Pet Sitting Oakwood

Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Oakwood, Find top rated pet sitting

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Leigh Ann E.
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Leigh Ann E.
Star Sitter
from
$19
per visit
5.0 out of 5 stars
• 29 reviews
12 repeat clients
37 years of experience
Annapolis, MD, 21403

“Leigh was very attentive with Karen! She played with her, spent time with her, wrote thorough reports on their time together, and was overall very communicative. She even left Karen a toy (which she loves, thank you!!!) Leigh went above and beyond and I would absolutely book her again.”

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Ezekiel P.
Sitter Profile Image: Elaine S.
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Elaine S.
from
$20
per visit
5.0 out of 5 stars
• 70 reviews
38 repeat clients
20 years of experience
Annapolis, MD, 21403

About: I get a lot of pleasure assisting busy professionals with their pet sitting needs. I provide a nurturing and loving environment for your special pets in a very tranquil setting. Your pets will be treated as if they were my own. My husband and I will treat your pet with the utmost care and attention. References available upon request.

Sitter Profile Image: Emma M.
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Emma M.
from
$15
per visit
5.0 out of 5 stars
• 3 reviews
3 repeat clients
16 years of experience
Annapolis, MD, 21403

“My kitties were vey happy with Emma. So was I. She did everything I asked for.”

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Joyce H.
Sitter Profile Image: Hannah B.
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Hannah B.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
• 31 reviews
10 repeat clients
15 years of experience
Annapolis, MD, 21403

“Hannah did a great job checking in on Arlo while we were out of town. She provided great updates and made sure to give him attention and affection. She was also very communicative and provided helpful updates after each visit. Highly recommend!”

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Cody H.
Sitter Profile Image: Amanda C.
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Amanda C.
from
$18
per visit
5.0 out of 5 stars
• 6 reviews
2 repeat clients
15 years of experience
Edgewater, MD, 21037

“I used Amanda the very first time that I have actually been away for a period of more than a couple of days! Everything was great and I will definitely be using her again!”

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April F.
Sitter Profile Image: Harrison S.
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Harrison S.
from
$16
per visit
5.0 out of 5 stars
• 18 reviews
3 repeat clients
4 years of experience
Annapolis, MD, 21403

“Harry was friendly, showed up on time, sent cute pictures and was very attentive to my elderly cat. Will definitely book him again!”

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Kate E.
Sitter Profile Image: Elizabeth G.
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Elizabeth G.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
• 50 reviews
22 repeat clients
10 years of experience
Annapolis, MD, 21403

“I booked Elizabeth pretty last minute to drop by to take care of my senior cat for a couple of days, and she was very responsive and did a fine job.”

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Miriam F.
Sitter Profile Image: Anya B.
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Anya B.
from
$14
per visit
5.0 out of 5 stars
• 9 reviews
3 repeat clients
8 years of experience
North Beach, Annapolis, MD, 21401

“Anya was incredible! She took care of my boys and was so responsive!”

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Blake K.
Sitter Profile Image: Elizabeth W.
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Elizabeth W.
from
$25
per visit
5.0 out of 5 stars
• 8 reviews
5 repeat clients
7 years of experience
Annapolis, MD, 21401

“Liz was fantastic in her care of my pup and my home. She arrived early to the visit and stayed the full length, communicated swiftly and saved us from any worry.”

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Colin M.
Sitter Profile Image: Jamie P.
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Jamie P.
Star Sitter
from
$28
per visit
5.0 out of 5 stars
• 127 reviews
50 repeat clients
45 years of experience
Annapolis, MD, 21403

“Jamie was very nice and extremely responsive! My cat is not the friendliest to strangers but Jamie handled her perfectly. We will definitely use her again!”

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Mallory H.
Sitter Profile Image: Gabriella L.
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Gabriella L.
from
$15
per visit
15 years of experience
Annapolis, MD, 21401

About: I have grown up with dogs and have been around/worked with them all my life. Needless to say I’m very comfortable with them. I’m confident in working and caring for a dog of any age and providing any care they might need. I have also been riding horses since I was a small child and feel comfortable with any needs they might need met. Feeding, mucking out (cleaning up poo and pee), giving meds to dogs, cats, horses are all tasks I feel confident in. Side note I also feel comfortable taking care of basic reptiles, but my experience is mostly in horses, cats, and dogs. I currently work full time in inner harbor from 8 am-4:30pm. I could possibly provide care before my regular working hours depending on location. Can definitely provide care after working hours. In my home my cats are fed both wet and dry food throughout day depending on their needs. At this time I do not provide the option of caring for an animal at my house.

Sitter Profile Image: Catherine N.
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Catherine N.
from
$40
per visit
5.0 out of 5 stars
• 17 reviews
2 repeat clients
30 years of experience
Annapolis, MD, 21403

“I was a little nervous to use rover for the very first time but as soon as my animals met Catherine they loved her. Catherine is so wonderful with animals -we have a very shy great Dane who just immediately loved her. She kept in contact with us the whole time and sent us pictures of the dogs playing. After our meet and greet we felt completely at ease leaving her the keys to our house and our precious dogs with her. We will 100% be calling again to use Catherine.”

