Dog Walkers in Winter Harbor Haven, VA
Book a dog walker to give your dog a 30-minute walk around your neighborhood.

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Top rated Winter Harbor Haven dog walkers
Prices are estimates per walk. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

“Both my dog and I think Claire is the best! She was professional, prompt and a good communicator. And - she went above and beyond - giving Coltrane long walks and lots of attention. I totally recommend her and Coltrane gives her a big paws up, too!”


About: Ivdd experience , medicine administered experience , senior dog care exeperience . Trained puppies. Good eye for noticing if a dog is not themselves . I am a very compassionate and passionate dog mom . Available to walk , feed , play whatever your daily pet needs . Even transport to an appointment if needed . I’ve loved dogs my whole life . Animals are a passion of mine . Anyone who knows me calls me the dog whisperer as I love to be with them , train them and just spend most of my days in their company . I grew up with so many different animals and even as a young girl I was always out doors soaking up the sunshine and hiking with animals . It’s an unconditional love . I can exercise you pet daily on leash or in your fenced in yard . Able to come a few times for potty walks or feeding . Medication experience . I’m here to help your pets have an exceptional day when you’re at work or away .

About: I've loved animals since I was a kid and have cared for many throughout my life! I was tasked with raising my family dog since she was a puppy when I was in high school, and I helped my college roommate with her puppy! I have walked/boarded many dogs and cats since moving to Virginia! Being in the military, my coworkers travel a lot so I have become the workplace's go-to "pet auntie." I genuinely love to spoil pets and providing them with a safe and homey environment while their loved ones are out! I have a fairly flexible work schedule so I can come back to my home or to your home to take care of your pet! Early morning, lunch, and evenings are especially free, so I can work around that depending on your needs. I do not own pets, so they will be here as a single child in the case they are boarded! Crates, food, litter boxes, etc will need to be provided as I don't own those things. I have access to many parks around my neighborhood, so walkability is not an issue!

About: I have taken care of animals since I was a child, I have always had a dog of my own as well as cared for cats and hamsters. I grew up with a mother that ran an animal sanctuary so I have seen and cared for them all! I love to stay active and would love to add a fur friend to that activity either on a walk or run! I work full time however I am home daily after 330pm and on weekends. I am available to have your fur baby stay in my home with a potty break mid day and lots of love after work or for a drop in and walk at your home. I have 2 dogs of my own, one is 5 years old and the other is 1 year old. Both boys are very friendly and love having other dogs to play with. I keep a gate on hand to separate them from our guest if need be because sometimes they just can’t stop playing and our guest need a break to relax.

About: I’ve never lived a day in my life without having a dog by my side, and I can confidently say that I can’t imagine it any other way. From puppies to our older friends, I love them just like they’re my own. After many years spent with different breeds, sizes, and ages, I am also well versed in pet first aid and common health conditions. I am especially fond of senior dogs and would be honored to care for them. I have recently begun a full time job in Richmond but still petsit often since I truly enjoy it. My schedule best suits check ins with pets in the mornings or evenings. You will never have to worry about how your baby is doing. Because of my own personal (and very anxiety inducing!) experiences with being away from my boy, I am very diligent about keeping pet parents in the loop.

About: I have had pets all my life! We have had cats and dogs growing up. As an adult, we have even had chickens! I love playing with all sorts of fur babies! Not to mention extra snuggles! I have been house-sitting and watching friends' dogs while they go on vacation and have loved every second of it! The job I have right now allows me a lot of free time and I work on my own schedule. So this would give me the availability I would need to help you and your busy schedule!! Your pets would be taken care of in your home. I feel this is the most comfortable and stress-free way for your pets. Whatever their routine is, they will have the same as if you were home with them!


About: I worked in a small animal emergency vet clinic for a year and a half where I was trained as a veterinary technician. Since then I have worked at 2 other vet clinics for a total of 5 years and counting. I have also had many pets of my own and have been caring for friend's and family's animals for most of my life. I currently have an Australian cattle dog, a fluffy cat, and a horse! I am very observant of your animals behavior and I will recognize the signs that something may be wrong. I enjoy caring for animals of every shape and size! I have references available that I would be happy to share with you and I am happy to answer any further questions you may have.

