House Sitting Cheapside

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

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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
9 reviews
3 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
9 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: Ethan G.
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Ethan G.
from
$35
per night
6 years of experience
Virginia Beach, VA, 23451

About: I’ve taken care of neighbors, friends and families dogs since I can remember. From single old pups to a house of 10 dogs and cats I’m currently off and free every Monday-Thursday after 2-3pm. Sometimes even as early as 10am. I’m open all afternoon and well into the next morning till 6am. I can only offer to take care of pets at your property, they’d rather be home anyways right? I find that animals prefer a new person in their own nest rather than in a strange new environment.

Sitter Profile Image: Hannah A.
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Hannah A.
from
$40
per night
1 repeat client
8 years of experience
Norfolk, VA, 23503

About: Dogs are my absolute favorite! I couldn't think of a better way to spend my days than loving on your pup! Dog walking, check ins, or overnights. I am available for anything to help. I am a travel CT tech. My schedule varies so just reach out to me and we can try to find something that works for both of us! I live in a complex so there are no busy roads and no fast driving. There is plenty of space for walks and playing in the yard. I am also willing and able to take your pet to a dog park if that is something you would like.

Sitter Profile Image: Ieashaw H.
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Ieashaw H.
from
$23
per night
7 years of experience
Norfolk, VA, 23505

About: I’ve been around animals my whole life, especially cats and dogs, so caring for them feels natural to me. I enjoy spending time with pets, giving them plenty of attention, exercise, and affection while making sure they feel safe, comfortable, and loved. I’m dependable, patient, and will always follow your pet’s routine and care instructions. I’ll treat your furry family member like they’re one of my own and keep you updated with photos and messages while you’re away. Pet care fits well into my schedule because I work PRN, which allows me to make my own hours. I occasionally work overnight shifts, and on Mondays and Thursdays I help with shipment at a clothing store from 6:00 a.m. to 10:00 a.m. Outside of those times, I have a flexible schedule and can plan around pet care. I’m committed to providing dependable, attentive care and will make sure your pet gets the time, attention, and love they deserve. When caring for pets in your home, I always respect your space and follow your pet’s normal routine as closely as possible. I’ll make sure they have fresh water, meals on schedule, exercise, playtime, and plenty of love and attention. I understand that every pet is different, so I’ll follow any instructions you leave, including medications, feeding schedules, or special care needs. My goal is to help your pet feel safe, comfortable, and happy while you’re away, and I’ll keep you updated with photos and messages so you can have peace of mind.

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

I have booked with Felicia three times now, and she has consistently provided a great experience. What stands out most is her attention to detail; she asks a lot of questions upfront to make sure she fully understands my dog's routine and comfort levels. It’s clear she wants to get everything exactly right, which gives me a lot of peace of mind while I'm away. She is reliable, communicative, and truly cares about the well being of the animals in her care. I highly recommend her if you’re looking for someone thorough and attentive!

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Mari R.
Sitter Profile Image: Emmanuel S.
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Emmanuel S.
Star Sitter
from
$50
per night
5.0 out of 5 stars
16 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: Elijah H.
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Elijah H.
from
$55
per night
4.8 out of 5 stars
10 reviews
1 repeat client
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: 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

So grateful for Alexandria stepping in for us over and over and love on our pups. Even with last minute plans, she has been always so professional and accommodating.

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Katie S.
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: Jennifer M.
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Jennifer M.
from
$50
per night
5.0 out of 5 stars
22 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: 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: Angelena P.
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Angelena P.
from
$65
per night
4.9 out of 5 stars
14 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: 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: Ciear J.
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Ciear J.
from
$52
per night
22 years of experience
Melfa, VA, 23410

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 available throughout the week to help out with your furry friends, Monday through Sunday. I can provide reliable, attentive care that fits easily into my daily routine, ensuring your pets receive plenty of love, attention, exercise, and companionship whenever they need it. 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: 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: morgan d.
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morgan d.
from
$30
per night
5.0 out of 5 stars
3 reviews
1 repeat client
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: Emma J.
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Emma J.
from
$55
per night
5.0 out of 5 stars
4 reviews
3 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: Crystal R.
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Crystal R.
from
$35
per night
3.6 out of 5 stars
5 reviews
1 repeat client
3 years of experience
Norfolk, VA, 23523

Crystal is AMAZING ! Love you ! Happy Mother's Day, Again!

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Stephanie 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
93 reviews
31 repeat clients
3 years of experience
Northwest, Virginia Beach, VA, 23462

I have to admit I was extremely anxious about using Rover.com. In the past, I have always known my dog sitters. And then a dear friend of mine, who is as passionate about her dogs as I am about mine, highly praised the website and uses the service quite frequently. I went on the website and I searched for sitters and narrowed it down to just a few and decided on Antonio from his picutres as it was quite obvious how happy the dogs looked under his care. And he appeared to engage the dogs in varied activities. He was very helpful with his messaging and assistence during the search process. Then with the "meet & greet" with my dogs Campbell and Charlie, I knew I had made the right choice. As he also was the House sitter, upon returning home found our house in perfect order. He was in contact duirng my days away posting pictures and keeping us well informed without being excessive. Always asked questions if he wasn't sure about something. For instance, we have a dog run on the property and he really didn't need to walk the dogs with a lease: just be with them while in the dog run. Then he messengered me and asked if he could take the dogs for a walk and I suggested he walk them separately as I do. He posted photos. Campbell & Charlie both looked happy and that was that. They all needed to get out of the house and spend some time together one on one. It's clear that Antonio really likes what he does and that he truly cares about the well being and happiness of the dogs under his care. He is quite personable and easy going all the while maintaining his professionalism. I will not hesitate to use him the next time I travel and in need of a sitter.

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James Alan S.
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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
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Why Choose Rover?

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Popular requests for house sitting - Cheapside

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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 August 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 August 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 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:

  • 95% 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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