House Sitting in Winter Harbor Haven
Find a loving dog sitter to watch your dog overnight in your home.

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

“So happy we found Taylor, she not only took care of our pup as her own she kept us updated throughout our trip and left the house in spotless condition. Excellent communication, from the meet and greet to the end of our stay, she is a gem. Looking forward to having Taylor take care of Lily and our home.”


“Anna was absolutely wonderful! She was very friendly and highly skilled with caring for dogs, Anna stayed at my house while I was away, and she bonded with my dog instantly. I was completely impressed with her ability to interact and connect with my dog. Anna was really good with following through with my requests regarding my dogs diet, and she followed up with me right away with any concerns. Anna is very reliable, trustworthy and honest, I highly recommend Anna to care for anyone’s pets. And FYI, she also willingly and lovingly cared for and fed my bird. Leaving my dog is hard for me, my heart aches to leave him behind, I never imagined I would find someone who could love my dog much ad I do, but Anna 100% exceeded my expectations.”


“Robin is amazing! She looked after my pups at my place for 4 days and sent me plenty of pictures and good communication. You could tell she loved my pups and they definitely loved her. Will definitely use her again!”


“Kasey was great. Made sure our dog was well taken care of. He made sure to meet all of our expectations. Our dog was happy and we knew that he was getting lots of love while we were gone. He made sure to send us pictures of everything each day. Our dog is reactive to other dogs on walks so he often doesn’t get out when we’re gone, but Kasey had no issues and got our guy plenty of exercise.”


“Cassandra was absolutely amazing with our cat and high energy dog who was recovering from knee surgery. She went above and beyond to make sure the animals and house were taken care of. I can't recommend her highly enough!”


“We've had less than positive experiences with boarding in the past and our dogs are a rambunctious bunch. They need constant supervision to keep them and the wildlife in our yard safe so house sitting is our only option. Macy took care of everything, stayed for the whole long weekend, and we came home to untraumatized dogs. Would definitely book again!”


About: I have experience in daycare/boarding settings, i have experience with high drive dogs, I do dog sports with my own personal dog so i am pretty confident in my handling skills. I have done years of research on dog related things some including understanding body language, knowing when a dog is uncomfortable or needs to be removed from a situation, what things are good and what are bad, how to use training tools properly if needed, learning the genetics of dog breeds and just over all temperaments that certain breeds have. I grew up on a farm full of dogs and other animals ive always owned dogs especially bully breeds ive been around dogs will all ages, behaviors and sizes my family and friends all know my love for animals and how good i am with them and how much i care about them even when they arent my own. I currently am unemployed, i am a stay at home dog mom and aside from the occasional grocery store run i am at home with my dogs. I will care for your pet to the best of my ability and under any instructions that may be given to me. I will care for your pet like they are my own and keep them as safe as possible while under my care!

About: Hi! I’m Tiffany,, a lifelong dog lover with 5 years of experience caring for dogs of all breeds, sizes, and energy levels. Whether your pup loves long walks, belly rubs, or just a cozy cuddle on the couch, I’m here to provide the love and attention they deserve while you’re away. I treat every dog like family — because they are. I’m reliable, detail-oriented, and always happy to follow your dog’s specific routine, medical needs, dietary needs, and quirks. From high-energy puppies to mellow seniors, I’ve cared for them all. Let’s make sure your dog feels safe, happy, and loved while you’re gone. I’d love to meet you both! 🐾 I do have a full time job that I work M-F 8-5. I am available to to swing by before or after work, as well as stop by on my lunch break so long as your house is in close proximity to my job. I am willing to stay at your home during the week as well to give your pet the attention and care they need around working hours. I have open a availability on weekends! With my home being small I am only able to accommodate inquiries that have me coming to your home. I will care for your home and pet as if they are my own! I ask that you leave me any specific details regarding routine (feeding times, medication times, etc.) to make the process easy and comfortable for your fur baby!

“Ashley was a wonderful sitter! She was very responsive and sent tons of pictures of my two dachshunds. She took such good care of the girls while we were away. We’d love to have her back anytime to sit for Harley and June. 🩷”



“Honestly we felt extremely comfortable leaving her with our two pets. My boy dog absolutely fell for her. She kept us updated and did informed us when something was out of her control. Will be rebooking when go for our next trip.”


