Dog Boarding Oakley

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Oakley, Find top rated dog boarding

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: Denise R.
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Denise R.
Star Sitter
from
$35
per night
5.0 out of 5 stars
• 150 reviews
59 repeat clients
5 years of experience
hollywood, MD, 20636

“Denise was absolutely amazing with dezl. She was very thorough and understand of dezls needs. I loved that she sent pictures and updates throughout dezls stay. If I could put more stars I would! Definitely will be using her again :)”

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Anna V.
Sitter Profile Image: Nikki G.
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Nikki G.
from
$32
per night
5.0 out of 5 stars
• 91 reviews
19 repeat clients
13 years of experience
Saint Leonard, MD, 20685

“Nikki was very responsive and sent picyures throughout my trip. My pup even had accidents. Thats right i said accidents with an s! And she was so sweet about it. My pup came home happy and i felt at easy the entire time. One less thing to worry about. I will rebook and i recommend you check her out if you need a dog sitter!”

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Jessica S.
Sitter Profile Image: Melanie & Randy W.
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Melanie & Randy W.
from
$40
per night
5.0 out of 5 stars
• 9 reviews
2 repeat clients
16 years of experience
Hollywood, MD, 20636

“I highly recommend Melanie and Randy to care for your pets! Our dog,Pax, can only have a certain type of dog toy, since he is a heavy chewer, and Melanie made sure that he would only have non-destructable toys to play with. She also gave updates with pictures to let me know how Pax was settling in. I felt very comfortable with Melanie and Randy caring for Pax and will definitely rebook with them on the future.”

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Jill G.
Sitter Profile Image: Amber M.
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Amber M.
from
$50
per night
4.4 out of 5 stars
• 9 reviews
10 years of experience
Mechanicsville, MD, 20659

“Hermione had a great experience with Amber. She loved playing with her children. Hermione’s first boarding experience was great. Looking forward to getting Amber again!”

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Freddie H.
Sitter Profile Image: Brooke H.
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Brooke H.
from
$35
per night
5.0 out of 5 stars
• 43 reviews
17 repeat clients
26 years of experience
Leonardtown, MD, 20650

“Brooke is the absolute best! I am very particular about who I leave my dog (Theo) with, particularly because of his small size and his separation anxiety. Brooke was phenomenal the entire week that we were on vacation and Theo was so happy. She took him on walks, played with him, let him take naps and snuggle with her, and she even worked on training to help with his anxiety. She even dropped him off for us after we'd been on the road all day. She sent regular updates, pictures, and videos, and he looked so happy every time and it was such a relief to not have to worry about him while we were away. Brooke absolutely goes above and beyond for her clients and I would highly recommend her to anyone! ♥️”

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Hailey and Troy L.
Sitter Profile Image: Anika C.
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Anika C.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 47 reviews
14 repeat clients
45 years of experience
Mechanicsville, MD, 20659

“My dog looked like he was enjoying himself so much, I wasn’t sure how to convince him to come home🤭 His previous stay away from home was terrible, and stressful, he returned with hotspots all over his body. I knew we found a good fit Anika because she only watches one dog at a time, more his speed. We received pictures and updates daily which eased his humans minds. I cannot thank Anika enough fo her care. See you soon!”

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Jennika I.
Sitter Profile Image: Haley W.
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Haley W.
from
$55
per night
5.0 out of 5 stars
• 45 reviews
8 repeat clients
10 years of experience
Lusby, MD, 20657

“Haley is the best! She accommodated my schedule & went above and beyond for my fur baby, Charlie. I was able to go on an overnight trip with no stress about how Charlie was doing.”

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Sierra R.
Sitter Profile Image: Kerri L.
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Kerri L.
from
$50
per night
5.0 out of 5 stars
• 14 reviews
6 repeat clients
20 years of experience
Lusby, MD, 20657

“Kerry and her family took amazing care of my dog Briggs while I was out of town. I got loads of adorable pictures, and he was returned groomed and fluffy with a new bandana. I highly recommend them and will be reaching out again when I travel.”

