Pet Sitting in Oakwood

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

End
Search

Every sitter passes an enhanced background check. Learn about RoverProtect

Top rated Oakwood pet sitters

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

1 / 1
Sitter Profile Image: Elaine S.
Verified Background Check
Elaine S.
from
$20
per visit
5.0 out of 5 stars
69 reviews
37 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: Ellie H.
Verified Enhanced Background Check
Ellie H.
from
$14
per visit
5.0 out of 5 stars
10 reviews
3 repeat clients
10 years of experience
Annapolis, MD, 21403

This is our second time booking Ellie and I can't say enough good things about her! Ellie was able to help watch our dog Piggy at the last minute and went above and beyond to take good care of her. Ellie alerted me to a concern about Piggy and was able to address the situation effectively. Ellie is a great communicator, shows up on time, and is enthusiastic about animals. We would definitely book Ellie again!! Thanks for your great work Ellie!!

Profile image
Joan D.
Sitter Profile Image: Shelby B.
Verified Enhanced Background Check
Shelby B.
from
$22
per visit
5.0 out of 5 stars
23 reviews
5 repeat clients
7 years of experience
Annapolis, MD, 21403

This is our second time working with Shelby, both times we needed last-minute assistance and she stepped in happily. She took great care of our dogs, gave them their medicine, let them frolic in the yard, and even brought in our packages and kindly turned off our oil diffuser that we had left on in a rush so we didn’t have to come back. We cannot recommend her enough, especially if you are looking for a sitter who is patient with skittish/anxious dogs.

Profile image
Cathlene D.
Sitter Profile Image: Laura D.
Verified Enhanced Background Check
Laura D.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
59 reviews
19 repeat clients
35 years of experience
Annapolis, MD, 21403

Laura was incredible! I requested two last minute drop-ins on a weekend day. Laura promptly responded, and we set up a meet-and-greet for the next day. Laura checked on both my dog and cat. All communication was clear, and I felt that Ranger and Renegade were well cared for. It's all we can ask as pet parents. Also, the pictures Laura took during the visit were excellent! Ranger and Renegade look forward to the next time Laura checks on them.

Profile image
Taylor M.
Sitter Profile Image: Andrew P.
Verified Enhanced Background Check
Andrew P.
Star Sitter
from
$19
per visit
5.0 out of 5 stars
65 reviews
18 repeat clients
15 years of experience
Annapolis, MD, 21403

Andrew is the best. We’ve been fortunate enough to be able to book him on several occasions. He is great with communication, fabulous with our pets and al trustworthy. We feel so blessed to have him.

Profile image
Marymai Q.
Sitter Profile Image: Leigh Ann E.
Verified Enhanced Background Check
Leigh Ann E.
Star Sitter
from
$19
per visit
5.0 out of 5 stars
7 reviews
3 repeat clients
37 years of experience
Annapolis, MD, 21403

Leigh Ann was very kind, caring, attentive, and professional when having a visit with my dog. I would not hesitate to book again in the future!

Profile image
Morgan O.
Sitter Profile Image: Beth W.
Verified Enhanced Background Check
Beth W.
Star Sitter
from
$28
per visit
5.0 out of 5 stars
71 reviews
32 repeat clients
25 years of experience
Annapolis, MD, 21403

My pups loved Beth W. They looked forward to her coming everyday. She was attentive and caring. I look forward to having her back the next time.

Profile image
Adelle J. D.
Sitter Profile Image: Stella N.
Verified Enhanced Background Check
Stella N.
from
$22
per visit
5.0 out of 5 stars
15 reviews
3 repeat clients
7 years of experience
Annapolis, MD, 21403

Thank you so much!!

Profile image
Erin D.
Sitter Profile Image: Thomas R.
Verified Background Check
Thomas R.
Star Sitter
from
$28
per visit
5.0 out of 5 stars
87 reviews
19 repeat clients
7 years of experience
Annapolis, MD, 21403

Thomas is great with our pups, and very reliable; even last minute! He’s pleasant, kind and responsible. I really enjoy seeing the Rover Cards with his notes, pictures and activities. We look forward to using him again!

Profile image
Heather C.
Sitter Profile Image: Sarah S.
Verified Background Check
Sarah S.
from
$23
per visit
5.0 out of 5 stars
437 reviews
132 repeat clients
13 years of experience
Annapolis, MD, 21403

Sarah was incredibly flexible and helpful while our plans changed (and we accidentally gave her outdated care instructions). She went out of her way to care for our kitties — and did a great job!