About: I, Clinique, have been raising animals since I was 8, growing up with around 15 pets alongside my family. Since moving to Virginia, the smallest number I've cared for at once has been two cats. My strength lies in building bonds through play and applying hands-on training techniques, especially inspired by the work I’ve done with my husky, Milio. My husband, Joseph, grew up with two cats and developed a deep sense of responsibility through caring for them. His specialty is general pet care he’s patient, attentive, and always tuned in to an animal’s needs, whether it’s daily routines or just making them feel safe and loved. Pet care is my daily routine. I do this full-time, so your pet gets my full attention. My schedule’s built around walks, feedings, playtime, and cuddles. Being available and reliable is huge for us, so you’ll never have to wonder if your pet is loved and cared for, they always are. We care for pets like they’re our family. We love cuddling, we love them on beds and furniture and most importantly we love positive reinforcement. We are consistent on any routine you set in your home or our. When we're in your home, respect will be given and rules followed.

About: I’ve taken care of pets since I was 17. I’ve help family and friends care for pets when I babysit their children. I loved being around the pets and children which is why I use my extra free time to provide attentive and loving care to others babies and fur babies as well! I currently work from home full time, so I have plenty of time to spend with your fur babies. They would have my attention and care at any time needed as I have more than enough time on my hands. I live in an apartment complex close to the beach, so I am open to caring for them in your home or mine! Whichever works best for you!

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 work at Banfield in Newport News as a vet assistant. I currently have a senior dachshund named Leo who’s great with other dogs and cats. My work schedule varies month to month. I can walk dogs or take care of pets in your home if my work schedule allows, or I can board in my house (dog friendly dogs/cats or small animals). I also have years of experience medicating dogs, cats, and small animals, and can trim nails on dogs and cats. I work 10 hour shifts, 4 days a week at Banfield. It varies each week but I do get a monthly schedule each month. I usually get my monthly schedule at the beginning of the previous month I usually take my dog out every 3-4 hours to go potty while I’m home. If your dog has a routine he/she follows, let me know and I can accommodate!

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.
Loving house sitters in your neighborhood
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Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.


Taylor-Laine F.Star Sitter

“So happy we found Taylor, she not only took care of our pup as her own she kept us updated throughout our trip and left the house in spotless condition. Excellent communication, from the meet and greet to the end of our stay, she is a gem. Looking forward to having Taylor take care of Lily and our home.”




Linda U.
Star Sitter


“Linda did an excellent job pet sitting our 5 mo old puppy. We will not hesitate to hire her again. She loves animals and is a competent, reliable and kind person.”


Anna Mei D.Star Sitter

“Anna was absolutely wonderful! She was very friendly and highly skilled with caring for dogs, Anna stayed at my house while I was away, and she bonded with my dog instantly. I was completely impressed with her ability to interact and connect with my dog. Anna was really good with following through with my requests regarding my dogs diet, and she followed up with me right away with any concerns. Anna is very reliable, trustworthy and honest, I highly recommend Anna to care for anyone’s pets. And FYI, she also willingly and lovingly cared for and fed my bird. Leaving my dog is hard for me, my heart aches to leave him behind, I never imagined I would find someone who could love my dog much ad I do, but Anna 100% exceeded my expectations.”


Robin P.

“Robin is amazing! She looked after my pups at my place for 4 days and sent me plenty of pictures and good communication. You could tell she loved my pups and they definitely loved her. Will definitely use her again!”


Kasey A.

“Kasey was great. Made sure our dog was well taken care of. He made sure to meet all of our expectations. Our dog was happy and we knew that he was getting lots of love while we were gone. He made sure to send us pictures of everything each day. Our dog is reactive to other dogs on walks so he often doesn’t get out when we’re gone, but Kasey had no issues and got our guy plenty of exercise.”


Cassandra T.Star Sitter

“Cassandra was absolutely amazing with our cat and high energy dog who was recovering from knee surgery. She went above and beyond to make sure the animals and house were taken care of. I can't recommend her highly enough!”


Macy F.

“We've had less than positive experiences with boarding in the past and our dogs are a rambunctious bunch. They need constant supervision to keep them and the wildlife in our yard safe so house sitting is our only option. Macy took care of everything, stayed for the whole long weekend, and we came home to untraumatized dogs. Would definitely book again!”


