House Sitting Windsor

Find a loving house sitter to watch over your pets and your home.

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Windsor, Find top rated house sitting

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

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Sitter Profile Image: Isaiah M.
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Isaiah M.
from
$55
per night
5.0 out of 5 stars
• 5 reviews
1 repeat client
5 years of experience
Chester, VA, 23836

“We are so grateful for Isaiah! We had to leave town last minute, and he worked with us every step of the way. He came by beforehand to meet our dogs and has a lot of experience. One of our dogs is a new adoption, and she really only likes me, but he was able to get her to a place where she was comfortable and not stressed around him. That alone says a lot about how good he is. He was accommodating to whatever we needed during the sit and was respectful of our home. When we got back, our pets were happy, relaxed, and acting completely like themselves. We’ve had experiences in the past where you could immediately tell the level of care they received, and this was the opposite. It truly felt like they had been cared for the way we would care for them. Isaiah was that person. We will definitely be reaching out to him again in the future.”

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Brienia B.
Sitter Profile Image: Triston N.
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Triston N.
from
$50
per night
5.0 out of 5 stars
• 13 reviews
1 repeat client
10 years of experience
Fulton, Richmond, VA, 23231

“Triston was incredible! We had to book last minute and Triston stepped up to take care of our 2 dogs and 4 cats! I will definitely be booking with Triston in the future!!”

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Taylor B.
Sitter Profile Image: Kaylynn H.
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Kaylynn H.
Star Sitter
from
$60
per night
5.0 out of 5 stars
• 13 reviews
4 repeat clients
18 years of experience
The Fan, Richmond, VA, 23220

“This was my first time hiring a pet sitter and Kaylynn couldn’t have been more perfect. She kept me updated, consistently checked in regarding my travel plans to support with care, provided quality care and walks and snuggles to my furbabies. I am so grateful for Kaylynn and will definitely hire her again for future pet sitting needs.”

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Maya B.
Sitter Profile Image: Jonathan W.
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Jonathan W.
from
$38
per night
5.0 out of 5 stars
• 5 reviews
6 years of experience
Richmond, VA, 23223

“Jonathan was great! He was attentive and thorough, and we came home to a happy and healthy dog. I wouldn't hesitate to book him again.”

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Mikaela P.
Sitter Profile Image: Nancy Marie B.
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Nancy Marie B.
from
$26
per night
1 repeat client
6 years of experience
Central Office, Richmond, VA, 23219

About: I have experience caring for both puppies (even during potty training) and senior pets with special medication or mobility needs. I have pet sit for numerous families with senior pets and have been successful in meeting all of their needs and providing the best care possible. I would love to do the same for your pet! I am in my 4th year of medical school, so my schedule is more flexible than an average full time job. I often have odd shifts or hours, so I can often tend to pets at times where others may not be able to! I am willing to fit caring for your pet into my schedule however I can. I currently have 1 cat who lives in my apartment. I am so excited for the day we move to a home where we can build him a cat patio (or catio as we lovingly refer to it as), but for now he loves sitting in the window and seeing all of the sights outside! I would be willing to travel wherever needed to pet sit or do pet check-ins/potty breaks/walks. I would care for your animal just like it was my own. My goal is to meet all of your pet's needs, from physical to emotional and psychological. I also strive to maintain great relationships with pet owners to make leaving pets less stressful and anxiety-inducing.

Sitter Profile Image: Mitchell I.
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Mitchell I.
Star Sitter
from
$60
per night
5.0 out of 5 stars
• 7 reviews
2 repeat clients
2 years of experience
Richmond, VA, 23224

“Mitch was great! He took good care of my dog while I was out of town and was easy to communicate with. He shared updates while I was gone and I would definitely recommend him and use his services again in the future!”

