House Sitting in Windsor

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

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Top rated Windsor house sitters

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: Annie D.
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Annie D.
from
$60
per night
5.0 out of 5 stars
85 reviews
24 repeat clients
10 years of experience
South Windsor, CT, 06074

Annie was AMAZING! She took such great care of our babies. Patches has anxiety, and unfortunately gets sick sometimes from it, and Annie went above and beyond on making sure she was OK. She also sent us pictures and a video while we were away. Highly recommend this young lady!!

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Joann V.
Sitter Profile Image: KiAnna H.
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KiAnna H.
Star Sitter
from
$70
per night
4.9 out of 5 stars
31 reviews
10 repeat clients
6 years of experience
Bloomfield, CT, 06002

KiAnna was willing to arrive by 6:45 AM so we could depart by 7:15 AM. She took great care of Chester and we will be asking her to house sit and take care of Chester again!

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Erin C.
Sitter Profile Image: Christopher M.
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Christopher M.
from
$75
per night
5.0 out of 5 stars
10 reviews
2 repeat clients
25 years of experience
East Windsor, CT, 06088

We had Chris come do an in-home stay for the first time with our reactive pitbull and he crushed it! Reactive dogs are not the easiest to find sitters for and Chris was very accommodating with setting up a meet and great before hand and had even done his own research ahead of time to make sure he was knowledgeable before going through the introduction process. Our dog warmed up to him right away and she was able to immediately identify him as a safe person since he was so calm and easy going with her. When it came time for him to stay, all that was needed was a quick reminder and they were best buds for the rest of the weekend. He quickly learns her quirks. He sent daily pictures and updates. Then when we returned, our mail was stacked on the counter and the house was very neat, just as we left it, which is always appreciated when someone stays in your home. During the introduction stage he even requested to be shown where our cleaning supplies were and when our trash gets taken out. Chris was not only an excellent dog sitter, but a great house sitter as well! We are frequent travelers and will definitely be continuing to use Chris.

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Allison R.
Sitter Profile Image: Jesey M.
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Jesey M.
from
$30
per night
5.0 out of 5 stars
15 reviews
5 repeat clients
7 years of experience
Windsor, CT, 06095

About: It's getting cold out. Your dog wants to go outside, but do you? Let me walk your dog for you. Cat sitting too. Jesey is open for business throughout the winter and spring! Proud roommate to the most perfect kitty ever created, friend of all things furry (or furless), and middle school music teacher. For over 10 years I have been taking care of delicate cats, big Australian shepherds, hyper Siberian husky puppies, grumpy felines, potbelly pigs, and everything in between. In the past I have slept over at a client's house to ensure that the little buddy gets let out, fed, etc. whenever they need to. I feel comfortable taking dogs out for evening/night walks, if your pet is a night owl. I love playing at the park or in the backyard, so let me hang out with your pet! I have worked with pets with allergies, dietary restrictions, and other various conditions. I have given cats and dogs their medicine in many different forms,(pills, oral liquid, injection, etc.) and am comfortable doing so. I'm working part time, so I will have plenty of time to take care of your beasts. Typically visit in the morning before 11am, and after 6pm for the evening. I care for everyone's pet like my own. Fresh water, food, litter, and lots of love every visit. skreet skreet pow skreet CRASH plop whoosh

Sitter Profile Image: Carol K.
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Carol K.
Star Sitter
from
$95
per night
5.0 out of 5 stars
120 reviews
37 repeat clients
15 years of experience
West Hartford, CT, 06117

Carol was wonderful with our dog, Brutus, while away on business trips. She was super comfortable with him, very experienced with a range of dog behaviors and medical issues, and provided frequent updates and photos. I would leave Brutus in her care any time and know he’s in great hands!

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Nathan R.
Sitter Profile Image: Madelyn C.
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Madelyn C.
from
$45
per night
5.0 out of 5 stars
3 reviews
1 repeat client
15 years of experience
Windsor, CT, 06095

About: I have 2 dogs and 2 cats. I have lots of experience feeding, walking, and taking care of them! I also have experience with senior animals! Mostly available evenings and weekends. I will work with you to schedule times that work for you and your animals. I will be as flexible as possible! For dogs, I can walk, feed, play with them, and give them medicine if needed. For cats, I can play, feed, change litter boxes, and make sure they are happy!

