House Sitting Windsor

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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: Daniel C.
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Daniel C.
from
$35
per night
5.0 out of 5 stars
61 reviews
16 repeat clients
10 years of experience
The Fan, Richmond, VA, 23220

Very happy with Daniel. He was very communicative and my dogs seemed to bond with him immediately. Highly recommend ! Thank you for all the help

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Keano C.
Sitter Profile Image: Journei F.
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Journei F.
Star Sitter
from
$28
per night
5.0 out of 5 stars
9 reviews
5 repeat clients
7 years of experience
Richmond, VA, 23234

10/10

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Matt W.
Sitter Profile Image: Meghan H.
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Meghan H.
Star Sitter
from
$40
per night
5.0 out of 5 stars
17 reviews
5 repeat clients
4 years of experience
Richmond, VA, 23234

Meghan did a great job with my dog and cat for a weekend stay. Took awesome care of the house and the animals are happy. Would highly recommend.

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Matt B.
Sitter Profile Image: Alexander S.
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Alexander S.
Star Sitter
from
$40
per night
5.0 out of 5 stars
33 reviews
8 repeat clients
47 years of experience
Old Town Manchester, Richmond, VA, 23224

Alex did a great job with our 2 pups. He took detailed notes at our meet and greet and followed their feeding and walking schedules carefully. Great communication and pics so we knew they were receiving good care. We’ve already booked Alex for our next time away

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Sally S.
Sitter Profile Image: Jennifer Z.
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Jennifer Z.
from
$40
per night
5.0 out of 5 stars
13 reviews
5 repeat clients
8 years of experience
North Chesterfield, VA, 23234

Jenni was a great choice to watch our fur baby overnight because of a last minute trip my partner & I had to take for a funeral. Due to our unexpected time constraint beforehand, she came over the same day of the booking and met our dog Hank & learned his routine. While we were away, she sent lots of pictures & gave us updates every so often so we were always in the know. We would definitely have Jenni watch Hank again in the future and highly recommend her for the pet sitting needs of other folks too!

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Peter C.
Sitter Profile Image: Marissa J.
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Marissa J.
Star Sitter
from
$40
per night
5.0 out of 5 stars
49 reviews
11 repeat clients
6 years of experience
Richmond, VA, 23221

Marissa was kind, communicative, calm, and flexible. My flight home got cancelled and I had to rebook my return trip a day later. Marissa immediately agreed to extend her services when I told her what was going on. When I (finally) made it home, Peaty was happy and well-cared for and my apartment was pristine. Would work with Marissa again in a heartbeat!

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Samantha T.
Sitter Profile Image: Emily B.
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Emily B.
Star Sitter
from
$55
per night
5.0 out of 5 stars
69 reviews
27 repeat clients
20 years of experience
The Fan, Richmond, VA, 23220

Emily was great! This was my first experience with Rover and I couldn’t have picked a better person. She was great with my puppy Lola and kept me updated during my whole work trip. She was trustworthy and really just made the whole experience so easy. My Lola was so happy when I got home and looked very well taken care of. Thank you Emily!

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Melissa L.
Sitter Profile Image: Isaiah M.
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Isaiah M.
from
$40
per night
5.0 out of 5 stars
2 reviews
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: Oli L.
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Oli L.
Star Sitter
from
$85
per night
5.0 out of 5 stars
109 reviews
35 repeat clients
18 years of experience
Hopewell, VA, 23860

This was my first time having someone stay at my house with my pup instead of bringing her somewhere. I completely trust Oli with her, it went well! I look forward to Oli helping my pup again for a wedding in September :)

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Allison H.
Sitter Profile Image: Mel C.
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Mel C.
from
$100
per night
5.0 out of 5 stars
47 reviews
19 repeat clients
12 years of experience
Gambles Hill, Richmond, VA, 23219

This was the first time leaving Gracie for several days. Mel did such a great job keeping her anxiety level low. We felt keeping Gracie in her own home environment would be the best. Mel did such a wonderful job taking care of Gracie. We will definitely use Mel the next time! I would highly recommend her!

