Dog Boarding Winsor Hills

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Over 105
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Winsor Hills, 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.

1 / 1
Sitter Profile Image: Veronica S.
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Veronica S.
Star Sitter
from
$49
per night
5.0 out of 5 stars
507 reviews
160 repeat clients
12 years of experience
Fells Point, Baltimore, MD, 21231

100000000000/10 recommend Veronica!! She treated our little Toaster like her own child! She had a beautiful home that was fully decked out to be a 5 star resort for puppies! She was so knowledgeable about dogs (you would think she was a Vet!) and made us feel so comfortable that our baby would be in the wat of hands!! She even sent us update photos so regularly that we felt like we were there with our baby!! Toaster made so many friends with all the sweet little angels she had and hardly wanted to come home after his stay because he had so much fun!! If you want your baby to stay with someone that will love them and give them as much (and probably even more) attention than you do, then look no further!! Veronica is hands down the best sitter in Baltimore and we cannot thank her enough!!!

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Hannah F.
Sitter Profile Image: Nicole T.
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Nicole T.
Star Sitter
from
$40
per night
5.0 out of 5 stars
53 reviews
26 repeat clients
3 years of experience
Lower Northwood, Baltimore, MD, 21218

Nicole was great! Gave us continual updates/pictures & kept my pup active and well taken care of. I would absolutely use Nicole again and recommend her to others!

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Hunter A.
Sitter Profile Image: Virginia & Steven G.
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Virginia & Steven G.
from
$34
per night
5.0 out of 5 stars
480 reviews
213 repeat clients
21 years of experience
Westgate, Baltimore, MD, 21229

We love sending out dogs to Virginia and Steve. They love on them so much! We use them to watch our dogs every time we are out of time. They truly treat our dogs like their own

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Moira A.
Sitter Profile Image: Liz & Jeffrey C.
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Liz & Jeffrey C.
Star Sitter
from
$50
per night
5.0 out of 5 stars
192 reviews
38 repeat clients
30 years of experience
Linthicum, MD, 21090

Our girls just love visiting Liz & the family ! It’s so nice to be able to relax when we are away knowing our girls are also having a blast and getting lots of cuddles.

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Kevin P.
Sitter Profile Image: Steven O.
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Steven O.
Star Sitter
from
$45
per night
5.0 out of 5 stars
263 reviews
148 repeat clients
25 years of experience
Pikesville, MD, 21208

Steven was an incredible host for our retired greyhound! He is incredibly communicative, thorough, and clearly cares deeply for his canine guests. He creates the perfect environment for a dog that prefers some peace mad quiet.

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Andrew D.
Sitter Profile Image: James & Mary H.
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James & Mary H.
Star Sitter
from
$50
per night
5.0 out of 5 stars
206 reviews
59 repeat clients
50 years of experience
Eldersburg, MD, 21784

This was Rui’s second stay with James and Mary. Mary and James take such great care of our boy when we are out of town. Rui loves them and looks forward to staying with them.

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Elaine G.
Sitter Profile Image: Erin L.
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Erin L.
Star Sitter
from
$60
per night
5.0 out of 5 stars
40 reviews
17 repeat clients
25 years of experience
Hamilton Area, Baltimore, MD, 21206

Erin was totally a pleasure and kind person to work with. From scheduling a meet and greet with our Maxx a few weeks before to sending updates with pictures. We never once had to worry about my our baby Maxx while chilling on the beaches in Cancun, Mexico.

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Sharon B.
Sitter Profile Image: Robin & Tyrone & Maritta A.
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Robin & Tyrone & Maritta A.
Star Sitter
from
$55
per night
5.0 out of 5 stars
139 reviews
55 repeat clients
40 years of experience
Halethorpe, MD, 21227

Robin promptly responded to all requests and provided a great experience for our Addie. Clearly comfortable working with dogs, has ample space indoors and outdoors for play. This was our first time and was great experience.

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David T.
Sitter Profile Image: Kelly & George B.
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Kelly & George B.
Star Sitter
from
$62
per night
5.0 out of 5 stars
213 reviews
89 repeat clients
12 years of experience
Glen Burnie, MD, 21061

Kelly and George were fantastic during Sophie's stay. From the pictures I could tell Sophie was relaxed, loved, and felt at home from the very first day. Will definitely board the pup with them again!

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Micah D.
Sitter Profile Image: Felice & Ken & Tyler & Morgan T.
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Felice & Ken & Tyler & Morgan T.
from
$50
per night
5.0 out of 5 stars
273 reviews
152 repeat clients
50 years of experience
Catonsville, MD, 21228

Feliz & Ken are the only people I trust my baby with. When Higgy is with them, he is with family and I have amazing peace of mind that is priceless!

