Dog Boarding in Winsor Hills, Baltimore

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

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Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Davida A.
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Sitter Profile Image: Davida A.
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1. Davida A.

Star Sitter
Let Me Be Your Fur Baby's BFF
Winsor Hills, Baltimore, MD, 21216
0.4 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
60 reviews
25 repeat clients
from
$50
per night

I just want to let anyone looking for a greater sitter, you need to take your dog to Davida. I feel like her home is my Angels second home. She gets excited when I'm walking her to the front door and I love that her family loves her as well. It's a win, win and I love it. I'm very particular and Davida checks all my boxes. I had an another sitter before her but since I've been going to Davida I don't need to look any further. My precious baby is well taken care of. Thanks Davida for all you do. Have a good day.

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Sitter Profile Image: Ash (they/them) N.
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Sitter Profile Image: Ash (they/them) N.
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2. Ash (they/them) N.

Star Sitter
Experienced and Friendly Dog Sitter
Roland Parl-Homewood-Guilford, Baltimore, MD, 21211
2.9 mi. away
Boarding, Drop-In Visits, Doggy Day Care
5.0 out of 5 stars
18 reviews
5 repeat clients
from
$50
per night

Ashley was excellent while taking care of my two pups. We ran into zero issues throughout the entire booking and Ashley's communication was superb. I highly recommend Ashley!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Ashante M.
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Sitter Profile Image: Ashante M.
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3. Ashante M.

Star Sitter
Seconds From Druid Hill Park🐕‍🦺
Mondawin-Walbrook Area, Baltimore, MD, 21217
1.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
110 reviews
51 repeat clients
from
$43
per night

Friendly and healthy dog environment. My dog had an amazing stay. Ashante has a dog who is very sweet and friendly. Overall I recommend this place for your pets.

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Sitter Profile Image: Ashley P.
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Sitter Profile Image: Ashley P.
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4. Ashley P.

Star Sitter
Ready to board your pets!!
Federal Hill, Baltimore, MD, 21230
4.4 mi. away
Boarding
5.0 out of 5 stars
18 reviews
6 repeat clients
from
$45
per night

Ashley was an outstanding sitter, sending regular pics and adjusting accordingly to my busy schedule. I would definitely use her again and recommend to anyone in the Baltimore city area.

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Sitter Profile Image: Mila B.
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Sitter Profile Image: Mila B.
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5. Mila B.

Rover 101
Star Sitter
Full time love and care!
Pikesville, MD, 21208
4.7 mi. away
Boarding, Doggy Day Care, Dog Walking
5.0 out of 5 stars
24 reviews
9 repeat clients
from
$40
per night

Horatio didn’t want to come home. So loving and caring. Pampered him just the way he likes. Have already booked her for two upcoming trips. Thank you Mila!

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Sitter Profile Image: Nautica E.
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Sitter Profile Image: Nautica E.
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6. Nautica E.

Star Sitter
Large fenced yard - Walk and Play
Forest Park, BALTIMORE, MD, 21216
0.5 mi. away
Boarding, Doggy Day Care, Dog Walking
5.0 out of 5 stars
32 reviews
12 repeat clients
from
$35
per night

Nautica was an excellent host for my busy little boy. She kept them an extra day because we've been having brownouts in my neighborhood. She even dropped him off and picked him up. I knew he was going to be spoiled rotten after enjoying a long weekend with the backyard. I will be using her again

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Sitter Profile Image: Shruti D.
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Sitter Profile Image: Shruti D.
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7. Shruti D.

Star Sitter
A PhD student and a dog named Hazel
Federal Hill, Baltimore, MD, 21201
4.2 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
12 reviews
5 repeat clients
from
$40
per night

Shruti is very caring and considerate of my dog who has separation anxiety. She worked with me to find the best solution for her. I've already booked her this time for an extended stay while I am travelling.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jessica D.
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Sitter Profile Image: Jessica D.
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8. Jessica D.

Star Sitter
Head over heels in puppy love!
Hampden-Woodberry-Remington, Baltimore, MD, 21211
2.7 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
65 reviews
34 repeat clients
from
$40
per night

Jess is simply amazing with my elderly and very high maintenance Havanese. He has serious separation anxiety but I never worry about him when I drop him off. She’s very attentive and patient and will go out of her way to make him comfortable. She’s really the only one I trust with my baby 🥰

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Felice T.
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Sitter Profile Image: Felice T.
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9. Felice T.

Rover 101
Star Sitter
Fur Babies Unlimited
Catonsville, MD, 21228
5.7 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
171 reviews
102 repeat clients
from
$50
per night

Bruno had such a good stay with Felice and Ken. It really seemed like he felt comfortable with them and he came home just as happy as ever. He has a little separation anxiety, but he settled right in with the family and their dogs. He had a great time running in their yard and being spoiled with attention and treats. She kept us updated throughout the stay so we knew he was doing well. Would highly recommend them and we plan on bring Bruno back again!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Kelly C.
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Sitter Profile Image: Kelly C.
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10. Kelly C.

Pet lover
Greater Rosemont, baltimore, MD, 21216
1.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
103 reviews
47 repeat clients
from
$50
per night

Kelly and her family were incredibly welcoming. I received daily picture updates of Charlee that helped me relax while she was away. Any time I am in the area, I will be going back to Kelly!

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Sitter Profile Image: Kelly H.
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Sitter Profile Image: Kelly H.
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11. Kelly H.

