House Sitting in Winsome Heights

Find a loving dog sitter to watch your dog overnight in your home.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
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Sitter Profile Image: Bronte B.
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Sitter Profile Image: Bronte B.
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1. Bronte B.

Star Sitter
Pampered Wagging Friends 🐾
Pikesville, MD, 21208
17.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$55
per night
5.0 out of 5 stars
92 reviews
32 repeat clients
Profile image

Bronte is amazing! Our dog absolutely loved her and they became instant friends. She even brought him a Bully Stick when she came (yes, she asked me for permission first!) Our dog is big and can be a little overbearing but she handled him perfectly. And our house was in perfect condition when we returned. Will DEFINITELY be rebooking! Thanks, Bronte!!!

Availability updated 17 days ago
Sitter Profile Image: John M.
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Sitter Profile Image: John M.
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2. John M.

Lifetime of pet care!
Hanover, PA, 17331
12.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$42
per night
5.0 out of 5 stars
230 reviews
110 repeat clients
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John is a kind and caring person who I've no doubt will take good care of your pets when you need extra help. My mini dogs are sensitive and each has their own quirks and needs John had an instant rapport with each one. My first booking was an overnight stay and I will be booking with him again!

Availability updated 3 days ago
Sitter Profile Image: Kerri L.
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Sitter Profile Image: Kerri L.
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3. Kerri L.

Star Sitter
Passionate about fluff!
Westminster, MD, 21158
6.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5.0 out of 5 stars
16 reviews
4 repeat clients
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Kerri is the BEST! She stayed at our house for over a week taking care of our dog and cat. Because our dog is large (70lbs) and sometimes anxious/reactive, it can be difficult to find a sitter that is a good fit. Kerri came prepared, asked lots of questions, sent daily updates, and our dog loved her. We will definitely book Kerri again -- highly recommended!

Availability updated 5 days ago
Sitter Profile Image: Delilah E.
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Sitter Profile Image: Delilah E.
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4. Delilah E.

Rover 101
Here to hangout with your pups:)
Westminster, MD, 21157
5.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$45
per night
5.0 out of 5 stars
10 reviews
1 repeat client
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I recently used the Rover app for the first time as I was in a pinch after plans for a a family member to pet sit fell through at the last minute. Enter Delilah — she was fantastic! She responded within a few minutes of the request, agreed to visit the day before she was scheduled to meet the animals and learn what she needed to know in terms of logistics. She was prompt in her arrival time and communicative throughout sending photos to let me know my fur babies were doing well. I’d definitely book with her again and recommend her to others who are in search of a pet sitter too! 🙌

Availability updated 9 days ago
Sitter Profile Image: Aaron L.
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Sitter Profile Image: Aaron L.
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5. Aaron L.

Star Sitter
Always Home High Availability!
Owings Mills, MD, 21117
12.6 mi. away
House Sitting, Drop-In Visits
from
$50
per night
5.0 out of 5 stars
20 reviews
5 repeat clients
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Aaron was great with our cat. He stayed in touch and sent pictures. Will definitely rebook! Thank you Aaron for taking great care of our Peppers.

Availability updated 13 days ago
Sitter Profile Image: Ryan H.
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Sitter Profile Image: Ryan H.
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6. Ryan H.

Rover 101
We treat dogs like family 🐾🦴
Owings Mills, MD, 21117
13.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$60
per night
5.0 out of 5 stars
88 reviews
27 repeat clients
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We absolutely love working with Ryan, and he takes such good care of PT! He sends the best videos and pictures, and even taught her a new trick - above all, we know that he loves dogs and can handle ours!!

Availability updated today
Sitter Profile Image: Katherine S.
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Sitter Profile Image: Katherine S.
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7. Katherine S.

Social worker with a love for pets!
Owings Mills, MD, 21117
14.2 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$45
per night
5.0 out of 5 stars
4 reviews
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Kat was absolutely amazing with Bunny and made us feel super comfortable while we were gone with regular checkins on how bunny was doing. We highly recommend her!

Availability updated 4 days ago
Sitter Profile Image: Elizabeth C.
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Sitter Profile Image: Elizabeth C.
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8. Elizabeth C.

Dog sitting and farm sitting.
Finksburg, MD, 21048
6.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$45
per night
5.0 out of 5 stars
2 reviews
1 repeat client

Elizabeth is a great pet sitter. She's reliable and caring. Her love for pets is present in the way she cares for animals. She will take the time to make your pet feel comfortable, happy, and safe. Elizabeth is always my first choice when it comes to pet care.

