Dog Walking Oakham

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

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Over 2
pet parents in Oakham have booked dog walking

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: Kaitlyn D.
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Kaitlyn D.
$23
total per walk
5.0 out of 5 stars
15 reviews
8 repeat clients
3 years of experience
Rutland, MA, 01543

Kaitlyn has been wonderful with our pups. We recently moved and she has jumped in to be a great fit with our dog Bowden easily and quickly. You can tell she has a real love for animals! Thank you for being so patient and wonderful with our furry baby!

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Liz M.
Sitter Profile Image: Erin H.
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Erin H.
$28
total per walk
5.0 out of 5 stars
5 reviews
3 repeat clients
15 years of experience
Rutland, MA, 01543

About: Hi there! I'm Erin, a dedicated mother and lifelong animal enthusiast. With a heart full of love for all creatures great and small, I've spent most of my adult life volunteering, fostering, and caring for animals. From dogs to cats and everything in between, I've had the pleasure of nurturing and pampering a wide variety of pets. My journey into pet care started years ago when I began volunteering at local animal shelters and fostering dogs and cats in need. Over time, my passion evolved into a profession, and I've been providing top-notch pet sitting and dog walking services ever since. What sets me apart is the personal touch I bring to every interaction. As a mother, I understand the importance of family, and that includes our beloved pets. That's why I love nothing more than including my own children in our pet visits and walks. Your furry companions not only get the care and attention they deserve but also the joy of interacting with a fun-loving family. At home, our household is a bustling hub of activity, filled with the laughter and energy of children. Alongside my small and sociable Jack Russell Terrier mix and clever cat, we create a warm and welcoming environment for pets of all shapes and sizes. With experience caring for various breeds, including the majestic Great Dane, I'm well-equipped to handle the unique needs and quirks of different animals. Whether your pup needs a leisurely stroll around the neighborhood or your cat requires some extra TLC while you're away, rest assured they'll be in loving and capable hands with my family. So, if you're seeking reliable and compassionate pet care services that treat your furry friends like family, look no further. Because when it comes to your pets, they deserve nothing but the best! Pet care is not just a job for me—it's my passion and my primary focus outside of being a mom and pet owner myself. With my schedule wide open and dedicated solely to pet care, I have the flexibility to tailor my daily and weekly routine to meet the needs of both pets and their owners. Each day, I prioritize spending quality time with the pets under my care, ensuring they receive the attention, exercise, and companionship they need to thrive. Whether it's morning walks, midday visits, or evening cuddle sessions, I'm there to provide personalized care and companionship every step of the way. My wide flexibility allows me to accommodate the unique needs of each pet, whether it's administering medication, adhering to specific feeding schedules, or simply providing extra TLC for pets with special needs. I understand that every pet is different, and I strive to create a routine that caters to their individual preferences and requirements. By limiting my bookings, I can ensure that each pet receives the care and attention they deserve without feeling rushed or overlooked. Whether it's a one-time visit or a long-term arrangement, I'm committed to providing top-notch care that exceeds both pet and owner expectations. In essence, pet care isn't just a part of my routine—it's the heart of my daily life, and I'm dedicated to making sure every pet feels loved, safe, and cherished in my care. Your pet's comfort and happiness are my top priorities. With a spacious 3-bedroom home and a large playroom addition, we offer a welcoming and secure environment for your furry friend to feel right at home. Whether your pet prefers the familiarity of their own surroundings or enjoys exploring new spaces, I can be flexible and accommodating to meet their needs. In our home, your pet will have plenty of room to roam and play, whether they're chasing toys, lounging in cozy corners, or enjoying some quality cuddle time. I understand that some pets may feel more comfortable in their own crates, and I am more than happy to accommodate those preferences to ensure they feel safe and secure during their stay. Outside of our home, we love to explore and embrace the great outdoors, making long evening walks around neighborhoods or adventures in the woods a regular part of our routine. Whether your pet enjoys a leisurely stroll or prefers a brisk run, we're committed to providing the exercise and stimulation they need to stay happy and healthy. Whether it's a staycation in our cozy home or a familiar visit to yours, you can trust our family to provide the personalized care and attention your pet deserves. Because when your pet is with us, they're not just a guest—they're a cherished member of our family

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: Rae D.
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Rae D.
$23
total per walk
5.0 out of 5 stars
6 reviews
2 repeat clients
25 years of experience
Hubbardston, MA, 01452

About: I've taken care of dogs for as long as I can remember. I've always been a very empathetic person and just love to wave and say hi to dogs going by. I've had dogs of all sizes. My most recent is experience with Chihuahuas. I just love them! I've raised 2 dogs from 8 weeks old. I love all stages of a dogs life, from puppy to senior. I also have experience with senior dogs who need special care and medication. I'm currently working for myself, so I have plenty of time to spend playing, caring, loving and walking with your pets. I'm available M-F 9-6 pm. I like to make sure the pet is comfortable. I want the pet to feel at home with me. The least amount of change from the pets daily activities are important for the pet to feel safe and happy.

