House Sitting Cheapside

Find a loving dog sitter to watch your dog overnight in your home.

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Over 4
pet parents in Cheapside have booked house sitting

Cheapside, 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: Heather K.
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Heather K.
from
$40
per night
5.0 out of 5 stars
• 2 reviews
45 years of experience
Exmore, VA, 23350

About: I left public education after 22 years. I will spoil your pets in your home whenever you are unavailable. I offer 1 hour walk/plays up to 1 month house sitting with animal and plant care. I work from home. I am open for scheduling. I am awake each morning by 5 am, I have 5 silkies and 3 bee hives. I will come to your home where your pet is most comfortable. I will take dogs on hikes if the owner requests. I am very flexible.

Sitter Profile Image: Monika D.
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Monika D.
from
$95
per night
5.0 out of 5 stars
• 25 reviews
6 repeat clients
20 years of experience
Northeast, Virginia Beach, VA, 23451

“Monika did a great job house sitting and watching my fur kids! Left the place spotless and my pets were well cared for! Recommend her for sure”

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Madeline B.
Sitter Profile Image: Alannah B.
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Alannah B.
from
$40
per night
7 years of experience
Northwest, Virginia Beach, VA, 23462

About: My name is Alannah and I am 20 years old. I love animals, I have experience pet sitting, I worked in a kennel and have helped deliver several litters of labs, I have had animals in my household since I was born, and I would love to help you keep your pets happy and cared for whenever you might need the extra help. I am in the military but work a shortened schedule, and I cannot have an animal of my own since I could go on deployments last minute. I love animals, dogs the most, and I would love so much to come take care of any pets and just lend some help. I currently work part time hours so I have plenty of time to care for animals. My average hours are 8-12 am. I have volunteered at some shelters to care for some cats and dogs, and I am actually considering fostering. I just love pets but am not in a stable enough environment to keep one with being in the military and I could have to leave for months on end with no notice. I am very respectful, will follow any and all restrictions / directions, and I have great decision making. I will know what to do to keep your pet safe and happy. Any sort of extra care I have no issue providing I am very attentive and very respectful of not only your wishes but also your space if you invite me to your home. I am eager and excited to help as needed.

Sitter Profile Image: Ana A.
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Ana A.
from
$120
per night
5.0 out of 5 stars
• 3 reviews
10 years of experience
Norfolk, VA, 23503

“Ana did a really good job with my shy girl and gave me lots of reassuring updates through out the weekend. She was also very flexible to do a weekend booking with short notice and she left my house tidy. You can tell that animals really like her.”

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Sanna S.
Sitter Profile Image: Emma J.
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Emma J.
from
$55
per night
5.0 out of 5 stars
• 8 reviews
4 repeat clients
10 years of experience
Norfolk, VA, 23508

“Emma was great and left our place clean. She kept us up to date with pictures. And even got Bear a Christmas present!”

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Jordan E.
Sitter Profile Image: Lacey L.
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Lacey L.
from
$36
per night
5.0 out of 5 stars
• 2 reviews
17 years of experience
Portsmouth, VA, 23701

“Lacey took care of our two dogs for 12 days and kept us updated the whole time. She was great with both of them and even our nervous dog loved her!”

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Sam S.
Sitter Profile Image: Zimir W.
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Zimir W.
from
$90
per night
4.8 out of 5 stars
• 50 reviews
12 repeat clients
21 years of experience
Portsmouth, VA, 23702

“We would highly recommend Zimir! He stayed with our Pit Bull, Cat, Parakeet, and Parrot. He took excellent care of each. Also maintained a clean home. We came to a very happy household. It was obvious that each pet was not only cared for but received attention and love. We would recommend him to any family and appreciated his professionalism and daily photos to assure us while away.”

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Amy Ellen D.
Sitter Profile Image: Helen M.
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Helen M.
from
$50
per night
5.0 out of 5 stars
• 4 reviews
20 years of experience
Norfolk, VA, 23510

About: My family has tradition of owning pugs and now I own my own pet. I've always been around animals from in my own home to looking after my friends pets. I have taken care of labs, poodles and collies to name a few breeds I have dog sat for. I have the patience, friendliness and responsibility to take care of any breed, age, gender and size. I look forward to making new canine friends and believe it will be mutual.

Sitter Profile Image: Hannah J.
Verified Enhanced Background Check
Hannah J.
from
$45
per night
4 years of experience
Chesapeake, VA, 23320

About: I offer peace of mind care to pets and their families when they are in my care! I have pet sat all kinds of pets from cats and dogs! I have well versed in caring for our beloved senior pets and taking care of more than one pet at a time! I come to you and your pet’s home so the pets can be more comfortable in their normal surroundings! I am currently a substitute teacher! I can shape my work schedule around the care for your pets! I am mostly available during the week and weekends. I care for your pets like they are my own! When I come into your home to watch your pets, I let them show me where they like to lay and all their toys. I go out in the yard with them when I let them out! I make sure everyone has enough water and eats all their food! I give treats at the appropriate times!

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The median cost per night for house sitting in Cheapside 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 to book house sitting

  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

    It's that easy! All payments are processed through Rover's secured platform.

Popular requests for house sitting - Cheapside

Select a filter and find qualifying sitters offering house sitting.

Sitters in Cheapside average 4
repeat house sitting clients

FAQs for House Sitting - Cheapside

Frequently asked questions about Rover

The average cost of House Sitting in Cheapside is $47 per night as of October 2026. Most bookings cost between $33 and $54 per night. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of October 2026, there are 1,051 sitters on Rover offering House Sitting across Cheapside. 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 Cheapside 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 Cheapside 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 Cheapside 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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet.

sitters on Rover set their own cancellation policy, which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.

Yes, you can find sitters who have experience with handling special pet needs in Cheapside. On Rover:

  • 89% of sitters can help with special care needs
  • 94% can help with giving oral medications or injections
  • 96% 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.


Rover offers the perfect alternative to dog kennels. The next time you head out of town and need someone to take care of your dog — and your home — turn to Rover for your Cheapside house sitting needs. On Rover, it's easy to find a loving dog sitter in Cheapside who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at home. Search from hundreds of trusted Cheapside house sitters near you, read sitter profiles, and reach out to sitters who seem like a good fit for you and your dog. We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your dog's stay all through Rover — it's easy, safe, and cashless. You get free premium insurance, a team of safety experts available 24/7, and cute photo updates throughout the stay. It's the easiest way to find trustworthy house sitters in Cheapside for your dog — people who'll treat him like family.

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