of 5 stars
• 89 reviews
22 repeat clients
5 years of experience
Pittsfield, MA, 01201

“Jess was so sweet. Our dogs were immediately interested in getting to know Jess and felt comfortable going with her into her home. Thankful for Jess’ flexibility during our pups’ stay since we had some last minute changes to our schedule. Thank you, Jess!”

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Matthew B.
Sitter Profile Image: Kathleen M.
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Kathleen M.
Star Sitter
$95
total per night
5.0 out of 5 stars
• 166 reviews
46 repeat clients
12 years of experience
Becket, MA, 01223

“Kathleen was so patient with my questions and worries prior to the visit. And when my pup was with her, her photos and videos let me see how happy and safe he was feeling. I wish she were based somewhere that I could use her all of the time, because I have never been so happy with a sitter. Her location is beautiful and perfect for dogs who like to adventure in the woods.”

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Katya C.
Sitter Profile Image: Carmela A.
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Carmela A.
$39
total per night
5.0 out of 5 stars
• 6 reviews
2 repeat clients
25 years of experience
Agawam, MA, 01030

“Carmela was super nice with my elder dog. My chihuahua suffered violence from a teenager and now his behavior is not the best. Carmela was so comprehensive and knew how to manage him to keep him feel safe in her home. I am so thankful that she received my baby in her home for the time I had to travel.”

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Virginia G.
Sitter Profile Image: Abigale & Eric F.
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Abigale & Eric F.
Star Sitter
$45
total per night
5.0 out of 5 stars
• 15 reviews
2 repeat clients
10 years of experience
Chicopee, MA, 01013

“Abigale was wonderful with Bailey our senior pup. She administered his special diet food and sent us great daily photo updates which gave us total peace of mind while we were away. They provided a safe, cozy environment and we joked that Bailey seemed to have made himself right at home! I would not hesitate to book with them again !”

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P G.
Sitter Profile Image: Jessiana V.
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Jessiana V.
$34
total per night
5.0 out of 5 stars
• 47 reviews
19 repeat clients
10 years of experience
Indian Orchard, Indian Orchard, MA, 01151

“Jessiana did great with Winter and Ollie! She sent me updates on a regular basis, and the dogs were so tired when they got home! She was understanding and it’s apparent she really cares about animals. Highly recommend her!”

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Ana B.
Sitter Profile Image: Emma G.
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Emma G.
Star Sitter
$69
total per night
5.0 out of 5 stars
• 60 reviews
14 repeat clients
15 years of experience
Northampton, MA, 01060

“Emma was great for our big, goofy, energetic young dog. She sent us a lot of updates and he came home happy. We will definitely use Emma again!”

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Josh B.
Sitter Profile Image: Irene T.
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Irene T.
Star Sitter
$73
total per night
5.0 out of 5 stars
• 24 reviews
8 repeat clients
20 years of experience
Pittsfield, MA, 01201

“Irene has been such a great find in the Berkshires! She always gives helpful communication with each stay, and Ruby seems to love her time with Irene (and her sweet dog Goldie). Thanks for all of the care that you give to Ruby - we'll see you soon!”

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Eric B.
Sitter Profile Image: Dorjee D.
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Dorjee D.
$67
total per night
4.9 out of 5 stars
• 53 reviews
26 repeat clients
15 years of experience
Amherst, MA, 01002

“So happy to have Dorjee as our go-to sitter for Ziggy! This past trip was the longest yet, and we received so many great pictures that helped put us at ease to see how much fun he was having while we were gone. Thank you again :)”

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Tristen M.
Sitter Profile Image: Francy & William S.
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Francy & William S.
$28
total per night
1 year of experience
Pittsfield, MA, 01201

About: We have one year of experience caring for small dogs. We are responsible, attentive, and ensure a safe, loving and confrable environment at all times We work from home, so we have plenty of time to take care of pets. Provide constant attention follow daily routines. And we are also available on weekends when needed. We have a fenced yard where pets can play safetly. And we can take them for once or two daily walks ensuring exercise, attention, and a conformable environment

Sitter Profile Image: Chris S.
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Chris S.
$56
total per night
5.0 out of 5 stars
• 23 reviews
8 repeat clients
28 years of experience
Westfield, MA, 01085

“Chris was amazing and took such good care of our pup! The communication was fantastic and my dog had so much fun in the yard and with Chris’s dog. I highly recommend Chris!!”