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Karen G.
Sitter Profile Image: Emily P.
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Emily P.
from
$20
per visit
5.0 out of 5 stars
• 5 reviews
2 repeat clients
20 years of experience
Harwood, MD, 20776

“Emily was available to help on short notice and did a great job!”

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Kyle P.
Sitter Profile Image: Brittanny A.
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Brittanny A.
from
$25
per visit
4.2 out of 5 stars
• 8 reviews
2 repeat clients
12 years of experience
Annapolis, MD, 21401

About: As someone who loves to travel, I know the importance of having trusted and communicative pet care. I have had two cats for 12 years and was lucky enough to become a dog mom when my husband I met 4 years ago. I have experience with walking and caring for our friends pets as well. I have a hybrid work schedule, so my availability is flexible for you and your fur baby’s needs. I can do early mornings, lunchtime, evenings, and overnights. We have a fenced in backyard that our dog enjoys and a covered porch that our cats enjoy. We can accommodate any animal and separate all the animals if feeding time is an issue.

Sitter Profile Image: Marley D.
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Marley D.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
• 59 reviews
20 repeat clients
15 years of experience
Annapolis, MD, 21401

“From the moment Marley met our two cats for the first time I knew I could rest easy on our long trip away. My cat was just coming off a bad reaction to sedation and has hyperasthesia, and she handled his meds and a setback in symptoms effortlessly and with care. She kept us thoroughly updated daily, followed all the instructions and notes I left! and made sure everything was clean on her last day. Most importantly Marley was a caring, loving presence and caregiver for our kitties every day, and was a very kind, compassionate person in all our interactions.”

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Hannah D.
Sitter Profile Image: Tiffany O.
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Tiffany O.
from
$20
per visit
5.0 out of 5 stars
• 4 reviews
1 repeat client
30 years of experience
Annapolis, MD, 21409

“Tiffany was a real trouper to come visit our 3 month old puppy. She is knowledgeable, organized and loves dogs. Communicates promptly, and is open to changing circumstances. I highly recommend her.”

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Shirley C.
Sitter Profile Image: Lindsay M.
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Lindsay M.
Star Sitter
from
$40
per visit
5.0 out of 5 stars
• 55 reviews
13 repeat clients
40 years of experience
Annapolis, MD, 21402

“I am so grateful to have found Lindsay. She's a natural with dogs -- relaxed, confident, loving, friendly and quite literally gets down on their level to connect. She was more than willing to come over for a meet & greet with our dog to help ease any concerns prior to her first booking. I loved her personality and level of customer service and her communication is exceptional. She's very punctual with her visits but also remains flexible knowing changes are sometimes needed. I look forward to continuing to work with Lindsay moving forward.”

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Ciri F.
Sitter Profile Image: sofia b.
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sofia b.
from
$40
per visit
5.0 out of 5 stars
• 8 reviews
1 repeat client
8 years of experience
Annapolis, MD, 21403

“Sofia is the warmest dog lover who cares for your pet with grace, attentiveness, and love. She came for a drop-in visit and soothed our dog who has been diagnosed with cancer. Our family is lucky to have found her! ❤️”

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Angie W.
Sitter Profile Image: Justine P.
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Justine P.
from
$20
per visit
5.0 out of 5 stars
• 73 reviews
34 repeat clients
31 years of experience
Pasadena, MD, 21122

“Justine was great. Bella warmed up to her immediately. She was on time for the drop in visits, prompt with communication, and sent many nice pictures.”

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Erik F.
Sitter Profile Image: Sarah M.
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Sarah M.
from
$14
per visit
1 repeat client
20 years of experience
Annapolis, MD, 21401

About: Besides my own dogs that I have taken care of since I was very young, I also have been relied on to take care of family and neighbor dogs. Most dogs that I have cared for have been geriatric, and I am extremely patient with them, and strong enough to even lift the larger dogs when they can’t lift themselves. Before coming to MD, I worked on a farm and interacted with dozens of dogs every day. I have never met a dog that hasn’t liked me, or one I haven’t liked. I work from home and so can easily step out for a drop-in or house sit and work from your home. I can do early morning or late evening according to need. I am unable to board your dogs. However, I am more than able to watch your dogs in your home. When in a client’s home, my philosophy is to only touch what is needed. The client’s direction and privacy is key to a good relationship, as well as my discretion.

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Pet parents share their Rover experiences - Oakwood

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5.0 out of 5 stars

Ali took great care of our cat Julian while we were away for the weekend! She was always communicative and responsive, and we loved the pictures she sent as well. We knew he was in great hands!

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Maura M.
Drop-In Visits
5.0 out of 5 stars

She is a very sweet person. Arrived on time. Stayed the whole hour. Shelby (my Lab) was well cared far and content when I came home.

