Dog Boarding in Oakwood, MD
Find a loving dog sitter to watch your dog overnight at your sitter's home.
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Top rated Oakwood dog boarders
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Our dog sitting experience with Shuling was wonderful. Lucky, our 4-year old mini goldendoodle, and his 2-year old beagle cousin looked like they were having a great time running around outside then relaxing inside. Shuling sent us lots of pictures. We would definitely contact her again if we need dog sitting coverage the next time we are in Annapolis.”
“Maizie is a very shy girl with people. So dropping her at a sitter is usually a bit difficult for her. Elaine had 2 other dogs arriving too which brings Maizie out of her funk. She had a blast running around the fenced yard. All in all she came home very happy.”
“Katie did a wonderful job watching Frankie for us for a long weekend! She sent regular pictures and updates and we could tell Frankie was very happy at Katie's. Would absolutely recommend Katie for any future boarding needs!”
“Willow had the best time with Shelby and her pup Ellie. Instant best friends. I felt totally confident that our 4 year old dog was having a vacation all her own the entire weekend. Lots of time outside, on walks, playing, and snuggling. 100% would recommend and feeling so happy we have a go-to sitter :) thank you guys!”
“Katelyn provided the most amazing care for our puppy!! He was spoiled with multiple walks, many treats, and tons of snuggles while we were away for a long weekend. He became friends with their sweet husky as well. Can’t wait for him to stay with her family again soon!! Thank you!!”
“Michelle was great! Our Birdie had a wonderful time and really felt at home with Michelle and her family. I appreciated the the pictures of Birdie hanging out, doing her thing. We know we left her in good hands!”
“After a meet and greet we decided to do an overnight trial and our dog loved it! The whole family is very warm and inviting and our dog felt at home the moment he walked in the door. Their house has a nice fenced in backyard as a plus. We have already booked our summer vacation and plan on booking other trips as well. Very happy to have found such a perfect fit.”
“Thomas and Melissa took excellent care of our large, energetic dog. They sent updates and pictures throughout the day and were flexible with their schedule. We will definitely be requesting their services again!”
“Beth was awesome with Bailey! Bailey is an older gal, and gets a bit stressed with change but Beth was very patient with her and Bailey settled down nicely during her stay. The video of Bailey wagging her tail and playing around proved such. Thank you, Beth, for taking such good care of her!”
“We thought we were having a good time until Tiffany sent pictures of our dogs. They were having the time of their lives! Tiffany is so kind and caring. She sent pictures of both dogs, cooked them food, let them sleep where they were comfortable. I couldn’t have picked a better person, and I will now only allow them to stay with Tiffany. Wonderful experience and big thanks to Tiffany!”
About: I've had dogs my whole life. Grew up in a house with 2+ dogs near constantly. All family dogs were 60+ lbs each with the largest being 110lbs. My 75lb dog crossed the rainbow bridge Sept 2025, I am not ready for a dog full time but I do miss the company. I will spoil your dog. I do not care about breed. I am looking for weekends. I work full time, so I am ready to go around noon on Friday and depending on the needs can be around all weekend. Generally I do leave the house during the weekend for a couple hours during the day to do chores and stuff but other than that can be a total home body. If the dog is good on leash I have a great neighborhood to take walks. If you are looking for me to stay at your house over the weekend, I can provide as much potty coverage as you request. If you want me to stay over the week, I do have a day job with my schedule being 7-3. I have a 8ft privacy fence the whole way around my backyard with a dog door. I do not have a crate, but I can use yours if you want your dog crated. I follow your food rules. I used to make hot breakfast/dinner for my dog. I do keep some dog treats in the house but I will check with you if your dog can have that specific treat first and if there are any dietary needs. If you want me to stay in your house, lets write the rules down and I'm happy to do whatever. If you have poor cellphone service, it'd be great to get a wifi password.
“Ashley was an absolute lifesaver! She came to our rescue at the last minute, and took excellent care of my Rebel. Ashley sent pictures everyday, and Rebel came home a happy boy.”
“Mady is AMAZING! She helped us out in a last minute pinch and made sure our pup had a fun, exciting day. She sends lots of pictures and gave Kiko lots of love! Thanks, Mady!”
“Oak really enjoyed her stay with Lindsay! She particularly enjoyed her kiddos! Lindsay made the pickup and drop off logistics incredibly easy! I really appreciated her flexibility. Thanks again Lindsay!”
“Blake was great with Murphy! She was very responsive and was able to support us as my scheduled sitter dropped out unexpectedly. Would highly recommend Blake boarding or watching a dog. Thanks Blake!”
“Celena was great! She sent tons pictures of our boy having a great time and she had plenty of updates. We also appreciate that she worked with us on our drop-off and pick-up times! We will definitely work with her again!”
Oakwood dog parents share their Rover experiences
Andy & Lydia did an outstanding job taking care of Bella. Andy was great at communicating how she was doing everyday & responding quickly to our texts. We were able to relax and enjoy our vacation knowing that Bella was having a fun time on her stay & being well taken care of. We will definitely use them again & recommend to others.
We thought we were having a good time until Tiffany sent pictures of our dogs. They were having the time of their lives! Tiffany is so kind and caring. She sent pictures of both dogs, cooked them food, let them sleep where they were comfortable. I couldn’t have picked a better person, and I will now only allow them to stay with Tiffany. Wonderful experience and big thanks to Tiffany!
Julia was wonderful! We left our doodle with her over the weekend and she seemed to have had a great time. Julia sent us multiple updates throughout the day with multiple pictures as well! Pick up, drop off, and communication went smoothly. We would definitely trust her to host our doggo again!
Alina was great! I got lots of pictures of Giles and he had such a fun playing with her pups. She already had a crate, so I brought in some blankets and a stuffie for him. She was also super flexible with times, which was wonderful. Her place looks perfect for doggies to play in and I am happy we used her to take care of Giles.
Popular requests near you
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It doesn’t happen often, but if your dog boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.
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Dog Boarding FAQs
Frequently asked questions about Rover
Typically, dog boarding sitters on Rover respond in under an hour, so you should be matched with the perfect sitter for you and your dog in no time!
Experience can vary widely from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when comparing sitters available in Oakwood.
Rover makes it easy to find Oakwood dog boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog boarding is great for:
- Dogs of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their 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 dog boarding sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your 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 dog boarding 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 dog boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
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