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Ravan R.
Sitter Profile Image: Virginia O.
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Virginia O.
Star Sitter
from
$45
per night
5.0 out of 5 stars
49 reviews
22 repeat clients
25 years of experience
Catonsville, MD, 21228

Virginia was amazing. Our dog loved being at her house with her two dogs and was thoroughly worn out after playing at her house all day. Will definitely be using Virginia again.

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Patrick A.
Sitter Profile Image: Megan H.
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Megan H.
Star Sitter
from
$35
per night
5.0 out of 5 stars
30 reviews
7 repeat clients
5 years of experience
Baltimore, MD, 21225

I had a great experience booking with this sitter for my dog Charlie. They took really good care of him, followed all of his instructions, and made sure he received his medication on time. I appreciated the photo updates because it helped me relax and know he was doing well. Charlie came home happy and calm. I would definitely book with them again.

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Kelli W.
Sitter Profile Image: Aida W.
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Aida W.
from
$45
per night
5.0 out of 5 stars
19 reviews
5 repeat clients
6 years of experience
Midway-Coldstream, Baltimore, MD, 21218

Aida sent pictures daily and made sweet observations about our pup, letting me know she sees him for who he is! She showed enormous patience and understanding. Will definitely rebook!

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Mepi N.
Sitter Profile Image: Diana B.
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Diana B.
Star Sitter
from
$48
per night
5.0 out of 5 stars
87 reviews
44 repeat clients
15 years of experience
Cockeysville, MD, 21030

Our dog Allie reported that she had an outstanding visit with Diane and family. Came home rested, relaxed, totally chill. Diane was a pleasure to deal with, was responsive, caring, informative. I hope we get back there.

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Bill S.
Sitter Profile Image: Brittanie & Ryan C.
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Brittanie & Ryan C.
Star Sitter
from
$55
per night
5.0 out of 5 stars
131 reviews
49 repeat clients
10 years of experience
Catonsville, MD, 21228

Brittanie and Ryan were wonderful sitters for our dog this weekend! She seemed to have gotten very comfortable in their home pretty quickly and had no issue coexisting with their dogs at all. They sent frequent update pictures and really went above and beyond bringing our dog to our wedding so she could be included in our pictures. Overall great first Rover experience and would happily use them again!

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Stacy S.
Sitter Profile Image: Charles W.
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Charles W.
Star Sitter
from
$45
per night
5.0 out of 5 stars
8 reviews
5 repeat clients
25 years of experience
Columbia, MD, 21045

Nino enjoyed his time with Charles and his family. I was updated with pictures and daily feedback. He was extremely quick with responding. Thanks again

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Mahasin I.
Sitter Profile Image: Olga L.
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Olga L.
Star Sitter
from
$31
per night
5.0 out of 5 stars
37 reviews
14 repeat clients
15 years of experience
Timonium, MD, 21093

Thank you Olga for taking care of our Darla while we were away. You always update us of your daily activities with photos & videos. Darla developed that connection already with you. I would definitely bring back Darla to you if need arises. Thank you again…

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Marissa A.
Sitter Profile Image: Julia L.
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Julia L.
Star Sitter
from
$65
per night
5.0 out of 5 stars
24 reviews
15 repeat clients
20 years of experience
Inner Harbor, Baltimore, MD, 21230

Junie comes back happy and healthy! We received lots of great pictures of her walks and hangout time with dog friends. Julia is quick to respond to messages and knows a lot about dog behavior.

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Justin H.
Sitter Profile Image: Melissa H.
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Melissa H.
Star Sitter
from
$45
per night
5.0 out of 5 stars
91 reviews
42 repeat clients
30 years of experience
Parkville, MD, 21234

Beau had a great week with Melissa! Daily photos of him settling in or playing with new friends helped us not miss him so much :) Thank you Melissa!

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Michelle N.
Sitter Profile Image: Shaun H.
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Shaun H.
Star Sitter
from
$40
per night
4.8 out of 5 stars
23 reviews
8 repeat clients
18 years of experience
baltimore, MD, 21225

Amazing! - Our dog stayed for a little over 2 weeks and we consistently received updates and proactive communication. We had to add a few days and it worked with scheduling. Thanks so much, will send her back!!

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Khalil U.
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The median cost per night for dog boarding in Winsor Hills is $50

Dog parents share their Rover experiences - Winsor Hills

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5.0 out of 5 stars

Ms. Jae is absolutely wonderful. She took my baby girl in as her own this past weekend and even had another energetic pup visiting that Cora could enjoy spending time with. Ms. Jae knew that I was worried given a few of my past experiences here in Baltimore and she made it her duty to send me multiple updates and photos throughout my time away from Cora. My was smiling the whole time, and I could really tell that she was happy and well cared for. You can tell that she really cares about making your pet feel safe, comfortable, and loved in her space. If I could give 10 stars I would. I will likely only send her to Ms. Jae from now on as long as she will have her ❤️❤️❤️❤️❤️❤️❤️

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Lauren O.
Boarding
5.0 out of 5 stars

I can’t say enough nice things about Sean and the wonderful way he took care of our fur baby, Taz. He kept me up to date with Taz’s daily activities and added pictures. I am so grateful for Sean and his excellent care of Taz. I will definitely use Sean again in the future!

