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.

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

Jessica was awesome! She clearly has a genuine love of animals and nature. We had a unique situation where we were vacationing in the area. Jessica was flexible to meet our unique needs on short notice and even provided local recommendations for things to do. She was super attentive to our pets and is a lovely person. I cannot recommend her highly enough!!

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Nancy N.
Sitter Profile Image: Margaret H.
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Margaret H.
from
$50
per night
5.0 out of 5 stars
7 reviews
3 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: Ciear J.
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Ciear J.
from
$32
per night
22 years of experience
Cape Charles, VA, 23310

About: Hi! My name is Ciear , and I’m a dependable, caring pet sitter who truly loves animals. I understand how important it is to have someone you can trust with your pets, and I treat every pet as if they were my own. I have experience caring for dogs and cats of different ages, sizes, and personalities — including feeding, walking, playtime, administering basic care, and giving lots of attention and love. I’m patient, calm, and attentive to each pet’s individual needs. I’m reliable, detail-oriented, and great at following instructions. I’ll make sure your pet sticks to their routine and feels safe and comfortable while you’re away. I’m also happy to send updates and photos so you have peace of mind. I have reliable transportation, flexible availability, and I’m comfortable with drop-in visits, dog walking, and overnight pet sitting. Your pet’s safety, happiness, and well-being are always my top priority. I’d love the opportunity to care for your furry family member — feel free to message me with any questions! I'm currently working part time, so I have plenty of time to work with your fur babies, weeken and weekdays im available after 1:30 pm I have plenty of ideas and things to keep your pet busy so they're never bored, I also have a fur baby myself who would love some playtime

Sitter Profile Image: Felicia H.
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Felicia H.
Star Sitter
from
$26
per night
5.0 out of 5 stars
24 reviews
7 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
$50
per night
5.0 out of 5 stars
15 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: Kathleen S.
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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: 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

I am so grateful Elijah was able to care for our dog Louie while my husband and I were out of town for the weekend. He was great at keeping us updated on how things were going, touching base several times a day and sending photos. When we arrived home, Louie seemed calm and relaxed. Our home was left neat and tidy. We look forward to working with Elijah again knowing that we can be at ease leaving Louie in his care.

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Cassandra B.
Sitter Profile Image: Meredyth G.
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Meredyth G.
from
$31
per night
4.3 out of 5 stars
6 reviews
2 repeat clients
11 years of experience
Chesapeake, VA, 23325

Meredyth was awesome with our Bootsy! Took him on lots of adventures with her and her kids which was so nice to see. He had a great time! Would recommend :)

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Bianca M.
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 was great. Lucy loves her. This is the 2nd time of house sitting we had with her and we came to a clean house both times. Will definitely recommend her and will call her up in the future.

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Rohit B.
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: Jennifer M.
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Jennifer M.
from
$50
per night
5.0 out of 5 stars
21 reviews
6 repeat clients
10 years of experience
Virginia Beach, VA, 23451

Jennifer was absolutely wonderful! My dogs loved her, the house was just the way I left it, and she even brought my mail in for me. I will definitely be biking with her again 🥰

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Justine S.
Sitter Profile Image: Monika D.
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Monika D.
from
$95
per night
5.0 out of 5 stars
21 reviews
5 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: Talaya S.
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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: Antonio & Taylor S.
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Antonio & Taylor S.
Star Sitter
from
$180
per night
5.0 out of 5 stars
92 reviews
31 repeat clients
3 years of experience
Northwest, Virginia Beach, VA, 23462

We have two Great Danes that can be intimidating when you first meet them, but Antonio was great with them. We came back from our trip to very happy dogs and cats! Antonio had great communication, was easy to work with, and treated our pets like his own. Will definitely use him again and highly recommend!

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Megan B.
Sitter Profile Image: Casey B.
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Casey B.
from
$26
per night
14 years of experience
Northeast, Virginia Beach, VA, 23451

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.