Sitter Profile Image: Megan L.
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Megan L.
$39
total per walk
10 years of experience
Rutland, MA, 01543

About: Hi! I'm excited to start offering pet sitting and walking services. I’ve always had a passion for dogs and animals of all kinds, and I understand how important it is to know your pet is safe, happy, and loved while you're away. I’m patient, attentive, and comfortable with high-energy dogs, walks, playtime, feeding routines, and lots of cuddles. Whether your pet needs exercise, companionship, or just someone to keep them company, I’m happy to help. I’ll treat your pets like they’re my own and make sure you feel comfortable and updated while you're away! With two dogs of my own, I know how important it is to find the right care. I will work my schedule around yours to provide the best care and normal routine for your furry friend! When caring for pets in their own home, I focus on keeping their routine as normal and comfortable as possible. I carefully follow your instructions for feeding, walks, playtime, medications, and any special care your pet needs. I make sure pets receive plenty of attention, exercise, and affection so they feel safe and relaxed while you’re away. I will also provide updates and photos so you can have peace of mind knowing your pet is doing well. My goal is for your pet to feel comfortable in their familiar environment while receiving reliable and loving care.

Sitter Profile Image: Melanie C.
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Melanie C.
$23
total per walk
5.0 out of 5 stars
3 reviews
1 repeat client
10 years of experience
Hubbardston, MA, 01452

Melanie handled the booking efficiently and arrived on time. My dogs, including my finicky husky, quickly took to her. She exudes a calm energy, and we would definitely book her again.

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Dwight D.
Sitter Profile Image: Julie D.
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Julie D.
$23
total per walk
5.0 out of 5 stars
4 reviews
2 repeat clients
20 years of experience
Rutland, MA, 01543

Julie is amazing I would definitely recommend her for dog walking

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Brittany W.
Sitter Profile Image: Jeffrey W.
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Jeffrey W.
Star Sitter
$23
total per walk
5.0 out of 5 stars
42 reviews
18 repeat clients
12 years of experience
Sterling, MA, 01564

Jeffrey is amazing! He was on time, personable and professional. He was patient with my dog and now Finn runs right away to Jeffrey. Rover is lucky to have him! As are we!

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Sharon E.
Sitter Profile Image: Christina C.
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Christina C.
$23
total per walk
20 years of experience
Holden, MA, 01520

About: Animals have always been part of my life. I’ve raised five dogs from puppyhood and have worked with many breeds, ages, and personalities. I also have experience caring for cats, reptiles, and small mammals, making me a reliable choice for families with diverse pets who need patient, knowledgeable support. I offer fully open availability, providing flexible, reliable care whenever your pets need support. My schedule is built around consistency and convenience for pet parents, and every visit reflects my commitment to animal welfare. As I grow my business, I’m also working toward my long‑term dream of opening a multi‑species rescue to help even more animals thrive. I care for pets in the way that keeps them happiest and most comfortable. In your home, I follow your routines exactly—feeding, walks, playtime, enrichment, medication, and any house rules your pet already knows—so their day feels familiar and stress‑free. In my home, pets enjoy a safe, supervised environment with structured potty breaks, cozy rest areas, and plenty of attention. Whether it’s walks, drop‑ins, boarding, or overnights, I make sure every pet gets individualized care, consistent communication, and a calm, loving experience.

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: Kayla C.
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Kayla C.
$28
total per walk
5.0 out of 5 stars
46 reviews
12 repeat clients
3 years of experience
Spencer, MA, 01562

Kayla is great! Our large breed lab mix loves her. Highly recommended.

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Troy R.
Sitter Profile Image: Cordelia C.
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Cordelia C.
$32
total per walk
5.0 out of 5 stars
6 reviews
3 repeat clients
11 years of experience
spencer, MA, 01562

She did a fantastic job with my new puppy and my three-year-old golden and very reliable. Highly recommend.

