Dog Boarding in Pittsfield

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Top rated Pittsfield dog boarders

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
131 reviews
33 repeat clients
25 years of experience
Pittsfield, MA, 01201

My dog came home happy and even better, tired! My pup loved her dog and kids. Brooke was great about communication and sent updates. Will definitely book again.

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Patricia D.
Sitter Profile Image: Irene T.
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Irene T.
Star Sitter
$73
total per night
5.0 out of 5 stars
17 reviews
6 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: Tetiana M.
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Tetiana M.
Star Sitter
$67
total per night
5.0 out of 5 stars
59 reviews
13 repeat clients
2 years of experience
Pittsfield, MA, 01201

Tetiana was a wonderful and caring caregiver to our two rambunctious pups. She not only gave them much love and affection, she walked them many times and spoiled them with couch and bed time snuggles. She took pictures regularly throughout their stay and shared them with us. She is a top notch person and was very accommodating and delightful.

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

This was the second time Aura & Nick watched Shannon. Shannon ran into their house to see them, excited to be there. It was very clear Shannon is happy to be there.

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Holly K.
Sitter Profile Image: Yenifer V.
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Yenifer V.
$73
total per night
5.0 out of 5 stars
23 reviews
4 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: Mahayla G.
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Mahayla G.
Star Sitter
$84
total per night
5.0 out of 5 stars
50 reviews
24 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: Jess L.
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Jess L.
$50
total per night
5.0 out of 5 stars
86 reviews
21 repeat clients
5 years of experience
Pittsfield, MA, 01201

Jess was good. We booked her while we were in Berkshires for our weekend ski/snowboard trip. It was a basically a 2 day noticed thankfully she was available. We enjoyed ourselves knowing that our Shiba girl Yumi was taken care of. Twice a day updates as requested. Whenever were in the area again, will rebook. Thanks Jess!

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Cheuck L.
Sitter Profile Image: Jennifer C.
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Jennifer C.
Star Sitter
$56
total per night
5.0 out of 5 stars
95 reviews
27 repeat clients
30 years of experience
Averill Park, NY, 12018

Our dog was very happy with Jennifer. We are so happy to have found her. She's kind and gentle and she worked with us when we had unknowns about our needs because of a funeral we had to travel for. We were trying to book without full details of when and where we had to be. We feel very fortunate she was willing to be flexible. Our pup was happy that he was the only one she had with her during his stay. He got all of her love and attention. Thank you, Jennifer.

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Gina M.
Sitter Profile Image: Reymon B.
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Reymon B.
$89
total per night
20 years of experience
Pittsfield, MA, 01201

About: Working in various Grooming/Training facilities. I'm currently working with Bumblebee Pet Care with 5 of my own clients. My conversations with the pets are amazing. I'm currently walking dogs 2 days out of the week looking for more to work with within the week. I have an open schedule and interested. I have separate spaces available for each animal. In my care at anytime, I will use provided equipment for transportation. Your pet safety is number one.

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

Kathleen was great! She has an amazing property for the dogs, keeps you updated with tons of pictures and videos of them, and is such a nice person that you know shes taking care of your pups as if they were her own, will definitely be using her moving forward!

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Ben G.
Sitter Profile Image: Amy H.
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Amy H.
$50
total per night
5.0 out of 5 stars
4 reviews
1 repeat client
5 years of experience
Blandford, MA, 01008

Amy and her family were fabulous. They made Takoda feel right at home. Takoda enjoyed making new friends, the walks and sleeping on the couch. Amy was very responsive and provided updates so we knew it was all going well. It was a wonderful experience for us and Takoda. We will definitely board Takoda with Amy again.

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Alexcia A.
Sitter Profile Image: Deanne R.
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Deanne R.
Star Sitter
$45
total per night
5.0 out of 5 stars
62 reviews
21 repeat clients
10 years of experience
Kinderhook, NY, 12106

This is our second time having our dog stay with Deanne. My dog has a great time with her. She has been extremely flexible with unexpected changes in our travel plans and the pup hates to leave her home. We will continue to use her services!

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Gonzo M.
Sitter Profile Image: Caitlin J.
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Caitlin J.
$56
total per night
5.0 out of 5 stars
4 reviews
20 years of experience
Windsor, MA, 01270

I had an amazing experience with Caitlin and her family. From the moment we met, it was clear how caring, responsible, and attentive they were with my dog. They kept me updated with photos and messages, which gave me so much peace of mind while I was away. My dog came home happy, relaxed, and clearly very well cared for. You can tell they genuinely love animals and treat them like family. I would absolutely book with them again and highly recommend them to anyone looking for someone trustworthy and compassionate to care for their pet

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David W.
Sitter Profile Image: Mary & Todd H.
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Mary & Todd H.
$50
total per night
5.0 out of 5 stars
38 reviews
11 repeat clients
40 years of experience
Chatham, NY, 12037

Mary & Todd are a dream come true! We were very nervous leaving our baby with someone we didn’t know, for the first time, and Mary made us feel so beyond comfortable. The photos, updates and check ins made us think Tilly may never want to come back home! Our pup went for rides, walks, runs, errands, ball chases and partook in endless fun for two straight days. I’m not sure how Mary & Todd could possibly have more energy than our dear Tilly but she’s officially exhausted and had the adventure of a lifetime. My husband joked that we should do this as a doggy camp once a month, we just may ask if they’d be down!

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Nadine L.
Sitter Profile Image: Katelynn R.
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Katelynn R.
$89
total per night
5.0 out of 5 stars
3 reviews
1 repeat client
15 years of experience
Pittsfield, MA, 01201

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.
Sitter Profile Image: Ivan O.
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Ivan O.
$67
total per night
5.0 out of 5 stars
6 reviews
20 years of experience
New Lebanon, NY, 12125

Ivan was a great host for Sadie. He sent photos and updates during her stay. He was also understanding and accommodating to my travel arrangements.

