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

Windsor, Find top rated house sitting
Prices are estimates per night for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“Olivia was amazing! She was so great with our big guy and sent lots of updates so we were aware of what was going on without feeling overwhelmed. Absolutely will be booking with her again!”

“Tara was so amazing with our dog and our cat. She sent us lots of updates while house sitting, took our dog for lots of walks, and gave them both lots of attention 😊 Great job with our pets and great communication. Would book her again in a heartbeat!”

“Caitlin was amazing! It was obvious that Ollie and Daisy loved her. She was very accommodating and took care of our pups with love and kindness. I would ask Caitlin to watch Ollie and Daisy again in a heartbeat! Thank you Caitlin!!”

About: I have pet/house sat multiple times over the past several years for friends and family, and have worked with several types of animals from small critters like guinea pigs and ferrets, cats, and even large dog breeds. I also have 2 years experience volunteering for a local shelter in socialization and vet transport, 3 years experience working for a doggy daycare and boarding facility, and I currently work part time for another local animal shelter. I am an experienced owner of dogs, cats, ferrets, chickens, guinea pigs, and more. I also have experience as a wedding dog handler, and would be happy to offer this service if requested so your furry companion can accompany you or someone you know on yours or their special day without any added stress, please let me know if this is something you'd be interested in! I currently work part time so I have lots of time to play with your pup, and hopefully can build savings towards a larger space to meet more people's needs! I am always looking to learn, grow, and provide better care for animals. Animal welfare is very important to me. At this point in time, due to the space I'm only able to accommodate smaller breeds that generally can get along with others. I do have a small fenced in yard, but I also have the bike trail and nearby hiking trails readily available, your dog will need to be on leash at all times when outside on walks/hikes, I do not provide "off-leash" trail experience as a safety precaution, thank you for your understanding! I am happy to provide pictures and updates of your pup whenever requested, please never be afraid to reach out!
“We got home and our dog was happy to see us, but she was so calm. She was clearly so comfortable with Skylar. Skylar left our house clean. She is great! We will use her again.”

“McKenna was able to help with our Aussie-doodle at short notice and we are so grateful! They had a fun day together and she helped him to be active and busy instead of in his kennel for a very long day. McKenna has a lot of experience and knowledge about what dogs need. She communicates regularly and sent some photos during the day as well. Thank you McKenna!!”

“Janet did a great job with the pups and with the house. Janet sent photos every day and kept us informed as to how the dogs were fairing. Both the dogs and the house were in perfect condition when we returned home. Thank you so much!”

About: I have cared for many pets my whole life. I love meeting new animals and learning about each and every personality. Had or cared for cats, dogs, and small animals, and willing to meet more! I am available most days and some nights. I can provide early morning care and mid day care, and night care but often after 10pm. I am always attentive to animal body language and keep an eye on how they are feeling in the environment or around me. I follow the guidlines closely that are given by owners on how to care for their pet.
“Keri is THE BEST!! Our dog is a bit shy around humans and it was honestly stunning how quickly they became friends. Not only was Keri extremely responsive when we were setting up this last minute booking, but she kept us updated regularly throughout our entire trip. It was clear that she showed him so much love, taking him on adventures and cuddling with him. We could tell Keri really understood his unique personality and she made our trip completely worry-free. When we got back, our house was even better off than it was before. If I could give 100 stars, I would!!”

About: Hello! I've had animals my whole life and love being around them. I'm available to walk dogs and give them good exercise for those that have a lot of energy. I am also available to stay overnight to take care of your house and animals. My love for animals has pushed me to study to become a veterinarian technician. I also currently work at Berkshire Veterinary Hospital so I'm comfortable bringing them to the vet in an emergency. I am also able to medicate (orally or injected) your animals. I'm also comfortable cutting nails. I have the most experience with cats and dogs but enjoy taking care of all animals whether they are furry, feathered, or scaled. I have a very calm personality so most animals trust me right away and if they don't, I'm very good at earning it. Let me earns yours and you won't regret it.
About: Working in various Grooming/Training facilities. I'm currently working with Bumblebee Pet Care with 5 of my own clients. My conversations with the pets are amazing. I'm currently walking dogs 2 days out of the week looking for more to work with within the week. I have an open schedule and interested. I have separate spaces available for each animal. In my care at anytime, I will use provided equipment for transportation. Your pet safety is number one.
About: I've grown up with dogs & cats. I am very involved in rescuing & fostering & have plenty of experience with all sizes, ages, temperaments & am experienced with most medical issues/medicating regimens. My schedule for work is Monday- Friday 7:30-4 pm. I'm available from 5-10 pm weekdays for drop ins and walks. I have open availability for weekends to house sit, go on walks and do drop in visits. I am currently in the process of relocating to New Hampshire permanently. I work full time Monday through Friday and offer pet care on evenings during the weekday, and full time on weekends :) I'm experienced with providing care for difficult dogs and cats and have no issues being able to give medications.
About: I have been a volunteer at the Berkshire Humane Society for about 6 months now working within the kennel and have been trusted with friends and family's dogs throughout my life! I have personally trained both of my large breed pups and have experience with both puppies and senior dogs! <3 I currently work part-time from Fri-Sun so I have full availability throughout the week to play with your pup(s)! I will always find the best time and place to give your pets what they need. I am not able to bring pets to my apartment, but will gladly give them all the care and attention they need in their home, or out and about!
About: Retired Military Veteran, 12 years of service. Very reliable and love animals. I love all breeds of dogs regardless of the stereotypes. Can’t wait to start watching your dogs. I have a vast background, military and emergency services. I’m in the process of becoming a nys emt and then will go on for my paramedic hopefully my flight medic. I’ve grown up with dogs and haven’t had a dog in a year. Feel free to look up my information in the military to know that I’m a veteran. I am always available even for a last minute vacation. My husband and I would love to help who ever needs that extra tlc while their owners go away. I’m home all day every day. I work overnights so my hubby could let your little or big pups out to go potty before work. They will have free range of the house unless they are specifically crated then I can put them in the crate and take them out when needed.
“Brenna was an amazing pet sitter for us. We have two dogs, both seniors, and one with significant health issues. It is always hard to leave him but had our son's wedding in Canada to attend. Brenna sent constant updates and photos to ease our mind while away. They were very well cared for and loved. I would use Brenna again in a heart beat!”