About: I’ve had dogs on and off my entire life. For the last 12 years our family has rescued/adopted 11 dogs. I have kept family and friends' dogs while they vacation as well as done drop ins at their home for walks, feeding and cuddling. I have also taken care of goats and chickens. I will treat your pets how I would want someone to treat mine. I am comfortable around all size and breeds of dogs and cats as well as goats and chickens. I am self employed and have a very flexible schedule. I am available almost any time, including nights and weekends. Most schedules can be accommodated. I have 5 acres which about 1/2 acre is fenced in with 6-foot fencing. I can snuggle your dog on the couch or crate them if they feel more comfortable like that. I have my own personal dogs but keep them separate from other people's pets. If you leave directions of what your pets routine in your home is like I can provide for them in that manner.

About: Ever since I was a child I have loved animals of every kind. I would love to care for your fur babies whether it’s overnight or just for a stroll. I am currently only working a few hrs. per week as I have made the decision to be home with my family more. Pet sitting would work perfectly for me. I’m available anytime that’s needed! I am able to keep a solid routine with the owners needs. Any services that are needed I can provide. Overnights, walking, play dates, etc.

About: I have been dog sitting and dog walking since I was the age of 12 and I have owned dogs and been around dogs since birth. I absolutely love going on dog walks and playing with dogs in my backyard. I believe that dogs are family and should be treated exactly like you would your little baby or child. I used to charge $5 to walk over to my neighbors house and either stay there with him overnight or just give him 3 long walks during the day while they were at work. I also have owned dogs ranging from Yorkies and dachshund size to german Shepard’s and mastiffs. I have had close contact with shelter dogs and puppies that we now own. I absolutely love dogs and pride myself on the excellent care I give them I currently am in the military but work days and my wife works nights so someone is almost always at home to give them walks meals and plenty of love I have a fenced in yard as well as hiking trails just a mile up from my house I love going to with my two pups. I treat your pets exactly as if they were my pets

About: I have owned, trained and taken care of a huge variety of breeds, temperaments and sizes. My current dog is a 120lb Shiloh Shepherd. My last was a 7lb Rat Terrier, Chihuahua mix! I'm currently in school online and self employed, so I can modify my schedule to fit your needs! From early mornings, to late in the evening, I have you covered! Pets are part of your family and as such, will be treated with the utmost care, respect and diligence. It is a big leap to trust a stranger with a family member, and I strive to provide the best care for you pet!

About: I have 50 years of experience caring for pets. We had a farm for 20 years, where I cared for horses, dogs and cats...my own and others. I am retired, so will be available most days and throughout the day. My schedule is very flexible, so will be able to accomodate your schedule. Currently, we have one senior dog. She is spoiled rotten, as all dogs should be! Every pet has unique needs and I do my best to accommodate each pet and pet owner.

About: I’ve worked at a petstore for 3 years and grew up with multiple types of animals and love all animals! Happy to help anyone! I Love cats and dogs I’m currently working part time right now as a cashier. As mentioned above I’ve worked at a petstore for 3 years and animals are my life. I do not own any animals right now but would love my own some day! I pride myself in taking good care of animals. If there’s anything I can do to make them comfortable and healthy I’ll find a way. Please note I DO NOT DRIVE! Most of my clients would have to come to me! I would be available weekends for drop ins and for boarding at dogs house! Weekends are available for walkings as well! I look forward to meeting your fur babies!

