Dog Boarding Pittsfield

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Over 445
pet parents in Pittsfield have booked dog boarding

Pittsfield, 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
• 139 reviews
36 repeat clients
25 years of experience
Pittsfield, MA, 01201

“Once again we are so please with Brooke and grateful we found a happy safe second home for our pups. We needed to leave out of town rather quickly and she was able to fit us in on short notice. We love the pictures and updates she sends of the pups. Thank you!!”

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Teena G.
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: Josselin M.
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Josselin M.
$73
total per night
5.0 out of 5 stars
• 3 reviews
5 years of experience
Pittsfield, MA, 01201

“Josselin did a nice job with our two little dogs. We would use her again.”

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Paul R.
Sitter Profile Image: Western B.
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Western B.
$84
total per night
5.0 out of 5 stars
• 4 reviews
20 years of experience
Dalton, MA, 01226

About: Dogs and I understand each other. I've always gotten them and they've always gotten me. Maybe because I grew up with three mammoth Samoyeds and Malamutes, and shared my life with Max, my sweet Cavalier, until he passed. Beyond love and care, I'm good at training and socializing, and dogs respond to my calm, confident leadership. I once cared for a reactive dog who barked at everyone who came near her, and I was the only one who could get her to settle and listen. After a month with a young Portuguese Water Dog, her owners told me she moped after I left. But mostly I think dogs feel good around me because they sense I genuinely care about them. I believe dogs are here to teach us to love and I want every dog to experience great care. For me, good dog care starts with getting to know the dog and the people who love them. I think dogs feel safest when their sitter truly knows them. Before any stay, I like to meet you and your dog, take a short walk together, and learn the little things that make your dog feel at home. That's why every stay begins with a meet and greet. What I offer that's different: - Pick-up and drop-off for longer stays: For stays of a week or more, I'll pick up and drop off your dog anywhere within a 30 minute drive of Dalton, including Lenox, Stockbridge, and Great Barrington. One less thing to manage before your trip. My home is calm and quiet, with a large, fully fenced backyard on a peaceful street in Dalton. I work from home, so your dog has company through the day, plus walks, play, and plenty of affection. I follow your instructions to the letter so your dog's routine stays as close to home as possible, and you'll get photos and a quick update every day so you can relax and enjoy your trip. Also happy to reinforce any training your dog is working on like leash manners. How I work: Every new client starts with a meet and greet, about 30 minutes with a short walk together, so your dog and I can meet before the stay. It helps make sure we're a great match, and your dog arrives already knowing a friendly face. Boarding in my home is a great fit if your dog: Settles comfortably for stretches after the initial sniffing and cuddles to get used to a new space. Is house-trained and walks well on a leash Is not a heavy shedder or super vocal Services Boarding: 2-night minimum House sitting: 2- night minimum, 2 night maximum for first sit I'd love to hear about your dog! I work from home so your dog will have plenty of companionship and attention from morning to evening. I usually walk dogs according to the schedule they are used to. In between, they can hang with me. IFeeding times will also coincide with your instructions. I'm an early riser so you are welcome to drop your dog off (with notice) as early as 7:30 am. I have a large three bedroom home with an huge fenced back yard on a quiet street near trails. It's single floor so no stairs for older dogs to contend with.

Sitter Profile Image: Mahayla G.
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Mahayla G.
Star Sitter
$84
total per night
5.0 out of 5 stars
• 54 reviews
25 repeat clients
15 years of experience
Adams, MA, 01220

“Our dog had a fabulous stay with Mahayla! Since it was our first time, Mahayla offered to come to our home to get to know our pup before caring for her the next day. They hit it off immediately and Mahayla explained her background in animal/dog behavior studies and reassured us that all would go well... and it did! Our pup had a blast trail hiking and also just relaxing at Mahayla's home. Mahayla clearly understands and loves dogs, and it was clear that she was focused on our dog's enjoyment, comfort level and care. She was also focused on our needs as the owners. Leading up to care day she was extremely responsive. On care day she sent photos and updates. A perfect stay...thanks, Mahayla!”

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Deb G.
Sitter Profile Image: Saskia C.
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Saskia C.
Star Sitter
$56
total per night
5.0 out of 5 stars
• 16 reviews
3 repeat clients
10 years of experience
Kinderhook, NY, 12106

“Saskia watched our two dogs at her home, and we had a great experience! They were both very well taken care of, and Saskia sent us several photos throughout their stay, which we really appreciated. Our dogs seemed to have a great time and got along really well with her dogs. It gave us peace of mind knowing they were in good hands while we were away. We will definitely be booking with Saskia again!”