Profile image
Natalie S.
Sitter Profile Image: Elizabeth G.
Verified Enhanced Background Check
Elizabeth G.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
43 reviews
20 repeat clients
10 years of experience
Annapolis, MD, 21403

Elizabeth was very prompt and professional. My pets are not used to me leaving and she went above and beyond what was expected for each visit. I felt like she was really paying attention to both of my pets specific needs and personalities. She was very flexible with my requests and worked with me to accommodate my pets. I will request her services again if I go out of town.

Profile image
Jennifer A.
Sitter Profile Image: Harrison S.
Verified Background Check
Harrison S.
from
$15
per visit
4 years of experience
Annapolis, MD, 21403

About: I’ve had dogs and cats my whole life growing up and been a pet owner for 18 years. I have walked, feed and cared for our family’s, friends, and neighbors. I’m am great with younger pets that need to release some energy and great with older pets that need a little bit more patience and time. I can’t wait to meet your pet and give a helping hand to your family. I’m completely flexible any days and times. Happy to do a meet and greet free of change! I currently own two pups named Dunkin and missy and a cat named bonnaroo. Which I care routinely. I don’t have any other big jobs right now so my main goal is focusing on the animals and making sure they get exercise. I love to get exercise and walk with my dogs. Also love to throw the ball with my dogs. By also Making sure they have food and water and stay healthy.

Sitter Profile Image: Mary H.
Verified Enhanced Background Check
Mary H.
from
$27
per visit
5.0 out of 5 stars
4 reviews
15 years of experience
Annapolis, MD, 21403

About: Hi! I’m Mary, but I usually go by Amber. I’ve raised and cared for dogs most of my life. I would love to help you with your check ins, walks, daycare, or boarding needs. I also have experience with medication administration if needed. I work part time, so I have a wide range of availability. I have a car and can drive to your location or host your loved one in my home. I have a single family house with a large fenced in yard. I also live in a big lovely neighborhood with plenty of space for walks. I do not currently have any pets, so your pet to have individual attention if required.

Sitter Profile Image: Alaina G.
Verified Enhanced Background Check
Alaina G.
from
$20
per visit
9 years of experience
Edgewater, MD, 21037

About: I’ve been surrounded by animals my whole life and have years of hands-on experience caring for dogs of all ages and sizes. My family has also fostered puppies for the past 5–6 years, which has given me experience with young dogs, routines, patience, and providing a safe, loving environment. Friends and family have always trusted me to walk, feed, play with, and care for their pets like they’re my own. I currently have a very flexible schedule and plenty of free time to dedicate to your pets before starting my full-time role in July. Once I begin, I’ll only be in office two days a week, so I’ll still have lots of availability. I’m available on both weekdays and weekends, and I’m happy to accommodate a variety of schedules and care needs. Your pet’s safety and comfort are my top priorities. I have a fenced yard and one friendly small dog who loves making new friends. Whether caring for your dog in my home or yours, I’ll make sure they feel loved, safe, active, and comfortable. I enjoy long walks, playtime, and giving pets lots of attention and care while you’re away.

Sitter Profile Image: Courtney A.
Verified Background Check
Courtney A.
Star Sitter
from
$28
per visit
5.0 out of 5 stars
13 reviews
4 repeat clients
15 years of experience
Edgewater, MD, 21037

My cats love Courtney! Especially my super shy boy comes out of shell when he sees her. I’m super happy with her taking care of my two little ones, she spends quality time with them and doesn’t cut her visits short. I also really appreciate the detailed write up and the cute photos. Thank you, Courtney!

Profile image
Anne-Katrin A.
Sitter Profile Image: Mark D.
Verified Enhanced Background Check
Mark D.
from
$20
per visit
5.0 out of 5 stars
3 reviews
2 repeat clients
30 years of experience
Annapolis, MD, 21403

Mark was great. Very professional, punctual and spent extra time with my dogs. I would definitely use him again.

Profile image
Karen K.
Sitter Profile Image: Kathryn U.
Verified Enhanced Background Check
Kathryn U.
from
$14
per visit
5.0 out of 5 stars
18 reviews
3 repeat clients
10 years of experience
Annapolis, MD, 21401

Kathryn went above and beyond caring for our senior dog Jackson! We were a bit nervous about using a dog sitter we didn’t know, but Kathryn put us at ease with her kindness and expertise. We’re so grateful for her help and would definitely recommend her to anyone looking for a great dog sitter.

Profile image
Luke A.
Sitter Profile Image: Alyssa B.
Verified Background Check
Alyssa B.
from
$20
per visit
5.0 out of 5 stars
11 reviews
3 repeat clients
10 years of experience
Annapolis, MD, 21403

Alyssa did an awesome job caring for my puppies. She was a great communicator and sent great pictures. I requested her pretty last minute but she was very responsive and I would recommend her to anyone!

