House Sitting Osborn Landing

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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.

1 / 1
Sitter Profile Image: Katy W.
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Katy W.
Star Sitter
from
$55
per night
5.0 out of 5 stars
71 reviews
15 repeat clients
12 years of experience
Toano, VA, 23168

Katy did a great job with Carmie! It was our first time using her and she was so easy to work with and flexible to come for a meet and greet. Great communication and sent regular updates with pictures.

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Deanna E.
Sitter Profile Image: Tracy D.
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Tracy D.
from
$50
per night
5.0 out of 5 stars
6 reviews
1 repeat client
50 years of experience
Lanexa, VA, 23089

Tracy is awesome! Our babies loved her. She was flexible and helpful. Definitely will want to work with her again. Thank you for loving on my babies! All 4 of them!!!

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Stephanie P.
Sitter Profile Image: Christina S.
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Christina S.
Star Sitter
from
$75
per night
5.0 out of 5 stars
251 reviews
117 repeat clients
15 years of experience
Williamsburg, VA, 23185

Christina is fantastic! Quick to respond and very friendly. She sent lots of photos and kept me updated during the visit. I will definitely be booking with her again!

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Jamie J.
Sitter Profile Image: Ashton V.
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Ashton V.
Star Sitter
from
$90
per night
5.0 out of 5 stars
50 reviews
14 repeat clients
10 years of experience
Williamsburg, VA, 23188

This is our second time using Ashton. The first time was for dog walking and this past week was for overnight home sitting for our dog and three indoor cats. Ashton did a great job of sending us updates and photos. She made sure to use the dog booties when it was scorching hot outside during walks. Our dog is anxious during storms and Ashton kept her close and snuggled with her to try to keep her calm. Good detailed instructions were helpful and appreciated. We are thankful for the care she provided.

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Sharon B.
Sitter Profile Image: Katilyn R.
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Katilyn R.
from
$35
per night
16 years of experience
Providence Forge, VA, 23140

About: Growing up on a small farm with cats & high-energy pups, I ended-up gaining experience as the neighborhood dog & cat sitter in my as a teenager. It was my favorite job I’ve ever had! ☺️ This included stops-in for daily walks, cuddle-times, & feedings; ensuring they play & move when their owners are away. Occasionally administering medications: (including medications that require a needle), and much more. As I got older, I gained experience working in a Veterinarian office. I’ve spent a lot of time with animals of all sizes and temperaments in these environments, including end of life care. I also have my own at home: two old boys. One sweet & feisty, almost thirteen-year-old blind and (nearly entirely) deaf Dachshund named Woody, who loves to be cuddled. Then, there’s my nearly ten-year-old American Foxhound sweetheart, Popeye, who wants to do nothing but play and be told how much of a “good boy” he is. They’re the best boys anyone could ask for. I look forward to hearing from you and how I can help! ☺️ I do same-day bookings for walks. Extra play-time, snuggles, and pets await. Currently, I am home, in-between waiting for Medical Assistant Certification classes to start in January, after 6 years of being a stay-at-home-mother. I am available 8:30AM-3:30PM & 5PM-8PM on M,T,W,TH,F & 8AM-8PM on S&S. I am extremely communicative and committed to respecting the boundaries of your home. If there are specifics to how you would like me to enter & lock your home, then it will be done. As far as taking care of your pets, they will be loved, played with, treated as if they are my own, and fed, walked, & watered (if specified for the job).

Sitter Profile Image: Joseph W.
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Joseph W.
Star Sitter
from
$40
per night
5.0 out of 5 stars
12 reviews
3 repeat clients
5 years of experience
Chester, VA, 23836

First time house sitting for our Bernedoodle and she was well handled by Joey. He took well care of her as usual, played, walked her and gave her medicine. 👍

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James K.
Sitter Profile Image: Oli L.
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Oli L.
Star Sitter
from
$85
per night
5.0 out of 5 stars
112 reviews
35 repeat clients
18 years of experience
Hopewell, VA, 23860

We were looking for someone to house sit for while we were overseas for a few weeks. From the moment we met Oli we knew our pets and home would be in good hands while we were away. Before our trip Oli took the time out to meet our pets and was happy to have all the detailed info about how to take care of them. Last minute our dog needed almost daily meds given while we were away and Oli didn’t hesitate to step up. She sent us multiple pictures and updates throughout the day which is as such a relief! When we came back our house was even cleaner than before and our pets barely greeted us. Which means they had an amazing time with Oli! Thank you so much Oli for your help and if you’re looking a reliable, communicative sitter, she’s your girl!

