Dog Walking Oakwood

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

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Over 1
pet parents in Oakwood have booked dog walking

Oakwood, Find top rated dog walking

Prices are estimates per walk. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Laura D.
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Laura D.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
62 reviews
20 repeat clients
35 years of experience
Annapolis, MD, 21403

Laura has been excellent for us. Our dog can be a handful around other dogs and Laura shows her expertise in keeping things calm during walks. Communication has been great and we’ve never had any scheduling issues. Laura’s rover cards are excellent and we get plenty of pictures! We’re really grateful we found Laura and that she had the availability for us. Highly recommend to anyone who is looking for a kind, reliable, trustworthy dog walker.

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John S.
Sitter Profile Image: Beth W.
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Beth W.
Star Sitter
from
$35
per walk
5.0 out of 5 stars
74 reviews
34 repeat clients
25 years of experience
Annapolis, MD, 21403

Beth helped me out in a pinch and was great!

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Dana H.
Sitter Profile Image: Leigh Ann E.
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Leigh Ann E.
Star Sitter
from
$17
per walk
5.0 out of 5 stars
21 reviews
7 repeat clients
37 years of experience
Annapolis, MD, 21403

About: I’ve cared for dogs of all breeds & sizes over the years. I am comfortable with puppies through senior age. Friends, family and clients have relied on me to feed, walk, play with, clean up after, and love their pups as if they were my own. I can administer medications, including injections, and sq fluids. I can practice obedience skills during my visits as well. I’m available for pet care visits on Wednesday & Thursday mornings as well as evenings, Friday afternoon-evening, and all day on Saturdays and Sundays. I am also available on major holidays. Mondays and Tuesdays are on a case-by-case basis. I am very safety conscious and will care for your pets as carefully as I would my own. I will follow whatever your normal household routine is so that your pets feel safe and comfortable. They thrive with routines! If they use a crate, need treats after potty breaks, want belly rubs after a meal, etc., I am there for it all!

Sitter Profile Image: Jessica B.
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Jessica B.
from
$25
per walk
5.0 out of 5 stars
12 reviews
5 repeat clients
12 years of experience
Edgewater, MD, 21037

Have had Jessica walk our dogs and also provide drop in visits while we were on vacation. She does a great job, lots of pics and our dogs love her. Would not hesitate to hire her again! Iggy and Obi love her.

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Hillary H.
Sitter Profile Image: Thomas R.
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Thomas R.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
88 reviews
20 repeat clients
7 years of experience
Annapolis, MD, 21403

Thomas is more than a terrific dog walker; he is amazing. He has patience with our 14 1/2 yo lab. He treats her like she is the only dog in the world. Scuppers looks forward to Thomas's visits!

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Dottie L.
Sitter Profile Image: Alexa D.
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Alexa D.
from
$25
per walk
5.0 out of 5 stars
7 reviews
2 repeat clients
13 years of experience
Annapolis, MD, 21401

Thank you so much!

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Elise C.
Sitter Profile Image: Stephanie M.
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Stephanie M.
from
$20
per walk
1 repeat client
7 years of experience
Annapolis, MD, 21403

About: Hi, I’m Stephanie and walking dogs is my favorite part of the day! I bring energy, love, and a calm presence to every walk. Whether your pup needs exercise, company, or a quick potty break, I’ve got you covered—rain or shine 🐾 I’m available from 8:00 AM–7:00 PM to let your pups out for a walk around the neighborhood or stop in for a quick drop-in visit. Happy to give your furry friends some extra love, exercise, and attention while you’re away! 🐶❤️ I provide loving, attentive care tailored to each pet’s routine and needs. I make sure pets are safe, comfortable, exercised, and given plenty of attention. I’m happy to follow feeding instructions, provide walks and playtime, and give pets the care and companionship they need while their owners are away.

Sitter Profile Image: Liza S.
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Liza S.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
100 reviews
20 repeat clients
20 years of experience
Annapolis, MD, 21401

Liza is awesome! I met her while she was walking another dog, and I was throwing a ball for my boy Francis. She was very sweet to both my boy Francis and his bro Elliott even though he ran up and barked at her at first. I said trust me he won't do anything, and I could tell she wasn't afraid in the least. Francis is on prednisone which caused him to develop a bladder infection and causes him to have to pee even more than the prednisone. I went on Rover yesterday around noon trying to book something for 5 the same day. Liza responded within 5 minutes that she would be able to do it and set up future Friday afternoon walks. She even wiped off his big dirty paws after the walk!