Airly S.
About: I have experience in daycare/boarding settings, i have experience with high drive dogs, I do dog sports with my own personal dog so i am pretty confident in my handling skills. I have done years of research on dog related things some including understanding body language, knowing when a dog is uncomfortable or needs to be removed from a situation, what things are good and what are bad, how to use training tools properly if needed, learning the genetics of dog breeds and just over all temperaments that certain breeds have. I grew up on a farm full of dogs and other animals ive always owned dogs especially bully breeds ive been around dogs will all ages, behaviors and sizes my family and friends all know my love for animals and how good i am with them and how much i care about them even when they arent my own. I currently am unemployed, i am a stay at home dog mom and aside from the occasional grocery store run i am at home with my dogs. I will care for your pet to the best of my ability and under any instructions that may be given to me. I will care for your pet like they are my own and keep them as safe as possible while under my care!


Tiffany M.
“I believe Tiffany is actually overqualified in regard to taking care of your fur babies. She goes above and beyond to care for your beloved fur babies. She does everything and more, and I can’t thank her enough for what she’s done for mine.💓 I couldn’t recommend Tiffany enough!!”


Ashley G.

“Ashley was a wonderful sitter! She was very responsive and sent tons of pictures of my two dachshunds. She took such good care of the girls while we were away. We’d love to have her back anytime to sit for Harley and June. 🩷”




Symone G.

“Honestly we felt extremely comfortable leaving her with our two pets. My boy dog absolutely fell for her. She kept us updated and did informed us when something was out of her control. Will be rebooking when go for our next trip.”


Joseph F.
“As someone who’s worked with Kuru training Millio (husky, 6 months), I’ve seen her pick up his quirks quickly, adjust her approach effortlessly, and always keep him comfortable and secure. She’s practical, considerate, and genuinely invested in each pet’s well-being. I trust her to deliver reliable, loving care every time.”


David S.

“David did a great job caring for our pups, and handled some extra responsibility at the last minute very well. I would definitely recommend him!”


Trevor T.

“Very good communication’s house was left clean and dogs seemed very happy.”


Jennifer R.
About: I’ve taken care of pets since I was 17. I’ve help family and friends care for pets when I babysit their children. I loved being around the pets and children which is why I use my extra free time to provide attentive and loving care to others babies and fur babies as well! I currently work from home full time, so I have plenty of time to spend with your fur babies. They would have my attention and care at any time needed as I have more than enough time on my hands. I live in an apartment complex close to the beach, so I am open to caring for them in your home or mine! Whichever works best for you!


Yuna L.
“Yuna is an amazing dog sitter and walker! My husband and I have had her keep our somewhat anxious and reactive dog Morty 3 or 4 times and every time Morty comes back to us content and ready to continue life at his normal pace and schedule without needing to be retrained on anything! She’s the best.”


jessie l.
About: I work at Banfield in Newport News as a vet assistant. I currently have a senior dachshund named Leo who’s great with other dogs and cats. My work schedule varies month to month. I can walk dogs or take care of pets in your home if my work schedule allows, or I can board in my house (dog friendly dogs/cats or small animals). I also have years of experience medicating dogs, cats, and small animals, and can trim nails on dogs and cats. I work 10 hour shifts, 4 days a week at Banfield. It varies each week but I do get a monthly schedule each month. I usually get my monthly schedule at the beginning of the previous month I usually take my dog out every 3-4 hours to go potty while I’m home. If your dog has a routine he/she follows, let me know and I can accommodate!


Kellee B.

“Kellee looked after Peluche for a week, and he had a great time! She sent us pictures of him and kept us updated. She left the house cleaner than she found it!”


Melanie H.

“Melanie was very communicative and my dogs seemed to love her!”


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.
How Rover works
1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
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 house 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.
House Sitting FAQs
Frequently asked questions about Rover
House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Winter Harbor Haven on Rover as of Aug 2025 was about $38 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.
As of Aug 2025, there are 349 house sitters in Winter Harbor Haven. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 91% of Winter Harbor Haven house sitters respond in under an hour.
House sitters in Winter Harbor Haven have an average of 17 years of experience. House sitters with repeat customers have an average of 4 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Winter Harbor Haven.
Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Winter Harbor Haven house sitters are great for:
- Dogs who’d prefer to stay on their home turf
- Cats and caged pets
- Pet parents on a tight schedule
- Keeping an eye on your home and plants while you’re away
Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your house sitter 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 house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.
