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 11%.

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Sitter Profile Image: Andrea L.
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Andrea L.
$39
total per walk
5.0 out of 5 stars
• 20 reviews
8 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: Ziv N.
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Ziv N.
$18
total per walk
20 years of experience
Pittsfield, MA, 01201

About: I've cared for dogs since I was ten years old. I've cared for puppies and senior dogs, and I have far too much experience with elderly dogs near the end of their lives. I love them all more than words, and it's a dream to get paid to play with new dogs! My first responsibility is as a dad (of human children), so I'm available for dogs from the minute the kids leave in the morning until the minute they walk in the door in the afternoon. I have wilderness emergency medical training, and carry basic dog supplies even on short walks around my own block. I treat dogs with the utmost love and care, and only want them to live good and happy lives.

Sitter Profile Image: Charlotte M.
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Charlotte M.
$18
total per walk
12 years of experience
Pittsfield, MA, 01201

About: Animals have been the touchstone of my life. I grew up taking care of animals and I prioritize each pet’s needs. I understand that each pet is different and will provide excellent care to your pets as if they were my own. I have experience caring for dogs at all life stages, and can administer medications confidently. Whether your dog loves to snuggle, play with toys, run around outside, or keep their distance, I can meet them where they’re at with patience and respect. I will provide photo and text updates for you, follow care instructions precisely, and be available for any questions you may have. The times listed are when I’m not working and fully available to take care of your pets! For drop in visits, I make sure I can spend at least an hour at your home and won’t be rushed. At my home, your pet will be with my two dogs and two cats, all of whom are friendly. There are plenty of dog beds, toys, and places to get cozy. We have a large, unfenced backyard, where your pup can play, supervised by me. We often let the dogs out at night leashed to ensure they stay close. I love to take the dogs for walks at the lake nearby or rail trail. I will be home with them all day.

Sitter Profile Image: Yasmin Jamal A.
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Yasmin Jamal A.
$18
total per walk
5.0 out of 5 stars
• 2 reviews
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: Brenna B.
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Brenna B.
$39
total per walk
5.0 out of 5 stars
• 7 reviews
1 repeat client
12 years of experience
Pittsfield, MA, 01201

“Brenna did a great job. She loves dogs & doing this donit is a win-win. Of course we recommend her.”

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Betts M.
Sitter Profile Image: Kelly H.
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Kelly H.
$56
total per walk
5.0 out of 5 stars
• 66 reviews
31 repeat clients
14 years of experience
Otis, MA, 01253

About: We LOVE and babysit all animals & dogs, we specialize in Pugs, English Bulldogs & French Bulldogs, we have a lot of experience with these breeds from having our own and caring for clients dog family! (We do travel up to 300 miles for in home stays, additional travel fee are quoted), (cross country house/pet sitting available upon request, special rates quoted). Our priority is their safety and comfort while remaining focused on them as individual pups each with their own unique routines, such as, maintaining their special diets, exercise and or supplements/MedX, which will be administered as determined by you. When we stay at your home we usually stay in a guest room, use one bathroom and the kitchen, tv/sitting room, we certainly don't require use of a full house. We are available to retrieving your mail, accept your packages, watering your plants and any other incidental services. We are a husband/wife team which is great because the pups are never left alone. I usually cook most of our meals. I vacuum, clean the bedding/towels, bathrooms & kitchen before we leave. We leave the house in order so that when you come back there is no mess or stress. We take our garbage and recycling with us. We also pick up after your pets, keeping the yard poop free. Our fee is $125/per night for up to 2 dogs and $150/night for 3-4 dogs.  Note: Extended stay will result in a modified price, hours of arrival and departure are between 11am and 4pm, outside these hours will be additional $60.00-$150.00, depending on arrival and departures. References upon request. We have enjoyed 11 wonderful years providing our services for and exclusively to a limited number of pets Per day/night. It is our policy "To meet and greet" prior to accepting "First timers, since We do provide "Your Home service" for Dogs of All sizes and breeds. So, allow us to provide your "Best friend/ friends" with the kind care that will satisfy your highest expectations. We are at your home 24/7, your pets are rarely left alone. We are available to arrive 8am and 6pm. Specialize; "Staying Home-Not Alone with Trusted Guardians." We specialize in; "Staying Home-Not Alone with Trusted Guardians." However we do offer our home for a very limited size dog(s), small to medium; "The Comforts of Home" is the quality care you have been searching for. We offer your Best Friend or Friends with indoor rooms, a backyard, lease only; your pup is in a protected area at all times to spread out as they relax and socialize with us as their guardians. We like to encourage everyone to bring your pets own bed; which allows them to feel at home. We provide gates at all doors to double the safety of your pet. Wedding sitting available, ceremony thru reception, starting at $300.00, inquire about rules. We currently house and pet sit full time. Allowing us to be with your pets 24/7, they are rarely left alone. "Staying Home-Not Alone with Trusted Guardians." We are vigilant, to be aware of where your dogs are at all times. If gates are needed at doors we put them to use.