Profile image
Caroline J.
Sitter Profile Image: Blinne F.
Verified Enhanced Background Check
Blinne F.
from
$19
per visit
5.0 out of 5 stars
20 reviews
6 repeat clients
20 years of experience
Annapolis, MD, 21403

Blinne was great with my pup, she went on long walks, my dog loved her, & she even did some training with her! I would definitely book with her again!

Profile image
Victoria E.
Sitter Profile Image: Halsey C.
Verified Enhanced Background Check
Halsey C.
from
$22
per visit
5.0 out of 5 stars
7 reviews
1 repeat client
4 years of experience
Annapolis, MD, 21403

Halsey did a great job of taking care of my cat Toby, would definitely hire her again for drop-ins! He was well-loved during a short trip while I was away.

Profile image
Sophia C.
1 / 1
View more sitters

Oakwood pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Elizabeth was great with our two cats! We had specific instructions about keeping them separate and mixing medicine into food, & she kindly agreed to a meet & greet to make sure she received the details & met our girls. We felt good about leaving them in her hands, & everything was the way we left it when we returned. Thanks Elizabeth!

Profile image
Julia H.
Drop-In Visits
5.0 out of 5 stars

This is our second time working with Shelby, both times we needed last-minute assistance and she stepped in happily. She took great care of our dogs, gave them their medicine, let them frolic in the yard, and even brought in our packages and kindly turned off our oil diffuser that we had left on in a rush so we didn’t have to come back. We cannot recommend her enough, especially if you are looking for a sitter who is patient with skittish/anxious dogs.

Profile image
Cathlene D.
Drop-In Visits
5.0 out of 5 stars

Camilla was amazing with my dogs! She checked on them regularly, made sure they were fed and walked, and handled their timid personalities with so much patience. Even though they were initially skittish even after a meet‑and‑greet. She took her time and let them warm up at their own pace. Her communication was excellent. She sent consistent updates and photos, which gave me total peace of mind and confirmed I’d made the right choice. By the end of the stay, my dogs were completely comfortable with her. I’m truly appreciative of the care she provided and will absolutely book Camilla again.

Profile image
Rebecca B.
Drop-In Visits
5.0 out of 5 stars

Laura is wonderful as always. Sending great descriptions of the visit plus a ton of pictures! Laura is great and we highly recommend!

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

Samantha is the best! She’s so responsible and loving to my cat. She is respectful of my home and I truly appreciate her.

Profile image
Trudi 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

Profile image
Tom C.
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!

Profile image
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.

Profile image
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!

Profile image
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’

Profile image
Catie C.
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

Profile image
James S.
Drop-In Visits
5.0 out of 5 stars

This is my 4th time having Ellie watch our dog Piggy. She is amazing!! She’s always prompt, communicates well and takes good care of Piggy. She has gone above and beyond by bringing in packages as well. I would highly recommend her.

Profile image
Joan D.
Drop-In Visits
5.0 out of 5 stars

Kristy has been so wonderful with our new pup Luna. She goes above and beyond when taking care of her. Kristy is reliable and responsible and brings us such peace of mind that Luna is taken care of while we are at work. She responds quickly, has been flexible, and is very attentive to Luna’s needs. Definitely recommend Kristy to anyone who wants their dog well taken care of!

Profile image
Rachel M.
Drop-In Visits
5.0 out of 5 stars

Meghan sent great pictures of my dogs and had great communication- will definitely have her back in the future!

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

Alyssa did an awesome job caring for my puppies. She was a great communicator and sent great pictures. I requested her pretty last minute but she was very responsive and I would recommend her to anyone!

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

I have probably said this before, but I always have such great peace of mind when Kylie looks after Guillermo. I am typically gone for a few days at a time — this time around I was gone for much longer but I felt at ease knowing he’d be in great hands. As always Kylie was communicative, caring and adaptive to the changes in Guillermo’s feeding routine. I can’t thank her enough for being so great with him!!

Profile image
Vanessa B.
Drop-In Visits
5.0 out of 5 stars

Michele was great with our puppy- she was communicative and kind, and Haze was happy as can be when we returned home! Would definitely book her again!

Profile image
Liza M.
Drop-In Visits
1 / 1
Find pet care near you

How Rover works

  1. 1. Search

    Read verified reviews by pet parents like you and choose a sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

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 pet 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.

Pet Sitting FAQs

Frequently asked questions about Rover

If you’re searching for a Oakwood pet sitter for the first time, visit the pet sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a pet sitter before, learn more about how to do this in the Rover app or on your computer.

Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, pet sitters on Rover respond in under an hour.

Experience can vary widely from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when comparing pet sitters available in Oakwood.

Rover makes it easy to find Oakwood pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:

  • Pets of all ages and abilities, including puppies
  • Pet parents looking for a safe, loving alternative to a kennel
  • Pets who’d love to socialize with their pet sitter’s pets

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your pet sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.