Availability updated 2 days ago
Sitter Profile Image: Jolene F.
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Sitter Profile Image: Jolene F.
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9. Jolene F.

Play, Sit, Walk, Stay
New Windsor, MD, 21776
12.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$31
per night
5.0 out of 5 stars
21 reviews
2 repeat clients
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Jolene was beyond amazing. We had something come up and our original plans for our boys got cancelled. She was available last minute, was very responsive, and she is extremely polite. She kept me updated with photos and videos. She loved on our boys like they were how own! I am definitely a crazy dog mom and she put me at complete ease! We will definitely use her again!

Availability updated 3 days ago
Sitter Profile Image: Josue H.
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Sitter Profile Image: Josue H.
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10. Josue H.

Your best friend is my best friend!
Owings Mills, MD, 21117
15.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5.0 out of 5 stars
16 reviews
2 repeat clients
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Josue was amazing with our Malamute during a 2 week trip! Malamutes can be a difficult breed but our pup took to Josue immediately. Josue took great care of our dog and house while we were gone, and we will happily work with him again for any future travel!

Availability updated 7 days ago
Sitter Profile Image: Carly B.
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Sitter Profile Image: Carly B.
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11. Carly B.

Nature and Animals-oh my!
Hampstead, MD, 21074
3.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$32
per night
5.0 out of 5 stars
2 reviews
4 repeat clients

About: It can take a lot for any animal to scare me, I’ve grown up around them and I know more often than not they’re more scared than we are, so I just want to offer them some help and attention! I’m fond of all types of dogs, and all type of weather so they’ll always get a walk in! Caring for pets is a great source of joy in my life, and hopefully a full time job! I want to help people and animals in ways I think can matter, so this is apart of my life! I’m can be more of a solitary person when it comes to people, but I love being with animals! So if you need a home sitter you can trust with your baby, I’m your woman! I’m fine with a fenced in yard to play or taking any age of dog on a nice walk!

Availability updated yesterday
Sitter Profile Image: Kristen M.
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Sitter Profile Image: Kristen M.
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12. Kristen M.

Love caring for Dogs and Cats🐾❤️
Sykesville, MD, 21784
9.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$40
per night
5.0 out of 5 stars
1 review

About: Hi I’m Kristen! I currently work for an amazing Dogwalking/ Pet Care company. I’m a former equestrian of 12 years and I have a dog & three cats. I’ve been taking care of animals (dogs, cats, horses) for as long as I can remember. I have experience with dogs of all sizes and most breeds. The most important thing is that your pets are treated with love and care! ❤️🐾 Please note that: for House Sitting services, I do not spend the night/ sleep in clients home. I leave to sleep at home and come back early morning. I have plenty of time for all services and I’m very accommodating. I take classes online so I’m available all weekdays and weekends to care for your pets. Morning, afternoon, and evenings as well. When a client trusts me with their pets and entry to their home, I put myself in their position and act as how I would want someone coming into my home to take care of my own pets 😊

Availability updated yesterday
Sitter Profile Image: Jason C.
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Sitter Profile Image: Jason C.
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13. Jason C.

Star Sitter
Your Fur Babies become my Family.
Reisterstown, MD, 21136
10.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$65
per night
5.0 out of 5 stars
12 reviews
6 repeat clients
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Jason is an excellent Rover!! He took great care of our two German shepherd dogs and house over thanksgiving. We will be booking with him again! He will follow all your instructions and send you pictures while you’re gone. Thank you Jason!

Availability updated 25 days ago
Sitter Profile Image: Lora M.
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Sitter Profile Image: Lora M.
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14. Lora M.

Pet lover - 22 years experience
Finksburg, MD, 21048
8.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$50
per night
5.0 out of 5 stars
8 reviews

Lora kept our dog the beginnning of the month and we are super happy. She communicated great, the dogs loved her, she sent me several pictures while they were there. There was no doubt they both had fun and were wore out when they came home.

Availability updated yesterday
Sitter Profile Image: Alexandra L.
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Sitter Profile Image: Alexandra L.
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15. Alexandra L.

Friendly dog and cat carer
Westminster, MD, 21157
7.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$40
per night
5 years of experience
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Alexandra is my Theo's new best friend. She sent pictures and stayed in contact while I was away, and she cared for him exactly as I asked. Alexandra will be my go-to sitter moving forward!

Availability updated 58 days ago
Sitter Profile Image: Brittany G.
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Sitter Profile Image: Brittany G.
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16. Brittany G.