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Sonya H.
Sitter Profile Image: Andrea G.
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Andrea G.
Star Sitter
$36
total per walk
5.0 out of 5 stars
96 reviews
36 repeat clients
11 years of experience
Ware, MA, 01082

Great communication, happy pup. Thank you!

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marguerite A.
Sitter Profile Image: Patricia H.
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Patricia H.
$28
total per walk
5.0 out of 5 stars
15 reviews
3 repeat clients
15 years of experience
Paxton, MA, 01612

Pat came and walked Leia again on Saturday and Leia was happy to see her. Leia was a little anxious as she had been recovering from dental surgery and had been more restricted for a couple of weeks, but Pat was able to build Leia's confidence and convince her to go further when Leia was initially reluctant. Pat is very good and patient with Leia's little quirks and helped her go further and enjoy the opportunity to go further beyond our yard. Leia was calmer and content with her walk.

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Barbara T.
Sitter Profile Image: Ella S.
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Ella S.
$28
total per walk
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 evenings and nights! I have open availability for all week days during those times, preferably 5pm up until midnight if you need me to! 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 that require high stamina. I will make sure your pet uses the bathroom, gets all its energy out, and is happy!

Sitter Profile Image: Lila P.
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Lila P.
$28
total per walk
5.0 out of 5 stars
11 reviews
3 repeat clients
15 years of experience
Brookfield, MA, 01506

About: I have taken care of cats, dogs, and horses for as long as I remember. I also volunteered at an animal shelter for a few years. Any family pets we've had (cats, dogs, and horses) have lived all the way up to their senior years (and even passed the "intended age range" of their breed). I'm working full time from Wednesday to Saturday 1 pm to 11:30 pm. But I'm available Sunday, Monday, and Tuesday. If it's just to walk your pet or drop in, I can come over before work. I can house sit starting Sunday, but can't stay until I have to go to work Wednesday. I absolutely love pets and will treat them like my own. I can't board or take them to my house. I'll keep them safe while in my care. I have always been an animal lover since I can remember. So their safe in my hands when I'm walking them, coming for a drop in, or house sitting. Due to my work schedule, I am available Wednesday through Thursday for walking, drop ins, and house/dog sitting. I can either spend part of my day or my whole day with your pet. I try to fit in as much time with my animals as I can. Taking my dog for a walk, groom my familys horses, and even cuddle with my cats. I can make some exceptions with house sitting and drop ins. HOUSE SITTING: I'll gladly accept! If i am in college as well, I'll bring my laptop to work on homework. DROP INS: I will come in before work to feed/walk them and I can come in after work for a check up. If your yard is fenced in, I will gladly sit outside with your pet. Maybe even take a book with me so your dog can stretch their legs, play for a little bit and get some fresh air for a while. I will treat your dogs and cats like their my own and give them as much care as I can along with play times.

Sitter Profile Image: Jacquie A.
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Jacquie A.
Star Sitter
$28
total per walk
5.0 out of 5 stars
20 reviews
6 repeat clients
20 years of experience
Holden, MA, 01520

About: My whole life as long as I remember I was the biggest pet lover. I had my own pets and I’ve taken care and walked the dogs of my neighborhood. I just love them. I work part time, which gives me a lot of time to do my favorite thing: pet sitting!!! I work part time and have a lot of time for my favorite hobby which is caring for these lovely creatures. I have a fenced in yard and I love walking in the woods with the doggies. I have a fenced in yard and I walk the dogs three times a day. My 2 lovely dogs will keep your dogs company. I will make sure they are spoiled.

Sitter Profile Image: lindsey r.
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lindsey r.
Star Sitter
$50
total per walk
5.0 out of 5 stars
36 reviews
10 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: Becca B.
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Becca B.
$32
total per walk
5.0 out of 5 stars
34 reviews
17 repeat clients
20 years of experience
Brookfield, MA, 01506

We have used Beeca for watching our fur baby at least a half dozen times. Becca is always in communication with us and sends the best pictures! Highly recommend

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

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

How Rover works

  1. 1. Search

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  2. 2. Meet & Greet

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Sitters in Oakham average 4
repeat dog walking clients

FAQs for Dog Walking - Oakham

Frequently asked questions about Rover

The average cost for Dog Walking in Oakham on Rover is $18.87 per walk (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

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

As of July 2026, there are 2,105 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 your Oakham. 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 Oakham.

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 Oakham. On Rover:

  • 92% of walkers can help with special care needs
  • 97% can help with giving oral medications or injections
  • 94% 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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