House Sitting Oakland

Find a loving house sitter to watch over your pets and your home.

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Over 5
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Oakland, 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: April H.
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April H.
from
$60
per night
5.0 out of 5 stars
7 reviews
3 repeat clients
40 years of experience
Oakland, MD, 21550

About: Dogs make me happy. I have a cozy house with a yard. Our mini dachshund recently passed away, he was such a sweet boy. We have not found it in our hearts to take in another sweet dog at this time. I own a business so my hours are flexible. I will care for you fur baby as if they were my own. I enjoy playing, walking, cuddling, and giving plenty of scratches behind the ears. Make sure I'm aware of any medications, special needs or allergies your dog may need. I've never met a dog that hasn't liked me. I feel I have a special connection with dogs. I look forward to meeting you and your dog, I can meet beforehand if necessary. Dogs make my heart smile and bring joy to my life. If you have questions feel free to ask. Thank you.

Sitter Profile Image: Jennifer H.
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Jennifer H.
from
$77
per night
5.0 out of 5 stars
31 reviews
2 repeat clients
12 years of experience
Bruceton Mills, WV, 26525

Jennifer and John took great care of our babies. They gave us updates and pictures throughout their stay. We were very hesitant to have strangers in our home but they took care of our home as if it were theirs, and we came home to a cleaner house than we left😊 highly recommend and would definitely use again. Our babies were happy, healthy and loved while in their care and that was the most important thing for us 💕

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Ellen H.
Sitter Profile Image: Thea L.
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Thea L.
from
$85
per night
5.0 out of 5 stars
10 reviews
1 repeat client
20 years of experience
Oakland, MD, 21550

Thanks very much, Thea! You were in touch before and during the time you watched Ringo. You even sent pictures, which we appreciated. We hope to book you again if we are in need.

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Richard O.
Sitter Profile Image: Laurie R.
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Laurie R.
from
$18
per night
4.4 out of 5 stars
8 reviews
2 repeat clients
8 years of experience
Elkins, WV, 26241

About: I am a 63 year old cancer survivor who is now disabled! I would love to babysit your pets for you in your home! Anytime! I have 2 dogs & 5 cats I now pet sit for. I am a true animal lover. I have 3 cats at home whom I love very much! This would be the perfect job for me. Although, I don't think of petsitting as a job. I would love to play with or walk your dogs for you. I would treat your pets with as much love as you do! Have been pet sitting for 4 years. I like to play with the dogs, take them for walks. Size or breed doesn't matter. All dogs are welcome! Why I love dog sitting I have been a dog lover for 25 years. I have had several (4) dogs in my life. The first was a german shepherd hybrid with wolf. She was beautiful! My husband had a little terrier mix who stayed in the house. We also had a black lab & a mutt named July. If I could have a dog now, I would; but I don't have a fenced-in yard. I really don't want to leave a dog on a chain all the time. My experience administering medication I can administer oral meds. I’m currently not working so im available week days & weekends. I’m very flexible & don’t need a lot of time before job. I really love animals! I can’t board animals. I don’t have the space. In other peoples homes I can play with their pets & enjoy taking them for a walk.

Sitter Profile Image: Bella S.
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Bella S.
from
$26
per night
5.0 out of 5 stars
1 review
4 years of experience
Reedsville, WV, 26547

Bella was amazing with my Yorkie. She stayed at my house, which made it so much better for Bluey. Would highly recommend Bella and definitely will use her again.

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michelle B.
Sitter Profile Image: Emma H.
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Emma H.
from
$100
per night
5.0 out of 5 stars
3 reviews
2 repeat clients
4 years of experience
Friendsville, MD, 21531

About: Overnight and long-term care🌙🏠, ☀️all season walks❄️, photos of your pets day to see their time in my care 📷 and experience in administrating medication routines. Pet sitting works well with my schedule, as I have a set part-time schedule right now that leaves room for me to give your pet the attention they deserve. When I care for a pet at home or on a walk, I make sure they are cared for and protected in the same ways their owners find right for them. Every pet I care for is treated and protected the same way I would treat my own.