Excellent Pet Care Available
Westminster, MD, 21158
6.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$35
per night
16 years of experience

About: I am currently a student in my second semester of undergraduate studies at UMBC, with a major in computer engineering. Up until recently, I have cared for my two senior Yorkie-poos at home. They both developed Cushing's Disease at around age 13, and one was just recently diagnosed as diabetic. This has given me a lot of experience in administering medicine and paying strict attention to the dog's behavior, to see if they are showing signs of discomfort. After moving out of my family home and into the Catonsville-Arbutus area, my sister and her husband purchased a Yellow Lab puppy, and I am responsible for caring for him on my sister's and brother-in-law's long days at work. This has given me a refresher in caring for puppies and in training puppies. Having lived in a house with pets my entire life, the transition to on campus life was made very challenging and lonely due to the lack of animals. I would love to be able to offer your pet great care in exchange for making a new friend. I'm currently on summer break and am not working. I am available at any time. Given that it's been so hot out, I tend to wait until the evening to take my dogs on a walk. I have 2 acres of land and 2 30 ft. leads for the yard. I have 2 friendly dogs at home (13 years and 4 years). My cattle dog requires, who was a rescue, requires a lot of stimulation throughout her day. I've found that she thoroughly enjoys learning new tricks! My dogs eat three times a day, but I am more than capable of accommodating your pup's feeding schedule. I also have plenty of time for frequent potty breaks!

Availability updated 2 days ago
Sitter Profile Image: Madelynn M.
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Sitter Profile Image: Madelynn M.
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17. Madelynn M.

A walk a day keeps the vet away! :)
Finksburg, MD, 21048
5.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$40
per night
5.0 out of 5 stars
6 reviews
4 repeat clients
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Madelynn pretty much saved our bacon this past weekend. The sitter we had previously booked had to cancel on the morning of our trip due to a family emergency. Madelynn was able to come and house sit for us with same day notice. She was able to come and meet our two dogs before we had to leave for the airport. She is a lovely young lady - and she is punctual which is very important to us. She took great care of our dogs - our younger dog is a ball of energy and Madelynn made sure she got plenty of playtime to wear her out. She took both of them on walks, made sure they were fed on schedule and loved them up. She sent us plenty of pictures and communicated with us regularly (and she responded to our texts very promptly). Madelynn helped make our weekend work and I highly recommend her. We will definitely make use of her services again.

Availability updated 32 days ago
Sitter Profile Image: Sennette F.
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Sitter Profile Image: Sennette F.
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18. Sennette F.

Pet/Home Sitter! 7 years Experienc!
Upperco, MD, 21155
3.7 mi. away
House Sitting, Dog Walking
from
$35
per night
2 reviews

Sennette watched my two Labs and our house while we were in Europe for 10 days. We were able to relax with daily updates on how our dogs were doing, and knowing someone was keeping an eye on them and our house. I would recommend Sennette to anyone looking for a responsible dogsitter.

Availability updated 80 days ago
Sitter Profile Image: Jaime T.
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Sitter Profile Image: Jaime T.
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19. Jaime T.

Just Two Animal Lovers!
Hampstead, MD, 21074
2.2 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$85
per night
5.0 out of 5 stars
34 reviews
9 repeat clients
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Jaime is a quantum jump above any housesitter and pet sitter I’ve ever had in the past 50 years. Not only is she conscientious and genuinely affectionate, learning each of my beasties individual wants and needs, she’s smart and resourceful in an unexpected emergency. When my elderly St. Bernard developed bloody diarrhea, Jaime assessed him and the situation, called us, and had already come up with the likely problem and solution. My daughter, who just got her doctorate in veterinary medicine was seriously impressed (and that happens rarely). Jaime and her daughter took turns through the night checking on Guinness hourly, giving us updates and truly nursing him back to health. I hesitated writing this review because she is the ONLY pet sitter I will ever want from here on out, and if everyone catches on to her skills and loving care, I may not be able to book her on short notice. WOW! Just WOW!

Availability updated 61 days ago
Sitter Profile Image: Emily D.
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Sitter Profile Image: Emily D.
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20. Emily D.

I will love your pet like my own!
Finksburg, MD, 21048
4.0 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$80
per night
5.0 out of 5 stars
8 reviews
3 repeat clients
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I was really anxious about leaving our pets with a “stranger,” but Emily immediately felt like a friend. She is the perfect blend of accountability and flexibility. She treated our dog’s ear infection daily as instructed, and she handled both a surprise visit from utility workers and a surprise dogfood delivery with ease. She kept our energetic spaniel busy and happy while we were gone. I received lots of pictures and overall communication was excellent. Emily really aims to please, and when we returned everything was just as we left it - better in some ways actually! Thanks again, Emily!

Availability updated 15 days ago

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