House Sitting in Chesapeake

Your pet stays in your home as a reliable pet sitter drops in feed and play with them

260 results for House Sitting in Chesapeake, VA

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Hannah W.

(29)
2 repeat clients
from $45.00
per night

Hannah was the perfect sitter for my dog Momo. Extremely accommodating and quickly picked up on all the nuances of caring for Momo. Loved the frequent updates and pictures I received! I have already booked her again and am sure Momo is in great hands when I am away.

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Brittany B.

(13)
6 repeat clients
from $40.00
per night

Brittany was amazing as always! She is my go to when I need my pup watched.

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Lillian S.

(9)
2 repeat clients
from $30.00
per night
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Kelsey W.

(43)
11 repeat clients
from $38.00
per night

Kelsey is awesome. This is the second time we've booked him and our dogs love him. He sends ample pictures and takes great care of our house and pups. We highly recommend booking with him.

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Damian H.

(35)
12 repeat clients
from $37.00
per night

Damian was great! Our girls seemed to really like him and it was nice not to worry about them. We are very appreciative of Damian and can't wait to book with him again.

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Ava D.

(18)
11 repeat clients
from $50.00
per night

Ava was great. Prompt, professional, and conscientious. Chico and Shotzy loved her. We would definitely recommend her and will also book her again if the need arises. TY Ava!

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Alyssia J.

(31)
6 repeat clients
from $47.00
per night

Alyssia house sat my pup for 3 days and she was fantastic. Every communication and meeting was very professional but of course friendly She requested a meet and greet before to make sure she was a fit for my dog and my dog was a fit for her, she took notes, said hello to my dog and asked loads of questions which was amazing, she definitely takes the job seriously. While I was away, she sent wonderful updates morning and evening (this was my request. One question she asked was how often I wanted to be updated and when) with the cutest photos! She was also happy to take him in the car to different walks which I really appreciated as there are no good woods/parks nearby my place and my boy needs his exercise! Every photo he seemed happy and relaxed and having a good time with Alyssia I then arrived home to the sweetest goodie bag for my dog filled with cute printed pictures, toys and snacks which was unbelievably sweet! I would 100% book again and definitely recommend. Thank you so much

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Hillary L.

(3)
2 repeat clients
from $40.00
per night
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Zara M.

(58)
19 repeat clients
from $60.00
per night

Zara is such a sweet person and her love for animals is obvious. She’s taken great care of my dogs twice now while I was out of town. She’s quick to respond to messages and keeps me updated.

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Miranda T.

(9)
1 repeat clients
from $34.00
per night

Miranda was amazing with our dog Finn. We also cannot thank her enough for being flexible to stay another day when our return flight was canceled due to government shut down and FAA requirements. Finn is happy and healthy and had a wonderful time with her.

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Garry G.

(12)
4 repeat clients
from $35.00
per night

Thank you so much for your care and flexibility with the meet & greet and with key drop off!! I really really appreciate that you spent so much time at the apartment with Eddie, it made me feel so much better knowing he wouldn’t be lonely 🫶🏻 thank you so much!!

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Kimberly H.

(9)
3 repeat clients
from $60.00
per night

We felt very comfortable leaving our senior dogs in her care. She did a great job and they were well taken care of. Excellent communication and she went above and beyond bringing in packages delivered while we were away and spending extra time with our eldest pup.

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Kelsey K.

(12)
3 repeat clients
from $50.00
per night

Kelsey is absolutely amazing! She arrived punctually and our pups loved having her around. She was very responsive when I messaged to check in and see how everything was going. She sent numerous pictures during her stay. I look forward to booking with her in the future!

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Chelsey M.

(67)
22 repeat clients
from $45.00
per night

We have used Chelsey multiple times for pet sitting and she does great with our animals each time! Our house is always left in great condition and our pets are well taken care of!

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Jazmin C.

(63)
28 repeat clients
from $45.00
per night

Jazmin was great! I came home to happy dogs. Jazmin sent me updates and pictures and had no problems taking care of my needy dogs. Definitely recommend!

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Brieana R.

(20)
7 repeat clients
from $65.00
per night

Another in home visit that allowed me to go see family and knowing that my fur baby was in wonderful hands. Communication was clear, received photos, followed medication and preference needs to a tee! I also had an unexpected travel delay and she was able to stay to do final feeding of the night.

