Dog Walking Middlefield

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Middlefield, 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: Kathleen M.
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Kathleen M.
Star Sitter
$30
total per walk
5.0 out of 5 stars
• 165 reviews
46 repeat clients
12 years of experience
Becket, MA, 01223

“Kathleen! Thank you for the last minute meet and greet / walk in the same day. It was so awesome to see Tessie fully open up to you. We are looking forward to many more hang outs!”

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

“You can tell McKenna is a big animal & dog lover. She was incredibly sweet & gentle during our meet & greet. She asked all the right questions and our pups felt instantly comfortable around her. We’re glad to establish a relationship with someone we can trust AND with someone who goes above & beyond during her visits. Thank you McKenna, we’ll be booking you again soon!”

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Graham S.
Sitter Profile Image: Janet M.
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Janet M.
Star Sitter
$34
total per walk
4.9 out of 5 stars
• 18 reviews
8 repeat clients
53 years of experience
Chesterfield, MA, 01012

“Janet is very responsive to msgs, shows up at the scheduled times, and provides summaries of her visit. Thanks Janet!”

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Allen B.
Sitter Profile Image: Trista S.
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Trista S.
$34
total per walk
5.0 out of 5 stars
• 23 reviews
10 repeat clients
30 years of experience
Pittsfield, MA, 01201

About: Animals kept me safe my entire life, now I return the favor by keeping your babies safe while you’re away. ❤️ I have been working with animals my whole life. At only 3 I moved in with my step father onto a small farm(yes this means I can feed your chickens, gather your eggs, clean your stalls, and feed your cattle, pigs, or even horses). I spent three years working in the veterinary field where I learned to better understand and triage animal emergency and how to deal with them calmly and safely. I have 3 dogs, and 2 cats of my own as well as a bearded dragon and a few chickens, whom I love more than life. I have minimal boarding experience, but have had or worked with everything from fish and birds, to dogs to cattle, from snakes to horses, and I love each one of these creatures just as much as the rest. I adore all animals, and cherish my pets so much, and finding some one you can trust to REALLY care for them can be a challenge, so let me make your life a little easier with flexible, reliable, patient and gentle care. As a pet mom to 11 furry, scaly, and feathered babies, I know how hard it can be to find reliable pet care. My animals are my children, my babies; the most important things in my world. I promise to love yours the way I’d love my own. I am currently unemployed and taking a leap. What I’d LOVE is to start my own pet care company. I know how hard it is to find pet care in and around the Berkshires, especially the holidays when all the day cares and well known sitters are booked - so let me take some of that weight off you. I’m flexible and reliable and can do drops ins, walks, day stays, over nights, or multiple day stays. I’m open to any animal type, including pocket pets, exotics and special needs. What can I say? Pets are really the only thing most of us like in this crazy world; so it’s kind of the perfect job. 😉 I am open to all types of care, all types of animals, and all types of situations. I have experience in vet medicine and have had elderly and special needs animals my whole life. No matter how long my interaction with your baby is, I assure you it will be filled with love.

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: Paisley R.
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Paisley R.
Star Sitter
$23
total per walk
5.0 out of 5 stars
• 20 reviews
5 repeat clients
10 years of experience
West Springfield, MA, 01089

“Milo had such a great experience today! 😊 Paisley was incredibly kind, attentive, and clearly cared about him. She made sure he got everything he needed, followed all of my instructions, and gave me peace of mind knowing he was in such good hands. It’s obvious she genuinely enjoy working with dogs, and Milo came back happy and well cared for. I would absolutely recommend her and will be continuously using her walking services. Thank you for taking such great care of my boy!”

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Kira K.
Sitter Profile Image: Reymon B.
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Reymon B.
$30
total per walk
5.0 out of 5 stars
• 4 reviews
1 repeat client
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: Brooke H.
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Brooke H.
$15
total per walk
5.0 out of 5 stars
• 4 reviews
4 years of experience
Holyoke, MA, 01040

About: I’ve worked hands-on with animals for years and currently volunteer/work at an animal sanctuary multiple days a week and The Good Dog Spot Northampton boarding location I’m very comfortable with feeding schedules, medication routines, cleaning enclosures, monitoring behavior changes, and handling animals safely and calmly. I’ve cared for dogs of different sizes, temperaments, and energy levels, including high-energy breeds and more anxious personalities. I’m very observant and take animal welfare seriously — I notice small behavior changes quickly and always prioritize safety and comfort.🩷 I will add photos of my happy dog customers to my profile! I also have my wildlife rehabbers license :) I currently just switched from full time to part time at the animal sanctuary and Good Dog Spot, so caring for animals is already built into my daily routine. Pet sitting allows me to gain even more hands-on experience while earning extra income doing something I genuinely care about. I’m available for drop-ins, walks, and house sitting outside of my Doggy Daycare shifts, and I manage my schedule carefully to ensure each pet receives consistent, attentive care. For everyone’s safety and comfort, I provide care in my client’s home only. I have a 14-year-old dog and two rescue hedgehogs who are territorial with unfamiliar animals, so I don’t host pets in my home. This helps prevent unnecessary stress for both my animals and yours. When caring for pets in your home, I follow routines exactly as instructed and prioritize keeping their environment calm, clean, and secure. I monitor behavior, appetite, and energy levels closely and will always communicate promptly if anything seems off. Your pet’s wellbeing and safety are my top priorities.