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Terri B.
Sitter Profile Image: Jacob H.
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Jacob H.
Star Sitter
from
$60
per night
4.9 out of 5 stars
21 reviews
5 repeat clients
25 years of experience
Oak Grove, Richmond, VA, 23224

Jacob performed a stand up service taking care of our four animals and our house while we were out of the country. He was always available to communicate updates, left our house looking very clean, and even worked with us last minute to add more time after we made a scheduling error. We would definitely recommend his services and will likely rebook should we need pet sitting again in the future.

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alex f.
Sitter Profile Image: Jenna S.
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Jenna S.
from
$75
per night
5.0 out of 5 stars
2 reviews
2 repeat clients
7 years of experience
Shockoe Bottom, Richmond, VA, 23223

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.
Sitter Profile Image: christine b.
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christine b.
from
$60
per night
5.0 out of 5 stars
27 reviews
10 repeat clients
8 years of experience
Randolph, Richmond, VA, 23220

Christine was so fantastic taking care of our babies! She was very responsive and cared so deeply about them, some of which are special needs or elderly and require medications, and she took great care to make sure each of their needs were met. She treated them like they were her own. She was respectful of our home and we would highly recommend her!

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Rebecca B.
Sitter Profile Image: Andrew C. T.
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Andrew C. T.
from
$65
per night
5.0 out of 5 stars
54 reviews
19 repeat clients
32 years of experience
Richmond, VA, 23224

Andrew was everything we want in a dog sitter. Kind, thoughtful, conscientious and funny. Our Oona can be a stubborn hound and we really appreciate him working with her quirks. He was flexible in meeting up with us to ensure we were comfortable leaving her, and he left the house better than he found it! A++

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Kate P.
Sitter Profile Image: Mary M.
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Mary M.
Star Sitter
from
$30
per night
5.0 out of 5 stars
10 reviews
3 repeat clients
10 years of experience
Richmond, VA, 23235

Mary did a wonderful job looking after our dog Maverick. We will definitely use her again in the future.

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Jimmy R.
Sitter Profile Image: Kaylynn H.
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Kaylynn H.
from
$60
per night
5.0 out of 5 stars
9 reviews
3 repeat clients
18 years of experience
The Fan, Richmond, VA, 23220

Kaylynn was super easy to work with, responded to messages quickly, and our dogs seemed to her! We wouldn’t hesitate to book her again when we need to.

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Morris B.
Sitter Profile Image: Alex K.
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Alex K.
from
$45
per night
5.0 out of 5 stars
84 reviews
28 repeat clients
20 years of experience
Richmond, VA, 23223

Our 2 dogs loved Alex from the moment they saw her. We left them for 6 days and Alex stayed with them night and day. They were so relaxed & healthy upon our return. Our neighbors reported that every time they saw the dogs, they were their normal happy selves. Our house was as clean as we had left it. We will definitely use Alex again.

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Diana C.
Sitter Profile Image: Elizabeth P.
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Elizabeth P.
from
$70
per night
5.0 out of 5 stars
11 reviews
3 repeat clients
16 years of experience
Richmond, VA, 23220

Over the moon with Ellie! She took great care of our two boys whilst we were gone easing so much anxiety. Ellie is responsive, professional, cared so well for the doggies, and went above and beyond!

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Emily C.
Sitter Profile Image: Jazmine A.
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Jazmine A.
Star Sitter
from
$100
per night
5.0 out of 5 stars
50 reviews
15 repeat clients
22 years of experience
Richmond, VA, 23075

Jazmine did a wonderful job taking care of my cat while I was away for a week. It’s a long time for me to be away, but I had total peace of mind knowing that Jazmine was spending time with my cat and looking after the house! She sent great updates, was very responsive, was flexible when I requested her to do another drop in after some travel delays, and I came home to a tidy apartment! Your pets and home are in great hands with Jazmine!

