Dog Walking Oakham

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Oakham, 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: Kimberly P.
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Kimberly P.
$19
total per walk
1 year of experience
Paxton, MA, 01612

About: My parents had a one year old dog when I was born so I started life with a canine sibling. A dog, or multiple actually, has always been by my side except between 7th and 9th grade, the loneliest two years ever. I lean towards the Irish Setter but I have raised Golden Retrievers, Boston Terriers, Yorkies and Standard Poodles. I currently have two Setters and one Standard. They speak fluent English and surf the Internet for creative ideas to keep mum busy. I am a retired high school teacher since one month and am looking for commitments on a flexible schedule. I want to be busy but not at the hectic pace that teaching requires. I spent 34 years in secondary education so teaching is natural for me. I have had a canine best friend for almost every of my 58 years and have done countless basic training classes. As a former division 1 athlete, I have an exercise centric lifestyle and thrive on being physically active. Retirement is leaving a void in my routine that I anticipate dog-walking will fill. I have a large property, the majority of which is fenced. The basement has a cage assembled, a cage in the closet and a large wooden pen that my three share when I am out. The furniture is dog friendly and I have enough leashes to walk a football team at once.

Sitter Profile Image: Ella S.
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Ella S.
$28
total per walk
5.0 out of 5 stars
• 1 review
1 repeat client
10 years of experience
Rutland, MA, 01543

About: I’ve had several pets all growing up, ranging from turtles, to birds, to dogs! I have had 5+ dogs that I’ve owned throughout my life! My friends and family go to me to walk/take care of their pets and/or give them advice about them. I am currently free during all time of the day! I have open availability for all week days, and could potentially be available some weekends as well. I will walk your dog for however long you need me to. I have no problem with long walks and lots of exercise as I’m usually in the gym about 5 days a week, leading me to be pretty fit and diligent for things like that. I will make sure your pet uses the bathroom, gets all its energy out, and is happy!

Sitter Profile Image: Bethany C.
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Bethany C.
$28
total per walk
5.0 out of 5 stars
• 3 reviews
32 years of experience
Oakham, MA, 01068

About: I am a lifelong animal lover, and have owned dogs, birds, bunnies, guinea pigs, hamsters and mice. Currently I own 2 cats with my partner named Rebel and Scout. Growing up my family dogs have included lhasa apsos, dandie dinmont terriers, a german shepherd, and a golden lab. I have experience sitting all types of dogs so whether you have a small medium or large dog, i am comfortable with all sizes. I also was an American Kennel Club junior handler for five years and during that time I showed my lhasa apsos. I have assisted with 4 four litters of lhasa puppies and am experienced with house training, puppy training, care etc. If you have any other questions I would be happy to answer them and look forward to the opportunity to become a friend to your precious pets! :) I am currently a homemaker, and am fortunate to have some flexibility! Just let me know the times/days you need. M-F preferred weekends are negotiable! My preference is to take care of pets at clients home. It is difficult to have other animals inside with the cats however I do have a fenced in area in my yard I can offer for them to be in!

Sitter Profile Image: Jenna Cathryn D.
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Jenna Cathryn D.
$43
total per walk
5.0 out of 5 stars
• 24 reviews
9 repeat clients
15 years of experience
North Brookfield, MA, 01535

About: I’ve been a pet owner my whole life since I was a little tike. Started with a beagle that I couldn’t get enough of. When I became older i adopted a red nose pittie named boo-boo and a few months later another named Meika. They were my best buds. After their passing I got into providing over night stays for my fur nephew cooper and a family friend whom has four German Shepard’s two horses a cat and dog. I was loving it! Later on I got a job in the four legged field walking dogs, play groups and providing simple behavioral training/commands with positive redirection. I recently adopted a puppy named Orion who is three months old. I really have a passion for animals and enjoy what I do. My services provided are walks with basic commands/training during those walks. If your away I can stay! Boarding can be hard and stressful for your pet. I do over night care so your fur baby can stay in the comfort of their home.

Sitter Profile Image: Sydney L.
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Sydney L.
$28
total per walk
5.0 out of 5 stars
• 2 reviews
1 repeat client
6 years of experience
Rutland, MA, 01543

About: I’ve been taking care of dogs for 6 years now! I have a medium size dog of my own named Remi. I have experience walking dogs, feeding, taking outside, and playing with dogs! I am currently working Part-time. I would love for the opportunity to play with and walk your pups! I’m so excited to meet them all! Unfortunately, I live on the main road so I am unable to do visits in my home, but I am willing to do what is needed to meet your dogs needs on our walk on in home visit!

