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

Every sitter passes an enhanced background check. Learn about RoverProtect
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.
“Ireland was amazing to work with! She was so great communicating, sending pics and updates through her stay. My pup absolutely loved being taken care of by her and was definitely sad when the trip ended. Definitely would book again!”
About: I have over 6 years of experience caring for a wide variety of dogs and cats. I am a dedicated pet caregiver comfortable working with everything from energetic large breeds to gentle small companions, meaning I can handle everything from high-energy power-walkers to smaller, more delicate breeds. What sets me apart is my commitment to your pet's routine and safety. I’ve lived with and cared for over five different cats, so I’m an expert at reading feline body language and providing the right level of attention. Whether your dog needs a vigorous walk or your cat needs a quiet companion for play and feeding, I provide detailed updates and photos so you have total peace of mind. I am reliable, punctual, and treat every animal like my own family. I am currently focused on pet care full-time while I am between jobs, meaning I have a very flexible schedule and wide-open availability. I can accommodate early morning walks, mid-day drop-ins for lunch breaks, or late-evening check-ins. Because I am highly available, I can provide your pet with plenty of focused attention and reliable consistency throughout the week. Safety is my top priority. When caring for pets in your home, I ensure all doors and gates are securely locked and follow your specific instructions to the letter. On walks, I am always alert and aware of my surroundings, especially when handling larger breeds. I believe trust is built through communication, so I always provide detailed check-in notes and plenty of photos so you know your pet is safe, happy, and well-cared for.
“I entrusted Christina with my beloved Prada while I attended a graduation, and she exceeded every expectation. I was away from home for nine hours. From the moment she arrived—right on time—it was clear that she genuinely cares about the animals in her care. Christina followed all of my instructions for Prada perfectly and kept me connected throughout the evening with sweet pictures that gave me such peace of mind. Prada took right up with her, which speaks volumes about Christina's gentle, confident approach with animals. What impressed me most was the combination of professionalism and genuine heart. Christina isn't just going through the motions—she truly loves what she does, and that makes all the difference. Knowing Prada was in such capable, caring hands allowed me to be fully present at the graduation without worry. I am more than pleased and would absolutely recommend Christina to anyone looking for a pet sitter they can trust completely. The peace of mind she provided was priceless. Thank you, Christina, for taking such wonderful care of our precious Prada! 🐾”


About: I have lived with dogs my whole life and am comfortable with all sizes and breeds, as well as cats. I am a collegiate soccer player, so any activity level is no problem for me! I have about 5 years of experience house and pet-sitting for neighbors and family friends. I am comfortable giving pets medication and taking them for long runs/walks. I am currently taking two online courses at Virginia Wesleyan University over the summer. I have responsibilities to practice and stay fit for the women's soccer team. I am free every day of the week aside from a few travelling trips and will devote all of my attention to your animals! I will be sure to provide the utmost standard of care to my client's homes and pets. No task is too much. Beyond caring for the animals, I can aid in chores and house upkeep. No pet will be put in an unsafe situation or made to feel stressed out under my watch.
About: I have taken care of all kinds of animals cats, dogs, fish, and even plants! I love to help my friends, family, and more with walking their dog, feeding their cat, or watering plants! I work only a few days a week because I’m a stay at home mother so I would give your pup all my love. I’m available during the week from 11am - 8pm. I take my dogs on walks as well as play fetch at least once a day! I feed them twice a day and let them out every 2-3 hours. If i dog/cat sit for someone I go to their house 2 times a day to feed, walk, or whatever else I’m instructed to do.
About: Hello! I am Julia Whatley. I am a young professional on the Hampton roads and richmond area.I am 25 years old. I am a triplet with a younger sister and I have 1 dog. I have taken care of my own dog for 7 years. I love all dogs and I can't wait to help out with other dogs. I will take great care your dog. I also babysit and love pets and kids. I have experience house sitting, pet sitting and babysitting. I currently work remotely and have a very flexible schedule. I work remotely full time and have a very flexible schedule. My routine varies week to week but also gives me a lot of flexibility and availability. My family has had a dog for 10 years and I have experience with many different dogs and cats. As I babysit and often as part of the responsibility includes pet-sitting. I can stay at your home or drop by to feed your pet and provide company. (whatever you may need)
“Jenny was wonderful!!! My two pups normally take a bit to warmup to new people but at the meet and greet they both clearly showed a liking to her. Jenny watched my pups in my home and messaged me several times a day and sent pics to let me know how things were going. This was very comforting for someone like me, with having anxiety with leaving them. My house was as clean as I left it, and I was very grateful that she brought in my packages as they were delivered. I would recommend Jenny, we will definitely be asking her to watch our pups again!!! Thank you so much Jenny, for easing my mind with my sweet babies and taking such great care of them😊!!!”

About: I am open to caring for any and all pets. As someone who currently has 3 Great Pyrenees, an Austrian Kelpie puppy, and other pets, I am experienced in all areas and types. I have open availability to care for pets. I work for myself so build my schedule around jobs and appointments as needed. I am very flexible with accommodations so please reach out if you have any questions. I do not offer overnight in home care at the moment due to all of my pets at home but will gladly stay at your home with your pet. I can send pictures and videos of your pet to you and don't mind cameras in the home so you can drop in any time and see your fur and/or scaly baby.
“If I could give Renee 10 stars I would. She is amazing - kind, responsive, thoughtful, genuinely cares and showed a lot of heart while taking care of our very elderly cat when we were out of town. She kept us posted, gave us updates, sent us pictures, and was simply a delight. When we returned from our trip Renee had taken care of everything, made sure everything was tidy, and my cat was relaxed and happy and clearly well loved. Knowing our beloved pet (and family member) was in such good hands allowed me to actually relax!!!, which is priceless. I recommend Renee with lots of enthusiasm and zero reservations. She's a lifesaver!”

