Dog Boarding In Cheswolde Area

Find a loving dog sitter to watch your dog overnight at your sitter's home.

Pick up
Search

Every sitter passes an enhanced background check. Learn about RoverProtect

Top rated Cheswolde Area dog boarders

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

1 / 1
Sitter Profile Image: Steven O.
Verified Background Check
Steven O.
Star Sitter
from
$45
per night
5.0 out of 5 stars
258 reviews
146 repeat clients
25 years of experience
Pikesville, MD, 21208

Leaving my dog to someone I had just met once caused some consternation. However, with that first meeting I had a "meet and greet" with Steven and his own dog, which turned out just right. I dropped my cocker spaniel off with confidence. Steven sent me pictures and an update as to how my Gabby settled in. I was able to feel comfortable and able to attend a function without concern for Gabby. When I picked her up she was happy and had received wonderful care! I have returned to the area after being gone 23 months. I lost some contacts that I had. I feel enormously relieved that I have someone professional, reliable, and kind to leave Gabby with should I need to do so in the future. You will not be disappointed should you leave your trust in Steven, nor will your dog.

Profile image
Blake or Kelly K.
Sitter Profile Image: Virginia O.
Verified Background Check
Virginia O.
Star Sitter
from
$45
per night
5.0 out of 5 stars
46 reviews
20 repeat clients
25 years of experience
Catonsville, MD, 21228

Virginia is wonderful. Rapha enjoyed his time socializing with her dogs. When he came home he was calm. We will definitely book again! Thank you!!

Profile image
Sabre W.
Sitter Profile Image: Shipra K.
Verified Enhanced Background Check
Shipra K.
from
$35
per night
5.0 out of 5 stars
6 reviews
1 repeat client
10 years of experience
Charles Village, Baltimore, MD, 21218

Shipra took good care of our dog. She walked and played with him. Her dog Trevor is very nice and well behaved. My dog is tiny but got along really well with him. I would love to keep my dog with her again!

Profile image
Sangha M.
Sitter Profile Image: Rodney & Marissa O.
Verified Background Check
Rodney & Marissa O.
from
$39
per night
5.0 out of 5 stars
422 reviews
217 repeat clients
10 years of experience
Randallstown, MD, 21133

My dog is a bit scared of strangers. We tried one day with Rodney and as I picked up Zuri, she was already friendly with Rodney. I got pictures of my dog playing with his dogs. Rodney replies quickly to any question pre booking and during the stay. Thanks for taking care of Zuri!

Profile image
Deepika V.
Sitter Profile Image: Ariel M.
Verified Enhanced Background Check
Ariel M.
Star Sitter
from
$45
per night
4.9 out of 5 stars
33 reviews
11 repeat clients
15 years of experience
Cheswolde Area, Baltimore, MD, 21209

Ariel is amazing with my dog - Fluffy. Fluffy seems to really like her and is very happy to be dropped off there. I trust Ariel completely and highly recommend her!

Profile image
Reva S.
Sitter Profile Image: Felice & Ken & Tyler & Morgan T.
Verified Enhanced Background Check
Felice & Ken & Tyler & Morgan T.
Star Sitter
from
$50
per night
5.0 out of 5 stars
261 reviews
145 repeat clients
50 years of experience
Catonsville, MD, 21228

Our dog Maizey had a great time with Felice, Ken et. al. Especially appreciate their flexibility in keeping Maizey an extra day due to the unexpected lengthening of my husband's hospital stay. Very friendly and caring folks!

Profile image
Elizabeth N.
Sitter Profile Image: Shannon R.
Verified Background Check
Shannon R.
Star Sitter
from
$52
per night
5.0 out of 5 stars
730 reviews
215 repeat clients
32 years of experience
Hampden-Woodberry-Remington, Baltimore, MD, 21211

Shannon kept us updated every day with how our girl was doing. It really put us at ease to know she was being cared for with such consideration.