About: I have loved animals all my life. I currently have the pleasure of caring for 3 dogs, a bird and an outdoor cat in my home. 1 of my dogs is senior and requires medication daily. I love birds and would board your bird in a heartbeat! I think pets just make life better. Until you need to find pet care and it’s super expensive! I offer low cost pet care in my home on the weekends so that you can go on a weekend trip. One day when I retire I hope to open that up to everyday of the week, but for now I work full time. My house has a large fenced backyard where dogs can roam and play. I also have a husky/border collie and a corgi mix who would love to be a companion to your dog for the weekend. They love when friends come to play. I currently care for my moms dog every time she goes on vacation and thought, hey, why don’t I start up this little pet sitting business on the side since I enjoy having furry buddies around. Everytime Brownie comes she gets treated like a queen with lots of attention and love. Don’t you want that for your dog, instead of a cold crate at the vet? Just hire me and your dog will feel like it’s on vacation too. I work full-time so a weekend situation would be best if you want your pet to have attention all day. Otherwise, I get home at 3 everyday and would be open to boarding during the week if you were okay with that. My dogs get let out around 10 am by my husband and just lounge and sleep all day until 3 pm when I get home. It works for us :) I have a fenced yard and 2 friendly dogs that can keep your dogs company. My other dog is senior and is separated from the bunch due to her being blind and deaf. She’s still loved like family, just in her own doggy play pen for safety. If you need senior dog care, I’m your sitter, as I have plenty of experience with my own shitzhu, Beauty. I always make sure there’s fresh water, and give snacks during the day. I dental bone a day and two meals. Whatever your dog’s food preferences are, I can do. I am used to giving medication daily as well.

About: I have taken care of animals since I was 15. I started working for a groomer as a bather for 7 years and have worked at Animal Care of Gloucester for 7 years. I am very well experienced in the their well being, animal behavior, walking, feeding, medicating, bathing. I would love to be able to help take care of animals in my free time. From puppies to seniors I have worked with them all. I am currently working looking for work but I would love to spend my free time taking care of animals. I do have my son every other weekend, so I will be available for pet sitting overnight every other weekend. I live at the end of a quarter mile dirt road off of the main streets, I do not have a fenced in yard but am able to leash walk as many times a day as needed. I have 5 babies of my own, 1 dogs, 2 cats, and a cockatiel that are very friendly and live other animals. I can easily crate if needed and provided and have a pet safe home. I am currently looking for work so anytime is perfectly fine. I do take & pick my son up from school everyday at 8:30am and 3:30pm. I can easily crate pets if needed. I live at the end of a quarter mile dirt road so there is very little traffic and plenty of space for walks.
Loving dog walkers in your neighborhood
Search Results
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.


Claire P.Star Sitter

“Both my dog and I think Claire is the best! She was professional, prompt and a good communicator. And - she went above and beyond - giving Coltrane long walks and lots of attention. I totally recommend her and Coltrane gives her a big paws up, too!”


Chelsea C.

“Very friendly, my dogs loved her!”


Bryan S.Star Sitter
“Nice to meet you, thanks for the walk Mike and pirate”


Rebecca M.
About: Ivdd experience , medicine administered experience , senior dog care exeperience . Trained puppies. Good eye for noticing if a dog is not themselves . I am a very compassionate and passionate dog mom . Available to walk , feed , play whatever your daily pet needs . Even transport to an appointment if needed . I’ve loved dogs my whole life . Animals are a passion of mine . Anyone who knows me calls me the dog whisperer as I love to be with them , train them and just spend most of my days in their company . I grew up with so many different animals and even as a young girl I was always out doors soaking up the sunshine and hiking with animals . It’s an unconditional love . I can exercise you pet daily on leash or in your fenced in yard . Able to come a few times for potty walks or feeding . Medication experience . I’m here to help your pets have an exceptional day when you’re at work or away .




Linda U.
Star Sitter


“Linda is great with pups. They love her right away. She treat them they way I do. Thank you Linda!!”


Yuna L.
“Yuna took care of my dog, Harley. She was great with him, was easily able to accommodate his feeding schedule and medical needs without any issue. She took him on walks with success and Harley still gets very excited to see her! I would trust her to watch Harley or either of any two cats anytime.”