“Talaya took excellent care of Duke, walks and enrichment activities. I think he’s disappointed she wasn’t back again today! Looking forward to the next trip knowing he’ll be in great hands. 🐾💜”

About: I’ve been a lifelong dog lover and have years of hands-on experience caring for dogs of different breeds, sizes, and personalities. I grew up with my own dogs, including a German Shepherd named Brownie and a Pitbull named Peanut, who both lived long, happy lives to 12 years old. Taking care of them taught me the importance of patience, routine, exercise, and lots of love. In addition to caring for my own pets, I have experience dog sitting for multiple dogs at once. I’ve cared for up to six dogs at the same time, managing different breeds, energy levels, and needs while making sure each dog gets attention, supervision, and proper care. I understand how important it is to trust someone with your pet, so I focus on keeping dogs safe, comfortable, and happy while their owners are away. Whether it’s walks, playtime, feeding, or just keeping them company, I treat every dog like they’re part of my family. Please Note: I Travel With My Children If you are interested in Housesits. Pet care fits naturally into my daily routine because I genuinely enjoy being around dogs and staying active. I work from home with a flexible schedule, which allows me to plan my day around walks, feeding times, playtime, and check-ins. This flexibility helps me give pets consistent attention and make sure they stay on their normal routine. Whether it’s daily walks or overnight sitting, I focus on keeping dogs safe, comfortable, and well cared for while their owners are away. When caring for pets, I focus on keeping them comfortable by following their normal routine as closely as possible. In a client’s home, I make sure pets are fed on schedule, have fresh water, get plenty of exercise through walks and playtime, and receive lots of attention so they feel safe while their owner is away. I also keep the home tidy and respect the pet’s space and habits. For walks and drop-ins, I make sure dogs get safe, enjoyable exercise while paying attention to their energy level, behavior, and surroundings. I always prioritize safety, including secure leashes, awareness of other animals, and making sure pets return home happy and relaxed. I treat every pet like they’re my own and aim to create a calm, caring environment where they feel comfortable and well looked after.

About: What sets me apart is my patience, reliability, and genuine love for animals. I take the time to learn each pet’s personality, routine, and needs so they feel safe and comfortable while their owner is away. I have experience caring for a variety of animals and understand the importance of maintaining feeding schedules, exercise, playtime, and a clean environment. I’m also attentive with shy pets, energetic puppies, and senior animals who may need extra patience and gentle care. My goal is to provide dependable care so both pets and their owners feel completely at ease. Caring for animals fits well into my daily routine because I enjoy being active and spending time with pets. I make sure my schedule allows time for feeding, walks, playtime, and check-ins so pets stay on their normal routine. I focus on giving them attention, exercise, and a safe environment so they feel relaxed and cared for while their owners are away. When caring for pets, I prioritize their routine, safety, and comfort. I follow the owner’s instructions closely for feeding, exercise, medication, and any special care they may need. I make sure pets receive plenty of attention, playtime, and regular check-ins. When caring for pets in a client’s home, I keep their environment clean and calm so they can stay comfortable in a familiar space. My goal is to provide consistent, loving care that keeps pets happy and owners worry free.
About: I’ve grown up with animals my entire life! My dream job was to be a veterinarian until I realized I’d probably get attached to the animals haha. I’ve been house/pet sitting for relatives for the past 4 years now and I love it!! I love being able to take them to dog parks, playing, or even just having a chill day! I also love to spoil the pets by buying extra toys to play with and some good snacks! I think doing rover and being able to care for others pets will be a great way to spend my time since I love animals! I update my calendar every 2 weeks and communicate through my inbox! If there’s a note given on specific times to feed or walk I’ll follow them exactly as written. I won’t ever do something without asking/notifying the owner. I’d spend quality time with the pet and try to get them to trust me and build a bond!
About: I have taken care of dogs since I was around nine years old. Growing up I had two dogs who were diabetic so as a result, I have learned how to deal with stressful medical situations regarding animals, including seizures and regular medication schedules. I also work at a doggy daycare currently, and as a result, I have picked up very useful skills for pet sitting, including medication administration, restraint, de-escalation procedures, and so much more! Pet care fits great into my schedule! I work early mornings starting at 6-6:30am In person. This means I can get up as early as your dog needs for breakfast, walks and other potential needs. I work Until about 1 pm and I am free the rest of the day with varying off days each week. Pets cared for in my home will be confined to a basement appt for roaming the house. They will have plenty of beds, toys and love coming from me and other members of my family. They also would have a fun little friend (my dog truffles). In your home It is relatively the same. I will not open any doors/ cabinets/ drawers I don’t need too. I will clean up after myself and your dog consistently and do any daily maintenance tasks for the animals required in your home. Basically I will follow whatever the house rules are!
About: I have my certification in Veterinary Science & I absolutely love animals. Just being able to care for them and make sure their lives are greatly met just makes me so happy I’m currently working part time so I’ll have plenty of time to care for your extended family members! If you get with me we can create a schedule that works best for the both of us I always make sure I have my eyes on the fur babies. Always want to make sure they are safe & in a healthy environment
How Rover works

1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets
2. 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 away
3. 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 night for house sitting in Winter Harbor Haven is $40
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.
Sitters in Winter Harbor Haven average 4 repeat house sitting clients
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 Jun 2026 was about $40 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 Jun 2026, there are 352 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.