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Devan C.
Sitter Profile Image: Kristen O.
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Kristen O.
from
$44
per night
5.0 out of 5 stars
• 7 reviews
30 years of experience
Chippenham Forest, Richmond, VA, 23225

“Kristen was wonderful! She took excellent care of Pepper and Merlin while we were away. She was attentive to their routines, followed all medication instructions, and made sure they received plenty of attention and quality time. Communication was great throughout, and she kept me informed, which gave me peace of mind knowing they were in good hands. She even went above and beyond by bringing in packages that arrived while we were away. Most importantly, I came home to two happy pups! I would absolutely book with Kristen again and highly recommend her!”

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Alicia D.
Sitter Profile Image: Conrad M.
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Conrad M.
from
$50
per night
5.0 out of 5 stars
• 12 reviews
5 repeat clients
13 years of experience
The Fan, Richmond, VA, 23220

“Conrad took great care of Finn and held down the fort at our house for a week. He was communicative and kept a very consistent routine with photos for peace of mind ☺️we would recommend him to anyone in need and will keep him at the forefront of our minds going forward.”

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Molly G.
Sitter Profile Image: Mel C.
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Mel C.
from
$100
per night
5.0 out of 5 stars
• 48 reviews
20 repeat clients
12 years of experience
Gambles Hill, Richmond, VA, 23219

“Mel was phenomenal! A superstar. Our two cats need to be kept separate, and we weren't sure anybody could handle what they needed, but Mel took care of everything no problem. Mel is incredible with animals and easily befriended some timid babies. Highly highly recommend, Mel will definitely become our go-to sitter from here on out.”

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Jack C.
Sitter Profile Image: Ezra A.
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Ezra A.
from
$50
per night
5.0 out of 5 stars
• 2 reviews
10 years of experience
Carver, Richmond, VA, 23220

“Ezra is wonderful. He took care of our dog Rev very well, and kept us updated while we were away. We came back to a clean house and a happy dog. We love that he took Rev for a hike and also to meet some people for socializing. I would definitely think of him again when we have other trips out of town.”

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Pai K.
Sitter Profile Image: Regina S.
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Regina S.
from
$40
per night
5.0 out of 5 stars
• 11 reviews
4 repeat clients
3 years of experience
Richmond, VA, 23224

“Regina was simply fantastic! She loved on our pug all weekend and he loves her! The communication was perfect and she really took care of him, taking him on multiple walks. She left our home spotless. Will use again!”

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Parker S.
Sitter Profile Image: Carla M.
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Carla M.
from
$85
per night
4.9 out of 5 stars
• 35 reviews
14 repeat clients
15 years of experience
Richmond, VA, 23219

“Carla was very responsive, punctual, professional, and friendly. She took wonderful care of our senior pup and sent lots of updates and photos.”

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Ellen C.
Sitter Profile Image: Alex K.
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Alex K.
from
$45
per night
5.0 out of 5 stars
• 87 reviews
29 repeat clients
20 years of experience
Richmond, VA, 23223

“Alex did a great job taking care of our 3 dogs while we were out of town at our son’s wedding. They were in very good hands while we were gone! We highly recommend Alex!”

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Torie A.
Sitter Profile Image: Andrew C. T.
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Andrew C. T.
from
$65
per night
5.0 out of 5 stars
• 56 reviews
20 repeat clients
32 years of experience
Richmond, VA, 23224

“Andrew was wonderful with our Mega Dane , Max and older girl, Bella. He was dependable and cognizant of the our fur babies’ needs. The house was neat and straight on our return. The pups enjoyed their activities with him and were disappointed when he didn’t show up the next day! Max runs to the door when I ask where’s Andrew! It was a very positive experience and we will definitely ask for his help again. Thank you Andrew.”

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Mary Lou M.
Sitter Profile Image: Kira S.
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Kira S.
from
$50
per night
5.0 out of 5 stars
• 9 reviews
7 years of experience
Richmond, VA, 23219

“Kira was amazing with our beagles. Kept in touch, took care of everything, and treated them like her own. We were so pleased with how well she cared for Luna and Neko and look forward to booking with her again. Excellent sitter and Luna and Neko’s new best friend!”