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James V.
Sitter Profile Image: Franny A.
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Franny A.
$56
total per night
5.0 out of 5 stars
• 7 reviews
30 years of experience
Great Barrington, MA, 01230

“Franny and her husband were absolutely wonderful!! They took extra great care of our pup! I highly recommend. It was soo convenient being right down the road from camp Pontiac, where we attended a wedding.”

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brittany R.
Sitter Profile Image: Diana G.
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Diana G.
Star Sitter
$67
total per night
5.0 out of 5 stars
• 10 reviews
2 repeat clients
5 years of experience
Valatie, NY, 12184

“Diana was very accommodating scheduling a meet and greet, and adjusting to our later-than-planned arrival due to bad weather. Journey was well taken care of and Diana kept us updated on his status. We are comfortable using Diana again.”

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Rick R.
Sitter Profile Image: Peter K.
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Peter K.
$62
total per night
5.0 out of 5 stars
• 33 reviews
7 repeat clients
8 years of experience
South Egremont, MA, 01258

“Peter and Monique were so attentive to our dog for a whole week. Peter was very thorough in asking all about Sooty’s needs and preferences. We really appreciated the updates and photos, our dog had a lovely time and was very well cared for. I booked Peter based on reading the reviews and would say exactly the same as others have. Definitely recommend and will be booking again in future.”

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Sarah T.
Sitter Profile Image: Kaitlyn B.
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Kaitlyn B.
$56
total per night
5.0 out of 5 stars
• 37 reviews
12 repeat clients
20 years of experience
Castleton, NY, 12123

“Kaitlyn was great with Hadley! She sent photo updates and booked very last minute which we are incredibly appreciative of. Her kids also adored Hadley so she felt right at home. Highly recommend!”

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Bianca P.
Sitter Profile Image: John S.
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John S.
Star Sitter
$86
total per night
5.0 out of 5 stars
• 126 reviews
24 repeat clients
20 years of experience
Norfolk, CT, 06058

“We feel in great hands whenever we leave our dog with John. While we're away he stays in touch with photos and texts and when we return it's always clear that she's had a wonderful time. Thank you, thank you, John!”

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Kathleen W.
Sitter Profile Image: Candice S.
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Candice S.
Star Sitter
$62
total per night
5.0 out of 5 stars
• 81 reviews
31 repeat clients
10 years of experience
Hudson, NY, 12534

“My dog didn’t want to come home! My communication and logistical coordination with Candice was super easy, accommodating, and professional. She took excellent care of my loved one. She is great and highly recommended.”

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Roc L.
Sitter Profile Image: Katherine M.
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Katherine M.
$56
total per night
5.0 out of 5 stars
• 23 reviews
4 repeat clients
4 years of experience
East Greenbush, NY, 12061

“Katherine was amazing taking care of Bogey for the first time! She was super responsive during the booking process, and sent loads of photos throughout his stay. It was clear Bogey was sad to leave given what a nice time he had in Katherine's home.”

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Eric M.
Sitter Profile Image: Laura G.
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Laura G.
Star Sitter
$45
total per night
5.0 out of 5 stars
• 51 reviews
22 repeat clients
5 years of experience
Rensselaer, NY, 12144

“I totally and wholeheartedly recommend Laura! This was my 1st time ever boarding my 2 small dogs, and she made me feel so at ease from the very beginning of this new process. Seeing all the great reviews, I was assured that my dogs were in good hands with Laura. She took awesome care of my dogs and stayed in touch daily with pictures and updates. Laura is my #1 when the need comes up again. Thank you so much Laura! You are a blessing to the dogs you take in!”

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Teresa E.
Sitter Profile Image: Ericca B.
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Ericca B.
$70
total per night
5.0 out of 5 stars
• 58 reviews
18 repeat clients
36 years of experience
Bennington, VT, 05201

“Ericca took great care of my dad's dogs while he was in the hospital. She was able to schedule with me last minute, over a holiday weekend, and extended the boarding by a day too. She was friendly, flexible, and kind. Recommended!”

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Asher C.
Sitter Profile Image: Logan S.
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Logan S.
$67
total per night
5.0 out of 5 stars
• 31 reviews
11 repeat clients
25 years of experience
Castleton, NY, 12033

“Logan was beyond awesome! He took amazing care of Mabibi and even took Mabibi on the doggy treadmill for his first time because I requested it which was so sweet of him to do. And he sent me adorable videos throughout Mabibi’s stay. ! I couldn’t be happier with Logan.”

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R. Kamela L.
Sitter Profile Image: Kelly H.
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Kelly H.
$84
total per night
5.0 out of 5 stars
• 66 reviews
31 repeat clients
14 years of experience
Otis, MA, 01253

“Kelly and Nabil were great! We had two very happy dogs, and we could relax knowing that they were being well cared for. Kelly really went above and beyond for us. We will definitely have them take care of our dogs again!”

