House Sitting Chesapeake Ranch Estates-Drum Point
Find a loving house sitter to watch over your pets and your home.
Over 66 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.
“My dogs were very comfortable with India; her calm and confident demeanor was helpful to my worrying about a predicted storm because of Gidgi's fears. She was instinctive in her suggestions and she seemed to like my dogs and cats.”
“Juliana was a joy to work with and took thoughtful care of my home and dog! She was knowledgeable, kind, communicative, and patient with Hugo getting used to her. Upon my return, she had followed instructions thoroughly and carefully, and Hugo was well cared for and happy. And so am I! Thank you, Juliana!”
“Shemoy was wonderful! We have had bad experiences with Rover dog sitters in the past, but she made us feel very at ease while watching our dog. She was very responsive and reliable. She even left the sweetest Christmas treats for my dog. You can tell she really cares about animals. I will definitely book with her again.”
“Leah is fantastic! We all know a “dog Mom” that doesn’t want to leave home because of her BABY!! (That’s me??♀️) Leah is patient and attentive, she went above and beyond for us on an extended stay. My dog, my home and my sanity were all in check with Leah. I can’t thank you enough, we will be booking again!”
“Anna was absolutely amazing! She kept me updated on how my furry babies were doing over the weekend. Had lots of questions and did a very good job at sticking to routine, which is important with a 15 week old puppy! She was clear about her need to get other things done over the weekend, even going so far to tell me when she was coming and going. Anna made it so that I could focus on my family this weekend with no concerns about how Nebula and Beethoven were being cared for, which was so welcome and reassuring after our last experience with a Rover sitter. We will definitely be using Anna again in the future. She is amazing and I would recommend her to anyone looking for a compassionate, reliable, dedicated, and caring pet sitter.”
“Samuel did a fantastic job watching our dog who is both quite reactive and recovering from ACL surgery. We already rebooked him for next month and highly recommend him for anyone needing peace of mind while they’re away from their fur baby.”
About: My name is Alexandra. I have 3 Chihuahuas. I also have a 17 year old dachshund. My pups are my world! My little fur babies as I like to call them. I absolutely love dogs. My whole life I have been an animal lover. I have 20 years plus years experience with dogs. I've never met a dog that didn't like me. My Schedule is very flexible. I am available is for walks and in home sitting/day visits. I can not do overnight visits. Please don't haste to contact me if you have any questions and concerns. Thank you for you time and I look forward to hearing from you and meeting your little fur babies! Have a wonderful day! Alexandra My schedule is open. Depending on when care is needed depends on how often I will come and how long I can stay. 24 / 7 I provide a safe, loving environment for pets to enjoy and feel comfortable in. Lots of pets and companionship will be provided for your loved one.
“Absolutely wonderful sitter!! April stayed in our home for a couple weeks with our two Shih Tzus. She sent daily updates with photos, handled their face and eye grooming (not easy for their breed!), was enthusiastic and communicative, and left our home clean and tidy. We really couldn’t have asked for more. We took a chance as she didn’t have reviews but I’m so glad we did. She did a fantastic job and I would definitely book her again. Thanks, April!!”
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!
“Elizabeth was attentive to Daisy's needs per the 'care & feeding' instructions we provided. Just as importantly, she treated Daisy as if her own, which was apparent by Daisy snoozling on Betsy's luggage as she prepared to leave.”
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!
“Taylor was amazing with our two dogs! 🐶💕 She was so attentive and caring, sent us plenty of pictures and updates, and always asked questions if she wasn’t sure about something, which we really appreciated. We have a 7-year-old and an 11-year-old, so knowing they were in good hands gave us such peace of mind while we were away. She was reliable, communicative, and clearly genuinely cared about making sure they were comfortable and happy. We came home to two very well-cared-for pups! 🥰 We would absolutely book Taylor again and highly recommend her to anyone looking for a sitter they can trust. 🤓☺️”
About: Hi! I’m Rosie — a lifelong animal lover and rescue-pet mom to one sweet pup and two cats. I’ve had pets since childhood and have always been drawn to helping animals who need a little extra love. I volunteer with a local shelter to support dog and cat socialization, and I also work with an island-dog rescue that brings pups from Puerto Rico to find their forever homes in the U.S. Whether it’s walks, playtime, or quiet company, I’m here to make your pet feel safe, loved, and well-cared for while you’re away. Pet care fits easily into my routine. I’m available early mornings, late afternoons, and evenings, with flexible weekends to ensure your pets get consistent, loving attention. In my home or yours, I focus on routines that build confidence and trust. I use gentle reinforcement, reward-based training, and plenty of love, cuddles, and playtime to help pets feel secure.
“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.”
“Ben took such good care of my sweet pup. He kept me updated about how she was eating, and how she was doing. She always gets mopey and doesn’t eat when we leave her. But she warmed up faster than usual, thanks to Ben.”
“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!”
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
Anna was absolutely amazing! She kept me updated on how my furry babies were doing over the weekend. Had lots of questions and did a very good job at sticking to routine, which is important with a 15 week old puppy! She was clear about her need to get other things done over the weekend, even going so far to tell me when she was coming and going. Anna made it so that I could focus on my family this weekend with no concerns about how Nebula and Beethoven were being cared for, which was so welcome and reassuring after our last experience with a Rover sitter. We will definitely be using Anna again in the future. She is amazing and I would recommend her to anyone looking for a compassionate, reliable, dedicated, and caring pet sitter.
Absolutely wonderful sitter!! April stayed in our home for a couple weeks with our two Shih Tzus. She sent daily updates with photos, handled their face and eye grooming (not easy for their breed!), was enthusiastic and communicative, and left our home clean and tidy. We really couldn’t have asked for more. We took a chance as she didn’t have reviews but I’m so glad we did. She did a fantastic job and I would definitely book her again. Thanks, April!!
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.
Why Choose Rover?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Meet local sitters who will treat your pets like family
1. Search
Browse profiles of sitters near you who offer house sitting
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests for house sitting - Chesapeake Ranch Estates-Drum Point
Select a filter and find qualifying sitters offering house sitting.Sitters in Chesapeake Ranch Estates-Drum Point average 4 repeat house sitting clients
FAQs for House Sitting - Chesapeake Ranch Estates-Drum Point
Frequently asked questions about Rover
The average cost for House Sitting in Chesapeake Ranch Estates-Drum Point on Rover is $54.39 per night (as of September 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 September 2026, there are 308 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 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 Chesapeake Ranch Estates-Drum Point. On Rover:
- 95% of sitters can help with special care needs
- 100% 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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