Sitter Profile Image: Meaghon R.
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Meaghon R.
$39
total per walk
5.0 out of 5 stars
• 20 reviews
6 repeat clients
20 years of experience
Princeton, MA, 01541

About: I have fostered dogs of all ages and health issues, have owned various breeds, have managed a boarding and daycare facility. Growing up and living with animals and my volunteer experience has taught me how to handle dogs of all backgrounds. I love all creatures and give them the love and respect they deserve. I will travel to care for your pet/s, my schedule is flexible with time and location. I prioritize you and your pets needs and will send updates daily with pictures. I love to hike and be outdoors so walks, runs, hikes, I'm all in for it. I am experienced and familiar with crate training if you need help and can accommodate as needed. Whatever is needed to create a safe, calm, quiet place for everyone is what I always want for my furkids.

Sitter Profile Image: lindsey r.
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lindsey r.
$50
total per walk
5.0 out of 5 stars
• 37 reviews
11 repeat clients
10 years of experience
Paxton, MA, 01612

“Lindsay was amazing! She took my request last minute due to a family emergency and was so kind and accommodating. We had a great meet and greet, and she took wonderful care of my shy dog, Georgia. She sent great updates and made me feel completely at ease. Georgia really took to her, which says a lot. I would absolutely book with Lindsay again!”

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Melanie R.
Sitter Profile Image: Brittany N.
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Brittany N.
$45
total per walk
5.0 out of 5 stars
• 12 reviews
4 repeat clients
20 years of experience
Barre, MA, 01005

“Brittney took great care of Otis. When I came home he was happy, fed and watered and she sent me some great pictures of him having fun in the snow. I appreciate the peace of mind I got from hiring her thank you very much.”

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Heather M.
Sitter Profile Image: Deepashree K.
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Deepashree K.
$23
total per walk
4 years of experience
Auburn, MA, 01501

About: Hi! I’m a caring and responsible pet lover with experience taking care of both cats and dogs. I’ve cared for pets in the past, so I understand how important it is to provide them with love, patience, attention, and a safe environment. I’m also a proud cat parent to my 6-year-old cat, which has given me years of experience understanding a cat’s needs, personality, and daily routine. Whether it’s going for walks, playing, feeding, providing companionship, or giving extra cuddles, I enjoy making pets feel comfortable, happy, and loved. I understand that every pet has a unique personality and routine, and I’m happy to follow your instructions to make sure your furry family member receives the best possible care. I’ll treat your pets as if they were my own and keep you updated with messages and photos while you’re away. Your pet’s happiness, safety, and well-being are always my priority. I look forward to meeting you and your furry best friend! 🐾 Pet care fits naturally into my daily routine because I genuinely love spending time with animals and making sure they feel happy, safe, and loved. I have experience caring for my family’s dog and my friends’ pets, along with being a proud cat parent to my 6-year-old cat. I’m familiar with daily feeding, playtime, walks, and giving pets the attention and affection they need. I enjoy getting to know each pet’s unique personality and making sure they feel comfortable and cared for. I’m happy to follow their usual routines and treat every pet with the same love and care I give my own. 🐾❤️ I prefer pet sitting in your home because I believe pets feel most comfortable and secure in their own familiar environment. Staying in their own home allows them to maintain their routines and feel less stressed while you’re away. I respect each pet’s boundaries, pay attention to their body language, and let them approach me at their own pace. I believe animals deserve the same kindness, patience, and respect as humans. My goal is to make every pet feel safe, understood, and loved, just as I would want someone to care for my own 6-year-old cat. 🐾❤️

Sitter Profile Image: Olivia P.
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Olivia P.
$28
total per walk
5.0 out of 5 stars
• 9 reviews
2 repeat clients
17 years of experience
Hubbardston, MA, 01452

About: I've been taking care of animals for over 17 years now, and I've been around animals for my entire life. I currently own 3 ducks, a horse, and a cat - I take care of them daily. Over the years I've had chickens, sheep, a bird, a dog, and guinea pigs. I love taking care of animals so much that I was involved in nursing one of my chickens back to health when she lost a wing to a predator. She stayed inside for a while but was more than okay to go back outside after she was healed. Once she was ready to join the rest of chickens, she thrived with the other chickens. For walking at home, I walk on different days for around 1 mile each way, and with animals I love to walk with them. I'm available during most times of the day, as my nights are usually unavailable due to overnights with pets. Right now, most nights will be available! Just a heads up is appreciated. I do not have a fence around my property, but I will walk your dog whenever is needed to let them outside. If you don't have a fenced area, I will do the same for your own pet!