Sitter Profile Image: Olivia S.
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Olivia S.
from
$32
per night
3 years of experience
South Windsor, CT, 06074

About: I’ve had a dog and 3 cats growing up. I am constantly around dogs and they all love me. My friends and neighbors have trusted to watch their animals when they are away. I just graduated college and looking for a fun job for over the summer! I have lots of free time so I am available to help with your animals whenever you need! I have one cat at home but he’s not the biggest fan of new animals. I love playing with animals and making sure they use most of the energy.

Sitter Profile Image: Allie H.
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Allie H.
from
$66
per night
5.0 out of 5 stars
30 reviews
9 repeat clients
15 years of experience
Manchester, CT, 06042

Allie was awesome with our two golden girls! She took such great care of them. The pictures and messages received were outstanding. Thank you again Allie!

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Michele G.
Sitter Profile Image: Samantha N.
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Samantha N.
from
$80
per night
5.0 out of 5 stars
59 reviews
17 repeat clients
13 years of experience
Windsor Locks, CT, 06096

Samantha is an awesome house sitter! Peaches takes to Sam when she arrives at our home! Sam was at our house for 3 weeks and she takes care of our home as if was her home!! She takes our call when we want to see Peaches! Thank you for the loving care of Peaches!!🍑 💕

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Marcia R.
Sitter Profile Image: Greg C.
Verified Enhanced Background Check
Greg C.
from
$50
per night
5.0 out of 5 stars
57 reviews
29 repeat clients
10 years of experience
windsor, CT, 06095

Heather and Greg were great with our two giant rescue pups. Heather stayed with them overnight for 10 days, and one of them was sad not to see her the first night we were back (looking for her in the guest room!). Hope to have them take care of pups again. Highly recommend this team to take care of your beloved family member pups.

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Nina A.
Sitter Profile Image: Sarah E.
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Sarah E.
from
$63
per night
5.0 out of 5 stars
37 reviews
15 repeat clients
16 years of experience
Windsor, CT, 06095

sarah was wonderful! she sent me pictures and updates every day! i came home to my apartment exactly as i left it, and i felt like my animals were very well taken care of.

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Sarah M.
Sitter Profile Image: Mary M.
Verified Enhanced Background Check
Mary M.
Star Sitter
from
$65
per night
5.0 out of 5 stars
64 reviews
27 repeat clients
3 years of experience
Suffield, CT, 06078

Mary was an amazing pet sitter to our dog. She sent photos and videos daily. I could tell by the videos and photos that our dog was very well taken care of while we were away and it took the stress out of traveling, knowing that she was in such good hands. I would definitely have Mary back to pet sit. Highly recommend!

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Renee L.
Sitter Profile Image: Jessica & Christopher F.
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Jessica & Christopher F.
Star Sitter
from
$45
per night
4.9 out of 5 stars
127 reviews
54 repeat clients
20 years of experience
Windsor, CT, 06095

Jessica was really great with our boys! They’re new to us and we didn’t know what to expect with a sitter but needed to attend a memorial today with short notice and reached out to Jessica just a couple days ago. Not only did she make herself available on short notice, she also made sure she could come by earlier today with her kids to see how everyone would interact. This was really helpful to familiarize everyone in advance and a big help to us to see how well our boys got along with “human puppies” - worked out so great! While we were gone, Jessica sent a bunch of FANTASTIC pics to keep us informed. Being new to our dogs and this being the first time we hired at home sitters for them, I think Jessica and I learned a few things simple we can do to clarify communication with each other in advance which went really well considering we had so little time to prepare! Would definitely welcome Jessica and the kids back again - our boys really loved them and enjoyed their time together - and they were happily exhausted when we got home still sleeping some 4 hours later! Thanks Jessica!

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Steve M.
Sitter Profile Image: Rebecca F.
Verified Background Check
Rebecca F.
Star Sitter
from
$120
per night
5.0 out of 5 stars
181 reviews
61 repeat clients
20 years of experience
Manchester, CT, 06040

Rebecca, per usual was wonderful. Really great communication while we were gone, took wonderful care of our home (was cleaner than we left it!). So looking forward to having her back on January!

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Erica D.
Sitter Profile Image: Berkley B.
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Berkley B.
from
$65
per night
5.0 out of 5 stars
4 reviews
2 repeat clients
4 years of experience
Windsor, CT, 06095

Kindly took a very last minute request, was able to squeeze in a quick visit, and did a fabulous job. Pups were content and happy to have them as company. Easy communication and very nice person all around. I’ll definitely be requesting again!