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Jim O.
Sitter Profile Image: Sarah S.
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Sarah S.
from
$23
per walk
5.0 out of 5 stars
443 reviews
133 repeat clients
13 years of experience
Annapolis, MD, 21403

Sarah has made a close connection with my Ausie Shepard-Golden-Collie pup Lucy. Sarah is also very responsive and responsible and an all around terrific person.

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Christopher H.
Sitter Profile Image: Nolan C.
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Nolan C.
from
$15
per walk
5.0 out of 5 stars
2 reviews
1 repeat client
10 years of experience
Annapolis, MD, 21409

About: I have taken care of different types of dogs and including in home stay, walks, puppies etc and had my own dog since I was 12. I have lots of experience in caring for animals from reptiles to mammals. I am very physically active and love to spend time outside so long walks and exercise is both fun for me and your pet. I am currently looking for a part time job my schedule is open for the relative future and any changes to my schedule will be minimal, I am fully available for a consistent walking or care schedule for your pet. I care for my dog with long walks, exercise/play time with his favorite toys or enrichment games. I also have a back and front yard at my house that my dog loves to play in with a park and beach access that allows dogs. When I care for bigger dogs I love to take them to the park in my neighborhood or one nearby to play fetch.

Sitter Profile Image: Allison G.
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Allison G.
from
$15
per walk
5.0 out of 5 stars
67 reviews
34 repeat clients
20 years of experience
Annapolis, MD, 21409

Allison has been walking my dog for a few weeks now and she’s been great! Great with communication of her schedule and Murphys needs. I would highly recommend Allison as a walker and boarder.

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Andrew L.
Sitter Profile Image: Ally V.
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Ally V.
from
$20
per walk
4.7 out of 5 stars
4 reviews
2 repeat clients
4 years of experience
Edgewater, MD, 21037

Ally was very responsive and reliable. Our dog loved her and i would get her again.

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Kathy T.
Sitter Profile Image: Donna R.
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Donna R.
from
$15
per walk
5.0 out of 5 stars
7 reviews
1 repeat client
24 years of experience
Glen Burnie, MD, 21060

Donna & Mars just connected. 💖 She must be the 🐶 pup whisperer !!

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Bennie H.
Sitter Profile Image: Andrew P.
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Andrew P.
Star Sitter
from
$19
per walk
5.0 out of 5 stars
66 reviews
19 repeat clients
15 years of experience
Annapolis, MD, 21403

Andrew did a great job this weekend! He walked my very large Labradoodle and St Bernadoodle and made sure both dogs and my 3 cats were fed and had water. He followed the care instructions, was extremely communicative and arrived promptly at the booking time. I will absolutely be using Andrew for future bookings, highly recommended!!

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Megan M.
Sitter Profile Image: Alexis H.
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Alexis H.
from
$25
per walk
5.0 out of 5 stars
7 reviews
2 repeat clients
13 years of experience
Annapolis, MD, 21403

About: I’ve been around animals my entire life and grew up caring for 3 dogs, 2 cats, birds, lizards, hermit crabs, fish, and rabbits. Taking care of pets has always come naturally to me. Since I was around 10 years old, I’ve helped walk my neighbors’ dogs and puppies, as well as pet sit their dogs and cats while they were away on vacation. I’m very patient, attentive, and love making pets feel safe, comfortable, and cared for like they’re part of the family. 🐾 Pet care fits naturally into my daily routine as a stay-at-home mom, which gives me a very flexible schedule and allows me to be home throughout the day for walks, feedings, playtime, check-ins, and lots of attention. My 5-month-old daughter and I spend a lot of time at home, so I’m able to provide consistent care, companionship, and updates for pet owners. I enjoy having animals as part of our daily routine and make sure every pet feels comfortable, safe, and cared for. In my home, pets are treated like family and are welcome on the furniture for comfort and companionship. I create a calm, loving environment where animals can feel safe and relaxed while away from their owners. My cats have access to food and water throughout the day, with their setup safely placed out of reach from dogs when needed. I do not crate animals unless specifically requested by the owner, as I prefer pets to feel comfortable and free in the home. I pay close attention to each pet’s routine, personality, and comfort level to make sure they receive individualized care, attention, and plenty of love.

