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Top rated Windsor house sitters
“Samantha is kind, knowledgeable, entirely reliable and more than fluent reader and astute observer of pups: a truly gifted person. She kept us up to date with photos and stories & we were reassured by her care and insight.”
“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!”
“Taz was amazing with my fur babies! She house sat for my two dogs and cat while I was away at my sisters wedding. She followed my care instructions, gave medication to my 10year old pup, and sent many photos while I was away. She notified me when my pup had vomited and did a great job cleaning up. She was easy to communicate with and responded quickly. I would definitely book her again!”
“KiAnna did a great job with our dogs! She was communicative and reliable and even got us out of a pinch last minute. We will definitely hire her again!”
“Finn was well cared for and very happy to have spent the day with Lucy. We will be scheduling more time with Lucy and would confidently recommend her to others.”
“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!!”
“Josh was great! Sent at least one picture or video per day and left the house cleaner than when he got there. This was a long trip for us, and we were very pleased with everything. Would definitely recommend.”
“Palma was on time, gave all necessary medications, sent photos, and left the house cleaner than she found it! She communicated well. Our babies were in great hands. Thank you Palma!!”
“This was the first time that I used a pet/house sitter for my dog and 2 cats. Alyssa came over for a meet and greet, and then again to go over details. This worked out really well with my pets having seen her twice before I left. She definitely put my mind at ease so I was able to have a relaxing get away. They all received plenty of attention in their own home. I will definitely be booking Alyssa again!”
“Zoey was absolutely wonderful while house sitting and caring for my dog, Mocha. From the start, her communication was excellent. She provided consistent updates, photos, and check-ins that gave me complete peace of mind while I was away. She followed all care instructions to a T and made sure Mocha was happy and loved the entire time. I came home to a calm, content dog and a spotless home. Zoey went above and beyond, and I truly couldn’t have asked for a better sitter. Highly recommend her to anyone looking for a responsible, kind, and reliable caregiver for their pets and home. Thank you again, Zoey!”
“Haven was absolutely lovely - excellent communication, kind, and a general pleasure to work with. We will absolutely be requesting her services again!”
“Alyanna was available to watch our dog when we made last minute plans and needed to be away overnight. She was wonderful with Maisie. She checked in upon her arrival and sent pictures and kept us updated on how Maisie was doing. We’d highly recommend Alyanna and have already asked her to watch Maisie in a few weeks.”
About: Over 10 years of pet experience! I provide safe, loving care and fun for your furry family - walks, cuddles, feeding, and personalized attention included. I’m currently a student at the University of Connecticut studying speech-language pathology. My schedule is very flexible and I’m open to any day of the week. Trusted in home care focused on safety, and routine. Comfortable crating pets as needed to maintain structure and reduce stress. I’ll follow your routine to ensure a calm/familiar environment.
“Aston was great! He handled out three dogs and one cat for a 7 day vacation. He was very good with them and they were quite relaxed when we returned home. We will definitely use him again.”
“Ayana was great! She took care of my boy and handles a couple challenges well. Very friendly person overall which made me so comfortable! Thanks Ayana!!”