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Katrina G.
Sitter Profile Image: Linda U.
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Linda U.
Star Sitter
from
$45
per night
5.0 out of 5 stars
137 reviews
48 repeat clients
30 years of experience
Gloucester, VA, 23061

Linda always goes above and beyond what’s required to take good care of the pups. The house is also perfect as well. We use her whenever we can get her.

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Nancy D.
Sitter Profile Image: Mindy J.
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Mindy J.
from
$50
per night
5.0 out of 5 stars
3 reviews
9 years of experience
Quinton, VA, 23141

Mindy was amazing especially with my grumpy senior dog. I have never seen Bucky take to a new person so quickly. She sent photos of my dogs on their walks and checked in with me each day. I can not recommend her enough.

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Samantha W.
Sitter Profile Image: Danielle H.
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Danielle H.
from
$45
per night
4.9 out of 5 stars
15 reviews
4 repeat clients
10 years of experience
Sandston, VA, 23150

Danielle was awesome with our pups and they loved her. She watched over our 2 dogs for several days while we were away, great communication throughout and came home to two happy pups.

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Scott A.
Sitter Profile Image: Michael R.
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Michael R.
from
$125
per night
4.9 out of 5 stars
14 reviews
4 repeat clients
50 years of experience
Quinton, VA, 23141

Michael exceeded my expectations in taking care of my two dogs. Prior to my trip, he came to visit my pups in order to get to know them, observe their behavior, talk about my daily routine, and any special needs. This interaction surely made me feel so much more comfortable in the fact that I could go away and not have to worry about my dogs while being away. I certainly looked forward to his many daily pics and information that he provided to me. In future trips, I will only request Michael because I never had to worry or be concerned about anything. He is definitely a KEEPER and highly recommend him to my family and friends.

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Pamela F.
Sitter Profile Image: Meaghan O.
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Meaghan O.
from
$45
per night
4.6 out of 5 stars
11 reviews
1 repeat client
20 years of experience
Williamsburg, VA, 23188

Meaghan did an awesome job sitting for our 12 week old puppy on Thanksgiving Day! She is an experienced and knowledgeable pet caretaker who loves animals. We highly recommend her.

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Cathy C.
Sitter Profile Image: Isaiah M.
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Isaiah M.
from
$45
per night
5.0 out of 5 stars
3 reviews
1 repeat client
5 years of experience
Chester, VA, 23836

We are so grateful for Isaiah! We had to leave town last minute, and he worked with us every step of the way. He came by beforehand to meet our dogs and has a lot of experience. One of our dogs is a new adoption, and she really only likes me, but he was able to get her to a place where she was comfortable and not stressed around him. That alone says a lot about how good he is. He was accommodating to whatever we needed during the sit and was respectful of our home. When we got back, our pets were happy, relaxed, and acting completely like themselves. We’ve had experiences in the past where you could immediately tell the level of care they received, and this was the opposite. It truly felt like they had been cared for the way we would care for them. Isaiah was that person. We will definitely be reaching out to him again in the future.

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Brienia B.
Sitter Profile Image: Jonas & Rex J.
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Jonas & Rex J.
from
$32
per night
25 years of experience
Williamsburg, VA, 23188

About: I’ve taken care of dogs of all sizes since I was just a kid. My partner Rex has also had dogs growing up. You can count on us to make sure that your pup is well cared for and loved while we watch them. Both myself and my partner have open availability and will be around. We will communicate with you should we need to step out for a moment for any reason. We have a dog of our own named Cap who is a lab/hound mix and four short hair cats (Anri, Mori, JoJo, and Astora). All of our pets have been fixed. When watching your pets we will ensure their safety and make sure that they are well cared for.