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Kate A.
Sitter Profile Image: Joanna R.
Verified Enhanced Background Check
Joanna R.
from
$65
per night
5.0 out of 5 stars
44 reviews
14 repeat clients
17 years of experience
East Hartford, CT, 06108

Joanna and her daughter were wonderful with our pups while we were gone!! Joanna was very responsive and attentive to our requests. We were grateful they showed our dogs lots of love and will definitely be reaching out to them again! Thank you, Joanna!

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Jen F.
Sitter Profile Image: Eleni F.
Verified Enhanced Background Check
Eleni F.
from
$70
per night
5.0 out of 5 stars
14 reviews
3 repeat clients
25 years of experience
Downtown, Hartford, CT, 06106

Eleni was great and super responsive. She was able to accommodate a last-minute request, and was great with our two large pups and their differing needs. She was communicative throughout and they were in high spirits when we returned!

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Larisa K.
Sitter Profile Image: Noelle K.
Verified Enhanced Background Check
Noelle K.
from
$60
per night
10 years of experience
Windsor, CT, 06095

About: I have cared for animals for about 10 years and have mostly worked with dogs, cats, and rabbits. I always am the first person my neighbors as for pet sitting as I am reliable and love spending time with animals. I love to give pets lots of attention and play with them and give lots of petting to make them as happy as possible. I currently have no other job at the moment so I have plenty of time to look after your pets! I am available all day during the week and on weekends. I have a cat that has to take pills daily and I am used to giving animals medicine and flea medicine so I am very capable of doing that for your animal. I also give my cat nail clippings and fur brushing to keep them clean. I also clean the litter box weekly and always pick up dog poop.

Sitter Profile Image: Kaeleene E.
Verified Enhanced Background Check
Kaeleene E.
from
$32
per night
5.0 out of 5 stars
4 reviews
1 repeat client
6 years of experience
Windsor, CT, 06095

About: I’ve taken care of many pets over the years. I’ve done both drop-ins for walking and feeding, as well as house sitting to provide enrichment and company. Every animal that I’ve met has liked me, even if their owner says they’re normally shy around new people, which I take as the highest compliment. I’ve administered medication, and the safety and wellbeing of the pet is my top priority. I respect any boundaries that the animal displays, whether it’s distance or petting, and I make sure to ask for any special routines or needs up front to make sure I can take care of them to the best of my ability. I work full time during the week while also being a full time online student, but I’m available to stop in before 8:45am and after 6:30pm. Weekends are usually open for drop-ins or house sitting. If there are any baby gates or areas restricted to the pets, I make sure to keep an eye on that. I wipe paws after being outside to keep the house clean, and if your pet needs company while they eat, I’ll absolutely sit with them.

Sitter Profile Image: Carla A.
Verified Enhanced Background Check
Carla A.
from
$75
per night
4.8 out of 5 stars
24 reviews
9 repeat clients
2 years of experience
West Hartford, CT, 06110

Carla is not only wonderful with pets she is a great human! We really enjoyed the experience of working with Carla and I know we will do so again many more times in the future. I would highly recommend her services to anyone out there looking for someone to trust with your pet.

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Valerie G.
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Over 10
pet parents in Windsor have booked house sitting

Windsor pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Sarah is great with our dogs! She takes such great care of them and keeps us updated with pictures while we’re out of town. Highly recommend her as a dog sitter.

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Maura R.
House Sitting
5.0 out of 5 stars

Our animals were so happy when we got home! Our dog is an old man and he was in great shape, the rabbit was also spry and happy. Will use Sarah again! So communicative and the house was as we left it.

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Lauren R.
House Sitting
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How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

The median cost per night for house sitting in Windsor is $60

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

    It doesn’t happen often, but if your house sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Sitters in Windsor average 3
repeat house sitting clients

House Sitting FAQs

Frequently asked questions about Rover

House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Windsor on Rover as of Jun 2026 was about $60 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.

If you’re searching for a Windsor house sitter for the first time, visit the house sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 1,334 house sitters in Windsor. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 88% of Windsor house sitters respond in under an hour.

House sitters in Windsor have an average of 17 years of experience. House sitters with repeat customers have an average of 3 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Windsor.

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Windsor house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.