Dog Walking Stockbridge

Book a dog walker to give your dog a 30-minute walk around your neighborhood.

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Stockbridge, Find top rated dog walking

Prices are estimates per walk for 1 dog. Pricing may vary based on your search and includes a booking fee of 15%.

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Sitter Profile Image: Valentina M.
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Valentina M.
$18
total per walk
6 years of experience
Stockbridge, MA, 01262

About: I grew up with 2 dogs and 2 cats. My family was part of helping a farm when i was little, I got to take care of ducks. They were so cute. I love animals and let me know if you had questions. I work at Marshall’s. I will be taking care of the animals during my days off. I will make sure they have everything they need I grew up with cats and dogs. I love all kinds of animals. I will take good care of them. I can bring them to my house as well.

Sitter Profile Image: McKenna P.
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McKenna P.
Star Sitter
$28
total per walk
5.0 out of 5 stars
382 reviews
146 repeat clients
8 years of experience
Lenox, MA, 01240

McKenna came to walk my pup today and I came home to a happy and tired dog. McKenna is a very reliable, punctual, and caring dog sitter. She is extremely trustworthy and I recommend her wholeheartedly. My dog loves her!

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Diana K.
Sitter Profile Image: Andrea L.
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Andrea L.
$39
total per walk
5.0 out of 5 stars
19 reviews
7 repeat clients
20 years of experience
Great Barrington, MA, 01236

Andrea was so, so wonderful taking care of my pup, even accommodating last minute changes when my travel changed. I absolutely recommend her for your pets!

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Tanya C.
Sitter Profile Image: Deborah G.
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Deborah G.
Star Sitter
$34
total per walk
5.0 out of 5 stars
14 reviews
4 repeat clients
7 years of experience
Lee, MA, 01238

About: Love spending time with furry friends. Have had my dog for seven years. I can’t get another dog at the moment, but I would love to share the moments with your loving pets. I work from home 3 days a week and am home most weekend. I can always take a break to look after your pet. Based on what you’re looking for. I have a backyard not fenced in. I would’ve want to offer an overnight stay. Just to come over and let your dog out or take your pet on walk.

Sitter Profile Image: Chenoe R.
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Chenoe R.
$28
total per walk
5.0 out of 5 stars
3 reviews
20 years of experience
Lee, MA, 01260

About: I am a registered nurse so I only work 3 days a week. I grew up with animals, I attended training classes and one point we had 3 dogs living in our home at once. I grew up with a Laborador Retreiever, a mini Shnauzer Poodle mix and a hound mix, so I have had experience caring for each type of dog and any accommodations they may require. I eventually want a dog of my own but I am unable to at this moment in my life. My goal is to help people give their dogs the best life they can lead. Life gets busy and one of the greatest joys in our lives are our furry best friends and I want to help you give them the life they deserve.

Sitter Profile Image: Adrienne L.
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Adrienne L.
$34
total per walk
1 year of experience
West Stockbridge, MA, 01266

About: I currently have one almost 2 year old chocolate lab who is sassy and has a lot of energy! I have taken care of many dogs, sometimes 3 at once in my life. I love to walk, and what better way to walk - is with a dog! I have had dogs ever since I was born, and have had both large and small dogs. Dogs are unique and I love getting to know their personality! I am a teacher, so taking clients for dog walks during the summer months, when I am away from the classroom. I am available for the vast majority of the summer! I care for dogs like they are my family. I will treat them like the good dogs they are and give them lots of petting and (if ok with you - treats)!

Sitter Profile Image: Keri H.
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Keri H.
Star Sitter
$39
total per walk
5.0 out of 5 stars
57 reviews
19 repeat clients
20 years of experience
Lenox, MA, 01240

Keri was absolutely wonderful with my dog! She was extremely communicative, obviously a dog lover, and so helpful. I will definitely use her again!

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Rebecca H.
Sitter Profile Image: Hannah L.
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Hannah L.
$23
total per walk
7 years of experience
Lenox, MA, 01240

About: I have many years of experience caring for dogs, cats, bunnies and chickens and am comfortable with feeding, walking, playtime and daily care routines. I understand that every pet has unique needs and will make sure they receive plenty of attention and proper care! I work remotely, providing me with a flexible schedule and plenty of time to care for your pets. I currently work remotely as a paralegal so I have plenty of time to tend to your pets. I do serve some nights but aside from that will be fully available for walks, potty breaks, feeding and all other activities. I have a large house with a big lawn. I also have a large crate and smaller carriers as well. I do have a pet bunny who will stay in my room and away from all pets.

