Dog Walking Winston Terrace

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

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Over 65
pet parents in Winston Terrace have booked dog walking

Winston Terrace, 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: Lauren K.
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Lauren K.
Star Sitter
from
$16
per walk
4.9 out of 5 stars
• 38 reviews
23 repeat clients
17 years of experience
Williamsburg, VA, 23188

“Lauren does very good work. She's clearly quite competent with Clove and concerned about her welfare. She's pleasant for conversation afterwards and is flexible. I recommend her highly.”

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Mae K.
Sitter Profile Image: Lauren W.
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Lauren W.
from
$20
per walk
5.0 out of 5 stars
• 25 reviews
3 repeat clients
25 years of experience
Williamsburg, VA, 23188

“Lauren is fantastic at sending pictures and taking wonderful care of my Shelby!”

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Erin B.
Sitter Profile Image: Genevieve B.
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Genevieve B.
from
$16
per walk
5.0 out of 5 stars
• 33 reviews
11 repeat clients
8 years of experience
Williamsburg, VA, 23185

“Genevieve was great with my Lexi! Kept me in the know of their walks and took good care of her for me. Will definitely use her again and recommend to anyone!!”

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Rebecca H.
Sitter Profile Image: Victoria L.
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Victoria L.
from
$20
per walk
4.8 out of 5 stars
• 58 reviews
26 repeat clients
6 years of experience
Williamsburg, VA, 23185

“Victoria is so good with our dog Dash! She’s so patient with him and makes sure he’s comfortable and has all the things they need (including treats!) for a successful walk! I’ll definitely be hiring her again!”

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Erika A.
Sitter Profile Image: Megan F.
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Megan F.
from
$20
per walk
5.0 out of 5 stars
• 2 reviews
1 repeat client
10 years of experience
Williamsburg, VA, 23188

“Very prompt with communication and action. Walked my dog on short notice with no issues. Definitely use her services again.”

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Joshua W.
Sitter Profile Image: Zander K.
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Zander K.
from
$14
per walk
10 years of experience
Williamsburg, VA, 23185

About: My family has had dogs forever, ranging from small medium and large so growing up with all kinds of dogs has given me experience in how to handle any situation with any dog! I’m currently a college student and away from my dog at home and am looking for any way to have more interactions with pets. Also, my most recent dog is now 2 years old and I did the majority of training, so if there are any needs or wants for training while I am sitting, I am more than capable. I’m currently a full time student and on the William & Mary Varsity Men’s soccer team, however, I have many breaks throughout my day. The only block of the day I’m usually completely unavailable is from 2-6PM When caring for pets in clients homes you can expect the utmost respect for the home but also a willingness to learn how you usually handle your dog at home. Whether that is using the crate and having some more strict guidelines, or if it is a more relaxed environment.

Sitter Profile Image: Bethany B.
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Bethany B.
from
$18
per walk
2 repeat clients
34 years of experience
Williamsburg, VA, 23185

About: I love animals, have grown up with dogs and cats, and have been fostering cats for the last 5 years, I including administering all sorts of medicine to cats and kittens. I work from home and go on daily walks, so why not take your pup for a walk as well! I also love to travel and am happy to help other people travel by helping take care of their fur family. I’ve been fostering cats and kittens for over 5 years, and have absolutely loved helping these animals find loving homes. I don’t currently have any animals of my own, which can help make your animal feel comfortable in my home if necessary. I understand a lot of animals require patience and space to warm up, and am happy to work with their comfort level.

Sitter Profile Image: Meaghan O.
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Meaghan O.
from
$25
per walk
4.6 out of 5 stars
• 11 reviews
1 repeat client
20 years of experience
Williamsburg, VA, 23188

About: I get a lot of joy from taking care of them and making them happy while getting to know their personality. I am comfortable with dogs and cats of all sizes and energy levels! Animals are certainly a woman’s best friend! I am a current law student that will have class in the mornings and early afternoons most weekdays, but will be able to care for your pets any time outside of that! I would love to have a furry friend to walk or play with during study breaks and can’t wait to get to know your baby! My utmost priority in caring for your pets is ensuring they are as safe, comfortable and at ease as possible. Animals are so special and deserve the kindest treatment in all circumstances, even when they make a mistake. I will ask for specific preferences or instructions and follow them in regard to feeding, walking, play time, medicine, potty breaks and any form of crating. I want to help your pet as much as possible through the nerve-wracking time of being away from their owner!