Profile image
Octavia S.
Sitter Profile Image: Shakiyla H.
Verified Enhanced Background Check
Shakiyla H.
Star Sitter
from
$50
per night
5.0 out of 5 stars
27 reviews
10 repeat clients
10 years of experience
Park Heights, Baltimore, MD, 21215

Baaz LOVED Shakiyla, when we arrived to pick him up he was hanging out on her porch like he was apart of the neighborhood. She kept us updated with how he was doing and maintained his same routine/schedule as if he were home. She sent videos and reassured me Baaz would be ok after he was feeling a little homesick the first night. She was always in communication and incredibly friendly. I would def book Shakiyla again! Thank you so much!

Profile image
Akhari D.
Sitter Profile Image: Danielle S.
Verified Enhanced Background Check
Danielle S.
Star Sitter
from
$40
per night
5.0 out of 5 stars
46 reviews
8 repeat clients
17 years of experience
Rosedale, MD, 21237

Danielle took great care of my dog while I was away! Sadie was happy and well cared for when I picked her up. Danielle was responsive and sent me regular updates so I knew Sadie was happy and safe. I highly recommend Danielle!!

Profile image
Kate F.
Sitter Profile Image: Steph P.
Verified Background Check
Steph P.
Star Sitter
from
$44
per night
5.0 out of 5 stars
61 reviews
16 repeat clients
40 years of experience
Parkville, MD, 21234

Steph took great care of Jill and kept us in the loop on the great time she was having with her two dogs. Jill was very happy and very tuckered out from a great couple days of playing when we picked her up.

Profile image
Bobby M.
Sitter Profile Image: Dorothy C.
Verified Enhanced Background Check
Dorothy C.
Star Sitter
from
$48
per night
5.0 out of 5 stars
12 reviews
4 repeat clients
28 years of experience
Towson, MD, 21286

Dorothy made us feel very good about leaving Penny. She looked very happy and content. We will definitely reach out next time we go on vacation when we can’t take her with us. Thank you Dorothy for taking such good care of our fur baby. 🥰

Profile image
Kimberly W.
Sitter Profile Image: Brittanie & Ryan C.
Verified Enhanced Background Check
Brittanie & Ryan C.
Star Sitter
from
$55
per night
5.0 out of 5 stars
119 reviews
41 repeat clients
10 years of experience
Catonsville, MD, 21228

Brittanie & Ryan were amazing! I had never used this service before and was a bit nervous. They were great and explained how it worked, and I met them before booking to make sure it was a good fit for all of us. It really was!! I could tell they took care of my dog as well as their own. They sent pictures throughout the week and texted back right away with any questions that I had. I can’t thank them enough and would definitely recommend them 100%! What a wonderful family and they loved Lucky and he was so happy with them and their family.

Profile image
Tricia O.
Sitter Profile Image: Marissa T.
Verified Background Check
Marissa T.
Star Sitter
from
$50
per night
4.9 out of 5 stars
49 reviews
28 repeat clients
20 years of experience
Govans, Baltimore, MD, 21212

Marissa is extremely caring and flexible and treats the dogs she watches like family! I consider her house to be a second home for my dog. Unlike a kennel I always know Marissa will be there to snuggle and play with the dogs and the dogs will get tons of time to play together.

Profile image
Kira B.
Sitter Profile Image: Casey M.
Verified Enhanced Background Check
Casey M.
from
$48
per night
5.0 out of 5 stars
9 reviews
1 repeat client
6 years of experience
Lutherville, MD, 21093

Casey and Marwa are the BEST! They spoiled our large dog Indiana to no end with multiple long walks every day, playtime, cuddles, and even grooming. There was plenty of space to roam freely in the house. They posted many pictures and videos every day. Their Pug Kevin is so cute and friendly! Indy came home well fed, nicely groomed, happy, and relaxed.

Profile image
Michaela M.
Sitter Profile Image: Ruth F.
Verified Enhanced Background Check
Ruth F.
from
$63
per night
5.0 out of 5 stars
142 reviews
46 repeat clients
6 years of experience
Baltimore, MD, 21209

Ruth & her family are amazing dog sitters! They sent adorable frequent updates & took the best care of our guy - he slept all day when he got home! He is a little high maintenance and we felt totally assured that he was loved and cared for while we were away. We would definitely recommend them to watch your pup!