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Anne Z.
Sitter Profile Image: Kimberly S.
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Kimberly S.
from
$45
per night
35 years of experience
Richmond, VA, 23235

About: I’ve taken care of pets for 35 years. I am able to administer medications including injectable’s if needed. I work with all breeds and temperaments, and do not shy away from pets that have behavioral issues. I’ve worked extensively with large farm animals to include horses, goats, donkeys, and cattle and have cared for the occasional parrot, chinchilla, and snake. Since pet sitting is my only employment, I am able to provide companionship to your fur family 14-18 hours daily including overnight care. I also am able to check mail, grab packages, and water plants at no additional charge. I keep to your pets normal daily routine, to include walks, potty breaks, feeding schedule, and of course nap times. Let’s set up a meet and greet to see if I’m a good fit. Currently I am only doing pet sitting and it’s my primary and only employment. This enables me to spend more time with your fur babies. I care for pets in your home as requested. I stick to their normal daily schedule. I also water plants and grab mail as needed.

Sitter Profile Image: Ada C.
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Ada C.
from
$60
per night
4.9 out of 5 stars
• 18 reviews
5 repeat clients
4 years of experience
Richmond, VA, 23236

“Ada is absolutely wonderful with my pets. My cat is a little bizarre ands likes to snuggle into and bite people’s hair if he likes them. It’s super weird and most people are intimidated by him because of it, but Ada sends me pictures of him snuggling in her hair and she still loves him. My dog was scared of thunderstorms and shaking and being super extra, but she comforted her and when I got home, they both look happy and well taken care of. She even helped when a leak happened in my house and she moved furniture and dried out the floor. She has gone above and beyond to take exceptional care of them ands I would absolute recommend her to anyone. This is the second time we’ve used her, ands we will definitely hire her in the future. She’s a gem.”

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Julie M.
Sitter Profile Image: Genevieve B.
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Genevieve B.
from
$40
per night
5.0 out of 5 stars
• 2 reviews
15 years of experience
Colonial Place, Richmond, VA, 23221

“Genevive watched my dog overnight while I was out of town. She was very sweet to my senior dog who is slow to warm up to strangers. Very happy with her care!”

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Kelsey P.
Sitter Profile Image: Sabrina F.
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Sabrina F.
from
$45
per night
5.0 out of 5 stars
• 7 reviews
2 repeat clients
6 years of experience
Richmond, VA, 23226

“Great with our dogs over a long weekend and left the house spotless. Reliable, concerned and communicative. Our boys were well taken care of.”

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John P.
Sitter Profile Image: Madelaine E.
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Madelaine E.
from
$65
per night
5.0 out of 5 stars
• 88 reviews
45 repeat clients
50 years of experience
Eastland Park-Dixie Plantation, Richmond, VA, 23230

“Madelaine was amazing with our 2 pups!!! They did a sleep over one night and they were so comfortable with her, they both slept through the night and were happy smiling pups when we got home from our weekend away. We were so happy, we have booked Madelaine for our next week away. 10/10 recommend!”

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Genny H.
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The median cost per night for house sitting in Windsor is $50

Pet parents share their Rover experiences - Windsor

1 / 1
5.0 out of 5 stars

There are no words to describe how fabulous Kelly is. In a way it’s sad because my cats are very sad when I come home and they stand at the door and they watch for her to come back, but they’re just gonna have to get over that until we go away again.

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Lauren W.
House Sitting
5.0 out of 5 stars

Morgan is reliable, professional, and super communicative in caring for our dog & cat. We were able to enjoy a weekend away without worrying about our boys, knowing they were in great hands. Definitely recommend Morgan - we will be using her again in the future!

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Cameron B.
House Sitting
5.0 out of 5 stars

Isaiah was a very caring, attentive and professional pet sitter. He followed our pets care instructions well, and they took to him quickly. He sent plenty of photos and updates. We felt assured our beloved animals were in good hands. We will book with him again!

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Miranda J.
House Sitting
5.0 out of 5 stars

Alex was reliable and checked in each day of my vacation. He took notes during our meet and greet and was a great communicator overall. He even let my dog share the bed with him. 10/10.

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Colby C.
House Sitting
5.0 out of 5 stars

Kendall did a great job caring for my cat. She was very communicative and sent lots of pictures, and she left the house a clean as when she arrived.