Sitter Profile Image: Courtney A.
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Courtney A.
Star Sitter
from
$27
per walk
5.0 out of 5 stars
18 reviews
8 repeat clients
15 years of experience
Parole, MD

About: Hi! I’m Courtney — a true dog lover, experienced pet caregiver, and someone who treats every pet like family. As a dog mom myself, I understand how important it is to trust the person caring for your pet. Whether your dog loves long walks, playtime, couch snuggles, or just a calm and reassuring presence, my goal is to make them feel safe, comfortable, and loved while you’re away. I have extensive experience caring for dogs with a wide range of personalities, energy levels, and care needs, and I pride myself on being dependable, communicative, and attentive to details. For house sitting, my standard rate includes typical care such as feeding, walks/potty breaks, companionship, overnight care, and lots of love. If your pet requires additional support — including senior care, medication administration, frequent potty breaks (every few hours), mobility assistance, separation anxiety management, or near-constant supervision — please let me know before booking, as these higher-needs situations may require custom pricing to ensure I can provide the level of care your pet deserves. Please be as detailed as possible about your pet’s routine, behaviors, and care needs so I can make sure we’re the right fit. Looking forward to meeting your furry family member!

Sitter Profile Image: Nicole L.
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Nicole L.
Star Sitter
from
$25
per walk
4.9 out of 5 stars
69 reviews
30 repeat clients
7 years of experience
Bowie, MD, 20716

Nicole is wonderful! Very attentive to my pup when they go on walks. Plus detailed notes and pictures and consistent communication before and after booked walks.

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Katie G.
Sitter Profile Image: Kaylee H.
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Kaylee H.
from
$17
per walk
5.0 out of 5 stars
4 reviews
2 repeat clients
4 years of experience
Lothian, MD, 20711

About: I have over 3 years of professional pet care experience through my roles at PetSmart, where I cared for pets, monitored their health and behavior, maintained a safe and clean environment for all of the animals we cared for in store as well as the ones pet parent's would bring in. I am certified in Dog and Cat CPR and have experience caring for dogs and cats of all ages, sizes, breeds, and temperaments. I have worked with energetic puppies, senior dogs, playful kittens, and shy or nervous pets who need extra patience and attention. During my time at PetSmart, I regularly cared for kittens in the adoption center and learned how important it is to make every animal feel safe, comfortable, and loved. I have also raised puppies of my own and helped care for pets belonging to family and friends. Whether your pet needs walks, playtime, feeding, companionship, or extra attention while you're away, I will treat them as if they were my own. I understand how important trust is when choosing someone to care for your pet, so I provide reliable care, plenty of updates, and open communication every step of the way. I look forward to meeting you and your furry family members! ***I offer discounts, Ask me!*** Pet care fits naturally into my daily routine. I have a flexible schedule and can provide consistent care, whether that’s feeding, playtime, walks, litter box cleaning, medication reminders, or simply keeping your pet company. I understand that every pet has different needs and will do my best to follow their normal routine to help them feel comfortable and stress-free while you’re away. Your pet’s safety and comfort are my top priorities. With over 3 years of experience working at PetSmart, I’m familiar with a variety of pet personalities and behaviors. I carefully follow all care instructions, provide regular updates, and take the time to build trust with each pet. Whether caring for your pet in your home or during drop-in visits, I’ll treat them with the same love, patience, and attention that I give my own cat, Luna.

Sitter Profile Image: Ryan L.
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Ryan L.
from
$27
per walk
5.0 out of 5 stars
9 reviews
1 repeat client
25 years of experience
Annapolis, MD, 21409

Highly recommend Ryan! He took the time to do a meet and greet and really understand my dog’s specific needs. He was very communicative and flexible whenever any changes came up, which I truly appreciated. What stood out most was how he followed my dog’s training routines and even used the exact phrases we’ve been working on. He handled my dog’s reactivity with care and confidence, and it made a huge difference. I felt completely at ease knowing my dog was in such good hands!