Profile image
Hannah H.
Sitter Profile Image: Erika D.
Verified Enhanced Background Check
Erika D.
from
$45
per night
4.8 out of 5 stars
58 reviews
32 repeat clients
11 years of experience
Pikesville, MD, 21208

Erika was friendly adaptable and kind. Our dog had a very nice stay. Erika sent us a few pictures and sent us periodic updates. We were pleased with her service and hope to use her again.

Profile image
Dan G.
Sitter Profile Image: Virginia & Steven G.
Verified Enhanced Background Check
Virginia & Steven G.
from
$34
per night
5.0 out of 5 stars
463 reviews
208 repeat clients
21 years of experience
Westgate, Baltimore, MD, 21229

I am so happy to find Virginia and her people and fur family. My previous sitter moved to California. Louie has anxiety separation issues and likes lots of attention. Virginia and her family gave Louie all the love and attention he needed. Virginia communicated frequently and sent lots of pictures. I was in a hurry when coming home and Virginia had Louie all packed up and ready for me to pick up. I am so relieved to find Virginia.

Profile image
Faith D.
Sitter Profile Image: Nicole T.
Verified Enhanced Background Check
Nicole T.
Star Sitter
from
$50
per night
5.0 out of 5 stars
47 reviews
24 repeat clients
3 years of experience
Lower Northwood, Baltimore, MD, 21218

Nicole and her family were amazing. I received a constant flow of updates and pictures. It was just a relief to know that my puppy was in such great hands.

Profile image
Naureen Q.
Sitter Profile Image: Kassandra P.
Verified Enhanced Background Check
Kassandra P.
from
$45
per night
5.0 out of 5 stars
6 reviews
1 repeat client
1 year of experience
Park Heights, Baltimore, MD, 21215

I’m so grateful that I found Kassandra to board my dog, Benji! The consistent updates and photos provided throughout, gave me such peace of mind while I was away. Kassandra and her adorable son will love your dog like their own to make the absence easier on your pup. Oh, and benji got spoiled with that amazing fenced in yard! 10/10 recommend.

Profile image
Tzila B.
Sitter Profile Image: Meredith & Kevyn B.
Verified Background Check
Meredith & Kevyn B.
Star Sitter
from
$45
per night
5.0 out of 5 stars
331 reviews
199 repeat clients
25 years of experience
Reservoir Hill-Bolton Hill Area, Baltimore, MD, 21201

I have boarded my puppy with Meredith & Kevyn for several months and they truly are the best! They take care of her as if she is their own. She is happy to be picked up & dropped off (such an added bonus they add to their service:)) and returns in in such good spirits. I highly recommend their pet services you will not be disappointed.

Profile image
Sara M.
1 / 1
View more sitters

Cheswolde Area dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Aaron was great. He communicated with me the entire time and sent plenty of pics! Dallas enjoyed his stay and came back as happy as can be!

Profile image
Kerrier M.
Boarding
5.0 out of 5 stars

Dimitri is super communicative and amazing with dogs. Took care of Simba for a weekend and gave updates throughout the boarding.

Profile image
Stevenson C.
Boarding
5.0 out of 5 stars

Ruth and her family are outstanding. Our dog is always happy, clean, and well fed when we pick him up. He is loved, exercised, and played with. Ruth communicates his daily events and responds quickly to texts. Grade A+ 100% satisfied!

Profile image
Zoe M.
Boarding
5.0 out of 5 stars

This has been my best rover ever! Extremely professional and knowledgeable. I needed to change my drop off and pick up time and she was very adaptable. Everyday I received meaningful updates with videos and pictures. I think I found a permanent dog sitter!

Profile image
Ashley D.
Boarding
5.0 out of 5 stars

I’m so grateful that I found Kassandra to board my dog, Benji! The consistent updates and photos provided throughout, gave me such peace of mind while I was away. Kassandra and her adorable son will love your dog like their own to make the absence easier on your pup. Oh, and benji got spoiled with that amazing fenced in yard! 10/10 recommend.