Sitter Profile Image: Alondra R.
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Alondra R.
$19
total per walk
15 years of experience
Holden, MA, 01610

About: I’ve cared for my own dogs since I was young. Responsible, patient, and attentive, I love connecting with dogs beyond the bare minimum, giving them real love and attention. I am a full time student, my classes end around noon time, the latest being 1:45 on Fridays. I have a part time job as well, but my work schedule is very flexible as I can pick the days I work in advance. My home is a safe and welcoming space for dogs. I have a large, fenced backyard where they can play and explore. I live with my parents, which just means even more love for the future pups! I have a small Chihuahua who mostly keeps to herself, but if any issues arise, there’s enough space in the house to separate them. If your dog needs a crate, I can accommodate for that too!

Sitter Profile Image: Jared V.
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Jared V.
$34
total per walk
5.0 out of 5 stars
• 8 reviews
1 repeat client
11 years of experience
Auburn, MA, 01501

About: *MY AVAILABILITY HAS BEEN UPDATED THROUGH THE END OF 2026!* Hi there, my name is Jared and I currently reside in central MA, Worcester area. I have been working with dogs for 11 years now, starting off as a groomer at Petsmart which was a 9 year career, a full time dog walker for a private business for a year and now dog sitting/walking on my own time. My full time job is a singer/dancer for Carnival Cruise Lines and when I'm home in between contracts, I am looking to make extra cash by lending my services and experience to whatever you may need. Along with grooming and dog walking experience, I have also house sat for numerous dogs ranging from puppy to senior. I'm comfortable with handling medications or special treatments that your pup might need. I hope you consider me and I can't wait to meet you guys! When I am home in between contracts with my full time job as a cruise ship singer/dancer, I have complete open availability. My schedule is set now until the end of 2026! I am vigilant, reliable, trustworthy and confident. I will make sure that your pet isn't out of my sight while I am taking care of it and treat it like my own!

Sitter Profile Image: Nicole L.
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Nicole L.
$39
total per walk
4.9 out of 5 stars
• 75 reviews
27 repeat clients
20 years of experience
Worcester, MA, 01604

“Nicole was awesome. Great communication, really dedicated to animals, my dog loved her. She did a meet and greet prior to the walks, very professional and showed great care for my doodle- who has a mind of her own.. Very impressed with Nicole.”

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Cheryl O.
Sitter Profile Image: Angelina O.
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Angelina O.
$43
total per walk
6 years of experience
West Boylston, MA, 01583

About: I am a registered nurse looking for some extra work! (Other than being stuck in a hospital all day). I truly love animals more than people and would be honored to spend some extra time with yours:) I've spent most of my life babysitting and dog sitting for friends and family and would love to branch out! I work two days a week as a registered nurse. I have plenty of time on my hands that I'm looking to spend doing something I love! I have two dogs of my own that I pour my heart and soul into. I would provide loving and reliable care in any way you desire for your pets!

Sitter Profile Image: Virginia A.
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Virginia A.
$28
total per walk
5.0 out of 5 stars
• 47 reviews
12 repeat clients
25 years of experience
Shrewsbury, MA, 01545

About: Grew up with animals, cats and birds and reptiles in my house, farm animals at grandma’s. I have a cat now, fostered a senior dog for a while years ago, and have lots of family and friends with dogs/cats. I also volunteer weekly at my local animal shelter. I work full time as a scientist but my hours are flexible and usually done around 3-4pm I’m currently working full time. However my hours are early and flexible, i usually leave between 3-4pm and will try to accommodate clients based on my availability and work Safety is always a priority.that means House doors locked behind me, windows closed, making sure your pet is fed/walked/played with and are happy when i leave them

Sitter Profile Image: Jaimie L.
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Jaimie L.
$28
total per walk
20 years of experience
Ware, MA, 01082

About: Ive bred and took care of newborn puppies. And the long term care the mother needed after birth. Helped keep her happy for the remainder of her life. Bathed and groomed more times than i can remember. Trained for practicality and for tricks! I volunteer in my town a lot. I am an assistant coach and i am about to be voted onto a town committee for the rail trail in our town. Also a full time care giver for my mother but i could have help with that if needed. A nice big open area to walk around in leashed.. and a big ole park (grenville park) just minutes away walking distance. Big apartment complex

Sitter Profile Image: Brianna S.
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Brianna S.
$34
total per walk
5.0 out of 5 stars
• 6 reviews
3 repeat clients
10 years of experience
Oxford, MA, 01537

