Dog Boarding Stockbridge

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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%.

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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
• 140 reviews
37 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 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: Jess L.
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Jess L.
$47
total per night
5.0 out of 5 stars
• 89 reviews
22 repeat clients
5 years of experience
Pittsfield, MA, 01201

“Jess was amazing with Rusty! She sent me daily updates and I saw that Rusty had fun with the other dogs in the yard and had cozy places to sleep and play with toys. Will definitely book her again!!”

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Jahna S.
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

“John was great with our two senior labs and they felt right at home. We were able to enjoy our time away knowing they were content. Also easy to coordinate the booking / drop offs and John was easy to communicate with as well. Would definitely hire him again for care.”

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Kimberly S.
Sitter Profile Image: Diana G.
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Diana G.
Star Sitter
$67
total per night
5.0 out of 5 stars
• 11 reviews
3 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: Yvette C.
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Yvette C.
$56
total per night
5.0 out of 5 stars
• 7 reviews
1 repeat client
9 years of experience
Winsted, CT, 06098

“Lovely experience leaving my foster pitbull with Yvette for a weekend. Right away I noted her nice calm demeanor. Maggie is a very nervous dog, but she responded well to Yvette on first meeting, so I felt good about that. Yvette also has all the needed supplies, lots of toys and a crate, which was nice because Maggie likes to have a place to feel safe when she’s nervous. I would feel very comfortable leaving Maggie with Yvette again. :)”

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Bailey B.
Sitter Profile Image: Kaitlyn B.
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Kaitlyn B.
$56
total per night
5.0 out of 5 stars
• 38 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: 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.
Sitter Profile Image: Sydney R.
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Sydney R.
$93
total per night
5.0 out of 5 stars
• 12 reviews
4 repeat clients
12 years of experience
Sheffield, MA, 01257

About: I’ve lived and worked with both dogs (all sizes) and cats since a young age. Friends and relatives have trusted me to care for their animals on a wide scale from dog walking to in-home stays. Additionally, I have spent time volunteering in animal shelters including fostering dogs from a few days to multiple month long stays working with them to find their forever homes! I am currently working part-time so I have ample time during the day to check-in on pets, take dogs on long walks, and any other care you’re looking for! I have experience with general dog training and crating if needed. I’ve worked with dogs that have a range of needs and am open to following whatever routine you normally follow with your pet!

Sitter Profile Image: Taylor F.
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Taylor F.
Star Sitter
$117
total per night
5.0 out of 5 stars
• 46 reviews
16 repeat clients
15 years of experience
Hudson, NY, 12534

“Taylor was SO loving with our dogs, so wonderful to interact with, and fed our dogs some of the fancy raw diet food her dogs have. It was a holiday treat for our pups!”

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Sarah H.
Sitter Profile Image: Meghan & Sean H.
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Meghan & Sean H.
$111
total per night
5.0 out of 5 stars
• 6 reviews
1 repeat client
10 years of experience
Germantown, NY, 12526

“We had SUCH a wonderful experience with Meghan & Sean—and so did our pup! Our 3yo dog is nervous around new people and can be reactive. We were worried about how she would do staying with a family with young kids. Meghan & Sean listed to our worries and helped up brainstorm ways to put our dog at ease. And it worked like a charm! We were so grateful to the extra time Meghan & Sean spent to make both the humans and the doggo feel positive about the plan. We loved getting pics of the crew on their daily walks. It was also really really REALLY nice to see how much love Meghan and fam have for all animals, and how positive they were about our sometimes tricky dog. Our dog had a great week and we will definitely return to Meghan & Sean for future doggy needs, whether it is another week or a shorter visit. Highly recommend, zero notes!”

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Gabrielle B.
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: Steve F.
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Steve F.
$84
total per night
5.0 out of 5 stars
• 2 reviews
2 repeat clients
12 years of experience
Lee, MA, 01108

“Steve communicated very directly. He had passion for caring for your dog.”

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Michael T.
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: David S.
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David S.
$98
total per night
5.0 out of 5 stars
• 1 review
22 years of experience
Ghent, NY, 12075

“David was a wonderful host to our Bug. His place is amazing with lots of area to roam far from any roads. I’m not completely sure Bug wanted to go home with us.”

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Ruth H.
Sitter Profile Image: Katherine H.
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Katherine H.
$73
total per night
5.0 out of 5 stars
• 20 reviews
8 repeat clients
12 years of experience
East greenbush, NY, 12061

“Katherine was so great with our girl Bella! I’m always afraid to leave my girl with someone I don’t know, but Katherine made sure to reassure me while we were gone with photos and videos every day! I think Bella loved her time there as well! Thank you Katherine!”

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Danielle F.
Sitter Profile Image: Zoey L.
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Zoey L.
$73
total per night
5.0 out of 5 stars
• 2 reviews
10 years of experience
Cheshire, MA, 01225

About: I have pet/house sat multiple times over the past several years for friends and family, and have worked with several types of animals from small critters like guinea pigs and ferrets, cats, and even large dog breeds. I also have 2 years experience volunteering for a local shelter in socialization and vet transport, 3 years experience working for a doggy daycare and boarding facility, and I currently work part time for another local animal shelter. I am an experienced owner of dogs, cats, ferrets, chickens, guinea pigs, and more. I also have experience as a wedding dog handler, and would be happy to offer this service if requested so your furry companion can accompany you or someone you know on yours or their special day without any added stress, please let me know if this is something you'd be interested in! I currently work part time so I have lots of time to play with your pup, and hopefully can build savings towards a larger space to meet more people's needs! I am always looking to learn, grow, and provide better care for animals. Animal welfare is very important to me. At this point in time, due to the space I'm only able to accommodate smaller breeds that generally can get along with others. I do have a small fenced in yard, but I also have the bike trail and nearby hiking trails readily available, your dog will need to be on leash at all times when outside on walks/hikes, I do not provide "off-leash" trail experience as a safety precaution, thank you for your understanding! I am happy to provide pictures and updates of your pup whenever requested, please never be afraid to reach out!

Sitter Profile Image: Lindsey V.
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Lindsey V.
$45
total per night
5.0 out of 5 stars
• 4 reviews
15 years of experience
Selkirk, NY, 12158

About: I’ve pet sit for multiple dogs, and my pup loves having friends. I telecommute and minimize my time out of the house on petsitting days. Occasionally I have foster dogs and won’t be available for services in my home on those days, but I’ll update my calendar. I live in a great neighborhood to walk dogs. I’m able to use lunch breaks to take your fur baby out for some mid day exercise. I have the sweetest dog to keep your fur baby company. I stay in the same room to make sure everyone is having a good safe time. I’m in a residential area so if boarding, your pup will have safe walks in my neighborhood.

Sitter Profile Image: Bryanna H.
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Bryanna H.
$56
total per night
5.0 out of 5 stars
• 11 reviews
2 repeat clients
15 years of experience
East Greenbush, NY, 12061

“Bryanna was an amazing host for our puppy Sunny! She provided frequent updates and pictures throughout his stay, which was much appreciated. After his stay, she gave us great feedback about our boy!”

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Varna N.
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The median cost per night for dog boarding in Stockbridge is $60

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  • 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?

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  • 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

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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

As of November 2026, there are 152 sitters on Rover offering Dog Boarding across Stockbridge. 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.

97% 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, 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 Stockbridge.

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 Stockbridge. On Rover:

  • 92% of sitters can help with special care needs
  • 95% can help with giving oral medications or injections
  • 97% 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 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 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 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.

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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