Sitter Profile Image: Sarah S.
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Sarah S.
from
$30
per night
1 repeat client
20 years of experience
Henrico, VA, 23231

About: I offer personalized, one-on-one care tailored to your dog’s unique needs, personality, and routine. With a focus on reliability and attentiveness, I make your dog’s comfort and daily schedule a priority. I strive to be a calm, loving presence your dog can trust, helping them feel safe, relaxed, and cared for while you’re away. As a full-time teacher, my weekdays follow a consistent and predictable schedule. I am available for afternoon visits after school, evening care, as well as overnight stays when needed. On weekends, holidays, and school breaks, I have more flexibility and can provide extended care, additional visits, or longer stays. This structure allows me to offer reliable, attentive pet care while maintaining clear communication and consistency for your pet. I care for pets with a focus on comfort, routine, and individual needs, whether in my home or in my client’s home. I follow each pet’s normal schedule for feeding, walks, playtime, and medication, and I take time to learn their preferences and personality. In a client’s home, I respect their space while providing attentive, one-on-one care and keeping pets in a familiar environment. I prioritize safety, cleanliness, and calm interactions, and I communicate regularly with updates so owners can feel confident their pet is happy and well cared for.

Sitter Profile Image: Gayle J.
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Gayle J.
from
$50
per night
40 years of experience
Henrico, VA, 23231

About: I’m 66 but I’m a young 66 year old women. I’d be honored to take care of your pets! I’d take care of them as if they were my own! I’ve had pets all my life (cats, dogs, and etc) I’m currently available at all times and everyday! I have my own transportation. I can always leave at any time to do a drop in for your pet! Night or day! I will follow your instructions closely and obey your house rules. I have many experiences with house sitting and pet sitting and pet sitting within my own home!

Sitter Profile Image: Ion D.
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Ion D.
from
$26
per night
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: Victoria L.
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Victoria L.
from
$65
per night
4.8 out of 5 stars
58 reviews
26 repeat clients
6 years of experience
Williamsburg, VA, 23185

Victoria is great, she is always very responsive and cares deeply for the pets she looks after. You can tell that she loves what she does and that she cares for your pet as if it were her own. My dog absolutely loves her and gets excited every time he sees her. I would definitely recommend her, and will absolutely hire her again in the future.

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Keenan O.
Sitter Profile Image: Caitlynn V.
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Caitlynn V.
from
$65
per night
4.9 out of 5 stars
19 reviews
4 repeat clients
8 years of experience
Quinton, VA, 23141

Caitlyn did a wonderful job watching my two dogs. She always responded in a timely manner and kept us updated. Would definitely book with her again!

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Jordyn F.
Sitter Profile Image: Arianna L.
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Arianna L.
from
$100
per night
5.0 out of 5 stars
73 reviews
22 repeat clients
14 years of experience
Williamsburg, VA, 23185

Arianna stayed at our house with our dog Stella again for over a week and took great care of her, as she’s done several times in the past. She’s a good house guest who always keeps the house the way we left it and Stella adores her. Highly recommend.

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Heather F.
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The median cost per night for house sitting in Osborn Landing is $50

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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
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

Why Choose Rover?

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  • 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.

Meet local sitters who will treat your pets like family

  1. 1. Search

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Popular requests for house sitting - Osborn Landing

Select a filter and find qualifying sitters offering house sitting.

Sitters in Osborn Landing average 4
repeat house sitting clients

FAQs for House Sitting - Osborn Landing

Frequently asked questions about Rover

As of September 2026, there are 1,272 sitters on Rover offering House Sitting across Osborn Landing. 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 Osborn Landing 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 Osborn Landing 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 Osborn Landing 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 Osborn Landing. On Rover:

  • 95% of sitters can help with special care needs
  • 97% can help with giving oral medications or injections
  • 99% 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.

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