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Suzanne W.
Drop-In Visits
5.0 out of 5 stars

Samantha was great and a huge help while we need to return to office. Great report out and I know our pup had a good mid day break.

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Maggie C.
Drop-In Visits
5.0 out of 5 stars

Luna and Dusty loved their visit from Shelby! She was prompt and sent lots of pics. Dogs enjoyed their playtime with her! Thank you so much!

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Yvonne B.
Drop-In Visits
5.0 out of 5 stars

Katie was wonderful to work with. She was very communicative, responsive and was great at getting to know and work with our sensitive cats. Even our grouchy cat opened up to her. She was also flexible in accommodating medication routines, the needs of a senior cat, and kind details like putting squirrel and bird food out to keep our cats entertained while we were away. We will definitely book with her again!

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Kelley S.
Drop-In Visits
5.0 out of 5 stars

Stephanie accommodated me on a last minute check-in. She arrived on time and my pup warmed up to her quickly!

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Amber E.
Drop-In Visits
5.0 out of 5 stars

Laura was great when we went away internationally! Took care of business as a dual! Always great to have watch our fur babies.

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Rhea L.
Drop-In Visits
5.0 out of 5 stars

Amber was very communicative and took good care of my cat Kora while we were on vacation. Would definitely book with her again in the future if needed.

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Emily C.
Drop-In Visits
5.0 out of 5 stars

Ellie was absolutely amazing! She took marvelous care of our cats and provided detailed notes as to how the cats were doing during each visit. The pictures she provided were adorable. We would gladly re-book her and recommend her for pet sitting.

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Sylvia M.
Drop-In Visits
5.0 out of 5 stars

Elizabeth did a great job helping us out last minute taking care of our dog. She was thorough and our puppy enjoyed having a companion to play with. Would highly recommend!

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Trevor S.
Drop-In Visits
5.0 out of 5 stars

Jessica is amazing! She was able to accommodate a short notice request to check in on our pets and feed them! She always provides first rate service and our pets love her. She also takes the best candid photos of our cat and dogs! She is our go to pet sitter

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Tom C.
Drop-In Visits
5.0 out of 5 stars

Julia was super great. Booked her last minute and really glad I did! She did everything we asked and arrived promptly. Will be using again!

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Pooja P.
Drop-In Visits
5.0 out of 5 stars

Andrew was timely, communicative, did everything asked, and successfully gave my senior cat her topical meds. I would book with him again without hesitation!

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Theresa D.
Drop-In Visits
5.0 out of 5 stars

Kayla took great care of our dogs, Wally and Pip, including taking them on walks and making sure they were happy and well cared for. She sent great updates and photos, which we really appreciated and made us feel completely at ease while we were away.

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Caroline J.
Drop-In Visits
5.0 out of 5 stars

Beth helped us out last minute to watch our cat, ReRe for a week. She made sure to make time to do a meet and greet with ReRe before we left. Like most cats she has multiple hiding places but Beth was able to spot her everyday and send a pic!

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Cyndi R.
Drop-In Visits
5.0 out of 5 stars

She’s so great! Super communicative and flexible. We’ll definitely be calling again. Our kitty loves her! Thanks MaKayla’

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Catie C.
Drop-In Visits
5.0 out of 5 stars

Arem was a great sitter! He made sure our cat was good, played with, fed, and everything was okay each day. He sent us daily updates with how she was doing along with photos of her, so we had a chance to see her as well. He was very communicative and made sure we were updated on everything. I would highly recommend him!

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Connor B.
Drop-In Visits
5.0 out of 5 stars

Gabriella is wonderful! Reliable and attentive to the needs of our sweet pup, she took her for walks daily even though it wasn’t required. Gabriella responds to messages quickly and kept us up to date about how our dog was doing with messages and pictures. Thanks Gabriella

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James S.
Drop-In Visits
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How to book pet sitting

  1. 1. Search

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FAQs for Pet Sitting - Oakwood

Frequently asked questions about Rover

Rover is the largest marketplace for local pet care. Whether you're looking for pet sitters, dog walkers, or house sitters who specialize in pet sitting, you can narrow your search by entering your ZIP code to find sitters within walking distance in your neighborhood.

You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.

Before booking, confirm:

  • the timing, length, and frequency of visits;
  • the care instructions the sitter should follow;
  • which parts of your pet’s usual routine should be prioritized;
  • how often you would like to receive messages, photos, or other updates.

Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.

If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.

The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.

Many pet parents provide a spare key or arrange a lockbox. You can also exchange keys during the Meet & Greet and show your walker how to use digital fobs or personalized codes. It helps to arrange access to your home, from spare keys to concierge introductions, before pet care begins.

If you live in an apartment or condo, don’t forget to discuss details like buzzer access, codes, or elevator etiquette. These details can help a pet sitter feel more comfortable going in and out of your building.

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 .

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.

Yes, you can find sitters who have experience administering medication or managing dietary requirements. You can also find pet sitters who accept only one pet at a time, which is ideal for anxious puppies 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 request a Meet & Greet to walk your sitter through your expectations.

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.

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