Sitter Profile Image: Skyler H.
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Skyler H.
from
$60
per night
5.0 out of 5 stars
4 reviews
20 years of experience
Oakland, MD, 21550

About: Dogs love me, and yours will too. Comfort, play, walks, and stays, care for your fluffy friend when you can't be there. Best with small to medium dogs in my location. Available for any size dog for walks, visits or off site stays. Additional experience with nervous and easily stressed, or startled dogs, always willing to make them feel safe, sitting with them and more. Long term experience with lots of different breeds and sizes, from large to miniature and anywhere between. Porch has two steps. I can change my schedule to accommodate some requests. We lost our little Mr Ham in 2025 at the age of 14. We no longer have any dogs in our home. So lots of room for boarding. We are searching for another mini-dachshund puppy to join our family. I can provide my own leash, bags, collar and more just ask. Prefer boarding here, but can make arrangements for other requirments. I need some advanced notice, although some same day requests may be possible to handle. I have an unfenced yard, however walks are easy around the house or around the neighborhood. Lots of attention avaliable. We lost our little Mr Ham in the summer of 2025 at the age of 14. We no longer have a dog in our house, so there is lots of room for bording. We are still looking for a mini-dachshind puppy to join our family.

Sitter Profile Image: Michelle G.
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Michelle G.
from
$100
per night
5.0 out of 5 stars
5 reviews
1 repeat client
21 years of experience
Terra Alta, WV, 26764

We needed a somewhat last minute sitter for our pups (in home) and Michelle was happy to help out! She was absolutely wonderful with our pups. She followed their routines and gave them lots of love which made me feel so reassured when we were away. She also communicated consistently and provided lots of pics of the pups. I will definitely reach out to her again if we need a sitter in the future!

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Erika L.
Sitter Profile Image: Jessica K.
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Jessica K.
from
$75
per night
5.0 out of 5 stars
69 reviews
15 repeat clients
10 years of experience
Grantsville, MD, 21536

Jessica was amazing with all of our animals when we were out of town. This was our first time using Rover and she exceeded all expectations.

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Amanda M.
Sitter Profile Image: Annie M.
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Annie M.
from
$55
per night
8 years of experience
Frostburg, MD, 21532

About: As a professional breeder and trainer, my Aunt taught me so much of what I know. I’m a homebody, looking to take fantastic care of your pets, plants, and even your sourdough starter 😁 With two degrees - graduating summa cum laude in both, I am sensitive to all your needs, care about the details, and am ready to work with you and the family to get the best results. Get ready for excellent house-maintenance & pet-care, you’ve found it here! I am a freelance musician who builds my own schedule - I am able to accept timely requests within my open availability and can schedule both teaching and preparation around your dates! I own no pets and am ready to fit the needs of yours! In-home services for long term care. If needed, I can host your pet for a few hours!

Sitter Profile Image: Rachel W.
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Rachel W.
from
$75
per night
5.0 out of 5 stars
4 reviews
20 years of experience
McHenry, MD, 21541

Rachel was absolutely the best Rover match to date! Her communication and reliability was exceptional and we hope our schedules align in the future! :-) Piper, Lake and Becket are already asking where their cuddle puddle friend went!

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Amy L.
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The median cost per night for house sitting in Oakland is $55

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. 1. Search

    Browse profiles of sitters near you who offer house sitting
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

Popular requests for house sitting - Oakland

Select a filter and find qualifying sitters offering house sitting.

FAQs for House Sitting - Oakland

Frequently asked questions about Rover

The average cost for House Sitting in Oakland on Rover is $88.8 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 38 sitters on Rover offering House Sitting across Oakland. 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 Oakland 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 Oakland 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 Oakland 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 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.

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