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Lyndsey W.
Sitter Profile Image: Franny A.
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Franny A.
$56
total per night
5.0 out of 5 stars
6 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: Maritza O.
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Maritza O.
$35
total per night
4.6 out of 5 stars
13 reviews
3 repeat clients
1 year of experience
North Adams, MA, 01247

Maritza took such wonderful care of my dog Waffles while we were out of town. Her dog Coco was a sweet little friend for him, and Maritza made sure he was spoiled the whole time. She sent lots of pics and communicated very promptly. I wouldn’t hesitate to book her again. She loves dogs and ensures they are happy puppers during their stay.

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Melissa M.
Sitter Profile Image: Iris F.
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Iris F.
$45
total per night
4.9 out of 5 stars
54 reviews
12 repeat clients
10 years of experience
North Adams, MA, 01247

About: I’ve been on Rover for 5 years now! I have lots of experience with animals and my education background is in biology and animal sciences I am available pretty much whenever to do drop ins or walks for your pets!! Let me know what you need and I can accommodate :) I always make sure to follow the owners instructions and communicate with them! Communication is important when taking care of someone else’s animals! I make sure to send lots of pictures as well

Sitter Profile Image: Nikki R.
Verified Background Check
Nikki R.
$28
total per night
34 years of experience
Adams, MA, 01220

About: Retired Military Veteran, 12 years of service. Very reliable and love animals. I love all breeds of dogs regardless of the stereotypes. Can’t wait to start watching your dogs. I have a vast background, military and emergency services. I’m in the process of becoming a nys emt and then will go on for my paramedic hopefully my flight medic. I’ve grown up with dogs and haven’t had a dog in a year. Feel free to look up my information in the military to know that I’m a veteran. I am always available even for a last minute vacation. My husband and I would love to help who ever needs that extra tlc while their owners go away. I’m home all day every day. I work overnights so my hubby could let your little or big pups out to go potty before work. They will have free range of the house unless they are specifically crated then I can put them in the crate and take them out when needed.

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Over 469
pet parents in Pittsfield have booked dog boarding

Pittsfield dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Irene was just wonderful with our pup Guthrie. Guthrie has seperation anxiety and gets a little jittery around other dogs initially (thanks, COVID!) but she was patient with him. Once he settled in, he had a great day lounging on her porch and hanging with her dog. (Irene sent us load of pictures). Guthrie came home relaxed and tired. Irene will be our go-to from now on!

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rochelle d.
Boarding
5.0 out of 5 stars

Tetiana is anlways absolutely wonderful with Dyce (my furry baby)! This was Dyce’s third stay with Tetiana, but his first longer boarding stay, and once again she was amazing! Having used her before, I already trusted her, but she truly went above and beyond during this extended stay. She kept me updated with messages and photos, which gave me so much peace of mind while I was away. It was clear that Dyce was happy, comfortable, and receiving lots of attention and care. Tetiana was responsive, professional, and genuinely caring throughout the entire booking. As a dog parent, it means a lot to know your dog is in good hands, and Tetiana consistently provides that reassurance. I am so grateful for the excellent care she gave Dyce and will absolutely continue booking with her in the future. Highly recommend!

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Keysa S.
Boarding
5.0 out of 5 stars

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.
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

Brooke was an absolute delight! She was incredibly helpful and accommodating, making me feel at ease leaving my dog with her for five days so I could finally enjoy a much-needed family vacation. I truly appreciated Brooke’s check-ins during this time, ensuring that my dog was doing well. It was a huge relief to know that my dog was in good hands.

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Kristina B.
Boarding
5.0 out of 5 stars

jess was very caring and accommodating with our fur babies! they had a great time with her and came home tired! one of our dogs is highly anxious but it was reassuring knowing our dogs were safe and in good hands. will book again. thank you, jess!

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Andrea F.
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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How Rover works

  1. 1. Search

    Read verified reviews by dog parents like you and choose a boarder who’s a great match for you and your dogs
  2. 2. Meet & Greet

    Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

The median cost per night for dog boarding in Pittsfield is $60

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

  • World-class support

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

Sitters in Pittsfield average 9
repeat dog boarding clients

Dog Boarding FAQs

Frequently asked questions about Rover

As of Jun 2026, the median cost of dog boarding in Pittsfield is $60 per night, including service fees. Boarding your dog for one week typically costs $420. Sitters on Rover set their own rates based on their qualifications, your dog's needs, and their space's amenities. As a result, most Pittsfield dog boarding rates can be found as low as $35 to as high as $66 per night.

If you’re searching for a Pittsfield dog boarding sitter for the first time, visit the sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, 53 sitters provided dog boarding in Pittsfield. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, dog boarding sitters joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple sitters about your booking. Typically, 89% of Pittsfield dog boarding sitters respond in under an hour.

Sitters who provide dog boarding in Pittsfield have an average of 16 years of experience. Dog boarding sitters with repeat customers have an average of 9 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters in Pittsfield.

Rover makes it easy to find Pittsfield dog boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog boarding is great for:

  • Dogs of all ages and abilities, including puppies
  • Pet parents looking for a safe, loving alternative to a kennel
  • Dogs who’d love to socialize with their sitter’s pets

There are 53 dog boarding sitters in Pittsfield on Rover, so you’re sure to find the perfect match for your dog! We understand that each dog is unique and may require specific instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog boarding sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog boarding sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your dog boarding sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your dog boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.