Sitter Profile Image: Kimberly R.
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Kimberly R.
from
$26
per walk
5.0 out of 5 stars
• 65 reviews
6 repeat clients
36 years of experience
Williamsburg, VA, 23188

“Kimberly was AMAZING!! We are traveling in our RV and she came out to our campsite and walked our dogs for us....She was professional, super nice and the dogs loved her.”

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Angie B.
Sitter Profile Image: Alesscia C.
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Alesscia C.
from
$22
per walk
5.0 out of 5 stars
• 7 reviews
2 repeat clients
18 years of experience
Williamsburg, VA, 23185

About: I have loved animals all my life, and my experience has ranged from caring for my own pets, to short-term and long-term fostering for friends and military families. I have cared for dogs, cats, hamsters, lizards, bunnies, birds and small livestock. I love them and treat them all as though they are my own. I am currently a currently a stay at home mom, and my children are now all school-aged. I care for my animals at home, and I have an open schedule, heart, and home to care for other animals. I have a about 1.3 acres of land with a dedicated (vinyl) fenced in area for dogs so I have plenty of room for outdoor playtime. Indoors, a few of my animals are crated at night based on their individual needs but all walk freely during the day. In your home, I am open to whatever is most comfortable for your pet.

Sitter Profile Image: Savanah G.
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Savanah G.
Star Sitter
from
$21
per walk
5.0 out of 5 stars
• 35 reviews
11 repeat clients
18 years of experience
Fort eustis, VA, 23604

“Savanah was great walking my 2 beagles. She was always on time and my dogs really liked her.. one of my dogs is a little special and Savanah seems to figure that out and made her feel more comfortable when walking with her. I would recommend her!”

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Daniela J.
Sitter Profile Image: Ion D.
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Ion D.
from
$16
per walk
10 years of experience
Williamsburg, VA, 23185

About: I’ve had dogs my entire life and genuinely love caring for them. To me, every dog deserves patience, kindness, and plenty of attention. Whether your pup loves long walks, playtime, or simply relaxing with good company, I’ll make sure they feel safe, comfortable, and loved while you’re away. I understand that every dog has a unique personality and routine, so I’ll follow your care instructions carefully—from feeding schedules and medications to favorite toys and walking habits. My goal is to treat your dog like a member of my own family, giving you peace of mind knowing they’re in caring, reliable hands. Please note, we board on family at a time, we do not cage the dogs. Pet care fits seamlessly into my daily routine because I work from home, and my wife is home full-time. This means your pet will receive plenty of attention, companionship, and supervision throughout the day rather than being left alone for long periods. We have a clean, safe, and pet-friendly home where dogs can feel comfortable and relaxed. Whether it’s regular walks, playtime, feeding, or simply providing affection and companionship, we’re committed to making every pet feel like part of the family while they’re in our care. I care for every pet as if they were my own. I follow each owner’s instructions carefully, including feeding schedules, exercise routines, medications, and any special needs or preferences. I make sure pets receive plenty of attention, affection, playtime, and regular potty breaks while maintaining their normal routine as much as possible. In my home, pets stay in a clean, safe, and comfortable environment where they are supervised throughout the day. Since I work from home and my wife is home full-time, your pet will have lots of companionship and won’t be left alone for extended periods. When caring for pets in a client’s home, I respect both the pet’s routine and the owner’s home. I provide reliable, attentive care, keep the space tidy, and send regular updates and photos so you can have peace of mind while you’re away.

Sitter Profile Image: Alexandria Y.
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Alexandria Y.
from
$25
per walk
4.9 out of 5 stars
• 9 reviews
4 repeat clients
15 years of experience
Williamsburg, VA, 23185

About: I have cared for kittens, cats, puppies and dogs for as long as I can remember; being my own or friends and family’s. I am a huge animal lover and would be honored to care for your baby’s! I am a stay at home mom of 2 (also animal loving) little ones. I can take your pup for a walk or care for any animal at any time of the day. My apartment complex has a dog park and we all love to go for walks here! Will also follow any want or need of any client.

Sitter Profile Image: Chelsea C.
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Chelsea C.
from
$20
per walk
5.0 out of 5 stars
• 17 reviews
9 repeat clients
6 years of experience
Newport News, VA, 23603

“Absolutely wonderful and best Rover I've worked with. Very responsive and has great communication, asks questions, and gives great feedback and updates.”

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Jasmine B.
Sitter Profile Image: Emma B.
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Emma B.
from
$20
per walk
5 years of experience
Newport News, VA, 23603

About: I have had animals in my home ever since I can remember! I am a professional dog groomer of 4 years and am CPR certified. I have worked with many different dog breeds and temperaments, as well as senior dogs, puppies and special needs dogs. At the moment I am usually available during the day for walks and drop ins and I am available in the evening with prior notice. I offer in home pet sitting, walks and drop ins services. A typical day would include filling up water and food bowl, walks up to an hour, and play time of course! I can also provide as many photo or video updates as you would like.

