House Sitting Chesapeake Ranch Estates-Drum Point

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Over 65
pet parents in Chesapeake Ranch Estates-Drum Point have booked house sitting

Chesapeake Ranch Estates-Drum Point, 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: Hannah A.
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Hannah A.
from
$65
per night
5.0 out of 5 stars
• 17 reviews
7 repeat clients
5 years of experience
Lusby, MD, 20657

“Very solid stay, lots of pictures nothing hidden. Very communicative! Will use here again.”

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Dan W.
Sitter Profile Image: Samuel H.
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Samuel H.
from
$30
per night
5.0 out of 5 stars
• 7 reviews
2 repeat clients
4 years of experience
Lexington Park, MD, 20653

“Sam was great as always. He took very good care of our babies, even scooped the cats litter box when he didn’t have to. He was able to calmly retrieve our dog quickly when he got out. He always leaves the house clean with the trash taken out”

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Cristianna N.
Sitter Profile Image: Shemoy S.
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Shemoy S.
Star Sitter
from
$95
per night
5.0 out of 5 stars
• 38 reviews
16 repeat clients
20 years of experience
California, MD, 20619

“Shemoy worked closely with us to make sure our dogs were comfortable before we left them. She treated our babies like her own and always kept us fully updated :)”

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Deanna G.
Sitter Profile Image: Shyann N.
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Shyann N.
from
$50
per night
5.0 out of 5 stars
• 5 reviews
1 repeat client
20 years of experience
Prince Frederick, MD, 20678

About: Hi, I’m Shyann and I’ve had pets as long as I could remember. Currently a cat owner! I will make sure your pet will feel comfortable, safe and cared for! I was a dog walker at a local shelter and have had multiple dogs of different breeds as well as taken care of family’s Great Dane/Irish wolf hounds! No dog is too big or small! Only accepting Spayed/ neutered pets! All pet ages welcome :) My schedule is pretty flexible as I work part time from home so I have plenty of time to care for your Furry family! <3 For dogs I love giving them plenty of walks and playing them a much as they desire, feeding them yummy treats and feeding them as needed! For cats I will scoop litter, they can get a bunch of play time with me, yummy treats and feed them!

Sitter Profile Image: Kathleen C.
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Kathleen C.
from
$100
per night
5.0 out of 5 stars
• 25 reviews
9 repeat clients
10 years of experience
Lexington Park, MD, 20653

“I highly recommend Kathleen for anyone looking for in home or not care. Kathleen allowed us to take a wonderful holiday vacation knowing our 16 year old boy with Kidney issues would be well loved and cared for as she sent pictures daily and was always available for a checkin. Kathleen also took care of our home and eneded her stay as if she had never lived their for 10 days. Just amazing! We were pleased more than we ever thought we would be. Highly recommend this wonderful gal who we did just meet as she came 3 times prior to my trip to ease my nerves. Real gem and she and her family are great with animals. Katu was comfortable right away, which is unusual. Thank you Kathleen. You are our sitter for Katu! Happy New Year! Loved your family Christmas card! Thank you so much!”

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Karen G.
Sitter Profile Image: Ren F.
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Ren F.
from
$60
per night
3 years of experience
Mechanicsville, MD, 20659

About: Ive taken care of many pets with specialized needs. This includes routine medicine and eye drops for the elderly, frequent belly band changes changes for those with bladder issues, and calming treats for those fearful of storms. Im quick to learn each dogs bathroom tells to avoid any unwanted accidents. I also have fishkeeping experience with 2 freshwater fish tanks at home. So if youre fish needs feeding or water quality checks I can handle that was well. I am currently working a part time internship with flexible hours, which allows me to care for furry babies in my free time! Weekends are typically busy, however with enough notice I can make them work. House rules are always respected, no matter how much a dog wants couch cuddles or if the cat likes the view from on top of the counter.

Sitter Profile Image: Mackenzie C.
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Mackenzie C.
from
$50
per night
6 years of experience
California, MD, 20619

About: I have 6 years of experience caring for pets and understand how important it is to have someone you can trust with your furry family members. I provide attentive, loving, and reliable care while making sure each pet feels safe, comfortable, and cared for. I’m happy to follow your pet’s normal routine, including feeding schedules, walks, playtime, potty breaks, medications, and plenty of attention and affection. I understand that every pet has their own personality and needs, so I take the time to make sure they receive individualized care and feel as comfortable as possible while you’re away. I am currently working full-time, mostly remote with one or two days in the office each month. Working from home gives me plenty of flexibility to provide regular potty breaks, walks, playtime, feeding, and lots of attention throughout the day. I’m also happy to accommodate each pet’s normal routine as closely as possible. Your pet’s safety and comfort are always my priority. I provide a calm, attentive environment and carefully follow any instructions you provide regarding feeding, medications, walks, routines, or special needs.

