Dog Boarding Stockbridge

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

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Over 3
pet parents in Stockbridge have booked dog boarding

Stockbridge, 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%.

1 / 1
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 was an absolute lifesaver for our family when we got in a tough spot with a home move and we had absolutely no options for our large, elderly matriarch of a dog. I would enthusiasticaly recommend her to anyone. Our dog needed so much extra attention and we are really indebted Brooke and her family for helping us out.”

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Rich M.
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: 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: 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

“I felt very comfortable leaving my pup with Mary and Todd. They have a lovely home and included my dog in all of their activities: walking, running, and much more. They also kept me up to date with pics and anecdotes. I would highly recommend Mary and Todd to anyone!”

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Deborah F.
Sitter Profile Image: Yenifer V.
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Yenifer V.
$73
total per night
5.0 out of 5 stars
• 35 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: Irene T.
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Irene T.
Star Sitter
$73
total per night
5.0 out of 5 stars
• 23 reviews
8 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: Jess L.
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Jess L.
$50
total per night
5.0 out of 5 stars
• 89 reviews
21 repeat clients
5 years of experience
Pittsfield, MA, 01201

“Jess was great with our 2.5 year old German shepherd mix, Moose! She was super communicative and flexible, and sent photos and videos which we really appreciated. We’ll definitely book her again!”

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Maria P.
Sitter Profile Image: Nicole P.
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Nicole P.
$89
total per night
5.0 out of 5 stars
• 31 reviews
6 repeat clients
34 years of experience
Elizaville, NY, 12523

“I would highly recommend Nicole to anyone looking for dog day care or boarding She communicates well and goes the extra mile to make your pet feel comfortable and happy Not only did Buddy have a Christmas themed neck scarf but also a Christmas toy! She clearly loves dogs and is proficient and skilled in all aspects of their care We had total peace of mind while we were away and she sent us some beautiful pictures of Buddy!”

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

“First time leaving our dog with John, and he's a keeper. Excellent communications. Quick responses and regularly sent pictures and updates. Large fenced backyard for dogs to run and he has a playful dog that ours enjoyed. John is also friendly and seems very responsible. Highly recommend and we plan on turning to again.”

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

“We left our pup with Deanne for a 7 day trip and she was incredible. It was all positive vibes from our first meeting onward. Our dog was clearly comfy, wonderfully cared for, and loved! Deanne will be our first call for future trips!”

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Zachary C.
Sitter Profile Image: Sarah & Noah P.
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Sarah & Noah P.
$39
total per night
5.0 out of 5 stars
• 3 reviews
1 repeat client
10 years of experience
Pittsfield, MA, 01201

About: I have years of experience caring for dogs and cats, including feeding, walking, administering basic medications, maintaining routines, and providing lots of love, attention, and companionship. I mostly work from home but when I’m not home, my fiancé (who will love your pets just as much as me) is! I am always available! I have a large yard and a 2,500 sq ft home so your babies will have room! I also have 2 friendly dogs to keep your pets company 😊 I have an extra room in my home for pets but if sleeping on my bed is more their style then that’s okay too!

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

“Peter was such a wonderful sitter. His updates were timely and detailed and I felt confident that Nutmeg was cared for, happy, and healthy during her stay. I will definitely ask Peter to sit again if I’m ever in the area again.”

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

“Diana was amazing and we felt at ease leaving our two pups with her. When picking them up after our quick trip it was very clear that she had already bonded with them.”

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Sophie G.
Sitter Profile Image: Chelsea H.
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Chelsea H.
$62
total per night
5.0 out of 5 stars
• 9 reviews
1 repeat client
22 years of experience
Nassau, NY, 12123

“Chelsea was great with my dogs. One of them has bad anxiety and she knew exactly how to make him feel comfortable. She also kept in touch throughout their stay.”

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Amy K.
Sitter Profile Image: Candice S.
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Candice S.
Star Sitter
$62
total per night
5.0 out of 5 stars
• 79 reviews
30 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: Kathleen M.
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Kathleen M.
Star Sitter
$95
total per night
5.0 out of 5 stars
• 165 reviews
46 repeat clients
12 years of experience
Becket, MA, 01223

“In a word: FANTASTIC. Kathleen is caring and adjusts her care to your dog’s needs. (My dog Rose, is a 6.5 year old 45 pound standard poodle.). Kathleen communicates well and kept me fully informed about my dog’s picky eating habit. (My dog ate better with Kathleen than she does at home.) You cannot appreciate the boarding facility until you visit Becket. The house is lovely with numerous happy dogs running about, playing and relaxing inside and out. From my observation, the place looked remarkably clean and orderly. The woods surrounding the house are lovely and with an acre of fenced in fields and forest. Kathleen is warm, intelligent and wants your pet to enjoy its vacation. I have the highest praise and appreciation for the home away from home Kathleen provided my beloved dog.”

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William B.
Sitter Profile Image: Yasmin Jamal A.
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Yasmin Jamal A.
$89
total per night
5.0 out of 5 stars
• 2 reviews
20 years of experience
Pittsfield, MA, 01201

“She was great.. very caring and responsible. I will use her again. Thank you Yasmin.”

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Vina P.
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 amazing! She helped us out when we were in a pinch and needed dog sitting for a weekend with only one days notice! We had never had Lucy boarded anywhere before and we were a bit nervous about the process, but it went so smoothly! She sent pictures to reassure my kiddos she was being well taken care of! I would definitely recommend her services and will be using her again for dog sitting in the future!”

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Jennifer D.
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: Jennifer C.
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Jennifer C.
Star Sitter
$56
total per night
5.0 out of 5 stars
• 99 reviews
30 repeat clients
30 years of experience
Averill Park, NY, 12018

“I felt great leaving our dog with Jennifer. She is so kind and clearly loves animals. She already had a number of pet supplies and toys which made things even easier since I was traveling at the time I had booked for boarding. She sent updates and was flexible with drop off and pick up times. I would definitely book with her again.”

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Ethan L.
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The median cost per night for dog boarding in Stockbridge 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 - Stockbridge

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Sitters in Stockbridge average 9
repeat dog boarding clients

FAQs for Dog Boarding - Stockbridge

Frequently asked questions about Rover

The average cost of Dog Boarding in Stockbridge on Rover is $59 per night as of October 2026. Most bookings cost between $54 and $64 per night. 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 154 sitters on Rover offering Dog Boarding across Stockbridge. 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.

100% of sitters in Stockbridge 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 Stockbridge 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 Stockbridge.

<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 Stockbridge 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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