About: I’ve had a passion for animals and pet care since I was a little girl. I have raised litters of kittens, pet sat for friends and strangers, and volunteered at rescue centers. I was a veterinarian technician and surgical technician at an animal hospital for 3 years. I have worked with animals of all kinds and sizes. I am pet CPR certified. Currently I am available week days and weekends, I have a reliable vehicle to either stop in or stay full days/nights while your pets stay in the comfort of their own homes. I do work 8 am - 4pm Monday through Friday. So I can visit before and after work or stay over and be there before and after. I care for my own pets the best I know how, along with giving them lots of love and cuddles. I have worked with healthy pets but also ones that need a little extra TLC, whether that is medication, extra time for introductions to make them feel comfortable, or special diets. I am willing to listen and follow any and all instructions on how to care for your pet. I want you to feel comfortable and confident with who is caring for your pet and how. I understand that your pet is your child and being apart from them can be very difficult.

Sitter Profile Image: Nicole A.
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Nicole A.
Star Sitter
$28
total per walk
5.0 out of 5 stars
• 26 reviews
14 repeat clients
9 years of experience
Upton, MA, 01568

“Nicole was great and exceeded my expectations. She came over to meet our dogs before we left on vacation and they instantly liked her. While on vacation she sent videos and pictures after every walk and was ALWAYS on time. She made my vacation worry free and I can’t thank her enough!”

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Laura M.
Sitter Profile Image: Bethany R.
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Bethany R.
$39
total per walk
32 years of experience
Leicester, MA, 01524

About: Animal lover offering dependable dog walking and in-home pet sitting. I’ll care for your pets in the comfort of their own home, giving them attention, exercise, and lots of love. I’m currently available for visits and walks, with limited weekend overnight availability. Caring for animals is something I truly enjoy, and I’m working on building more of my routine around dog walking and pet sitting. I offer dog walking, in-home pet sitting, and animal transportation services, including helping with trips to vets, groomers, or even transporting pets or rescue animals to different towns or states when needed. I typically work weekends, but I have good flexibility during the week and can often adjust my schedule to meet your pet’s needs. I’m dependable, communicative, and committed to making sure your pets are safe, comfortable, and well cared for. When caring for pets in a client’s home, I always follow their established routines and instructions closely—whether that’s feeding schedules, walk times, medications, or preferred habits. I know consistency is important for pets, so I do my best to keep everything as familiar and stress-free as possible. I’m also happy to assist with things like vet visits or grooming appointments if needed. And most importantly, I will treat your babies as if they are my own. With my own pets, I maintain a consistent daily routine with feeding in the morning and evening at the same times each day, along with regular exercise and enrichment—we start our mornings with a drive to a fun walking spot, even during the winter months. I also stay on top of routine vet care and grooming to keep them healthy and well cared for. I bring that same level of care, structure, and attention to every pet I work with.

Sitter Profile Image: Hillary L.
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Hillary L.
$23
total per walk
5.0 out of 5 stars
• 3 reviews
7 years of experience
Marlborough, MA, 01752

About: I have been taking care of our bull dogs for seven years now. We adopt and had three before our oldest recently passed away. Bull dogs provide quite a bit of high maintenance care such as cleaning all folds multiple times a day, tail pockets, monitoring skin for yeast or allergies and of course… wiping butts after potty time. At least two walks or forms of exercise a day to keep them in shape for their health and breathing issues; if you see my babies photos, they are in super shape! So caring for three I feel shows my love, responsibility, managing skills and understanding of how to properly and lovingly care for pets. For many years now, I have also cared for a variety of my family members dogs and cats, whether that involves feeding, walking/ exercise, over nights, and loving attention. I am Corporate Life Coach & Counselor so I have a flexible schedule that I make myself, in a variety of towns in Massachusetts ( which is why my radius is so big) I also have a rental house in Dennisport MA, so providing pet care in the Cape is an option too! I love my fur-babies and providing love, exercise and quality time is what your pet deserves too! I will be providing services at your household, so any and all safety protocol will be provided that suits you and your pet to the fullest!

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

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Popular requests for dog walking - Oakham

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FAQs for Dog Walking - Oakham

Frequently asked questions about Rover

As of November 2026, there are 2,043 sitters on Rover offering Dog Walking across Oakham. 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 Oakham. 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 Oakham 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 Oakham. On Rover:

  • 89% of walkers can help with special care needs
  • 92% can help with giving oral medications or injections
  • 95% 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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