House Sitting in Cheapside

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

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Top rated Cheapside house sitters

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: Margaret H.
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Margaret H.
from
$50
per night
5.0 out of 5 stars
5 reviews
2 repeat clients
10 years of experience
Cape Charles, VA, 23310

About: I have always loved animals and always been around them in my home. I have years of experience with feeding, exercising, and providing enrichment for both cats and dogs. I understand the importance of making sure they feel comfortable as well as respected during our time together. My goal is to ensure that your pet is happy, healthy, and cared for when you need a little extra help! I’m currently working part time, and have plenty of time to hangout with your fur babies. With my current seasonal hours slowing down, your pets can be guaranteed a sitter with pretty open availability! I have a large backyard and one level home for your fur baby. I have access to 5 miles of shaded and accessible trails as well as a dog friendly beach. My furniture is meant to be enjoyed by four-legged friends and I love taking them on “field trips” to many of the natural areas I have access to!

Sitter Profile Image: Anna Mei D.
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Anna Mei D.
Star Sitter
from
$30
per night
4.9 out of 5 stars
111 reviews
42 repeat clients
13 years of experience
Greater Wythe, Hampton, VA, 23661

I am so glad we found Anna to take care of our dogs while we’re away. She sent me daily photos, updates, and communicated any questions or concerns in real time. I have a puppy who is very anxious/skittish around new people. Anna recognizes her body language and works with her to meet her needs at her comfort level - by the end of Anna’s stay at our home, my puppy was willingly sitting in her lap! She doesn’t do that for ANYONE so to me this is an excellent reflection of the way my pets were cared for while in Anna’s care. She did a great job following their routines and went above and beyond to keep them happy while we were gone. My home was treated respectfully and in the same condition I left it when I returned. We already have Anna booked for another stay and look forward to working with her again in the future.

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Clarissa T.
Sitter Profile Image: Felicia H.
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Felicia H.
Star Sitter
from
$26
per night
5.0 out of 5 stars
18 reviews
4 repeat clients
5 years of experience
South Norfolk, Chesapeake, VA, 23324

Felicia was amazing! We came home to happy dogs and a clean home. Thank you for everything. We’ll be in touch for another upcoming trip we’ll need your services for!

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Tiffany L.
Sitter Profile Image: Emmanuel S.
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Emmanuel S.
Star Sitter
from
$40
per night
5.0 out of 5 stars
14 reviews
5 repeat clients
10 years of experience
Norfolk, VA, 23508

Emmanuel was an amazing pet sitter! He watched my 5 fur babies while I was gone for a week and they got along with him so well! He was very attentive to my fur babies and he enjoyed time spent with them! He treated them like they were his own. He was very communicative, providing me daily updates with adorable pictures and videos! He even got my antisocial cat to warm up to him and interact with him, which was a 1st! He also did a great job keeping the place clean while caring for the fur babies. I feel like my pets definitely lucked out with having an amazing sitter and new friend! I would highly recommend booking Emmanuel as your next pet sitter!

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Frantaisia R.
Sitter Profile Image: Alondra A.
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Alondra A.
from
$15
per night
4.5 out of 5 stars
9 reviews
1 repeat client
4 years of experience
Norfolk, VA, 23518

Alondra was a joy to work with and the dogs loved her!

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Erin D.
Sitter Profile Image: Elijah H.
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Elijah H.
from
$55
per night
5.0 out of 5 stars
8 reviews
4 years of experience
Norfolk, VA, 23509

Elijah was polite and friendly to us and our reactive rescued pocket bully. He was willing and able to handle her complex feeding instructions, walking peccadillos, and anxieties about people and dogs. Farah looked more relaxed with him in photos he sent than she did with her last pet sitter. Elijah also offered to do any light housekeeping chores we needed, wiped down counters before he left, and even did his own laundry and made up the bed again. Highly recommend!

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Katherine A.
Sitter Profile Image: Alexandria A.
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Alexandria A.
from
$24
per night
4.7 out of 5 stars
10 reviews
5 repeat clients
17 years of experience
Northwest, virginia beach, VA, 23455

Frequently checked in and spent time with our dogs while we were out of town. It gave us such an ease of mind that they were being so well taken care of care of.