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Carly G.
Sitter Profile Image: Margot B.
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Margot B.
from
$65
per night
5.0 out of 5 stars
34 reviews
13 repeat clients
7 years of experience
Stratford Hills, Richmond, VA, 23225

Margot was absolutely amazing. We got constant updates and photos which we so appreciated. When we got home the house was just as we left it and so clean. She left the guest room so clean which we didn’t except given we’ve had other pet sitters who have left the house very dirty. When we met her we fell in love and will definitely be rebooking if she’ll allow us!! 10000/10 🤍🤍🤍

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Alessandra A.
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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

Fantastic pet sitter for both my reactive dog and cat! Patient, attentive, and responds quickly. Highly reccomend :)

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Ty D.
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

Marissa is the best and our go to sitter! She’s responsive and send updates with pictures. You can’t go wrong with her!

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Rachel S.
House Sitting
5.0 out of 5 stars

Isaiah was great watching our dogs! He was very responsive and communicative during the day. Our dogs were happy and our home was clean after a long weekend. Will definitely be using him again!

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Alexis H.
House Sitting
5.0 out of 5 stars

Fran did a great job house sitting for my sweet cat. She left the housecleaning and sent several pictures while I was away.

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Darlene K.
House Sitting
5.0 out of 5 stars

Kelly is the best ever. We have used her countless times. . . . and will use her over and over again.

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Lauren W.
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

Sam got along great with my cat Annie and she was very communicative and flexible to work with. She sent several pictures each day. I’d book with Sam again!

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Darlene K.
House Sitting
5.0 out of 5 stars

Camryn was amazing! She took excellent care of our medically complex dog and was fantastic with communication. Really appreciate her and would definitely book with her again!

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Tori F.
House Sitting
5.0 out of 5 stars

Liesel is so great with my reactive dog, it’s such a relief having someone who understands my dog’s quirks and takes such good care of her.

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Laura P.
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
5.0 out of 5 stars

Alexis is wonderfully attentive and communicative and did an excellent job with our senior dogs! We were gone for a week and knew they were in good hands. She was very receptive to our directions and keeping the little old ladies safe and loved. We highly recommend Alexis!

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Lauren D.
House Sitting
5.0 out of 5 stars

Molly took great care of our three dogs while we were away and kept us updated throughout. Molly was especially patient and understanding with our older Chihuahua. It was clear that our dogs were well cared for and comfortable. We would happily trust her with our pets again and highly recommend her to others.

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Dakota C.
House Sitting
5.0 out of 5 stars

Savannah was awesome! She played with my boys everyday and kept them entertained. She kept them on the same schedule I had them on and her communication was great! I’d definitely recommend to book her when you need overnight sitter

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Jeremiah P.
House Sitting
5.0 out of 5 stars

Ginny took such amazing care of my Tillie-Bean! She kept me updated with plenty of photos and messages, which made being away from my sweet pea so much easier. Tillie had such a great time that I’m pretty sure she’ll be requesting Ginny as her sitter again in the future! 🐾💕

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Jenn B.
House Sitting
5.0 out of 5 stars

Macee was fantastic to have help watch our two dogs (including a 5month old puppy!). She was communicative, sent updates, and overall just great to work with.

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Lauren T.
House Sitting
5.0 out of 5 stars

Nancy did a wonderful job caring for our home and our three very different dogs while we were away. She was responsible, communicative, and great about checking in whenever she had questions. She carefully followed all instructions, and it was clear our dogs were well cared for and comfortable in her care. We came home to happy dogs and a house that was in great shape. We truly appreciated the peace of mind she gave us and would absolutely recommend her to others.

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Mary J.
House Sitting
5.0 out of 5 stars

Bianca and Conrad took excellent care of the pups while housesitting. Excellent communication and lots of pictures. Dogs looked well taken care of and the house looked great. Highly recommend!

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Zohaib A.
House Sitting
5.0 out of 5 stars

Erica was incredible as always! I really appreciate Erica, because when she is watching my dog, I do not have to worry about a single thing. She always treats her with love and follows all of her care instructions.

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Kendall V.
House Sitting
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