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
• 2 reviews
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: Bella G.
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Bella G.
$39
total per walk
5.0 out of 5 stars
• 13 reviews
2 repeat clients
10 years of experience
lanesborough, MA, 01237

About: I have my own dog walking/Pet Sitter business called “Canine in motion” On facebook and instagram. I’m super excited to have new clients reach out to me that need a dog walker/pet sitter. I’ve worked at an animal shelter, a doggy day care and I also used to volunteer at a nearby animal shelter to help walk dogs. Through those experiences i’ve learned so much about different dog breeds and other small animals. I’m currently working part-time, so I’ll have plenty of time to play with your pup! I’m available for pet sitting/dog walking Monday-Friday. My weekends are also free. Why should I look after your dog while you're on vacation or unable to look after them? I give genuine love and passion to dogs. I understand their needs, both physical and emotional, and i’m dedicated to providing them with the utmost care and attention. My patience and attentiveness allow me to anticipate their needs and respond accordingly, ensuring their comfort and well-being. I have a keen eye for detail, noticing subtle cues and behaviors that may indicate their mood or health. I’m responsible, I follow instructions diligently, whether it's regarding feeding, exercise, or medication. My calm and nurturing presence creates a safe and secure environment, allowing dogs to feel at ease in my care. With me, dogs will find a trustworthy and compassionate companion, someone who will go above and beyond to ensure their happiness and safety.

Sitter Profile Image: Michael B.
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Michael B.
$23
total per walk
5.0 out of 5 stars
• 4 reviews
24 years of experience
Deerfield, MA, 01342

“Michael is an amazing dog walker for Theo. He is always available for us, even if it’s only a day or so warning and Theodore absolutely adores him. He sends photo updates to me which makes me so happy to see Theo when I’m gone from work! Thank you Michael!!!”

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laura g.
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: 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: Brittany F.
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Brittany F.
$20
total per walk
5.0 out of 5 stars
• 8 reviews
5 repeat clients
20 years of experience
Longmeadow, MA, 01106

“This is our second time using Brittany, she was prompt, communicative and sent plenty of pictures and notes. Would highly recommend!!”

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Lauren W.
Sitter Profile Image: Lilly T.
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Lilly T.
$23
total per walk
5.0 out of 5 stars
• 9 reviews
3 repeat clients
19 years of experience
Belchertown, MA, 01007

“Lilly was great to work with, as well as reliable and responsive to a small last l-minute adjustment. I loved getting the photos of Trina. I will definitely ask Lilly to care for Trina again!”

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Susanne P.
Sitter Profile Image: Anna C.
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Anna C.
$28
total per walk
5.0 out of 5 stars
• 21 reviews
9 repeat clients
20 years of experience
East Longmeadow, MA, 01028

About: Dogs have and will always be a huge part of my life. We got our first family dog when I was just 3 years old and the rest is history. My husband Jack is extremely passionate about animals as well and is my partner in all of this so you get two dog sitters for the price of one. Between the two of us your pet will get so much love, cuddles & exercise. We guarantee a level of attention and care that I feel confident your pet won’t get anywhere else; between this and Rover taking it’s fee our prices might be on the high side but they reflect our level of personalized and professional level of care. I also just want to add that our love for dogs extends to all animals so cats etc are all welcome to come hang with us :) Important Note: if you are reaching out for house sitting my husband and I only take those if we both are allowed to stay the night. We prefer to do this for safety as well as enabling the best care possible for your pet. Your pets will be my top priority & my main focus when they stay with us! I feel pretty confident that they will get more quality time, attention & lovin with me then any other pet sitter! I have a smoke free home and do not have any dogs currently living at my house so your pets will be my only focus! Also a child free home!

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: Diana G.
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Diana G.
$34
total per walk
5.0 out of 5 stars
• 6 reviews
1 repeat client
5 years of experience
Valatie, NY, 12184

“Wonderful, accommodating, and great with my normally shy poodle! Will be booking again. Thank you so much 💕”

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Dayna F.
Sitter Profile Image: Sydney D.
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Sydney D.
$38
total per walk
20 years of experience
Southwick, MA, 01077

About: I’ve been an animal lover for as long as I can remember! I grew up with Labs, so I’m very familiar with big personalities, lots of energy, long walks, playtime, and plenty of slobbery love. 🐾 I also adopted a cat, which taught me that sometimes the best way to win a pet over is to let them come to you (and maybe offer a few treats!). Although my own pets have since passed, they gave me years of experience, amazing memories, and a genuine love for caring for animals. I’m patient, playful, attentive, and always focused on making pets feel safe and comfortable. Whether your pet wants an adventure outside, a game of fetch, or just some extra love and company, I’m happy to be their new buddy while you’re away! ❤️ I currently own my own business and make my own hours and work from home, so I can easily make my own schedule fit around any pet care! I'm lucky to have an open, comfortable and clean home where I can walk animals on the many acres I live on. I can also crate animals if that's how they are trained. When in other people's homes, I'm incredibly conscious of being considerate, following directions to respect their space, and understanding how the animal uses and loves the space.

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The median cost per walk for dog walking in Middlefield is $23

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Popular requests for dog walking - Middlefield

Select a filter and find qualifying sitters offering dog walking.

Sitters in Middlefield average 3
repeat dog walking clients

FAQs for Dog Walking - Middlefield

Frequently asked questions about Rover

As of October 2026, there are 760 sitters on Rover offering Dog Walking across Middlefield. 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 Middlefield. 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 Middlefield 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 Middlefield. On Rover:

  • 95% of walkers can help with special care needs
  • 98% can help with giving oral medications or injections
  • 98% 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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