Dog Boarding Berkshire

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

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Berkshire, 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

“Brooke and her family were kind and loving to Millie! She hasn’t been with anyone but us and she isn’t a very easygoing pup so we were so relieved when Millie was so relaxed and happy in Brooke’s home. Brooke kept us updated and sent many adorable photos! I would absolutely book with Brooke again and will recommend her to anyone needing care for their fur children.”

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Kisti O.
Sitter Profile Image: Jess L.
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Jess L.
$49
total per night
5.0 out of 5 stars
• 89 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: 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 was absolutely fantastic! She took such wonderful care of our two energetic dogs and our energetic cat, and we couldn't have been happier. She truly went above and beyond, staying in constant communication with us the whole time we were away and sending photos and updates that really put our minds at ease. She put an incredible amount of heart into caring for our pets—she easily gave one hundred and fifty to two hundred percent—and her response time was incredibly fast.”

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tamas u.
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: Sheronda L.
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Sheronda L.
Star Sitter
$50
total per night
5.0 out of 5 stars
• 29 reviews
14 repeat clients
20 years of experience
Troy, NY, 12180

“Sheronda was a great sitter for my elderly poodle! She provided updates and photos and was very conscientious about a couple of special instructions I left. Sheronda is highly reliable and very personable. I highly recommend her!”

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Karen E.
Sitter Profile Image: Deanne R.
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Deanne R.
$45
total per night
5.0 out of 5 stars
• 75 reviews
24 repeat clients
10 years of experience
Kinderhook, NY, 12106

“Jasper seemed very happy and well cared for when we picked him up. He needed a bit of extra care in the beginning of his stay. Deanne followed all of the instructions perfectly. Deanne sent lots of updates and pictures during his stay.”

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

“Mary and Todd did an excellent job watching my Tobi. He has separation anxiety and they took good care of him, sending pictures and updates. I will definitely use there services again.”

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Michael T.
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 took wonderful care of my 14 year old Charlie overnight. She’s a very kind person and Charlie felt completely comfortable with her. He also got along well with her dog. I will definitely be using her again.”

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Terri L.
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: 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: Christopher H.
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Christopher H.
Star Sitter
$49
total per night
5.0 out of 5 stars
• 32 reviews
6 repeat clients
16 years of experience
Menands, NY, 12204

“Chris was attentive to my dog's need and was easy to communicate with and was flexible to work with. My dog enjoyed his time under Chris' care. Would highly recommend”

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Mitesh M.
Sitter Profile Image: Darcy J.
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Darcy J.
$56
total per night
5.0 out of 5 stars
• 9 reviews
1 repeat client
36 years of experience
Castleton-on-Hudson, NY, 12033

“Darcy was fantastic with my dog, Blaze! Her own dog is so sweet and Blaze had a wonderful time. I got updates and pictures throughout his stay. We will definitely be using Darcy as a sitter again!”

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Rosemary F.
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

“Laura is a very caring dog lover, evidenced by all the senior dogs she takes into her care. She understands dogs and provides them with a safe and loving environment. Communication was easy and consistent, and Laura was flexible about dropoff given problematic weather conditions. I highly recommend her!”

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Deb S.
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: Joni M.
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Joni M.
$56
total per night
5.0 out of 5 stars
• 6 reviews
12 years of experience
Albany, NY, 12207

“Joni was great. Communicated ahead of our drop off. Flexible on timing. Kept us updated during Teddy’s stay. He was a happy pup at pick up and had a great time.”

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Mike C.
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 did an awesome job taking care of Lola. She sent me frequent updates on how things were going while I was away that put me at ease. I would definitely use her again she’s highly recommended.”

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Wanda H.
Sitter Profile Image: Marc S.
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Marc S.
$62
total per night
5.0 out of 5 stars
• 71 reviews
3 repeat clients
20 years of experience
Bennington, VT, 05201

About: Lifelong dog person, I have cared for dozens of furry friends, mine and others. I currently have a 4 year old Shepherd Mix. Former PETCO employee and rescue volunteer I am currently working part-time and unavailable 2pm to 7pm Monday- Friday. There is some flexibility, so please ask about your specific timing needs. Thanks I will follow your instructions as well as your pet's needs, mood, and personality. I do my best to let your fur baby be comfortable and themselves.

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 took such good care of my puppy during her first time away from home and communicated with me throughout her stay. He shared videos and photos and it was clear she was treated very well and was having a blast. She loved his dog, too, which was a great added bonus. We will definitely be back!!”

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Kathryn G.
Sitter Profile Image: Jose A.
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Jose A.
$56
total per night
4.9 out of 5 stars
• 46 reviews
21 repeat clients
1 year of experience
West Hill, Troy, NY, 12180

“jose helped w a last minute holiday booking for a few weeks in december, communication was smooth and easy. would definitely rebook in the future”

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Maria P.
Sitter Profile Image: Danielle C.
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Danielle C.
$67
total per night
4.8 out of 5 stars
• 10 reviews
1 repeat client
30 years of experience
Hillsdale, NY, 12529

“We had a wonderful experience! Danielle responded promptly, shared pictures and updates, and was so kind. Our dog seemed happy and comfortable in their cozy home. We’d happily book again!”

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Jane G.
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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 - Berkshire

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FAQs for Dog Boarding - Berkshire

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 Berkshire 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 Berkshire.

<b>Tip:</b> 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 Berkshire 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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