Sitter Profile Image: Camille B.
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Camille B.
$30
total per walk
5.0 out of 5 stars
8 reviews
3 repeat clients
5 years of experience
Great Barrington, MA, 01230

Camille was extremely reliable and caring for our two dogs! She came everyday rain or shine and would even check the weather and make recommendations to adjust the timing of the walk based on the weather that day. When she noticed the health of one of the dogs was not normal that day she notified us immediately so we could help the dog. She included updates about the dogs health in the following days. She was exactly what the doggies needed and she will be greatly missed while she is on her research trip!

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Madison K.
Sitter Profile Image: Robert W.
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Robert W.
$36
total per walk
5.0 out of 5 stars
4 reviews
2 repeat clients
10 years of experience
Lee, MA, 01238

Robert and McGee seemed to do very well today for their 1st walk/visit. I appreciate Robert’s being so diligent and caring for McGee. I would like to continue with Robert and I hope he enjoyed McGee‼️

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Liz P.
Sitter Profile Image: Sally A.
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Sally A.
$62
total per walk
5.0 out of 5 stars
45 reviews
13 repeat clients
50 years of experience
Richmond, MA, 01254

About: Born with Stormy the spaniel & Jane the tabby, I participated in the love and care of Lance the setter, Tippy the happy boy and Snickelfritz and Tidy the calico kitties. My pets were my favorite toys! In adulthood I adopted rescue puppy Kino and blue-eyed kitten Shasta, elegant Jazz-girl, and some other great pets. Now I have Tigra Carmela, my wild-child calico who came skinny and scared from the woods and now loves her tummy rubbed. Family & friends going on vacations give me plenty of hands-on house and pet caretaking experience. I offer pet & TLC home & property care . ME: I love dogs and cats, and also sing old songs and play guitar at senior establishments, and am a watercolor artist. I believe a world without pets is colder place. • Dedicated pet care, Pet First Aid Certification. Includes: Household maintained to pre-arrival condition or better. Plants & gardens are watered, Porches & paths are swept/shoveled, household systems problems are dealt with. My Home & Pet Care will leave you worry-free! • Fee adjustments per conversation. • Mileage fee may be added, at the current IRS rate, 2025 of .70% per mile. • TIPS: Optional, and Appreciated, this is a service job, with prices based on a US custom of tipping (20% for excellent service is very much appreciated).

Sitter Profile Image: Caitlin H.
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Caitlin H.
$17
total per walk
5.0 out of 5 stars
17 reviews
3 repeat clients
4 years of experience
Pittsfield, MA, 01201

About: I acknowledge that routine is important with pets and therefore will mold my style to fit your pets norm. (This includes your rules for your pet, anything you are training them to do, and any medication). Before taking care of your pet I make sure I fully understand their daily routine to make sure their schedule isn’t thrown off. I have experience administrating medicine to pets. I also have experience giving baths to pets as long as their grooming supplies are supplied. Also I have taken care of pets for around 3 years and am very flexible as I want to make it as easier on you as possible. I am a teacher so I have all day to spend with your pup during summer months. Also during the school year, I get off in the late afternoon on Weekdays so I can be there to take care of your pup by early evening. I respect my clients space and I am also happy to take care of any additional things around the house (watering plants, bringing in mail, etc.) if asked.

Sitter Profile Image: Karla C.
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Karla C.
$18
total per walk
5.0 out of 5 stars
7 reviews
7 years of experience
Lenox, MA, 01240

About: I love to care for my dog and love to meet other dogs. I am open to any dog and its unique personality. I have taken care of all sizes of dogs and always want to meet their needs. I don't mind taking them on walks around the neighborhood and am happy to take pictures or videos of how they are doing. I am primarily available on the weekends but will make time for weekday evenings. I am currently applying to other weekday jobs and will update my schedule accordingly. I’m moving to Amherst on August 26th so I recommend not booking after this date. I will not be in the area I let my dog outside when he asks for it and keep a close eye on him. I also supervise all dogs outside, making sure they don't go into places they should not go. I will also provide baths when asked and can give oral medication.