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Jacquelyn I.
Sitter Profile Image: Jessica L.
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Jessica L.
from
$45
per night
5.0 out of 5 stars
2 reviews
1 repeat client
28 years of experience
Cape Charles, VA, 23310

About: From a very young age, my family had all kinds of animals. I have experience with many breeds of dogs, including Rottweilers, pit bulls, hunting dogs, and rescues, along with horses, pigs, a variety of birds, and hampsters, chinchillas, and a guinnea pig! I was a large animal vet tech (horses, cattle, goats and farm dogs!) before becoming a nurse, and I also grew up with a dog who had diabetes, and have helped several friends treat their puppies at home for Parvo. Also being a nurse, I'm very comfortable with giving injections, wound care, and coaxing your fur baby to take meds :) I work full time, but that still gives me 4 days off a week. I love to be outside and spend my time with animals, walking dogs is a great way to do both! I can be pretty flexible and early morning/late night visits to check on your critters aren't an issue at all for me. Hope to hear from you soon!

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

Before booking Monika, I was pretty nervous about leaving Rosie with someone I didn’t know. I felt so much better after our meet and greet because of how sweet and professional she was. Throughout the whole process of being away Monika was very communicative, providing ample pictures and Rosie updates. I seriously couldn’t have asked for a better experience or a better person to watch Rosie. I highly recommend her as a top quality caregiver for anyone’s pup!

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Kevin W.
Sitter Profile Image: Antonio & Taylor S.
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Antonio & Taylor S.
Star Sitter
from
$180
per night
5.0 out of 5 stars
91 reviews
31 repeat clients
3 years of experience
Northwest, Virginia Beach, VA, 23462

Antonio did a great job with my crew. He was incredibly responsive and thorough. I have a head strong arthritic German shepherd, a pit mix (couch potato), and a relatively anxious/hesitant husky mix…as well as a cat who acts like he’s a dog and attempts to escape whenever possible. I’m always hesitant whether a sitter is prepared to manage multiple large dogs, but Antonio had no issues. We came home to a clean home and happy pets, which is all I can ask for!

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Adina D.
Sitter Profile Image: Emma J.
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Emma J.
from
$55
per night
5.0 out of 5 stars
4 reviews
2 repeat clients
8 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: Brittany B.
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Brittany B.
from
$40
per night
5.0 out of 5 stars
13 reviews
7 repeat clients
10 years of experience
South Norfolk, Chesapeake, VA, 23324

Brittany was fabulous and even my Lab who is afraid of everyone accepted Brittany pretty quickly. She was great with pictures and updates!! Highly recommend!

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Scott J.
Sitter Profile Image: morgan d.
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morgan d.
from
$30
per night
5.0 out of 5 stars
3 reviews
8 years of experience
portsmouth, VA, 23464

⭐⭐⭐⭐⭐ If you are looking for someone to trust completely with your fur babies, look no further than Morgan — she is absolutely exceptional! We were away for two full weeks on an international trip to Dubai and Egypt, and the only reason we could truly relax and enjoy every moment of our travels was knowing that Zack and Gia were in Morgan's loving, capable hands. That peace of mind is priceless. Morgan didn't just "watch" our dogs — she genuinely cared for them as if they were her own. Two weeks is a long time to be away from your pets, and she made the whole experience seamless and stress-free. We came home to two happy, healthy, well-loved pups who were clearly comfortable and content the entire time we were gone. Her communication was top-notch — responsive, reassuring, and she kept us updated without us ever having to wonder how Zack and Gia were doing. That level of attentiveness says everything about her dedication and professionalism. Morgan is warm, trustworthy, and truly passionate about the animals in her care. She has earned a client for life, and we cannot recommend her highly enough. If you want your pets treated like royalty while you're away, Morgan is your person — 10 out of 10, without hesitation!

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Dionne W.
Sitter Profile Image: Angelena P.
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Angelena P.
from
$65
per night
4.9 out of 5 stars
13 reviews
4 repeat clients
15 years of experience
Northeast, Virginia Beach, VA, 23454

Angie is absolutely amazing. Took a last second booking and was able to stay at the house and watch the dogs. The dogs loved her, the house was taken well care of during her visit. Would recommend 10/10. If we leave town, we will be rebooking.

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Dylan C.
Sitter Profile Image: Ashiyah P.
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Ashiyah P.
from
$22
per night
5 years of experience
Mercury Central, Hampton, VA, 23666

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.