About: Hi! I’m Megan, a lifelong dog lover based in Manchester and South Windsor, Connecticut. I had the joy of caring for my amazing Pittie—Samantha—for 13 years. She was my shadow, my jogging buddy, and my heart. Through her, I gained hands-on experience with leash training, handling strong breeds, and recognizing subtle behavior cues that helped her feel safe and loved in every situation. I know how important it is to trust someone with your dog—and I treat every pup I meet with the same love, patience, and respect I gave to Samantha. Whether your dog is full of energy and needs a good walk or prefers a quiet sniff around the block, I adapt to their style and needs. In addition to walking and drop-in visits, I also offer house sitting for pet parents who want peace of mind while they’re away. I keep your pets comfortable in their home environment and maintain routines so everything feels familiar and safe. It’s important to me to stay in a clean and tidy space while house sitting, and you can expect me to maintain your home with the same care I’d give my own. I’m happy to keep things neat, water plants, bring in mail, and make sure everything feels just the way you left it. I’m calm, dependable, and genuinely love spending time with animals. I’m happy to send photo updates after every walk, drop-in, or overnight stay so you can stay connected with your furry friend while you’re away. What You Can Expect: ✅ One-on-one attention & personalized care ✅ Experience with large breeds & strong pullers ✅ Patience with shy or reactive pups ✅ Clean-up, water refresh, and playtime included ✅ Photo & text updates after every visit ✅ Respectful care of your home during house sitting ✅ Sticking to your pet’s routine for meals, meds, and rest ✅ Light household tasks like mail pickup, plant watering, and tidying up ✅ Overnight presence to keep your pets company and your home secure Let’s set up a meet & greet—I’d love to learn more about your pup and how I can help! Walking and Drop-Ins Schedule: • Weekdays: • Early mornings: 5:00 AM – 7:00 AM • Lunchtime (South Windsor only): 1-hour window available (perfect for midday potty breaks!) • Evenings: 4:00 PM – 8:00 PM • Weekends (Sat & Sun): • Available all day: 5:00 AM – 8:00 PM House Sitting Schedule: I work 7:30 - 4:00 PM during the work, if you're within a 5-10 mile radius of South Windsor I can do an afternoon drop in. Weekends I'll be able to stick to whatever your normal routine is! I love walking and jogging. I can tailor my service to your pups preference. A relaxing stroll, or a light jog depending on energy level. I’m available for in-home visits and overnight stays while you’re away for a stress free vacation. My 14 year old pittie passed away peacefully of old age recently, and I have a lot of love to share with your fur babies!
“Jessica was absolutely amazing! We were nervous to leave our pup for the first time (we were away for 8 days)-she made us feel so comfortable and at ease right away. Every day we received at least 10-20 pictures of our dog Artie. She treated him like her family:) He enjoyed walks/hikes and even introduced him to her dog and they immediately became best friends. I will definitely use her in the future. Thank you so much Jessica!!!”
About: I have been raised in a household with all sorts of animals. From ducks, to pigs (an indoor pig, duh), to birds, I can handle it all! On top of that, I was an employed dog walker and babysitter! I am currently working part-time at a coffee shop. That leaves me with plenty of time to play with your fur babies. I do not have a set schedule at work, but will do my best to accommodate to both jobs!! At home, I have a big yard with two friendly playful dogs and a pig (who mostly keeps to himself). We have a fenced in area. Of course at your home, I will abide by your rules and give your pet lots of loving!!
“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.”
“Jarrett was great! He stayed for 3 days at my house watching my dog and 2 cats. He sent me multiple pictures and updates throughout the day, and promptly answered any messages I sent him. He left the house in the same condition I left it in and did not make or leave any messes, in fact he cleaned a few while I was gone. 10/10, will definitely be booking him again. :)”
Loving house sitters in your neighborhood
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Samantha L.Star Sitter
“Samantha is kind, knowledgeable, entirely reliable and more than fluent reader and astute observer of pups: a truly gifted person. She kept us up to date with photos and stories & we were reassured by her care and insight.”
Mary M.Star Sitter
“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!”
Tazesha W.
“Taz was amazing with my fur babies! She house sat for my two dogs and cat while I was away at my sisters wedding. She followed my care instructions, gave medication to my 10year old pup, and sent many photos while I was away. She notified me when my pup had vomited and did a great job cleaning up. She was easy to communicate with and responded quickly. I would definitely book her again!”
KiAnna H.
Star Sitter
“KiAnna did a great job with our dogs! She was communicative and reliable and even got us out of a pinch last minute. We will definitely hire her again!”
Lusianna M.Star Sitter
“Finn was well cared for and very happy to have spent the day with Lucy. We will be scheduling more time with Lucy and would confidently recommend her to others.”
Annie D.
“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!!”
Joshua N.Star Sitter
“Josh was great! Sent at least one picture or video per day and left the house cleaner than when he got there. This was a long trip for us, and we were very pleased with everything. Would definitely recommend.”
Palma T.Star Sitter
“Palma was on time, gave all necessary medications, sent photos, and left the house cleaner than she found it! She communicated well. Our babies were in great hands. Thank you Palma!!”
Alyssa W.