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Angela K.
Sitter Profile Image: Lori W.
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Lori W.
from
$45
per night
5.0 out of 5 stars
• 80 reviews
32 repeat clients
20 years of experience
Chesapeake Beach, MD, 20732

“She loves dogs truly. She let our little dog to sleep on her bed first night to let him feel like home. She updated and sent photos twice a day. The little dog seems to make the furry friends and like his stay”

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jess d.
Sitter Profile Image: Ashley T.
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Ashley T.
from
$40
per night
5.0 out of 5 stars
• 22 reviews
6 repeat clients
10 years of experience
Colonial Beach, VA, 22443

“Ashley T. was terrific! With many years of experience, this mild-mannered, petite yet confident dog sitter immediately knew how to care for and manage my Giant Pyrenees Doodle- all 75 pounds of him. I felt good about leaving my huge fur baby with her for my out of town trip. During my dog's stay, Ashley periodically sent photos and updates. This was most comforting and I was able to enjoy my long needed trip. I highly recommend Ashley T. and will hire her again and again.”

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Abenaa P.
Sitter Profile Image: Daniela H.
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Daniela H.
from
$40
per night
5.0 out of 5 stars
• 3 reviews
5 years of experience
Prince Frederick, MD, 20678

“Daniela was an amazing puppy sitter! Bruno absolutely loved her and her sweet family. While we were out of town, Daniela communicated with us daily and sent us the cutest photos and videos the entire time. We are so thankful that she was able to accommodate our last-minute request. With all the belly rubs and cuddles, I’m sure our furbaby had an amazing time and we’ll definitely be rebooking with her next time!”

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Melissa G.
Sitter Profile Image: Rena L.
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Rena L.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 82 reviews
27 repeat clients
30 years of experience
Waldorf, MD, 20603

“Great Service as always. Can’t explain enough how I can leave my dog with Rena and feel at peace while traveling knowing my dog is treated like he is a part of their family.”

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Nicholas B.
Sitter Profile Image: Kimberly T.
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Kimberly T.
Star Sitter
from
$80
per night
5.0 out of 5 stars
• 152 reviews
47 repeat clients
20 years of experience
Lusby, MD, 20657

“Kimberly took exceptional care of our pups! Highly highly recommend to anyone looking for an attentive care taker for your fur babies while away. I will not hesitate to call Ms. Kimberly again to watch Greta and Bow again.”

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Barbar E.
Sitter Profile Image: Richardine L.
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Richardine L.
from
$50
per night
5.0 out of 5 stars
• 3 reviews
2 repeat clients
10 years of experience
Waldorf, MD, 20602

“She did a phenomenal job taking care of my baby while I went on a work trip. Kept me well informed & plenty of pictures.”

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Patrice M.
Sitter Profile Image: Donna A.
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Donna A.
from
$40
per night
5.0 out of 5 stars
• 4 reviews
1 repeat client
10 years of experience
Leonardtown, MD, 20650

“Was very appreciative that Donna took Kodi at the last minute when her usual border wasn't available. She seems so pleasant. Kodi was fine. I will definitely use her again if necessary. I gave her a cash tip which I always do so that they can get full benefit of it.”

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Jayne S.
Sitter Profile Image: Jasmine H.
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Jasmine H.
from
$39
per night
5.0 out of 5 stars
• 2 reviews
1 repeat client
6 years of experience
California, MD, 20619

“Jasmine was great with my boy. She provided tons of updates and pics of him enjoying his stay. I will definitely use her again the next time we are out of town.”

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Keegan U.
Sitter Profile Image: Michelle M.
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Michelle M.
from
$45
per night
5.0 out of 5 stars
• 19 reviews
7 repeat clients
25 years of experience
Chesapeake Beach, MD, 20732

“Michelle was fantastic with our pup! He had so much fun playing with her sweet dog and friends, and she sent us pictures throughout his stay so we could see how happy he was! She was great at arranging pickup and drop off, to make sure it worked with our schedule too. Will definitely be rebooking when we need.”

