Dog Boarding Chesterfield

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Chesterfield, 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.

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Sitter Profile Image: Jie M.
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Jie M.
Star Sitter
from
$55
per night
5.0 out of 5 stars
• 57 reviews
10 repeat clients
10 years of experience
Swanzey, NH, 03446

“Lou had a wonderful time with Jie! Great communication all around, and extremely accommodating. I highly recommend Jie to look after anyone’s pups!”

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Jessica B.
Sitter Profile Image: Nicole S.
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Nicole S.
Star Sitter
from
$65
per night
5.0 out of 5 stars
• 87 reviews
23 repeat clients
25 years of experience
Greenfield, MA, 01301

“Nicole runs a 5-star boarding operation! Her home is relaxed, welcome and very pet- friendly, and the fenced backyard is excellent for zoomies!”

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Kate J.
Sitter Profile Image: John M.
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John M.
Star Sitter
from
$70
per night
5.0 out of 5 stars
• 161 reviews
62 repeat clients
15 years of experience
Turners Falls, MA, 01376

“John provided Lilly with excellent care. Lilly had been traumatized by a two-day visit last year to a kennel last year. We vowed never to do that again. But her visit with John was just wonderful. Lilly will definitely be hanging out with John in the future!”

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Pete M.
Sitter Profile Image: Alicia W.
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Alicia W.
from
$49
per night
5.0 out of 5 stars
• 16 reviews
5 repeat clients
10 years of experience
Keene, NH, 03431

“Alicia and her sweet family welcomed Ollie into their home for a 10 day stay. This was Ollie's first stay away from home and Alicia did her best to make him feel safe and comfortable during his stay. Upon pickup he was healthy and happy - would not hesitate to book again!”

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karin a.
Sitter Profile Image: Laura P.
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Laura P.
Star Sitter
from
$65
per night
5.0 out of 5 stars
• 100 reviews
25 repeat clients
43 years of experience
Wilmington, VT, 05363

“Pepper stayed with Laura for 3 nights while we went away. We felt at ease leaving her, knowing she would be well taken care of. We were not wrong. When we went to pick her up I could tell she had made a new friend and was comfortable with Laura. I am so thankful we picked Laura to take care of Pepper.❤️”

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James G.
Sitter Profile Image: Heather M.
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Heather M.
from
$40
per night
5.0 out of 5 stars
• 6 reviews
3 repeat clients
10 years of experience
Ashburnham, MA, 01430

“Heather was great with Charlie! We responded very fast and sent lots of photos!!”

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Emily S.
Sitter Profile Image: Stephanie M.
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Stephanie M.
from
$75
per night
5.0 out of 5 stars
• 5 reviews
1 repeat client
40 years of experience
Greenfield, MA, 01301

“Stephanie took great care of our two dogs - took them on long walks, treated them with love, and they had a great time. Will definitely be in touch with her again when we're back in the area!”

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David C.
Sitter Profile Image: Tessa H.
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Tessa H.
Star Sitter
from
$100
per night
5.0 out of 5 stars
• 12 reviews
3 repeat clients
8 years of experience
Springfield, VT, 05156

“Tessa was fantastic with our Riley girl! 10/10 recommend her services. Riley had the best time and her communication was phenomenal the entire stay. Thanks Tessa!”

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Victoria C.
Sitter Profile Image: Mike & Laura O.
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Mike & Laura O.
from
$125
per night
5.0 out of 5 stars
• 13 reviews
2 repeat clients
25 years of experience
Putney, VT, 05346

“Mike and Laura were the absolute perfect fit for our little rescue chihuahua, Topo, who needs some specific care and management. We felt extremely comfortable and confident leaving him with them while we were on holiday and our dog came back even more relaxed and happy then when we dropped him off. Very communicative and they clearly showed our dog all the love and care and walks we could have asked for. Thank you! Topo is looking forward to coming back.”

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Rosalie J.
Sitter Profile Image: Tosca D.
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Tosca D.
from
$76
per night
5.0 out of 5 stars
• 4 reviews
25 years of experience
Greenfield, MA, 01301

“Tosca took great care of our elderly dog while we visited family for a week. She was a proactive communicator and willing to be flexible when it looked like our travel plans may have been delayed. She was diligent about our dogs medications, and he came back to us calm, relaxed and happy. Its clear Tosca took exceptional care of him.”

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Liz G.
Sitter Profile Image: Sean O.
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Sean O.
from
$70
per night
5.0 out of 5 stars
• 9 reviews
1 repeat client
2 years of experience
Wilmington, VT, 05363

“Sully came home a tired and happy boy. Reliable and dependable. A+”

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Amy S.
Sitter Profile Image: Grace M.
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Grace M.
from
$125
per night
5.0 out of 5 stars
• 7 reviews
15 years of experience
Athens, VT, 05143

“Grace took fantastic care of our puppy, Arrow. He has plenty of play time, love and affection, and came home tired from having a wonderful time. We will definitely board with Grace again.”

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James D.
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The median cost per night for dog boarding in Chesterfield is $60

Book with peace of mind

  • 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

Select a filter and find qualifying sitters offering dog boarding.

Sitters in Chesterfield average 13
repeat dog boarding clients

FAQs for Dog Boarding - Chesterfield

Frequently asked questions about Rover

As of November 2026, there are 105 sitters on Rover offering Dog Boarding across Chesterfield. Enter your ZIP code to see which available sitters are closest to your home.

If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.

The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.

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.

94% of sitters in Chesterfield can provide daily exercise during dog boarding stays. Depending on the sitter, their home environment, and your dog’s needs, this 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.

Yes, you can find sitters who have experience with handling special pet needs in Chesterfield. On Rover:

  • 92% of sitters can help with special care needs
  • 95% can help with giving oral medications or injections
  • 94% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

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 NH 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.

Adding another pup to the pack? Most sitters and walkers offer a reduced rate for additional dogs. You’ll find these exact rates listed under the "Services" tab on any sitter's profile. Since every dog is unique, final pricing may vary depending on the level of care required.

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