House Sitting Osborn Landing

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Osborn Landing, 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.

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Sitter Profile Image: Katy W.
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Katy W.
Star Sitter
from
$50
per night
5.0 out of 5 stars
70 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: Christina S.
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Christina S.
Star Sitter
from
$75
per night
5.0 out of 5 stars
250 reviews
115 repeat clients
15 years of experience
Williamsburg, VA, 23188

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!

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

We have found our forever pet sitter! Oli was there for my husband and I as we welcomed our son into this world (a week early!) and the comfort she provided by taking such diligent care of our pets was invaluable. Oli is kind, organized and genuinely loving towards animals.

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Emma H.
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 love having her stay with them! She loves on them and treats them the way we do. Thank you for being amazing and so helpful. Will definitely work with her again.

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

Ashton was great with our two huskies for a week-long stay. She kept us updated with pictures and the pups clearly loved their walks and cuddles. She was in regular communication and very responsive. We hope she will be available in the future for another stay!

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Mariruth L.
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: 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: Allyson B.
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Allyson B.
from
$40
per night
4.8 out of 5 stars
58 reviews
17 repeat clients
15 years of experience
Henrico, VA, 23231

Allyson was responsive and always sent pictures and updates while we were away, which put my mind at ease! My dog and cat seemed very happy and calm with her care, and everything with our home was in order / clean upon our return. Would use Allyson again to watch our fur babies!

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Emma W.
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: 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: Chelsea W.
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Chelsea W.
from
$75
per night
5.0 out of 5 stars
11 reviews
2 repeat clients
14 years of experience
New Kent, VA, 23124

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.

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Kathleen S.
Sitter Profile Image: Isaiah M.
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Isaiah M.
from
$40
per night
5.0 out of 5 stars
2 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: 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: Samantha K.
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Samantha K.
from
$50
per night
1 repeat client
20 years of experience
Shacklefords, VA, 23156

About: I have experience with all animal types including dogs, cats, horses, livestock, birds, pocket pets and some reptiles. I am a licensed vet tech so I am also comfortable medicating animals that need it. I have 7 dogs and 3 cats, all of which are friendly with other animals. I will treat your pets as if they are my own no matter if they are being boarded or just going for a walk. Please feel free to ask any questions regarding your pets and their needs while you are working, vacationing, etc. I can care for pets early before work, mid-day and late after work. On weekends my schedule can be more flexible depending on what activities I have going on. Any dogs that come into my home will be treated as if they were my own. I have a fenced backyard for the dogs to play in. Boarding dogs will have their own room to hang out in.

Sitter Profile Image: Melanie C.
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Melanie C.
from
$65
per night
4.7 out of 5 stars
27 reviews
4 repeat clients
17 years of experience
Church Hill, Richmond, VA, 23223

Melanie was amazing! She watched our dog for the weekend, and saved us after another sitter had cancelled. She was communicative and kept us updated the whole time with photos and videos. She’s super sweet and reliable. We will definitely book her for future stays.

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Carter D.
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

Caitlynn is the best! My dog can be very stubborn with strangers but he warmed up to her immediately. She took great care of him and of the house while I was away, can’t recommend her enough and I will definitely be using her again in the future!

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Rhett M.
Sitter Profile Image: Nicole S.
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Nicole S.
from
$50
per night
15 years of experience
Williamsburg, VA, 23185

About: I’ve take care of pets since I was 12 years old. I currently own 2 German Shepherds, a golden retriever, a Australian Shepherd/husky mix and 3 chinchillas. I’ve kept puppies all the way to senior dogs, cats even cared for horses before. Currently I work full time but would be available to stay overnight and check in mid day. My schedule is typically M-F 7am to 6pm with a two hour break from 12-2. At this time I only offer in your home sitting. I will walk your babies for as long as needed or let them in the yard if it is fenced and play with them. I can crate if needed while I’m gone. Rest assured your babies will be spoiled to bits by the time you come home (:

Sitter Profile Image: Marina S.
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Marina S.
from
$30
per night
5.0 out of 5 stars
3 reviews
10 years of experience
Richmond, VA, 23225

Marina was fantastic highly recommend her great communicator and Butch loved having her watch him

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Babs P.
Sitter Profile Image: Alexandria Y.
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Alexandria Y.
from
$27
per night
4.9 out of 5 stars
8 reviews
4 repeat clients
15 years of experience
Williamsburg, VA, 23185

Ally is great and I appreciate how much she cares about Muffin

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Sharon R.
Sitter Profile Image: Lauren K.
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Lauren K.
from
$55
per night
4.8 out of 5 stars
6 reviews
1 repeat client
30 years of experience
Hopewell, VA, 23860

Lauren was great. Super friendly and could tell she truely cared about taking care of our dog and 2 cats. She sent pictures and updates and asked questions to make sure she was doing everything right. She was accommodating with a more last minute booking to house sit for a weekend. Would definitely reccomend Lauren!

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Leila C.
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The median cost per night for house sitting in Osborn Landing is $50

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.

Meet local sitters who will treat your pets like family

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

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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 August 2026, there are 1,244 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:

  • 94% 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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