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Cayla K.

(30)
9 repeat clients
from $30.00
per night

Cayla was great. She was accommodating when my travel plans changed last minute. Always answered my texts promptly. Gave daily pictures. Would book woth her again.

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Kage S.

(4)
1 repeat clients
from $50.00
per night
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Lindsey V.

(12)
5 repeat clients
from $35.00
per night

This is my 2nd time working with Lindsey and Austin and both times they’ve been phenomenal to work with! Both requests were for in-home house sitting. Fast facts about my pets: Roo: a 4yo, 55lb husky/cattle dog mix who is hyper anxious around new people and likes chewing electronics and other random things Gypsy: 9yo, 74lb arthritic, tri-paw German shepherd who is dog-reactive, dominant, and sometimes requires someone to lift her if she’s struggling to get on a bed or couch The Cat: a 3yo cat…who acts like a dog half of the time Suffice it to say, finding a pet sitter who’s comfortable caring for a people-anxious medium size dog and a large dominant GS with medical conditions is a tall order. Yet this duo has been absolutely fantastic to work with! We started with a meet and greet where I got to meet both of them and learned Austin (husband) would do overnights and Lindsey (wife) will provide day-care. Honestly, my pets had more care throughout the day than when it’s just me! Made me feel way more comfortable going out of town for sure. Communication was through Lindsey although Austin relayed messages frequently. The home visit went very well. They weren’t anxious with Roo barking incessantly or Gypsy barreling forward (she packs more of a punch when moving bc of the 3 legs). They asked all the right questions and were open about any concerns or lack of experience. IE: they had no prior experience with a tripaw dog. I was totally fine with that seeing as we had no experience either until it became a medical necessity. Ultimately, I was seeking someone who was comfortable around dogs who are large and dominant. They showed immediate comfort with Gypsy and I knew that Roo would chill with time. Although it was great to see that Roo approached them while they were visiting!! The first house stay was while I went out of the country for a week. It was my first time leaving the dogs since one of crew passed away. I was pretty anxious but Lindsey kept me posted to make me feel more at ease. I failed to mention to them that Roo likes to chew pens. Inevitably she got one and they were up front and told me rather than trying to hide it (I’ve had a sitter try to hide issues before). I truly appreciated it because it reminded me to add that to Roo’s care notes. Also showed me that I could trust that Lindsey and Austin would alert me to any concerns which was a massive relief! (Side note: I don’t blame them for that at all. Roo gets into a lot of things and there’s only so much a person can do, especially when I didn’t tell them to look out for that). Additionally, there was a thunderstorm which makes Gyspy problematic. Lindsey was creative and figured out a way to ease Gypsy outside (Roo follows gypsy’s lead) so that they could go to the bathroom. I’ve had Gypsy since she was a pup and never thought of trying what Lindsey did! My 2nd house sitting request was a debacle at first. The key I had left was SUPER cute but, as we discovered, it was also very flimsy. It broke in the door lock and I was already 4-5hrs away! Of course the spare key was with my neighbor…who also happened to be out of town. Long story short, Lindsey and Austin communicated everything with me and my neighbor to find a solution. Austin was a saint, willing to climb through a window to get into my house since a locksmith couldn’t change the locks without me present. Seriously, I cannot fathom my fortune finding this couple…they 100% prioritized the safety and well-being of my crew with both visits! They even offered to stop by my place to let them out again/give them dinner if traffic delayed me getting home. The house looks just as I left it, my animals are happy and healthy, and they both have been a pleasure to work with each time. I truly appreciate both of them and will continue to reach out to them anytime I’m looking for a house sitter!

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Sara M.

(6)
1 repeat clients
from $37.00
per night

Sara was fantastic, and she even won over my people-selective weirdo pup, Phoebe! HIGHLY recommend her.


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Are you looking for house sitting in Chesapeake to take care of your beloved pet? You are in the right place! We currently have 260 experienced, loving and background-checked house sitters in Chesapeake. Our sitters offer a variety of pet services such as home dog boarding, dog walking and doggy daycare. Make an informed decision based on reviews, response rates and contact at least 3 approved house sitting professionals. Your dog will be delighted to be looked after by our loving house sitters.