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Heather D.
Sitter Profile Image: Kim M.
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Kim M.
Star Sitter
$62
total per night
5.0 out of 5 stars
• 73 reviews
26 repeat clients
20 years of experience
Westfield, MA, 01085

“Kim was great with my high energy dog. It was the first time he had stayed overnight with somebody outside of my family and it went great. Would have him stay over again!”

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Abby W.
Sitter Profile Image: Saktah K.
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Saktah K.
$45
total per night
5.0 out of 5 stars
• 11 reviews
5 repeat clients
30 years of experience
Upper Hill, Springfield, MA, 01109

“Saktah did a great job taking care of my elderly and rather unfriendly kitty, Koshka, for two weeks while I was vacationing. She was very professional, organized, and caring, kept me updated on how my kitty was adjusting, and showed genuine affection and concern for her. She's driven to get things right and wants your pet to be as comfortable as they can be while you're gone. So if you (like me) have a pet that needs extra love and care, and you'd like to relax during your vacation knowing they're in good hands, go with Saktah. She's got you covered.”

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Blink B.
Sitter Profile Image: Amy H.
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Amy H.
Star Sitter
$56
total per night
5.0 out of 5 stars
• 30 reviews
10 repeat clients
25 years of experience
East Longmeadow, MA, 01028

“If Arthur could write this review himself he would. He has had a few sleepovers with Amy and Mayzie. Every time he arrives he sprints to her door with tail wagging and pure joy. When he gets back home it’s KO. Snoring like he ran a marathon and had the time of his life doing it. I would trust Amy again, and again. 🐾”

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Mellanee H.
Sitter Profile Image: Jillian M.
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Jillian M.
$56
total per night
4 years of experience
Amherst, MA, 01002

About: I’m an active, outdoorsy person who loves getting outside and enjoying some fresh air with a dog by my side. I especially enjoy walks, exploring new trails, and giving dogs plenty of time to play and get their energy out. I’m comfortable caring for dogs with different personalities and energy levels, and I’m happy to follow their normal routines for meals, walks, playtime, and downtime. I want every dog in my care to feel comfortable, safe, and well cared for while their people are away. I’ll also keep you updated with photos and messages along the way! I work remotely 5 days a week and have plenty of time to hang with your pup! Working from home gives me the flexibility to let your dog out for potty breaks as frequently as needed. I live close to a network of trails that your dog will love! My friendly Bernedoodle is always looking for friends and will keep us company!

Sitter Profile Image: Ali S.
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Ali S.
Star Sitter
$56
total per night
5.0 out of 5 stars
• 31 reviews
7 repeat clients
5 years of experience
Belchertown, MA, 01007

“Our dog boarded with Ali for a week. We had a very positive experience at every stage of the process. He was easy to communicate with and very responsive. He was kind and attentive with our dog and we were able to relax and enjoy our vacation knowing that our dog was being so well cared for while we were away. I would highly recommend Ali!”

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Hayley S.
Sitter Profile Image: Russ & Janet W.
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Russ & Janet W.
Star Sitter
$62
total per night
5.0 out of 5 stars
• 66 reviews
31 repeat clients
11 years of experience
Longmeadow, MA, 01106

“Russ and Janet are great. Sophie was in 7th Heaven with them. Walked and played with and cuddled. I didn’t have to worry about a thing. Having just moved to the area, we’re thrilled to now have a go-to sitter for our pooch.”