Sitter Profile Image: Teona & Louelyn M.
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Teona & Louelyn M.
Star Sitter
from
$35
per walk
5.0 out of 5 stars
• 205 reviews
61 repeat clients
17 years of experience
Williamsburg, VA, 23188

About: Your dog will be treated like part of our family! I work remotely from home, so your pup will have plenty of attention, companionship, and care throughout the day. They are rarely left alone at most, about an hour on the occasional grocery trip or quick walk around the neighborhood. My husband also works primarily from home, running his own home services business, so there is almost always someone here with your dog. We understand how important it is for pets to feel safe, loved, and comfortable, especially when they’re away from home. Whether your pup loves to play, cuddle, or simply relax, we’ll make sure they receive personalized care, regular potty breaks, plenty of affection, and a calm, loving environment. We treat every dog as if they were our own and will keep you updated with photos and messages, so you can enjoy peace of mind while you’re away. I’m home most of the time, except for quick grocery trips. I’ll be available to give your dog plenty of attention and care throughout the day. We keep your pups active during the day so they’re ready to settle in at night. Dogs usually sleep in their room with their own bed or blanket (if provided), which keeps them safe and cozy. We have a separate room to ensure they’re comfortable and relaxed. Feel free to message us with any questions—we’d love to make sure both you and your pup feel at ease!

Sitter Profile Image: Mikayla V.
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Mikayla V.
from
$20
per walk
5.0 out of 5 stars
• 3 reviews
20 years of experience
Lanexa, VA, 23089

About: I’ve had pets and taken care of a wide variety of animals from a very young age. They’re furry family members who need just as much love and care as we do! It fits well into my schedule throughout the week. Being able to take care of pets in one of the best ways to find work. I can assure you that your furry friend will be taken care of exactly how you want. My baby is 10 years old and has lived a very fun, spoiled life thus far. It’s only fair to share the care!

Sitter Profile Image: Destiny T.
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Destiny T.
from
$18
per walk
10 years of experience
Newport News, VA, 23608

About: I ensure a comfortable and stress-free experience for your furry, scaly, or finned friends while you're away. Whether it's a lazy stroll for your pup, ensuring your cat's needs, or tending to your aquatic or reptilian companions, rest assured that they're in loving and capable hands! I’m currently unemployed so I have all the time in the world to take care of your furbabies, I’m just a call away if there is an immediate need! I’m available at just about all times! I care for pets in my clients home and fur-babies as I do my own, if there is a fenced in yard I always double check that gates are locked. I make sure to check their food, water, look around the home to make sure there isn’t anything that needs to be tidied up. I make sure any non-safe objects are out of reach.

Sitter Profile Image: Bailey B.
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Bailey B.
from
$16
per walk
5.0 out of 5 stars
• 2 reviews
3 years of experience
Newport News, VA, 23602

About: I love animals with all my heart!! I currently have a high energy large German Shepard and Lab at home who I adore. I am great with all breeds and not scared of reactive dogs. I am very patient and dedicated to making sure all pets are safe, happy and well taken care of. I don’t own any cats, but I love them just the same and I am more than willing to accommodate!! I am currently a student and I do most of my school work from home leaving lots of free time for pet care, I am very flexible with my hours and I can do early mornings / late nights My German Shepard Waylon and our roomates lab, Carl, are my responsibilities most days of the week. I spoil them with walks, pup cups and car rides daily. We do projects at home and I honestly treat them like real kids. I will gladly do the same for other people’s pets. I know each pet is different with their own personalities and needs.

Sitter Profile Image: Lily & Philip E.
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Lily & Philip E.
from
$22
per walk
5.0 out of 5 stars
• 194 reviews
38 repeat clients
9 years of experience
Toano, VA, 23168

“This is a great team who really took care of our Dog walks for a week when we were unable to walk him. Courteous, on time, snd pleasant people. They quickly got to know Eddie’s quirks and behaviors. Highly recommend!”

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Alan K.
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The median cost per walk for dog walking in Winston Terrace is $20

Dog parents share their Rover experiences - Winston Terrace

1 / 1
5.0 out of 5 stars

Very prompt with communication and action. Walked my dog on short notice with no issues. Definitely use her services again.

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Joshua W.
Dog Walking
5.0 out of 5 stars

Wilhelmina was especially engaging with Larka, running her through our agility course, dock diving, and brushing. We highly prize her skills.