“This was the first time that I used a pet/house sitter for my dog and 2 cats. Alyssa came over for a meet and greet, and then again to go over details. This worked out really well with my pets having seen her twice before I left. She definitely put my mind at ease so I was able to have a relaxing get away. They all received plenty of attention in their own home. I will definitely be booking Alyssa again!”
Zoey C.
“Zoey was absolutely wonderful while house sitting and caring for my dog, Mocha. From the start, her communication was excellent. She provided consistent updates, photos, and check-ins that gave me complete peace of mind while I was away. She followed all care instructions to a T and made sure Mocha was happy and loved the entire time. I came home to a calm, content dog and a spotless home. Zoey went above and beyond, and I truly couldn’t have asked for a better sitter. Highly recommend her to anyone looking for a responsible, kind, and reliable caregiver for their pets and home. Thank you again, Zoey!”
Haven H.
“Haven was absolutely lovely - excellent communication, kind, and a general pleasure to work with. We will absolutely be requesting her services again!”
Alyanna G.
“Alyanna was available to watch our dog when we made last minute plans and needed to be away overnight. She was wonderful with Maisie. She checked in upon her arrival and sent pictures and kept us updated on how Maisie was doing. We’d highly recommend Alyanna and have already asked her to watch Maisie in a few weeks.”
Ashley S.
“Is very friendly with pets. She has done it for years and is very responsible. She has cared for some very needy dogs and cats”
Aston J.
“Aston was great! He handled out three dogs and one cat for a 7 day vacation. He was very good with them and they were quite relaxed when we returned home. We will definitely use him again.”
Ayana W.
“Ayana was great! She took care of my boy and handles a couple challenges well. Very friendly person overall which made me so comfortable! Thanks Ayana!!”
Megan S.
“I can’t say enough good things about Megan. She is kind, reliable, and clearly have a genuine love for animals. My pup absolutely adores her and is always excited to see her. I feel completely at ease knowing my dog is getting excellent care, lots of attention, and plenty of playtime while I’m away. It’s such a relief to have someone I trust. I highly recommend Megan for your pet sitting and walking needs!”
Jessica & Christopher F.Star Sitter
“Jessica was absolutely amazing! We were nervous to leave our pup for the first time (we were away for 8 days)-she made us feel so comfortable and at ease right away. Every day we received at least 10-20 pictures of our dog Artie. She treated him like her family:) He enjoyed walks/hikes and even introduced him to her dog and they immediately became best friends. I will definitely use her in the future. Thank you so much Jessica!!!”
Angela M.
“First of all, Angela is an all around animal lover of animals!!! She comes from a family that has had over 10 dogs through out her life, many chickens, and a pig! I know this because she has watched our dog several times and have learned this from being with her. I highly recommend Angela to care for and walk your dog(s).”
Greg C.
“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.”
Jarrett G.
“Jarrett was great! He stayed for 3 days at my house watching my dog and 2 cats. He sent me multiple pictures and updates throughout the day, and promptly answered any messages I sent him. He left the house in the same condition I left it in and did not make or leave any messes, in fact he cleaned a few while I was gone. 10/10, will definitely be booking him again. :)”
Over 88 pet parents in Windsor have booked house sitting
Windsor pet parents share their Rover experiences
This is my second time having Sarah stay with my dogs- she is communicative, sends cute update pictures and is super kind and flexible. She took great care of our babies and would definitely book again!
Sarah stayed at our house for 10 days and took care of our 2 dogs and 1 cat. She sent photo updates twice a day and responded quickly if I had any questions. She left the house neat and tidy upon her departure. I would hire Sarah again and would recommend her to anyone needed a pet sitter.
Sarah was great! She was very professional, easy going, took amazing care of my two dogs (who can be a little rambunctious!) while we were out of town for the holidays. I appreciated the ease of communication, as well as all the picture updates while we were out of town! Would definitely recommend and book again!
As first timers with Rover, we were so fortunate to have found Melissa to watch our puppy. Her communication was excellent (loved the pics, videos and updates!) and she navigated a few obstacles with ease and a great attitude. We’ve already booked her for our next family trip! Thank you, Melissa!
How Rover works
1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets
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. 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 $50
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 Jul 2025 was about $50 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.
As of Jul 2025, there are 1,080 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 16 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.
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