Dog Boarding Stockbridge

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

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.
Sitter Profile Image: Irene T.
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Irene T.
Star Sitter
$73
total per night
5.0 out of 5 stars
19 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: 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: Yenifer V.
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Yenifer V.
$73
total per night
5.0 out of 5 stars
25 reviews
5 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: Nicole P.
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Nicole P.
Star Sitter
$84
total per night
5.0 out of 5 stars
28 reviews
6 repeat clients
34 years of experience
Elizaville, NY, 12523

Nicole took excellant care of Baxter and Oliver during our vacation. Daily updates and photos showed my pups happy and loved in my absence. Thank you so much for taking the worry away.

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

Deanne is an excellent communicator, sending many updates and photos of our Odin. He was well looked after and happy as ever! We would definitely come back again! Thank you!!!

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Ryan M.
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

I couldn't be happier with the care my pup gets when he stays with Tetiana. He is a bit neurotic and has separation anxiety - he is not an easy customer. Tetiana and her mom are excellent with him -- they give him lots of love, attention, and walks-- and he always comes home in a great mood. Thank you, Tetiana!

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rochelle d.
Sitter Profile Image: Peter K.
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Peter K.
$62
total per night
5.0 out of 5 stars
29 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: John S.
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John S.
Star Sitter
$86
total per night
5.0 out of 5 stars
113 reviews
24 repeat clients
20 years of experience
Norfolk, CT, 06058

Mr. Darcy had a blast as usual, he loves hanging with John and his lively dog Dolly, and we go away with no worries. He comes home super tired, which is a great sign

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Cynthia H.
Sitter Profile Image: Candice S.
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Candice S.
Star Sitter
$62
total per night
5.0 out of 5 stars
58 reviews
22 repeat clients
10 years of experience
Stottville, NY, 12172

Candice was amazing and we could tell our dog Zoey had a great time with their family! Very responsive and punctual with both pick up and drop off. Highly recommend for anyone looking for a sitter!

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Wesley E.
Sitter Profile Image: Jess L.
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Jess L.
$50
total per night
5.0 out of 5 stars
88 reviews
21 repeat clients
5 years of experience
Pittsfield, MA, 01201

Jess was awesome and took wonderful care of our dog Wiley. She sent lots of photos of him and kept us up to date on how he was doing, the nice walks they went on and other dog buddies he met. We would definitely board with Jess again.

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Lily D.
Sitter Profile Image: Rebecca L.
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Rebecca L.
$73
total per night
5.0 out of 5 stars
7 reviews
20 years of experience
Lenox, MA, 01240

Thanks to Rebecca, we enjoyed an amazing concert on our vacation and didn't worry about our dog for a second. She put me at ease before I ever met her. She happily anwered my questions and she asked questions that showed me that she really wanted to make our dog's stay pleasant. Her warmth and love for dogs was apparent as soon as I met her. And it was apparent to my dog, too-- she immediately connected to her. I told Rebecca that our dog loves to play fetch, and Rebecca played fetch with her as we drove away. While we were at our concert, Rebecca texted me to let me know our dog was doing great. She told us that our dog was playing with her dogs and that she and her husband had taken all three on a walk. She also sent along a few photos. When we went to pick our dog up, she was happy. to see us but didn't run to our car. She went back to Rebecca-- maybe to say goodbye! We had such a wonderful time at our concert and it was all thanks to Rebecca. We will definitely book her again! And we know our dog will be thrilled to see her!!

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Carolyn 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: 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

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.
Sitter Profile Image: Yasmin Jamal A.
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Yasmin Jamal A.
$45
total per night
20 years of experience
Pittsfield, MA, 01201

About: I waitress, have taken care of seniors and am a certified yoga instructor. I have had cats, dogs, chicks, fish, hamsters. I currently do not own any pets. Pets to me are precious friends who are to be taken care of like children. With full attention, support and love. I work from home so I am able to provide that kind of care. I work from home (virtually) and can accommodate boarding weekdays and weekends. I keep a clean and tidy home and have a gorgeous park very close by. Pet care fits in my routine as I used to have a cat until recently. I care for pets with respect and integrity. Showing them love and care. Keeping them and the area around them clean. Accommodating to their needs by always keeping an eye for out for them.

Sitter Profile Image: Garrett & Deanne G.
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Garrett & Deanne G.
$45
total per night
5.0 out of 5 stars
3 reviews
9 years of experience
Kinderhook, NY, 12106

Garrett & Deanne were really great! Ruby seemed to have a great time with them. They kept me updated on how she was doing (especially with the fireworks over July 4th). I'll definitely be having them watch my girl in the future!

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

Kathleen was an excellent overnight sitter for our dog! She gave frequent updates with photos and made sure the pup was well fed, well exercised, and well taken care of. This was our first experience with Rover and we are very likely to use the service again (and Kathleen if we are back in the area).

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Ashley S.
Sitter Profile Image: Cheyenne F.
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Cheyenne F.
$62
total per night
5.0 out of 5 stars
8 reviews
3 repeat clients
20 years of experience
Kinderhook, NY, 12106

Cheyenne watched our dog Nellie for the first time last night . Nellie seemed to love it and Cheyenne’s dogs . It was a great experience! Thank you !

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Darcy C.
Sitter Profile Image: Martin D.
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Martin D.
$56
total per night
25 years of experience
KINDERHOOK, NY, 12106

About: I have years of experience with many different types of dogs. I watch dogs on a regular basis. For younger dogs I can offer a mountain hikes and for older dogs I can walk them on boardwalk trails that are easy on the joints, yet give the dog the sense of walking in the woods. I don't mind larger dogs at all. I also am willing to cook food for dogs. I very much enjoy the company of dogs and find that when they are well fed and exercised they are really pleasant to be around. Please give me honest description of your dog so I can plan His/Her visit accordingly. My house is set back (1000 feet) from a country road . I can pick up dogs in NYC , Great Barrington , Hudson, or Albany for a fee. I have watched many dogs over the years. Usually I try to walk them as much as possible. I feed them well , but make them follow the sit command before being fed and multiple times a day. All dogs have to be on a slip proof leash when outside or dropped off. Dogs often don't behave as they do at home . Once off a leash it can be very difficult to recapture a dog. In the house I don't crate dogs . We can only watch a few dogs at once. If your dog is very difficult let me know in advanced. Also Corgies get 10% off.

Sitter Profile Image: Jennifer C.
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Jennifer C.
Star Sitter
$56
total per night
5.0 out of 5 stars
96 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.
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The median cost per night for dog boarding in Stockbridge is $55

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  • 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.

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Sitters in Stockbridge average 9
repeat dog boarding clients

FAQs for Boarding - Stockbridge

Frequently asked questions about Rover

The average cost for Dog Boarding in Stockbridge on Rover is $58.85 per night (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog Boarding easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Boarding. For more information on service fees, click here .

As of July 2026, there are 159 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 rhythm and routine, but most will follow the flow that keeps your dog happiest. Sitters can give meals on your dog's regular schedule, provide a comfortable place for sleep, and plenty of one-on-one attention.

100% of Stockbridge sitters also include daily walks in the neighborhood during dog boarding stays. You can also request photo and message updates throughout the stay so you can see which Stockbridge landmarks or neighborhoods your dog is enjoying.

If your dog is a little shy, consider booking a one-night trial stay! This practice run can boost your and your dog’s confidence before your trip.

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.

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.

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