Sitter Profile Image: Jennifer R.
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Jennifer R.
from
$50
per night
5.0 out of 5 stars
• 2 reviews
15 years of experience
Lusby, MD, 20657

About: I’ve had dogs my whole life and have been taking care of them since I was a kid! I have two dogs and a cat of my own who are family! So I understand how important it is to trust someone with your pets! Im currently a stay at home mom and wife I have plenty of time to walk, play and cuddle your fur baby’s! Any time of day or night I can be there for you and your family I can take you dogs for a walk around the neighborhood or around your yard! I am comfortable putting them in crates and feeding or any type of play what ever you need I can do!

Sitter Profile Image: Virginia E.
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Virginia E.
from
$60
per night
5.0 out of 5 stars
• 20 reviews
9 repeat clients
40 years of experience
Clements, MD, 20624

“Really good with the animals… 2 cats and and a Velcro dog. Appreciated updates. Highly recommend Virginia and will use her again.”

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Debby M.
Sitter Profile Image: Christina C.
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Christina C.
from
$80
per night
5.0 out of 5 stars
• 13 reviews
6 repeat clients
8 years of experience
Lexington Park, MD, 20653

“Christina was very attentive with Mr. Moo and her pictures helped us get through the long weekend without our chunky monkey. She left our house and our cat in excellent condition and he wasnr even mad at us when we got back, which is always a giod sign that he was well taken care of! We wouldn't hesitate to work with her again.”

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Anica L.
Sitter Profile Image: Kristina B.
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Kristina B.
from
$85
per night
1 year of experience
Ocean city, MD, 20636

About: I’m already someone who loves being home, going on peaceful walks, and keeping things cozy, so adding a furry friend to the mix just makes everything better. I treat pets like little VIP guests and I make sure they get plenty of attention, affection, and a routine that feels calm and predictable for them. I always try to match whatever your pet is used to so they feel safe and comfortable. If I’m watching your pet in your home, I keep their routine exactly how you have it. They will have their meals on time, daily walks, play breaks, and plenty of cuddles. I’m very detail-oriented, so I pay attention to the small things like their favorite toy, how they like to be greeted, or where they prefer to nap. If I’m caring for them in my home, they get a clean, cozy environment, lots of love, and a peaceful space to relax. Whether your pet is energetic, shy, or somewhere in between, I adjust to what makes them feel happiest. I genuinely treat every pet like they’re my own and give them spoiled-in-a-good-way kind of love. I’m patient, observant, and good with pets who may be a little shy or anxious. I have a patient personality and animals tend to trust me quickly. I’m also extremely reliable and communicative, so you’ll always know how your pet is doing. I’ve cared for a variety of pets from rambunctious puppies to senior dogs. I tailor my care to each pet’s personality and needs.

Sitter Profile Image: Vanessa S.
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Vanessa S.
Star Sitter
from
$85
per night
5.0 out of 5 stars
• 82 reviews
37 repeat clients
30 years of experience
Prince Frederick, MD, 20678

“Vanessa did house sitting for five nights watching our 13 year old dog who is deaf, partially blind and has pretty bad arthritis. She did an excellent job! The best part is she kept in constant touch with us sending pictures (via text) of our dog in the morning, during the day and just before bed. This gave me great peace of mind since this was the first time she was watching our dog. Also my old dog doesn't normally eat very well when we are away but Vanessa was very successful getting him to eat. I was so impressed. Another surprise....when we came home she had washed the bed sheets and towel she had used and my house looked spotless. My dog had so much energy when we returned and seemed so calm and happy. What more can you ask for?”

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Deb M.
Sitter Profile Image: Jeanine H.
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Jeanine H.
from
$40
per night
1 repeat client
25 years of experience
Prince Frederick, MD, 20678