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Darlene K.
House Sitting
5.0 out of 5 stars

Camryn once again took wonderful care of our pets and our home. I especially appreciate her care of our cranky little dog and his sensitive tummy.

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Jennifer W.
House Sitting
5.0 out of 5 stars

Amelia took incredible care of my senior pup. She took his health challenges in stride, navigating his pill dispensing and bathroom breaks with ease. She sent pictures and updates, left my home immaculate, and was so lovely during our meet and greet. Easily an above and beyond sitter, thank you again Amelia!

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Claire K.
House Sitting
5.0 out of 5 stars

Emily was amazing and an absolute life savior with my last minute booking when my other plans fell through to watch my sweet Goldendoodle!

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Kat G.
House Sitting
5.0 out of 5 stars

Liesel rocks! I came home to a healthy happy pup and a clean organized place like I never left. Liesel even hung around a bit longer than scheduled to make sure my anxious pup got through a thunderstorm. Thank you!

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Todd A.
House Sitting
5.0 out of 5 stars

Samariah has stayed with my cat Annie a few times now, and things have gone well each time. Would book with her again

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Darlene K.
House Sitting
5.0 out of 5 stars

Fran is the best - watched our two dogs while we were away for 10 days, and I felt they were in great hands the entire time. Our dogs absolutely love hanging with Fran!

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Anna D.
House Sitting
5.0 out of 5 stars

Nora was great! Dogs were well taken care of and house was so clean when we got back. This was the second time Nora watched our dogs and will certainly hire her again!

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Allie S.
House Sitting
5.0 out of 5 stars

Marissa was a great house sitter. She left the house clean and took good care of our dog while we were gone. I would absolutely use her again!

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Trevor L.
House Sitting
5.0 out of 5 stars

Alexandra was great with our senior dog, Stella. Stella has separation anxiety and is terribly afraid of thunderstorms but Alexandra did a great job keeping her comfortable and communicating with us while we were away for the week.

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Elizabeth W.
House Sitting
5.0 out of 5 stars

Triston did an excellent job house sitting and taking care of my animals! I will definitely use him again!

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Wendy C.
House Sitting
5.0 out of 5 stars

Jenna is amazing! She took such great care of our 3 dogs and even taught them new tricks! She is extremely communicative and sent us photos and videos often. She left our house spotless and even watered my plants for me. She is now our go to person!

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Payton Y.
House Sitting
5.0 out of 5 stars

I recently had Estella watch my dog, Levi, for a full week, and I couldn’t be happier with the experience. Levi is an overly anxious, high‑energy, and sometimes reactive dog, so leaving him with someone new is never easy for me. Estella handled him beautifully. He seemed calm, comfortable, and well‑cared‑for the entire time. Her communication throughout the week made a huge difference. Because of her thoughtful check‑ins, I was actually able to relax and enjoy my vacation. When I returned home, my house was in perfect shape, and Levi looked great. I highly recommend Estella to anyone looking for a reliable, kind, and capable pet sitter. She gave me peace of mind and took wonderful care of my boy.

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Julie B.
House Sitting
5.0 out of 5 stars

Kristine took good care of our kitties and our home while we were away on vacation. She made it easy for us to relax, knowing they were in good hands.

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Monique M.
House Sitting
5.0 out of 5 stars

Carson stayed with our two German Shepherds over the Fourth of July weekend, and we couldn’t have asked for a better sitter. He was communicative throughout the stay, sent regular photo updates, and gave us peace of mind while we were away. He also took great care of our home, leaving everything clean and exactly as we left it. Our dogs were happy, well cared for, and clearly comfortable with him. We’d absolutely recommend Carson to anyone looking for a reliable and trustworthy pet sitter, and we’d be happy to have him watch our dogs again in the future.

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Tyler G.
House Sitting
5.0 out of 5 stars

Mitch was great! He took good care of my dog while I was out of town and was easy to communicate with. He shared updates while I was gone and I would definitely recommend him and use his services again in the future!

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Devan C.
House Sitting
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