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Stacie Z.
Sitter Profile Image: Kennedy E.
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Kennedy E.
from
$15
per walk
5.0 out of 5 stars
3 reviews
2 repeat clients
10 years of experience
Crofton, MD, 21114

About: With over 10 years of experience caring for dogs and being a proud dog owner myself, I’m dedicated to providing loving, reliable, and attentive care for every pet. From daily walks and playtime to personalized attention and specialized care, my goal is to make sure every dog feels safe, happy, and comfortable. Pet sitting fits naturally into my routine, allowing me to provide dependable care while giving pets the attention they deserve. Whether it’s walks, feeding, play sessions, or companionship, I enjoy creating a positive and stress-free experience for both pets and their owners. When caring for dogs in my home or a client’s home, I focus on safety, comfort, and maintaining each pet’s normal routine. I begin by learning about their schedule, preferences, and specific needs to ensure personalized care. I provide regular exercise, enrichment, affection, and follow all feeding and medication instructions carefully. Throughout each stay, I keep owners updated with messages and photos so they always feel connected and reassured. Now that it is summer I am free mostly all of the time! I have a few vacations, and possibly other things that may come up but I will always make sure my schedule is clear! At home I let my dogs out every 2-3 hours, I feed them at the same time everyday, and make sure they have plenty of exercise! I really enjoy playing with my dogs at home as well, weather thats running around out back, playing tug-of-war, or even just going on a walk! Overall my favorite time of day with my dogs at home is bed time, my puppies sleep with me every night!

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The median cost per walk for dog walking in Oakwood is $20

Dog parents share their Rover experiences - Oakwood

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5.0 out of 5 stars

Ali was able to accommodate a last minute booking. She arrived on time and stayed the full length of the visit. Very happy with her services.

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Charles V.
Dog Walking
5.0 out of 5 stars

Beth was so helpful, caring, and just generally great with my pup! I will definitely book again in the future!

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Caitlin I.
Dog Walking
5.0 out of 5 stars

We can’t recommend Kayla highly enough. Throughout the last year of our elderly dog’s life, her anxiety increased as her physical capabilities and comfort decreased. Kayla was always responsible, gentle, and kind with our sweet old girl. She was also a great communicator during planning and if anything unusual came up during walks/visits (like the time we had to get her to go room to room in our house because the dog was too spooked by a recent thunderstorm to come to the door when Kayla arrived — Kayla found treats and coaxed her out from under the bed!)

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Katy L.
Dog Walking
5.0 out of 5 stars

Jessica is fantastic and I don’t think I could feel any more comfortable when traveling out of town. My pups are always in the best of care with Jessica.

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Drew M.
Dog Walking
5.0 out of 5 stars

Megan was prompt, communicative, and sent lots of cute photos of Baker! Look forward to having her take care of our pets again.

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Alexa E.
Dog Walking
5.0 out of 5 stars

Ella has been an excellent dog walker for Cannon. She is extremely reliable and a great communicator. We would highly recommend her to care for your pets!

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Sadie S.
Dog Walking
5.0 out of 5 stars

Blinne was fabulous with my highly energetic pup and offered great feedback as to Kali’s behaviors after every walk. Kali would wait excitedly at the door each day for Blinne’s arrival. I will definitely reach out to Blinne again!

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Alison W.
Dog Walking
5.0 out of 5 stars

Ellie was great with my dog. She stayed in close communication and was both trustworthy and very sweet. I would hire her again.

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Mary R.
Dog Walking
5.0 out of 5 stars

I really appreciate MaKayla she is always on time and keeps me posted on what is going on. I feel like we make a great team for Cooper.

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Debbie E.
Dog Walking
5.0 out of 5 stars

Arem was reliable and great with Lexi. He consistently did an excellent job and I’d absolutely use him again.

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Elsie V.
Dog Walking
5.0 out of 5 stars

Kristine is our go to dog walker in the Annapolis area. She is reliable and we feel confident that our dog is getting great exercise and being well cared for when she comes.

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Devon D.
Dog Walking
5.0 out of 5 stars

Stella is awesome with a great personality! She is timely and very reliable. We have 2 dogs and 1 puppy. She did an excellent job caring for them. She definitely loves animals. We felt so comfortable and had no worries leaving our fur babies with her.

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Charisse B.
Dog Walking
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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.

Why Choose Rover?

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  • Reservation protection

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

  • World-class support

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

Meet local walkers who will treat your dogs like family

  1. 1. Search

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Popular requests for dog walking - Oakwood

Select a filter and find qualifying sitters offering dog walking.

Sitters in Oakwood average 4
repeat dog walking clients

FAQs for Dog Walking - Oakwood

Frequently asked questions about Rover

The average cost for Dog Walking in Oakwood on Rover is $22.2 per walk (as of August 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 August 2026, there are 13,132 sitters on Rover offering Dog Walking across Oakwood. 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 Oakwood. 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 Oakwood.

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 Oakwood. On Rover:

  • 90% of walkers can help with special care needs
  • 96% can help with giving oral medications or injections
  • 96% 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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