Rebecca P.
About: I have taken care of animals since I was a child, I have always had a dog of my own as well as cared for cats and hamsters. I grew up with a mother that ran an animal sanctuary so I have seen and cared for them all! I love to stay active and would love to add a fur friend to that activity either on a walk or run! I work full time however I am home daily after 330pm and on weekends. I am available to have your fur baby stay in my home with a potty break mid day and lots of love after work or for a drop in and walk at your home. I have 2 dogs of my own, one is 5 years old and the other is 1 year old. Both boys are very friendly and love having other dogs to play with. I keep a gate on hand to separate them from our guest if need be because sometimes they just can’t stop playing and our guest need a break to relax.


Jenna A.
“Jenna has been an absolute lifesaver for me and my two boys, Bramble and Scout. She is always on time, reliable, and is just the sweetest thing! Whether it's a regular walk or watching over them while I’m away on trips, I always know they’re in the best hands with her. She goes above and beyond; me and my boys really appreciate her!”


Kellee B.
“When I say there is no one better to trust with your dogs, I don’t make that statement lightly. Kellee is friendly, attentive and treats your dogs as if they are her own. My dog doesn’t trust new people easily. As soon as she met Kellee she curled up next to her with her head in Kellee’s lap. If you want to be able to travel with piece of mind then Kellee is the perfect choice.”


jessie l.

“Oatmeal loved his walks with Jessie!”




Kelsey M.
About: I worked in a small animal emergency vet clinic for a year and a half where I was trained as a veterinary technician. Since then I have worked at 2 other vet clinics for a total of 5 years and counting. I have also had many pets of my own and have been caring for friend's and family's animals for most of my life. I currently have an Australian cattle dog, a fluffy cat, and a horse! I am very observant of your animals behavior and I will recognize the signs that something may be wrong. I enjoy caring for animals of every shape and size! I have references available that I would be happy to share with you and I am happy to answer any further questions you may have.


Melanie H.
About: I’ve had dogs on and off my entire life. For the last 12 years our family has rescued/adopted 11 dogs. I have kept family and friends' dogs while they vacation as well as done drop ins at their home for walks, feeding and cuddling. I have also taken care of goats and chickens. I will treat your pets how I would want someone to treat mine. I am comfortable around all size and breeds of dogs and cats as well as goats and chickens. I am self employed and have a very flexible schedule. I am available almost any time, including nights and weekends. Most schedules can be accommodated. I have 5 acres which about 1/2 acre is fenced in with 6-foot fencing. I can snuggle your dog on the couch or crate them if they feel more comfortable like that. I have my own personal dogs but keep them separate from other people's pets. If you leave directions of what your pets routine in your home is like I can provide for them in that manner.


Charity P.
“Charity has pet sit for me outside of Rover many times. She’s very responsible and has many pets of her own. (The cat whisperer:)She’s a very loving human being with a big heart. You can count on her spur of the moment and long term. Very friendly and outgoing, Charity is. She’s the best!”


Connor D.
“Always treated my dogs like a priority and is punctual and kind. Able to handle bigger dogs and has never reported a problem she couldn’t handle.”


Samuel J.
About: I have owned, trained and taken care of a huge variety of breeds, temperaments and sizes. My current dog is a 120lb Shiloh Shepherd. My last was a 7lb Rat Terrier, Chihuahua mix! I'm currently in school online and self employed, so I can modify my schedule to fit your needs! From early mornings, to late in the evening, I have you covered! Pets are part of your family and as such, will be treated with the utmost care, respect and diligence. It is a big leap to trust a stranger with a family member, and I strive to provide the best care for you pet!


LeeAnn R.
About: I have 50 years of experience caring for pets. We had a farm for 20 years, where I cared for horses, dogs and cats...my own and others. I am retired, so will be available most days and throughout the day. My schedule is very flexible, so will be able to accomodate your schedule. Currently, we have one senior dog. She is spoiled rotten, as all dogs should be! Every pet has unique needs and I do my best to accommodate each pet and pet owner.


Heather T.

“Heather is great with my pup and gives her extra attention!”


Brittany S.
“I’ve known Brittany for years and she used to be my pet sitter. She’s went above and beyond with taking care of my animals! She is very trustworthy and tries her hardest keeping her animals happy and safe.”