Sitter Profile Image: Leona O.
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Leona O.
$20
total per walk
4.8 out of 5 stars
• 13 reviews
3 repeat clients
10 years of experience
North Adams, MA, 01247

About: I’ve taken care of dog of many sizes and health conditions, I have had a cat for 9ish years and have cared for friend and families dogs for years. I am a student, I am relatively free but lots of work to do! I like to go on walks already! I am able to be flexible. I know how to feed animals and care for them, can follow special instructions as I know they are important. As much as I would love to care for your fur baby at my home, I cannot.

Sitter Profile Image: Logan S.
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Logan S.
$28
total per walk
5.0 out of 5 stars
• 31 reviews
13 repeat clients
25 years of experience
Rensselaer, NY, 12144

About: I've been taking care of a wide variety of animals for a long time. I have experience in all around basic boarding care for dogs, cats, and various reptiles and small animals; dog training basic obedience, fear or frustration aggression/reactivity, high drive dogs, and anxiety behaviors. Pet Care is not only an important part of my life, but it's a passion of mine. Caring for your animal like I do my own is what makes life rewarding for me. When your pet is with me it becomes a part of my family and is treated as such. I look forward to training or caring for your animals! I can train your dog in a multitude of ways. I work a lot of animals with anxiety and behavioral issues. I can easily crate your dog, cat or any other animal if needed. I have access to multiple fenced in yards for your pet to run around in and play. I have a fully trained purebred smooth collie who is extremely gentle and can make friends with anything. I have multiple rooms and spaces in order to accommodate your fur baby's needs. I pay attention to detail and carry out all care with the highest level of standards I can.

Sitter Profile Image: Amad E.
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Amad E.
$28
total per walk
5.0 out of 5 stars
• 34 reviews
7 repeat clients
15 years of experience
Northampton, MA, 01060

About: I've been house and pet sitting for ten years plus, besides that I've been an owner of many dogs and cats. There is nothing that makes me happier than the well-being of them. When you choose me for the care of your fur babies, they'll be taken care of to the maximum comfort and standard. I'm flexible in that I work remotely... So i huge amount of the time i will be around to cater to your pets. And also will be able to walk them often and keep them stimulated I'll make sure their safety and the environment they're in are safe and nurturing. If it's the owner's house I won't change a thing, if it's my house I'll have them have access to all that they would have at their home.