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Karen W.
Sitter Profile Image: Victoria S.
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Victoria S.
Star Sitter
$45
total per night
5.0 out of 5 stars
• 10 reviews
4 repeat clients
5 years of experience
Maple High-Six Corners, Springfield, MA, 01105

About: Feeding, entertaining, and walking pets. Friends and family have trusted me in caring for their pets like my own when needed. I have had pets of all kinds growing up and have a passion for caring for dogs, cats and small animals such as guinea pigs. I currently work full remote and have flexibility to add in drop ins during the work day. I also have availability during weekends if you’re taking a trip, for multiple drop ins a day as needed. I currently have two cats who are my best friends. I have grown up around dogs and have dog sat for many years for friends and family. Walking and pop ins are the best part of my day.

Sitter Profile Image: Shelby P.
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Shelby P.
$56
total per night
5.0 out of 5 stars
• 11 reviews
4 repeat clients
15 years of experience
Amherst, MA, 01002

About: I’ve cared for dogs most of my life and truly treat them like family. I grew up in a home with four dogs, so I’m very comfortable with different personalities, sizes, and energy levels. I also adopted and lovingly cared for a difficult senior dachshund for years, which gave me valuable experience with patience, senior dog needs, routines, and extra attentiveness. Today I have a large Bernedoodle, so I’m confident handling bigger dogs as well as energetic pups who need exercise and structure. I’m active and love taking dogs on walks, runs, and outdoor time when appropriate, while also making sure they get plenty of affection, snuggles, and supervision. What sets me apart is that I’m dependable, attentive, and genuinely love dogs. I understand every dog is different, and I’ll make sure your pet feels safe, comfortable, and cared for while you’re away. I work remotely from home, which gives me a very flexible schedule and allows me to be present throughout the day for the pets in my care. Because I’m home most of the time, dogs get plenty of attention, regular potty breaks, walks, playtime, and companionship instead of being left alone for long stretches. My flexible routine also makes it easy for me to stick to your pet’s normal schedule for feeding, medications, exercise, and any special needs. I’m able to provide attentive, consistent care and make sure your pet feels comfortable, safe, and loved while you’re away. Safety and comfort are always my top priorities. I provide a calm, loving home environment where pets can feel relaxed and cared for. I have a friendly, social dog who enjoys having visitors and does well with other dogs, while always making sure introductions are done thoughtfully and safely. I have a yard for outdoor time, and while it is not fenced, I use a secure runner/tie-out system and close supervision so dogs can safely enjoy fresh air, potty breaks, and time outside. I also keep dogs leashed on walks and anytime they are outdoors for added safety. If your dog is crate-trained or more comfortable with their own space, I’m happy to accommodate crating and follow your normal home routine. I always aim to keep pets on their regular schedule for feeding, exercise, rest, and any medications or special instructions. I treat every pet like my own—with patience, attentiveness, and lots of love.

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  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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

  • World-class support

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

How to book dog boarding

  1. 1. Search

    Browse profiles of sitters near you who offer dog boarding.
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit.
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform.

Popular requests for dog boarding - Chesterfield

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FAQs for Dog Boarding - Chesterfield

Frequently asked questions about Rover

Rover is the largest marketplace for local pet care. Whether you're looking for pet sitters, dog walkers, or house sitters who specialize in pet sitting, you can narrow your search by entering your ZIP code to find sitters within walking distance in your neighborhood.

Every sitter on Rover has their own routine. Depending on the arrangements you agree on before the stay, a sitter can follow your dog’s regular feeding schedule, provide a comfortable place to sleep, offer companionship, and support their usual exercise and play needs.

Depending on the sitter, their home environment, and your dog’s needs, daily exercise may include walks, outdoor play, indoor enrichment activities, or supervised play with compatible dogs. These activities are not automatically included with every booking, so ask the sitter what a typical day looks like.

During the Meet & Greet, discuss your dog’s usual exercise and play routine, whether they can safely interact with other dogs, and any activities or restrictions the sitter should follow. You can also ask the sitter to send photo and message updates during the stay so you can see how your dog is spending their time.

Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Chesterfield home-away-from-home, 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 Chesterfield.

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 Chesterfield 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 , 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 .

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 MA 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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