Jessica S.
About: I have loved animals all my life. I currently have the pleasure of caring for 3 dogs, a bird and an outdoor cat in my home. 1 of my dogs is senior and requires medication daily. I love birds and would board your bird in a heartbeat! I think pets just make life better. Until you need to find pet care and it’s super expensive! I offer low cost pet care in my home on the weekends so that you can go on a weekend trip. One day when I retire I hope to open that up to everyday of the week, but for now I work full time. My house has a large fenced backyard where dogs can roam and play. I also have a husky/border collie and a corgi mix who would love to be a companion to your dog for the weekend. They love when friends come to play. I currently care for my moms dog every time she goes on vacation and thought, hey, why don’t I start up this little pet sitting business on the side since I enjoy having furry buddies around. Everytime Brownie comes she gets treated like a queen with lots of attention and love. Don’t you want that for your dog, instead of a cold crate at the vet? Just hire me and your dog will feel like it’s on vacation too. I work full-time so a weekend situation would be best if you want your pet to have attention all day. Otherwise, I get home at 3 everyday and would be open to boarding during the week if you were okay with that. My dogs get let out around 10 am by my husband and just lounge and sleep all day until 3 pm when I get home. It works for us :) I have a fenced yard and 2 friendly dogs that can keep your dogs company. My other dog is senior and is separated from the bunch due to her being blind and deaf. She’s still loved like family, just in her own doggy play pen for safety. If you need senior dog care, I’m your sitter, as I have plenty of experience with my own shitzhu, Beauty. I always make sure there’s fresh water, and give snacks during the day. I dental bone a day and two meals. Whatever your dog’s food preferences are, I can do. I am used to giving medication daily as well.


Melissa C.
“Melissa has the unique and special ability to bond with animals, especially dogs. Animals are drawn to her as they inherently understand her love and compassion for them. Bonus - she has an amazing personality and positive attitude that is a joy to be around. Melissa has over 17 years of professional experience taking loving care of all types of dog breeds which makes her the only one I would trust with my precious fur babies!”
How Rover works
1. Search
Read verified reviews and choose a dog walker who’s a great match for you and your dog2. Meet & Greet
Meet either virtually or in-person with a walker to discuss the level of care needed for your dog3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per walk for dog walking in Winter Harbor Haven is $18
Why Choose Rover?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your dog walker has to cancel, we’ll work with you to find a new walker.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Sitters in Winter Harbor Haven average 3 repeat dog walking clients
Dog Walking FAQs
Frequently asked questions about Rover
Dog walkers on Rover are free to set their rates. The median cost to hire a dog walker in Winter Harbor Haven on Rover as of Aug 2025 was about $18 per walk, after factoring in Rover’s service fees. A dog walker’s rate may also change as you customize your booking to fit your and your dog’s needs.
As of Aug 2025, there are 592 dog walkers in Winter Harbor Haven. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, dog walkers joining Rover must pass a background check for you and your dog’s safety.
Rover makes it easy to reach out to multiple dog walkers about your booking. Typically, 84% of Winter Harbor Haven dog walkers respond in under an hour.
Dog walkers in Winter Harbor Haven have an average of 18 years of experience. Dog walkers with repeat customers have an average of 3 repeat clients. Experience can vary from dog walker to dog walker, but you can view reviews, years of experience, and number of repeat clients when you compare dog walkers in Winter Harbor Haven.
You can’t always predict a super busy day at work, but you can anticipate your dog’s needs. Instead of rushing home at lunch, book a dog walker to give your dog a 30- or 60-minute dog walk. Your dog walker can stop by as many times as you need—on whatever days you need them. With the Rover app, get a comprehensive Rover Card from your dog walker that includes:
- Start and stop times
- A map of their walk with total distance
- Pee, poo, food, and water breaks
- Cute photos and a personalized note
There are 592 dog walkers in Winter Harbor Haven on Rover, so you’re sure to find the perfect match for your dog! In Winter Harbor Haven, 97% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, all dog walkers on Rover have been background checked for you and your dog’s safety.
Yes! Dog walkers joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog walker through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog walker has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your dog walker requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your dog walking service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog walker’s cancellation policy.