Sitter Profile Image: Patricia H.
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Patricia H.
$34
total per walk
5.0 out of 5 stars
• 6 reviews
2 repeat clients
20 years of experience
Poughkeepsie, NY, 12601

About: I have been a pet lover & pet care advocate for as long as I can remember! I’ve been caring for dogs of all breeds, sizes, and personalities my entire life. I’ve taken care of kittens, pups, rescued cats, & cared for other pets like bunnies, fish, & hamsters. Over the years, friends, family, and neighbors have trusted me to walk, feed, and love their pets like my own which I do with a smile. Whether it’s an energetic puppy who needs to play & burn off some energy, or a sweet senior pup who needs extra patience and care, I adapt to their unique needs and personalities. I’m not just a sitter, i’m an emotional support human & a dependable companion for your pet while you’re away. I believe in consistent communication, lots of love, and making sure your pet feels safe, happy, and cared for. I love & care for them as if they were my own. I’m experienced with administering medications, sticking to routines, and keeping pets calm and comfortable in their own environment. Your comfort, peace of mind, & your pet’s happiness are my top priority! As someone who works from home and takes online classes, my schedule is super flexible; perfect for giving your pet the attention they deserve! I’m home throughout the day, which means your pet won’t be left alone for long stretches. Whether it’s a midday walk, playtime, or just some company while they nap, I can be there when they need it most. My routine allows me to be fully present and responsive to your pet’s needs. I can stick to their feeding and walking schedule, provide consistent companionship, and make sure they feel safe, loved, and entertained while you’re away. Being home all day also makes me a great fit for puppies, senior pets, or dogs who need a little extra TLC. When I care for pets in their own home, my goal is to keep their routine as familiar and stress-free as possible. I follow your pet’s routine closely & I make sure they’re comfortable in their space, following their usual schedule for walks, meals, playtime, and cuddles. Whether it’s sticking to their favorite walking route or knowing exactly how they like their food prepared, I pay close attention to every detail you share. I know how much the little details matter! Being in their own environment helps your pet feel more relaxed, and I’m there to make sure they feel loved every step of the way. I’m experienced in administering a variety of medications, including flea and tick ointments, oral chewy meds, and pills; whether they’re hidden in a treat or given directly. I stay calm and patient to make the process as stress-free as possible. I’m comfortable managing multiple pets and giving each one the attention and care they need. I treat your home with the same respect and care I give to your pet: clean, secure, and exactly how you left it. I provide regular updates with messages & photos so you can feel confident your pet is safe, happy, and in good hands & know everything is going smoothly while you’re away.

Sitter Profile Image: Daniel A.
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Daniel A.
$18
total per walk
5.0 out of 5 stars
• 2 reviews
2 years of experience
Wilbraham, MA, 01128

About: I’ve always taken care of pets and volunteered at local shelters. Your doggies will have the option of treats, dog walks, dog park trips, bark toys, and the option to socialize with other dogs if that is an option! What’s different with me is every dog that stays here with me and comes home with a brand new BARK BOX toy if the parent allows ! I’m currently a stay at home dad so this works perfectly with my schedule! With my wife working full time, this makes a household that much more at home! All of my dogs are trained and with the huge yard in our back yard it provides the perfect area for exercise and potty time! We also have a dog park right down the street!

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The median cost per walk for dog walking in Stockbridge is $25

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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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    It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.

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    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

How to book dog walking

  1. 1. Search

    Browse profiles of walkers near you who offer dog walking.
  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 walking - Stockbridge

Select a filter and find qualifying sitters offering dog walking.

Sitters in Stockbridge average 4
repeat dog walking clients

FAQs for Dog Walking - Stockbridge

Frequently asked questions about Rover

As of November 2026, there are 461 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 bookings, your dog walker can send a Rover Card with details about your dog’s walk. Rover Cards require at least one photo and may include a map of the walking route, the total walk time and distance, and any pee or poop breaks recorded by the walker.

The route map lets you review where your dog was walked in Stockbridge after the booking. It is not live GPS tracking.

Have specific details you would like included? Message your dog walker in the app before the 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:

  • 92% of walkers can help with special care needs
  • 94% 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.

A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your walker interacts with your pet 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. Meet & Greets are a great way to prepare your pet and walker for longer stays or first-time bookings. Read our tips for your first Meet & Greet.

walkers on Rover set their own cancellation policy, which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

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

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