Sitter Profile Image: Grayson Y.
Verified Enhanced Background Check
Grayson Y.
from
$26
per night
2 years of experience
Virginia Beach, VA, 23455

About: I’m patient, reliable, and great with all pets! I have experience with basic puppy training and making sure pets stay active and happy. Your pet will get lots of love and attention while you're away! Pet care fits really naturally into my daily routine. As a nursing student, I spend a lot of time studying, so having a pet actually helps me stay balanced. I like to use walks as study breaks because they give me a chance to clear my head and reset, especially when coursework gets intense. Morning walks are my favorite—they help me start the day feeling calm, focused, and energized. Caring for a pet fits well with my schedule because I’m already used to planning my time carefully, and it’s something I genuinely enjoy rather than see as a chore. I provide a safe, comfortable space and follow your pet’s routine. Whether in my home or yours, I make sure they get food, exercise, playtime, and plenty of attention!

Sitter Profile Image: Lisa Marie S.
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Lisa Marie S.
from
$105
per night
5.0 out of 5 stars
9 reviews
4 repeat clients
20 years of experience
NORFOLK, VA, 23503

Lisa did an amazing job house sitting the week we were out of town. She was very accommodating with our last minute request/booking, and was very knowledgeable on working with pets, therefore streamlining this whole process. She was very communicative and always kept us in the loop of the wellbeing of our pets while we were gone. As a house sitter, Lisa displayed many signs of etiquette and respected our property. All-in-all, I'm in a much more calmer state of mind knowing that whenever I need to take vacation, I know who to call. Thank you so much Lisa! <3

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Ethan J.
Sitter Profile Image: Kathleen S.
Verified Enhanced Background Check
Kathleen S.
from
$50
per night
8 years of experience
Virginia Beach, VA, 23455

About: I grew up in a home with at least two dogs and a cat, so it’s no surprise I’m the person at a gathering who ends up saying hi to the pets first. I’ve always had an easy connection with animals, and I’m comfortable reading their body language while respecting their routines, boundaries, and comfort levels. Over the past few years, I’ve become the go-to sitter in my friend group (and for friends-of-friends) because I’m dependable, attentive, and genuinely love spending time with pets. I have experience with both dogs and cats of all sizes and ages—from playful puppies and curious kittens to sweet senior pets who need a slower pace. Whether your pet loves long walks and playtime or prefers quiet companionship and cuddles, I’ll make sure they feel safe, cared for, and happy while you’re away. I’m happy to follow detailed instructions (including how long your pet can be alone), and I can provide regular photo updates. I’m also comfortable administering oral medications and supporting pets with health-related care needs as directed. I have an extremely flexible schedule and work from home, so pet care fits naturally into my day. Because I’m in full control of my routine, I can adjust my availability around you and your pet’s needs—whether that means morning/evening walks, midday drop-ins, frequent potty breaks, or keeping your pet company throughout the day. I’m reliable about sticking to feeding and medication schedules, and I’m happy to tailor my visits to match your pet’s normal routine. I tailor my care to each pet’s routine and comfort level! I grew up with dogs and cats and have experience with pets of all sizes and ages (from puppies/kittens to seniors), so I’m comfortable adjusting my approach based on energy level, temperament, and any special needs. For every service, safety and consistency come first: I follow your instructions closely, keep feeding and potty schedules on track, and make sure pets get the right balance of exercise, play, and calm companionship. I love long walks and outdoor time for dogs who enjoy exploring, and I’m equally happy providing quieter care for pets who prefer a slower pace. I’m comfortable administering oral medications as directed and supporting pets with health-related routines. If I’m caring for pets in your home (drop-ins, walks, or house sitting), I treat your space with respect, keep things tidy, and aim to keep your pet’s day feeling as normal as possible. When house sitting, pets aren’t left alone for more than 4 hours. In my home (boarding or daycare), pets get a calm, attentive environment with plenty of supervision, affection, and structured breaks, and I only take pets I can safely and comfortably care for. Throughout every booking, I provide regular photo updates so you can relax knowing your pet is happy and in good hands.

Sitter Profile Image: Talaya S.
Verified Enhanced Background Check
Talaya S.
from
$30
per night
5.0 out of 5 stars
1 review
1 repeat client
5 years of experience
North King St, Hampton, VA, 23669

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. 🐾💜

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Bridget J.
Sitter Profile Image: Yazmine L.
Verified Enhanced Background Check
Yazmine L.
from
$60
per night
5.0 out of 5 stars
3 reviews
7 years of experience
Newport News, VA, 23601

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!

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  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 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. 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 Cheapside is $45

Why Choose Rover?

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  • 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 Cheapside 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 Cheapside on Rover as of Jun 2026 was about $45 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.

If you’re searching for a Cheapside house sitter for the first time, visit the house sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 560 house sitters in Cheapside. 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, 87% of Cheapside house sitters respond in under an hour.

House sitters in Cheapside have an average of 15 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 Cheapside.

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. Cheapside 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.


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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