About: Hey there! I’ve been caring for animals for over 25 years…or really, my whole life! From dogs and cats to birds, hamsters, bearded dragons, and even fish, I’ve shared my life with animals of all kinds. I currently live with four cats who have taught me even more about patience, play, and intuitive communication. I’ve also helped friends with pet care, walked dogs of all sizes, and provided loving attention to pets while their humans were away. Animals tend to gravitate toward me, and I feel deeply connected to them. I believe in meeting each animal where they are, tuning into their energy, and ensuring they feel safe, seen, and nurtured. Whether it’s a playful walk, cozy check-in visit, or overnight care, I’m committed to showing up with love, attentiveness, and a calm, grounded presence. Your pet will be treated like one of my own! Pet care fits beautifully into my current schedule. I’m seeking flexible work that keeps me close to home so I can care for my four cats and continue pursuing my passion for baking. My days are open and adaptable, and I love spending time with animals. I’m currently available most days and times, and I genuinely enjoy being outside for walks or tending to pets’ unique needs. This work is a natural extension of my lifestyle. I treat all pets like family, tuning into their needs with care and calm energy. Whether in my home or yours, I create a peaceful, loving environment. I’m attentive to each pet’s unique personality, maintain clean spaces, and follow feeding or medication routines exactly. My four cats are well-loved and cared for, and I bring that same intention and presence to every animal I care for.

Sitter Profile Image: Amanda S.
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Amanda S.
from
$50
per night
5.0 out of 5 stars
• 11 reviews
3 repeat clients
21 years of experience
Huntingtown, MD, 20639

“She gave my pups so much love, and even fed my anxious one my hand, and waited patiently for Nala to come to her. She gave them extra treats and stayed with them for long periods of time. She’s amazing!!”

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Sharon S.
Sitter Profile Image: Amaun H.
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Amaun H.
from
$55
per night
17 years of experience
Mechanicsville, MD, 20659

About: Every pet is different, and I take the time to truly understand their unique personality, preferences, and needs. My love for animals isn’t just a job — it’s a real passion, and I treat every pet like family. One thing that sets me apart is that I’m home all day and have wide availability. That means your pet gets more attention, more playtime, and more one-on-one care — especially helpful for pets who need extra love, routine, or supervision. I keep pet parents in the loop with regular updates, photos, and detailed notes, so you always know how your furry friend is doing. I go beyond the basics with enriching activities and interactive play that help keep pets mentally and physically happy. You can count on me to be punctual, consistent, and reliable — creating a stress-free experience for both you and your pet. Whether it’s a special request or an unexpected situation, I’m always willing to go the extra mile to make sure everyone is safe, comfortable, and cared for. I’d love the chance to meet you and your pet — feel free to reach out any time! Pet care fits seamlessly into my daily routine because I’m home throughout the day and have a very flexible schedule. I build my days around the pets I care for — making sure they get walks, playtime, meals, and companionship on a consistent schedule. I’m not rushing in between other jobs or obligations, which means I can give pets my full attention, especially those who need a stable routine or extra care. Whether it’s early morning drop-ins, midday playtime, or evening feeding, I’m available and fully present. I genuinely enjoy caring for animals, so making it part of my everyday life doesn’t feel like work — it’s just what I do. Every pet is different, and I take the time to truly understand their unique personality, preferences, and needs. My love for animals isn’t just a job — it’s a real passion, and I treat every pet like family. One thing that sets me apart is that I’m home all day and have wide availability. That means your pet gets more attention, more playtime, and one-on-one care — especially helpful for pets who thrive on routine or need extra supervision and love. When caring for pets in a client’s home, I do everything I can to keep their environment calm, familiar, and consistent. I always begin with a meet and greet to learn your pet’s habits, health needs, and any household preferences. I follow feeding, walking, and play routines closely and provide plenty of mental and physical stimulation through personalized activities. Cleanliness and safety are top priorities — I keep your home tidy, clean up after pets, wipe paws when needed, and ensure food and water areas are fresh. I respect your space, follow house rules, and take home security seriously by locking up and following any protocols you’ve shared. I also provide frequent updates, photos, and notes, so you always know how your pet is doing. Whether it’s a special request, last-minute change, or emergency situation, I’m committed to going the extra mile to make sure both you and your pet feel confident and cared for. You can count on me to be consistent, punctual, respectful, and above all, deeply invested in your pet’s well-being. I’d love the chance to meet you and your furry friend — feel free to reach out any time!

Sitter Profile Image: Landry S.
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Landry S.
from
$25
per night
2 years of experience
Great Mills, MD, 20634

About: Ive taken care of Dogs since i was 12. Family and friends have always worked with me if they need any pet service, not just for dogs! i have two dogs at home but i usually work on a horse farm where i take care of horses, a rabbit and two cats! I have a large fenced in yard with lots of toys and 24/7 available attention. both of my dogs are create trained, so i can easily crate yours if needed. long walks are available as well as lots of play time.

