Dog Boarding Chesterfield

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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: Jessica C.
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Jessica C.
Star Sitter
$33
total per night
5.0 out of 5 stars
• 59 reviews
19 repeat clients
35 years of experience
Sunderland, MA, 01375

“Josie loves dogs and took great care of our Pip. The family made Pip feel good about spending the weekend with them and seemed to love her, even forgiving her for getting food off the counter. 😬 we feel fortunate to have found them.”

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Mary J.
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
2 repeat clients
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: Katelyn S.
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Katelyn S.
Star Sitter
$35
total per night
5.0 out of 5 stars
• 14 reviews
5 repeat clients
25 years of experience
Westfield, MA, 01085

“Posy had a great time with Katie and the dogs! She loved getting to play in the yard and get some outside time. Sue came home happy and ready for a nap!”

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Auri C.
Sitter Profile Image: Sandra C.
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Sandra C.
Star Sitter
$44
total per night
5.0 out of 5 stars
• 43 reviews
15 repeat clients
30 years of experience
Indian Orchard, INDIAN ORCHARD, MA, 01151

“I am so grateful and appreciative of Sandra‘s loving care of Lulu while I was gone for 13 days. Lulu has a seizure disorder and Sandra was amazing with giving her medication and keeping me updated every day with her status and sending pictures of how well loved and cared for she was. Sandra and her husband John invited Lulu into their home and treated her as though she was theirs!”

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Kristin 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 is the best! She is very responsive and caring with our slightly neurotic dog. 🐶 He always comes home happy and calm. Irene has a great setup for playtime (fenced yard, screened porch).”

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rochelle d.
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 great! She was super flexible on a last-minute booking. My pup has almost boundless energy, but she came home happy and pretty worn out. We'll definitely be sending her to Jess again!”

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Mike L.
Sitter Profile Image: Yenifer V.
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Yenifer V.
Star Sitter
$73
total per night
5.0 out of 5 stars
• 37 reviews
7 repeat clients
3 years of experience
Pittsfield, MA, 01201

“Yenifer took excellent care of my dog. He was so happy with her! She made sure she communicated everyday with us during the stay, sent us pictures and updates. We are very happy with her services and would strongly recommend her. Thank you, Yenifer.”

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Divya C.
Sitter Profile Image: Krystal N.
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Krystal N.
$40
total per night
5.0 out of 5 stars
• 2 reviews
1 repeat client
7 years of experience
Williamstown, MA, 01267

“Krystal is great! We brought our mini cockapoo, Nella, over for a sleepover. Krystal sent us photos throughout the day and gave us notes about specific things she noticed. Nella can be a shy little pup, but Krystal’s dog Soju is a sweetheart and very gentle. Would definitely book again!”

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Jean G.
Sitter Profile Image: Wendy A.
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Wendy A.
$39
total per night
4.9 out of 5 stars
• 8 reviews
3 repeat clients
30 years of experience
Westfield, MA, 01085

“Wendy was great! I needed a dog sitter at the last minute and came across her profile. I loved that she was so close to my home, and she made the entire experience stress-free. During my dog's stay, I received nightly text updates along with photos and videos, which I really appreciated. This was the first time I'd traveled over 13 hours away from my sweet girl, so I was super nervous. After the first day went so well, all my worries disappeared, and I was able to fully enjoy my trip knowing she was in great hands. I will definitely book with Wendy again and maybe next time she'll even get to meet my kitty too!”

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Sarah H.
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: Jessiana V.
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Jessiana V.
$34
total per night
5.0 out of 5 stars
• 48 reviews
21 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: Mindi S.
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Mindi S.
Star Sitter
$50
total per night
5.0 out of 5 stars
• 7 reviews
4 repeat clients
15 years of experience
LUDLOW, MA, 01056

“Hailey loved staying with Mindi and her family and is looking forward to her next sleepover.”

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Jr G.
Sitter Profile Image: megan b.
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megan b.
$50
total per night
4.9 out of 5 stars
• 143 reviews
42 repeat clients
20 years of experience
South Hadley, MA, 01075

“Staying with Megan was awesome, as always! I know I can always trust her with my “baby boy!” He plays with her dogs and follows her around - just like he does with me. I know he loves it there and I am grateful he is in good hands with Miss Megan.”

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Diane M.
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: 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: Karen T.
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Karen T.
Star Sitter
$55
total per night
5.0 out of 5 stars
• 25 reviews
8 repeat clients
10 years of experience
East Forest Park, Springfield, MA, 01118

“Karen is fantastic! My dog Jackson loves staying at her house with her two little dogs. She sends lots of photos and Jackson always looks happy. She is a great sitter!”

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Erin P.
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: Lissette R.
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Lissette R.
$62
total per night
4.6 out of 5 stars
• 45 reviews
12 repeat clients
6 years of experience
Enfield, CT, 06082

“Lissette took great care of our pup, kept him happy and safe! She was prompt in her response times, good communication, so I knew he was in good hands. I’ll definitely keep her in mind for future bookings!”

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Siobhan G.
Sitter Profile Image: Amanda B.
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Amanda B.
$23
total per night
5.0 out of 5 stars
• 4 reviews
8 years of experience
Chicopee, MA, 01020

About: Hi! I'm a lifelong animal lover and proud pet parent to Raven (7 female dog), and Miles (8 female cat) I know how important it is to find someone you can trust to care for your pets, and I would love to provide them with the same love and attention I give my own! I work from home, so I'm able to give pets plenty of attention throughout the day and provide frequent potty breaks, playtime, and companionship. I also have a fenced yard where dogs can safely get fresh air and exercise. My home is used to being around both animals and kids. I understand that every pet has their own personality, routine, and needs. Whether your pet needs company, playtime, walks, or just a comfortable and caring place to stay, I will treat them like part of the family!

Sitter Profile Image: Aura G.
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Aura G.
$67
total per night
5.0 out of 5 stars
• 24 reviews
6 repeat clients
10 years of experience
Pittsfield, MA, 01201

“Our 15 year old puppy received so much love and care. They were managed her unique old lady needs with grace and kindness. Our puppy fell in love with both of them. We appreciated the regular updates and photos. Our dog can’t wait to go back. Fabulous caregivers.”

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Holly H.
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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?

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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

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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, 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 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 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 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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