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Eric L.
Sitter Profile Image: Davis B.
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Davis B.
Star Sitter
$84
total per night
5.0 out of 5 stars
• 47 reviews
13 repeat clients
10 years of experience
BENNINGTON, VT, 05201

“We did a trial night with my dog. I knew immediately she was perfect for my special needs fur baby! She knew exactly how to care for him and I felt at ease. She went above and beyond with Boomer We have booked Boomer next stay . I highly recommend Davis .”

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Tonia H.
Sitter Profile Image: Hillaree H.
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Hillaree H.
$69
total per night
5.0 out of 5 stars
• 31 reviews
10 repeat clients
40 years of experience
Conway, MA, 01341

About: My family has always had dogs, and I feel that they enhance the family unit. No discrimination against certain breeds. German Shepherd, Rottweiler, American Staffordshire, Boxer, makes no difference to me. I adore all the four-legged kids! I have my own four-legged kid, and truly appreciate the help I’ve received through Rover.com, while being at work or out of town. It’s such a relief to know that the he is taken care of, so I can continue working to provide for him. Updating you on the visit with pictures and/or videos, so you can see your four-legged kid(s) have been cared for, would be my pleasure. Dogs are family, and I would gladly treat yours as part of my pack. I would be happy to perform drop-in visits or walk your dog(s) during the day, or into the night hours, as my schedule allows. Currently, I am unavailable for midday drop-ins and walks Mondays through Thursdays. Updating you on the visit with pictures and/or videos, so you can see your four-legged kid(s) have been cared for, would be my pleasure. I happily treat your fur kids as lovingly as my own. Always checking that food and water bowls filled as needed. Utilizing the crate should they need it upon my leaving.

Sitter Profile Image: Danielle & Charles T.
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Danielle & Charles T.
$78
total per night
5.0 out of 5 stars
• 2 reviews
30 years of experience
Averill Park, NY, 12018

“We had an absolutely fantastic experience with Danielle and her family! We were looking for a warm, home environment for our dog Tanner rather than a kennel, and we couldn’t have found a better fit. We booked just two days in advance, and Danielle responded immediately. After a quick meet and greet, we knew she was the perfect choice—we had full confidence from the start, and that trust was reinforced throughout Tanner’s entire stay. Her communication, kindness, and genuine care were exceptional. I can’t recommend Danielle highly enough.”

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gavin c.
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The median cost per night for dog boarding in Pittsfield is $55

Dog parents share their Rover experiences - Pittsfield

1 / 1
5.0 out of 5 stars

Coco's experience, and therefore mine, was excellent. Sarah and Noah cared for her with love and caring as if she were one of their own. I could not be more pleased. When the occasion arises, I will definitely call on them again.

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rmrabm40@yahoo.com
Boarding
5.0 out of 5 stars

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.
Boarding
5.0 out of 5 stars

My mind is always at ease with the knowledge that my dog is being loved when she is with Brooke and her family.

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Tory S.
Boarding
5.0 out of 5 stars

Once again, Tetiana and her mom Maria took excellent care of my senior dog, Edna. They are kind and trustworthy people. Tetiana is calm and friendly and has a great understanding of dogs’ needs and wants. She sent multiple pictures daily of Edna on walks, playing with her and testing various napping spots. I hope we are lucky enough to book with her again. 🐕

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Ann D.
Boarding
5.0 out of 5 stars

Leaving my lil anxious pup with strangers can be so hard, but I felt so comfortable and confident leaving him with Aura and Nick. They were so attentive to my dog’s needs and a calming presence for him while I was away. They are lovely and I hope to have the chance to use their boarding services again!

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Katherine M.
Boarding
5.0 out of 5 stars

Jess exceeded my expectations. She was sweet, kind and efficient, easy to deal with, and interacted well with Cosmo.

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Steven L.
Boarding
5.0 out of 5 stars

Luna had a great time! They were super communicative and sent several photos and updates which I appreciated.

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Jeremy B.
Boarding
5.0 out of 5 stars

Katelynn and her pet family and small 6 month old were and are amazing to have your beloved pet taken care of!! Copine settled in right away. I got a daily update with pics! Could not be happier with how the pet sitting went for my beautiful pup!

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Laura Y.
Boarding
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Sitters in Pittsfield average 10
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FAQs for Dog Boarding - Pittsfield

Frequently asked questions about Rover

The average cost of Dog Boarding in Pittsfield is $47 per night as of October 2026. Most bookings cost between $34 and $72 per night. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of October 2026, there are 227 sitters on Rover offering Dog Boarding across Pittsfield. Enter your ZIP code to see which available sitters are closest to your home.

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.

96% of sitters in Pittsfield 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 Pittsfield 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 Pittsfield.

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 Pittsfield 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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