Star Sitter
Korvie Pet Homestay - Care and Free
Catonsville, MD, 21228
4.2 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
34 reviews
9 repeat clients
from
$47
per night

Kelly was amazing! She took such good care of my dog and kept him entertained and active the entire time. You can tell she is an animal lover and really treats your pet like part of her family. My dog was sad to leave! Loved the frequent photos and updates as well. Highly recommend.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Brittanie & Ryan C.
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Sitter Profile Image: Brittanie & Ryan C.
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12. Brittanie & Ryan C.

Star Sitter
Your pet is like our pet
Catonsville, MD, 21228
5.0 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
27 reviews
14 repeat clients
from
$55
per night

Our dog had the best time. Brittanie & Ryan sent us daily photos and updates. They took wonderful care of our dog. We will be using them again for boarding and for walking. So comforting to know our “baby” is in good hands.

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Sitter Profile Image: Ruth F.
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Sitter Profile Image: Ruth F.
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13. Ruth F.

Responsible “family” of watchers
Baltimore, MD, 21209
4.3 mi. away
Boarding, Drop-In Visits, Doggy Day Care
5.0 out of 5 stars
79 reviews
35 repeat clients
from
$51
per night

Ruth and her family were absolutely beautiful, they have a beautiful and welcoming home as well! They took great care of our puppy son/brother during his very 1st overnight stay with someone other than his grandmother. We were/are very pleased with and definitely will be using them again! Thanks Ruth and family!!

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Sitter Profile Image: Nicole T.
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Sitter Profile Image: Nicole T.
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14. Nicole T.

Star Sitter
Here to love your fur baby
Lower Northwood, Baltimore, MD, 21218
5.3 mi. away
Boarding
5.0 out of 5 stars
16 reviews
4 repeat clients
from
$50
per night

Loved loved LOVED Nicole. King’s transition was so smooth. She stayed in communication. Made us feel comfortable from the beginning to the end. King will definitely be back.

Sitter Profile Image: Adrienne T.
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Sitter Profile Image: Adrienne T.
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15. Adrienne T.

Star Sitter
A Lover of Dogs
West Baltimore, Baltimore, MD, 21223
3.1 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
29 reviews
11 repeat clients
from
$40
per night

Adrienne was very wonderful with my dog and very responsive to me. My dog was in great spirits when I picked her up and I would definitely use Adrienne again!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Brandon B.
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Sitter Profile Image: Brandon B.
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16. Brandon B.

Animal lover ready to serve you!
Greater Rosemont, Baltimore, MD, 21216
0.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
8 reviews
2 repeat clients
from
$31
per night

Brandon was a great dog sitter. Would this be my first time he really made me feel comfortable. I appreciate him sending me pictures and videos of my dog having a great time highly recommend him

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Veronica S.
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Sitter Profile Image: Veronica S.
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17. Veronica S.

Star Sitter
Home all day. Only pups under 25 lb
Fells Point, Baltimore, MD, 21231
5.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
264 reviews
102 repeat clients
from
$45
per night

Veronica is the most genuine and dog-loving person I have ever met. I knew that my pup was in great hands (and that he was being spoiled!). Her experience with dogs should put anyone at ease and take this as your sign to book with her!

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Sitter Profile Image: Maria H.
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Sitter Profile Image: Maria H.
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18. Maria H.

Star Sitter
Pawsitive Vibes Only ❤️🐾
Reservoir Hill-Bolton Hill Area, Baltimore, MD, 21217
3.1 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
13 reviews
6 repeat clients
from
$50
per night

Had a wonderful experience with Maria - she sent photos everyday, and I could tell Pearl was having a great time. My anxious dog received so much love and attention. Will use her again, for sure!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Crissy A.
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Sitter Profile Image: Crissy A.
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19. Crissy A.

Star Sitter
Reliable and experienced provider
Hamilton Area, Baltimore, MD, 21214
7.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
69 reviews
38 repeat clients
from
$45
per night

Our Bellatrix's first time with Crissy and she had a wonderful time. Crissy was great keeping in touch and sending pics. Thank you Crissy. Bellatrix will see you and Dublin again soon ☺️

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Meg C.
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Sitter Profile Image: Meg C.
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20. Meg C.

Rover 101
Ask me my favorite dog joke!
Chinquapin Park-Belvedere, Baltimore, MD, 21212
5.3 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
11 reviews
4 repeat clients
from
$50
per night

Meg was great and could accommodate all of our dogs weird quirks! Unfortunately our dog and Meg’s dogs did not get along or we would definitely be using her services again.

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Rover also offers Dog Boarding in these neighborhoods:

Rover also offers other services in Winsor Hills:

Dog owners in Winsor Hills, Baltimore, MD love booking dog boarding with sitters on Rover.com. Over 2462 pet owners have reviewed dog sitters in Baltimore, giving them an average rating of 5.0/5 stars. Booking dog boarding can be super affordable, no matter where you live. Trust us, we think you'll be pleasantly surprised. Curious what it might cost to book dog boarding with Rover? Check out our average dog boarding rates to get an idea before reaching out and starting a conversation with a dog sitter near you in Winsor Hills.

Rover.com offers the perfect alternative to dog kennels and traditional dog sitting. The next time you head out of town and need someone to take care of your dog, turn to Rover for your dog boarding needs. It's easy to find a loving Winsor Hills dog sitter on Rover who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at their sitter's home. Search from hundreds of dog sitters in Winsor Hills, Baltimore, MD, read sitter profiles, and reach out to sitters who seem like a good fit for you and your dog. We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. With Rover, pet boarding is guilt-free, cashless, and convenient. That way, you can hit the road happy knowing your dog's in loving hands while you're away.

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