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Roger G.
Dog Walking
5.0 out of 5 stars

Kira is always amazing. She’s is great with buddy and he just loves her . She’s always accommodating with schedule changes and extremely flexible.

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Justin C.
Dog Walking
5.0 out of 5 stars

Allison was great! She was super responsive, was flexible and the dogs loved her. She provided great updates and was very thorough! Will definitely work with her again for care of our two pups!

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Michael D.
Dog Walking
5.0 out of 5 stars

As my dog gets older, his care has become more specialized, so I’ve become much more discerning when it comes to finding someone I can truly trust with him while I’m away. I feel incredibly lucky to have found Kate on Rover. Kate watched my dog for an entire week while I was out of town, and during that time, he unfortunately became sick and also started acting out in ways that were out of character for him. Kate was immediately on top of everything. She kept me informed whenever something happened, reassured me when he was improving, and was incredibly proactive about finding creative solutions to make sure he was comfortable and well cared for. Knowing that Kate was attentive to his needs and genuinely cared about him took an enormous amount of stress and worry off my shoulders. I never had to wonder whether he was in good hands, as I knew he was. Kate was truly one of the best decisions I could have made for my dog. She is attentive, caring, knowledgeable, communicative, and incredibly thoughtful. Most importantly, she gave me something that is priceless when you’re away from your pet: complete peace of mind. I would recommend Kate wholeheartedly to anyone looking for someone they can genuinely trust with their dog. She is wonderful!

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Nicolas P.
Dog Walking
5.0 out of 5 stars

We were able to book Jared for drop in visit and walk on short notice. He was very responsive and came to meet Rooney prior to visit. He sent pictures and updates after walks. We will definitely book with him again.

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Stacey E.
Dog Walking
5.0 out of 5 stars

Eloise was the best dog walker! She took such great care of my special boy and paid attention to all his quirky needs. My dog is begging for her to come back. Definitely will be booking her again soon!

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Erika G.
Dog Walking
5.0 out of 5 stars

Lauren does very good work. She's clearly quite competent with Clove and concerned about her welfare. She's pleasant for conversation afterwards and is flexible. I recommend her highly.

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Mae K.
Dog Walking
5.0 out of 5 stars

Jessica is so great with our dog, Honey! I have booked with her several times and she is always very reliable, trustworthy, and caring. Honey loves her! I definitely would recommend her to others!

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Andrea K.
Dog Walking
5.0 out of 5 stars

Tess is always fantastic and makes me feel so secure that my dogs are always in good and loving hands!!! I am so thankful for her!

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Margaret C.
Dog Walking
5.0 out of 5 stars

Honey is the absolute best! So incrediblely thorough and takes wonderful care of our dogs! We are so grateful for her.

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Lily S.
Dog Walking
5.0 out of 5 stars

Kayla was perfect for our lovable but sometimes unpredictable dog. They bonded immediately in a meet and greet. They walked and played fetch. Great communication with us for this 5 day care. Will definitely for ask her for our next time away.

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Roger G.
Dog Walking
5.0 out of 5 stars

Rebecca was punctual and seemed to like Soffie. She is very nice and friendly, and I certainly would like to have her again.

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Lana W.
Dog Walking
5.0 out of 5 stars

Always great communication and great care with buddy . Will be rebooking anytime available to walk buddy on days we need someone

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

How to book dog walking

  1. 1. Search

    Browse profiles of walkers near you who offer dog walking.
  2. 2. Meet In Person

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Popular requests for dog walking - Winston Terrace

Select a filter and find qualifying sitters offering dog walking.

Sitters in Winston Terrace average 3
repeat dog walking clients

FAQs for Dog Walking - Winston Terrace

Frequently asked questions about Rover

The average cost of Dog Walking in Winston Terrace is $22 per walk as of October 2026. Most bookings cost between $16 and $31 per walk. On Rover, walkers set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of October 2026, there are 895 sitters on Rover offering Dog Walking across Winston Terrace. 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 Winston Terrace. 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 , 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 Winston Terrace 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 , 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 .

Yes, you can find walkers who have experience with handling special pet needs in Winston Terrace. On Rover:

  • 89% of walkers can help with special care needs
  • 93% can help with giving oral medications or injections
  • 97% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

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

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your walker interacts with your pet or the new environment.

During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your walker questions about their skills and expertise, and make sure the fit feels right for everyone. Meet & Greets are a great way to prepare your pet and walker for longer stays or first-time bookings. Read our tips for your first .

walkers on Rover set their own , 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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