Sitter Profile Image: Sydney R.
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Sydney R.
$36
total per walk
5.0 out of 5 stars
6 reviews
12 years of experience
Great Barrington, MA, 01230

Sydney was fantastic!! Chloe was so happy!! I would highly recommend Sydney to anyone! Chloe would too🐾❤️ certainly took the worry out of my days away knowing she was being taken care of so wonderfully!!

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Joanne B.
Sitter Profile Image: Chloe O.
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Chloe O.
$32
total per walk
5.0 out of 5 stars
9 reviews
8 years of experience
Lee, MA, 01238

Chloe was always quick to respond and kept me updated with pictures. She was fantastic with my energetic pup!

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Renee A.
Sitter Profile Image: Steve F.
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Steve F.
$56
total per walk
5.0 out of 5 stars
1 review
2 repeat clients
12 years of experience
Lee, MA, 01108

About: I'm very happy to be around pets. Have experience taking care of pets as I have had pets growing up I have been called to dog wisper because I have that connection with dogs. Your pet will be well cared for and loved in my care I'm open mornings and at night.i do food delivery and housekeeping part time.i can usually be available for whatever times you need just reach out and let me know I have a eye for detail and.very alert so your pet will be safe. What ever kind of pet sitting you need I can do

Sitter Profile Image: Janet C.
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Janet C.
$25
total per walk
4.7 out of 5 stars
13 reviews
11 repeat clients
20 years of experience
Great Barrington, MA, 01230

Janet was wonderful

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Leslie T.
Sitter Profile Image: Reymon B.
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Reymon B.
$23
total per walk
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: Makayla F.
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Makayla F.
$50
total per walk
5.0 out of 5 stars
14 reviews
3 repeat clients
10 years of experience
Great Barrington, MA, 01230

About: I've always carried a deep passion to care for animals since I can remember. I love dogs that are not mine as if they were my own! I have many years experience caring for dogs and other animals. Ive always had jobs in kennels and daycares. I am confident your pet will be very happy in my care. I have taken care of dogs who need extra medical attention, older dogs, puppies, etc. I am more than happy to meet your expectations and accommodate your needs for your furry friend. I am offering day long care for your pet. We can do walks, hikes, swimming, even a play day at the park. Single walks, hikes, swimming, trips to the park. Drop ins to your home for up to 2 hours at a time. Available late night and early morning. I take pride in loving your pet like my own and I hope we can work together :) I have a lot of available time to help your pets in need! My schedule is very flexible. I am currently transitioning from being a stay at home mom. I’m very trustworthy and make sure your pet is safe at all times! Whether off leash walks are allowed or on leash at all times. I will make sure your pet is always treated as if it were my own.

Sitter Profile Image: Lindsay L.
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Lindsay L.
$28
total per walk
5.0 out of 5 stars
4 reviews
20 years of experience
Canaan, NY, 12029

Thank you Lindsay! You were exactly on time and a last minute life saver for us - we had a great evening out. Great communications too. 🐶

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Teri T.
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The median cost per walk for dog walking in Stockbridge is PLN 25

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Sitters in Stockbridge average 3
repeat dog walking clients

FAQs for Dog Walking - Stockbridge

Frequently asked questions about Rover

As of June 2026, there are 477 sitters on Rover offering Dog Walking across Stockbridge. Enter your ZIP code to see which available sitters are closest to your home.

Whether you want a solo or group walk depends on your dog's personality. Solo walks can be beneficial for dog parents with reactive dogs, puppies, or dogs who are anxious around unfamiliar animals. Many dog walkers on Rover offer private, one-on-one walking services.

Group walks are a good fit for social dogs who enjoy structured walks. If your dog prefers the energy of a group stroll, ask your dog walker about group walks in your Stockbridge. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.

For dog walking services, you can request a report card update with specifics about your dog’s walk. Report cards require photos and can include a map of the walking route , total walk time, poop and pee breaks, and distance traveled, so you know exactly where your dog has been walking in Stockbridge.

Got specific details you'd like the dog walker to include? Message them in the app before your dog’s walk begins.

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 walker 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 .

Yes, you can find walkers who have experience with handling special pet needs in Stockbridge. On Rover:

  • 94% of walkers can help with special care needs
  • 100% can help with giving oral medications or injections
  • 100% 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.

A Meet & Greet is a short introductory meeting between you, your dog, and a walker. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your walker or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your walker questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and walkers on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement walker.

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