Sitter Profile Image: Rae W.
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Rae W.
from
$55
per night
5.0 out of 5 stars
• 9 reviews
2 repeat clients
23 years of experience
Bryantown, MD, 20617

About: I have a genuine love for all animals and perhaps a special affinity towards man’s best friend! I have had the pleasure of taking care of and owning animals of various kinds throughout the entirety of my life, from cats and dogs, to ferrets and bunnies! I am able to offer basic puppy training, senior dog care/disabled dog care and also administer medicines. Follow our journeys at themanyminiadventures on IG. I work part time from home and have availability to care for your furry friends doing drop ins and pet sitting! I’m available on short notice and pet sitting has reallly helped me manage since the loss of my Dad and becoming a caregiver for my mom! I treat your fur babies like they’re our fur babies while they are here with the exception of following their diet and your specific instructions. We also: walk dogs on a leash. Play outside. provide potty and exercise walks while leashed to allow for new scents as well. Feed pups separately unless they came together and we have been notified they eat well together by the owner(s). notify you immediately in the case of any abnormalities/concerns or emergencies. provide you with pictures and updates throughout the stay!

Sitter Profile Image: Amanda D.
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Amanda D.
from
$80
per night
5.0 out of 5 stars
• 7 reviews
2 repeat clients
30 years of experience
North Beach, MD, 20714

About: Promo Code for $40 off first time booking for Pet Owners that it is their first time using Rover- AMANDD61392 Friends and Family call me the animal whisperer. I have had a dog/dogs my whole life. I have taken care of dogs from brand new puppies, to babies that were at the end of their life. I'm currently not working full time away from home, so for any boardings that are on week days or weekends, you and your fur babies are good to go. I do have one small dog at home BUT, if you prefer your dogs to be alone while here, my dog is easily brought to his grandparents house:), which they are always happy about. I will update when my work schedule changes. I have a fenced yard (tall privacy wooden fence with sliding deadbolt), and can easily crate dogs if needed. Any animals would have free range of the house and the yard. Your babies are my babies while I am taking care of them.

Sitter Profile Image: Christopher S.
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Christopher S.
from
$50
per night
5.0 out of 5 stars
• 4 reviews
1 repeat client
13 years of experience
Cheverly, MD, 20784

“We continue to be grateful for Chris and his excellent care of our cats. He is very conscientious to send pictures regularly while we're away and the cats really seem to like him. He's now done in house cat sitting for us twice and I totally recommend him for your pet care needs!”

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Lavender K.
Sitter Profile Image: Ella M.
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Ella M.
from
$55
per night
5.0 out of 5 stars
• 1 review
2 years of experience
Annapolis, MD, 21401

“Simply the best!!! Very communicative, my Karma loved their walks!! Thank you for taking care of our baby!!!!”

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Christa G.
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The median cost per night for house sitting in Chesapeake Ranch Estates-Drum Point is $50

Pet parents share their Rover experiences - Chesapeake Ranch Estates-Drum Point

1 / 1
5.0 out of 5 stars

Betsy took great care of our dog and house. Great communication and we loved getting pictures of our dog while we were away. I would happily recommend her to anyone.

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Mike B.
House Sitting
5.0 out of 5 stars

Beau was GREAT! He is extremely responsive and my dog was comfortable with him immediately. 10/10 recommend!

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Adrienne M.
House Sitting
5.0 out of 5 stars

Kim is absolutely amazing! I have used Rover for years and she is by far the best sitter that I have ever had. Our dogs adore her and I felt completely secure and comfortable on my vacation, knowing that my pups were safe. Thank you, Kim! ❤️

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Lea W.
House Sitting
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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
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How to book house sitting

  1. 1. Search

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  2. 2. Meet In Person

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Popular requests for house sitting - Chesapeake Ranch Estates-Drum Point

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Sitters in Chesapeake Ranch Estates-Drum Point average 4
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FAQs for House Sitting - Chesapeake Ranch Estates-Drum Point

Frequently asked questions about Rover

The average cost of House Sitting in Chesapeake Ranch Estates-Drum Point is $54 per night as of October 2026. Most bookings cost between $28 and $87 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 296 sitters on Rover offering House Sitting across Chesapeake Ranch Estates-Drum Point. 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 Chesapeake Ranch Estates-Drum Point 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 Chesapeake Ranch Estates-Drum Point 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 Chesapeake Ranch Estates-Drum Point 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 , 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 .

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 .

sitters on Rover set their own , 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 Chesapeake Ranch Estates-Drum Point. On Rover:

  • 90% of sitters can help with special care needs
  • 95% can help with giving oral medications or injections
  • 95% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

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