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

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

“Linda is my go-to dog and house sitter. When planning a trip, the first thing I do is try to get on her calendar! She always goes above and beyond when staying with Harley, and makes my being gone so easy and worry free.”

“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!”

“Christina did a great job of taking care of our pet family! They were all very healthy and happy when we got home! She was very communicative and sent many pictures which was very much appreciated!”

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: 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.
“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😊!!!”

“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 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.
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)
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: 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 around pets my entire life, especially pit bulls, and I’m very comfortable caring for strong, energetic, and affectionate dogs. I understand the importance of structure, patience, and positive reinforcement, and I treat every dog with the same love and respect I give my own. In addition to dogs, I’ve also cared for two beautiful tuxedo cats, so I’m familiar with meeting cats where they are—whether they’re playful, independent, or just want a quiet companion. Having pets of my own has taught me how important trust, routine, and attention are, and I always make sure animals feel safe, loved, and at home while in my care. I work from home, which gives me a very flexible schedule and allows me to be fully present for the pets in my care. Because I’m home throughout the day, I’m able to provide frequent potty breaks, walks, playtime, feeding, and lots of attention rather than leaving pets alone for long periods. I can easily adjust my day to match your pet’s routine, whether that includes early morning walks, mid-day check-ins, medication reminders, or extra cuddle time. My flexible work-from-home schedule also allows me to respond quickly to any needs that come up and gives me the freedom to focus on keeping pets comfortable, happy, and well cared for at all times. Safety and trust are my top priorities when caring for pets. I live in a pet-friendly apartment community with plenty of dogs and a designated dog park, which provides a safe and social environment for pets to get exercise and enrichment. I always supervise playtime at the dog park and only allow interactions that are positive and appropriate for each pet’s temperament and comfort level. In my home, I maintain a clean, calm, and pet-safe environment. I follow each pet’s routine closely, including feeding schedules, potty breaks, walks, medications, and any special instructions provided by owners. Pets are never left unattended outside, and I ensure doors, leashes, and gates are always secure. When caring for pets in a client’s home, I respect their space and stick to their pet’s established routine to minimize stress. I provide regular updates, photos, and communication so owners feel confident and at ease while they’re away. Whether in my home or yours, I treat every pet with patience, attentiveness, and the same level of care I would want for my own animals.
About: I am a dog lover and I’m comfortable with all breeds. I had multiple pets including a dog and cat that I took care of growing up. I currently have no pets but have recently taken care of friends’ dogs. This has included overnight and daytime boarding at my house while taking care of all walking, playing, and feeding needs. I’m currently working PRN (part time) as a physical therapist and I have a lot of flexibility and freedom in my schedule. I’m looking to fill some of this free time with something that I’ve always enjoyed, taking care of pets. I am trustworthy, clean, and respectful of others homes when entering to care for their pets. I am happy to walk your dog wherever they normally like to go around your home.
“Chelsea is an amazing and professional dog sitter. She made the extra effort to gain our rescue dog’s trust before we left town with get to know visits. While we were gone she gave regular updates and photos. I always felt confident and secure leaving our dogs in her care. She is transparent and trustworthy. My dogs were secure and happy on our return.”

The median cost per night for house sitting in Winter Harbor Haven is $45
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.

Why Choose Rover?
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 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.
How Rover works
1. Search
Browse profiles of sitters near you who offer house sitting2. Meet & Greet
Schedule a free in-person Meet & Greet to find the perfect fit3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests near you
Select a filter and find qualifying Winter Harbor Haven sitters!Sitters in Winter Harbor Haven average 4 repeat house sitting clients
FAQs for House Sitting - Winter Harbor Haven
Frequently asked questions about Rover
As of June 2026, there are 862 sitters on Rover offering House Sitting across Winter Harbor Haven. Enter your ZIP code to see which available sitters are closest to your home.
Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:
- Mail & deliveries: Collecting letters and packages so they don't pile up.
- Plant care: Keeping your indoor or outdoor garden hydrated.
- Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
- Home security: Sitters can stay overnight to keep your home occupied.
The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Winter Harbor Haven walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.
It’s helpful to think of house sitting as a "home base" service. Most sitters in Winter Harbor Haven maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:
- Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
- Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
- Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.
Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Winter Harbor Haven choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.
All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.
Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .
If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.
For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.
Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.
A Meet & Greet is a short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter 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 sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.
Yes, you can find sitters who have experience with handling special pet needs in Winter Harbor Haven. On Rover:
- 94% of sitters can help with special care needs
- 98% can help with giving oral medications or injections
- 100% 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.