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Stephanie L.
Sitter Profile Image: Sarah B.
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Sarah B.
from
$40
per night
4.8 out of 5 stars
• 25 reviews
10 repeat clients
31 years of experience
Saint leonard, MD, 20685

“Sarah was amazing with our dog! She was so good to our dog and even gave us a new collar because our dog chewed through hers. Sarah is very sweet and thoughtful, she took our dog for a run and made sure she felt right at home! I highly recommend her!!”

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Jenna C.
Sitter Profile Image: Tara G.
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Tara G.
from
$45
per night
5.0 out of 5 stars
• 41 reviews
13 repeat clients
20 years of experience
White Plains, MD, 20695

“Bella had a great stay and wanted to stay longer! Tara and her family are very sweet and accommodating. Tara sent photos and updates about Bella throughout her stay as we requested.”

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Joy J.
Sitter Profile Image: Kareema L.
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Kareema L.
from
$55
per night
5.0 out of 5 stars
• 6 reviews
1 repeat client
15 years of experience
White Plains, MD, 20695

“I had a great experience with Kareema! She was reliable, communicative, and took great care of my pup while I was away. I really appreciated the updates and knowing he was in good hands. This is my second booking and would definitely recommend her and book again!”

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Abighail O.
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The median cost per night for dog boarding in Oakley is $45

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.

How to book dog boarding

  1. 1. Search

    Browse profiles of sitters near you who offer dog boarding.
  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 dog boarding - Oakley

Select a filter and find qualifying sitters offering dog boarding.

Sitters in Oakley average 11
repeat dog boarding clients

FAQs for Dog Boarding - Oakley

Frequently asked questions about Rover

As of November 2026, there are 393 sitters on Rover offering Dog Boarding across Oakley. Enter your ZIP code to see which available sitters are closest to your home.

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.

Every sitter on Rover has their own routine. Depending on the arrangements you agree on before the stay, a sitter can follow your dog’s regular feeding schedule, provide a comfortable place to sleep, offer companionship, and support their usual exercise and play needs.

96% of sitters in Oakley can provide daily exercise during dog boarding stays. Depending on the sitter, their home environment, and your dog’s needs, this may include walks, outdoor play, indoor enrichment activities, or supervised play with compatible dogs. These activities are not automatically included with every booking, so ask the sitter what a typical day looks like.

During the Meet & Greet, discuss your dog’s usual exercise and play routine, whether they can safely interact with other dogs, and any activities or restrictions the sitter should follow. You can also ask the sitter to send photo and message updates during the stay so you can see how your dog is spending their time.

Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Oakley home-away-from-home, we recommend packing:

  • Health and safety essentials such as their ID tags, vaccination records, medication, and emergency vet or secondary caregiver contacts.
  • Food and gear such as harnesses, collars, food (portioned by day), and an item that smells like you.
  • Special instructions such as a list of training cues, medical administration needs, or favorite hang-out spots in your Oakley.

Tip: You can upload your dog’s routine and medical info directly onto their profile so your sitter always has the details at their fingertips.

Yes, you can find sitters who have experience with handling special pet needs in Oakley. On Rover:

  • 86% of sitters can help with special care needs
  • 95% can help with giving oral medications or injections
  • 96% 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.

You and your Oakley sitter can schedule drop-off and pick-up in a way that works best for the both of you—and your dog. Most sitters offer flexible times for drop-off and pick-up but the easiest way to confirm those times will be through in-app messaging. Confirm your arrival time the day of pick-up and drop-off can also help keep the process smooth and organized.

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.

While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.

Many sitters in MD ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies.

By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.

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 dog to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your dog 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.

Adding another pup to the pack? Most sitters and walkers offer a reduced rate for additional dogs. You’ll find these exact rates listed under the "Services" tab on any sitter's profile. Since every dog is unique, final pricing may vary depending on the level of care required.

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