Profile image
Tzila B.
Boarding
5.0 out of 5 stars

Steven is truly the best and cares deeply for his clients! He tended to our dog very diligently after an unexpected injury required some extra care during her stay.

Profile image
Andrew D.
Boarding
5.0 out of 5 stars

Ariel is so pleasant and accommodating. She treated Mylo like her own. I will always choose her first.

Profile image
Tiara A.
Boarding
5.0 out of 5 stars

Kierra was excellent with Snowflake. I wouldn't have minded more pictures of her activities, but other than that, all was well.

Profile image
Letty M.
Boarding
5.0 out of 5 stars

This man was an absolute blessing to my family. I have two dogs who have two completely different temperaments. He was able to take both of them last minute and care for them like they were family. If that wasn’t enough he is so sweet and extremely considerate of people and animals. I will be using him every time I need a dog sitter going forward and so should everyone else.

Profile image
MyStephanie F.
Boarding
5.0 out of 5 stars

Victoria’s understanding of dogs in general is a gift! She is absolutely amazing. Whenever she did have to call for my anxious fur babe, she was so kind and positive. She gave my husband and I peace of mind while being out of the country. Our guy is tough, especially post covid, but Victoria took amazing care of him!! Highly highly recommend!

Profile image
Metta E.
Boarding
5.0 out of 5 stars

Another great stay for my little Tofu. Jhane and Emjay take good care of my little guy, send lots of photos and are great at communication. Highly recommend them.

Profile image
Tiffany G.
Boarding
5.0 out of 5 stars

They are absolutely wonderful!! Layla enjoyed her stay with Leah and Shawn. They will now be where I take Layla each time. She had such a good time with them.

Profile image
Tia J.
Boarding
5.0 out of 5 stars

Erika took such great care of my 6 month old puppy, she had a blast and came home safe and sound. Thank you so much!

Profile image
J D.
Boarding
5.0 out of 5 stars

Melanie was great with our 2 year old corgi! He seemed to have had a lot of fun :) Melanie was also very patient with us with our delayed schedule.

Profile image
Rosa L.
Boarding
5.0 out of 5 stars

Whitley was wonderful with our girl and we didn't worry about her for a minute! She came home happy and healthy and we will definitely use Whitley in the future. Highly recommend!

Profile image
Shelley Z.
Boarding
5.0 out of 5 stars

Good care, great communication! Esp appreciated the easy-going response when we had to make a schedule change.

Profile image
Hilary R.
Boarding
5.0 out of 5 stars

Samantha was totally awesome! She was great with Ozzie, who, at the last minute had an eye issue and needed meds for it. Samantha is so easy going and accommodaing! I would highly recommend her for sitting!

Profile image
Harriet W.
Boarding
5.0 out of 5 stars

As a first time Rover user of the sitting service, Mila eased my anxiety with the care she provided to my senior dog. I was had not worries while out of town. She updated me and kept in communication along with sending pics. She is wonderful and my dog took to her beautiful energy. Thank you Mila for your exceptional service!

Profile image
Monica K.
Boarding
5.0 out of 5 stars

Ty has a great time with Julia and Lyra! I am always confident that Ty will be well cared for -- and might even be disappointed to see us come back, LOL!

Profile image
Linda & Don A.
Boarding
5.0 out of 5 stars

Was available last minute when previous sitter quit responding. Sent update/photos. My girl was happy to have a playmate!

Profile image
Naomi S.
Boarding
1 / 1
Find pet care near you

How Rover works

  1. 1. Search

    Read verified reviews by dog parents like you and choose a boarder who’s a great match for you and your dogs
  2. 2. Meet & Greet

    Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs 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 dog boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.

  • World-class support

    We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.

Dog Boarding FAQs

Frequently asked questions about Rover

If you’re searching for a Cheswolde Area dog boarding sitter for the first time, visit the sitter’s profile and select the Contact button.

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

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 Cheswolde Area.

Rover makes it easy to find Cheswolde Area 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.