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Mary G.
Boarding
5.0 out of 5 stars

Jeremy took excellent care of Sebastian during his stay. He was attentive, dependable, and made me feel comfortable knowing Sebastian was in good hands. Sebastian came home happy and well cared for. I would definitely book with Jeremy again!

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Demetrius M.
Boarding
5.0 out of 5 stars

I really had a great experience with Jamella she was professional a she really took time too get a clear understanding about pepper’s routine I will highly recommend

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tammy s.
Boarding
5.0 out of 5 stars

As per usual, Victoria comes through in a clutch. Max is always well taken care of and i always get 1-2 check in depending on his length of stay. Victoria and her family are quite friendly and responsive.

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Zi J.
Boarding
5.0 out of 5 stars

Cheryl was awesome! She welcomed my fur baby into her home and treated him like her own. She provided updates, pictures, and videos. And as a bonus my fur baby got to hang out with her beautiful daughter. I could not ask for a more "genuinely" compassionate, and loving family to leave my boy with. I would completely use her again. Thank you so much Cheryl!!!

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Shawne D.
Boarding
5.0 out of 5 stars

Olivia is friendly, positive, accommodating, loving, communicative and very responsible -- in short, everything you could want in a sitter for your four legged fur baby! We drive 30 minutes **each way** specifically so we she can care for our beloved pup when we have to go out of town. She checks in often and sends plenty of pictures so we know our pup is getting the best care (and behaving!) Her home is lovely -- spacious, welcoming and just right for a pup who might sometimes be a little too curious for her own good. We highly recommend Olivia! You cannot go wrong with her.

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Fifi R.
Boarding
5.0 out of 5 stars

Great petsitter!!! My dogs were so happy being there and coming back home. Nautica kept my daughter and I updated daily with videos and pics of their journeys. One of dogs has anxiety problems and she made sure he was comfortable. Nautica followed our feeding directions and walking schedules. My dogs did not have any accidents while in her care.

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Dee L.
Boarding
5.0 out of 5 stars

I really appreciate Shakiyla. I contacted her in short notice due to my daughter being in the ER and not being able to find anyone to watch Reign. She responded immediately and was great with my dog. I was very nervous using this app for the first time, but She sent videos and kept me posted about how Reign was doing. She was a life saver. Thank you so much.

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Jay D.
Boarding
5.0 out of 5 stars

Ashley was absolutely amazing! We have two older gals and she took such incredible care of our girls. Great communication, easy to contact and my girls were happy and healthy! We will definitely be asking Ashley to help watch our girls again. Thank you!!

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Claire L.
Boarding
5.0 out of 5 stars

Benn & Thinh K. were exceptional. They treated my baby like their own. You would be lucky to have them watch your furry companion. I have the utmost respect for them and hopefully they would accept Max in the future.

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Michele J.
Boarding
5.0 out of 5 stars

Kieth takes the dogs out for plenty of walks and backyard time! My dog is always very excited to go to Kieth’s place.

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Grace K.
Boarding
5.0 out of 5 stars

Rhiannon was fantastic! Easy drop off and pick up, and very diligent in sending updates during our dog's stay. I'd recommend Rhiannon to anyone looking for pet boarding services.

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Hill P.
Boarding
5.0 out of 5 stars

The best communication was amazing, updates and pictures the whole time. My dogs came back happy and healthy.

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Jennifer C.
Boarding
5.0 out of 5 stars

Carolina was great with Buddha! She made sure he was comfortable, and kept me updated. Thank you Carolina!

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Tiffany A.
Boarding
5.0 out of 5 stars

Nina was such a blessing to find as I was looking for last minute care for my pup! She welcomed Sweet Pea into her home and within the evening she was settled and I could tell she felt at home. She shared pictures throughout the stay and was super communicative which I appreciated greatly! She came home tired and so happy - couldn’t ask for more!

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Katie N.
Boarding
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!

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Kerrier M.
Boarding
5.0 out of 5 stars

It’s Carti’s second time with Robert and she is pretty much family! She even has a nickname now! ❤️ 😂

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CHAMARA J.
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.

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Tzila B.
Boarding
5.0 out of 5 stars

Melanie is a fantastic sitter for our little girl Luna ! She provides updates with plenty of pictures , which we appreciate greatly! Thank you for looking after our little Luna!

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Lisa L.
Boarding
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