Sitter Profile Image: Richie A.
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Richie A.
from
$28
per night
20 years of experience
Chesapeake, VA, 23325

About: I'm a remote voice actor with a flexible schedule, so your pets get lots of companionship—not just quick drop-ins. As a longtime homeowner and property manager, I also understand the importance of keeping your home clean, secure, and well cared for. I've cared for dogs and cats of all ages, including energetic breeds, senior pets, multi-pet households, and pets with unique routines. I'm comfortable with crate training, positive reinforcement, basic medications, and dogs that need a little extra patience on walks. Whether it's a long hike, a game of fetch, or a quiet afternoon with a cuddly cat, I adapt to each pet's personality and routine. Clear communication is important to me, so you'll receive regular updates and photos while you're away, giving you peace of mind that your pets and home are in great hands. Pet care fits naturally into my daily routine. I work remotely as a voice actor, so I have the flexibility to schedule walks, feeding, playtime, and potty breaks throughout the day rather than trying to fit them around a traditional office schedule. I genuinely enjoy being active, so daily walks, hikes, and outdoor time are something I look forward to. When I'm home, I like providing a calm, consistent environment where pets can stick to their normal routines and get plenty of attention and companionship. Whether it's a quick neighborhood walk, a game of fetch, or simply keeping a cat company while I work, I enjoy making pets feel comfortable and cared for. When caring for pets in a client's home, my goal is to keep their routine as normal as possible. I carefully follow feeding schedules, walking routines, medications (if needed), and any training or household guidelines you provide. I believe pets are happiest when their daily routine stays consistent. Since I work remotely, I'm home much of the day, giving pets plenty of companionship and reducing the amount of time they're left alone. Whether it's long walks, playtime, belly rubs, or simply keeping a cat company while I work, I adjust my care to each pet's personality and needs. I also treat every home with the same respect I would my own—keeping it clean, secure, and well cared for. You'll receive regular updates and photos, so you can relax knowing your pets and home are in good hands.

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: 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

Morgan did a fantastic job while my husband and I had to leave the state to attend a family emergency. We have a 3 year old husky and 2 year old lab both full of energy. She sent us pictures of how the boys were doing as well as letting us know when our husky was getting a lil separation anxiety and not really eating. Our lab was on 2 medications and Morgan made sure our lab was staying on track and when our lab ran out of salami to hide the pills in she had purchased some with her own money to make sure he was okay. 1000% recommend and in the future will definitely look to see if she is available.

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Brian D.
Sitter Profile Image: Grayson Y.
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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: Taylor Y.
Verified Enhanced Background Check
Taylor Y.
from
$60
per night
5.0 out of 5 stars
5 reviews
1 repeat client
10 years of experience
Northwest, Virginia Beach, VA, 23455

Thanks for taking care of Chester and Chicken Taylor!

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Benjamin D.
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The median cost per night for house sitting in Cheapside is $45

Pet parents share their Rover experiences - Cheapside

1 / 1
5.0 out of 5 stars

Jessica was awesome! She clearly has a genuine love of animals and nature. We had a unique situation where we were vacationing in the area. Jessica was flexible to meet our unique needs on short notice and even provided local recommendations for things to do. She was super attentive to our pets and is a lovely person. I cannot recommend her highly enough!!

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Nancy N.
House Sitting
1 / 1
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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?

  • 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. 1. Search

    Browse profiles of sitters near you who offer house sitting
  2. 2. Meet & Greet

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

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Sitters in Cheapside average 4
repeat house sitting clients

FAQs for House Sitting - Cheapside

Frequently asked questions about Rover

The average cost for House Sitting in Cheapside on Rover is $47.08 per night (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of House Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for House Sitting. For more information on service fees, click here .

As of July 2026, there are 1,053 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 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 Cheapside. On Rover:

  • 94% of sitters can help with special care needs
  • 99% can help with giving oral medications or injections
  • 98% 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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