About: I grew up with dogs my whole life. My parents also run a dog sitting business on cape cod and I help out there when I can! I am also fully insured! I’m a current second grade teacher, so I’m completely free on the weekends and the summer months, as well as school vacations to take care of your furry friends! I will love your dog like my own! I’m a diligent, reliable and clean person that will leave your home and dog happier than I found it. I am also fully insured!
About: ive had a couple of dogs growing up in my childhood, a sweet old black lab and a super crazy dingo.. in my free time after school and during summer i used to walk them, no amount of walking could satisfy my dingo..! id have her pull my bike to get all her energy out since we didnt have any closed in areas she could run off in.. ( i dont do this anymore! i realize its not very safe! she absolutely loved it for sure though) i love pups big and small old and energetic theyre all very unique and id love some new friends to get me out of the house. id ask you beforehand of course if youd be okay with them swimming, theres a pond i can bring them to after walking to cool off at. i have two cats, so id like to know how your dog reacts around small creatures, if they cant be in contact i can always but them into a room while the dog is over. most likely theyd be outside keeping me company! lots of shade and id keep em well hydrated and happy :3 i currently have been on a job hunt since what feels like forever, my schedule is very. very open.. since i dont have a car, but I have an electric scooter thanks to a helpful couple I babysat for! drop off would be ideal, if youre close enough to walk to i can do that too! my cats get their waters filled and cleaned almost daily, lots of love of course and are very spoiled. i dont have any dogs at the moment, so of course id love to chat about what youd expect and need for your lovely pup! im good with communication and friendly, special needs id be extra attentive to. im very good at remembering small things, though id still write em down incase!

About: I have two chocolate labs at home. I have cared for these dogs for 8+ years, and I have also dog-sat plenty of my neighbors', community members', friends', and relatives’ dogs over the years. I love to adventure with my dogs, but I can accommodate whatever adventure means for each dog, based on ability and the owner's desire. Also, I have done training with my oldest dog, have experience giving medication upon the owner's instructions, and have sat with quite sick dogs (my attentiveness to needs in this department is high). Overall, excited to sit for you! And let me know if you have further questions for me! I’m currently working part-time, so I have plenty of time to devote to your pups! I’m available for watching on both weekends and weekdays when you need my help! I will have work throughout the week, but I can pick up times to watch as my schedule is flexible. I spend a lot of time with my dogs when they go outside, and I walk/run them every day. I can easily crate your dog if needed. I also have experience ensuring owners’ dogs receive their medications and the correct dosages. Overall, I can adjust to all your pup’s needs!
The median cost per night for house sitting in Windsor is $60
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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 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.
Meet local sitters who will treat your pets like family

1. Search
Browse profiles of sitters near you who offer house sitting
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
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Popular requests near you
Select a filter and find qualifying Windsor sitters!Sitters in Windsor average 4 repeat house sitting clients
FAQs for House Sitting - Windsor
Frequently asked questions about Rover
As of July 2026, there are 361 sitters on Rover offering House Sitting across Windsor. Enter your ZIP code to see which available sitters are closest to your home.
Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:
- Mail & deliveries: Collecting letters and packages so they don't pile up.
- Plant care: Keeping your indoor or outdoor garden hydrated.
- Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
- Home security: Sitters can stay overnight to keep your home occupied.
The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Windsor walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.
It’s helpful to think of house sitting as a "home base" service. Most sitters in Windsor maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:
- Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
- Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
- Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.
Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Windsor choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.
All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.
Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .
If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.
For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.
Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.
A Meet & Greet is a short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.
Yes, you can find sitters who have experience with handling special pet needs in Windsor. On Rover:
- 92% of sitters can help with special care needs
- 100% can help with giving oral medications or injections
- 92% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.
Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.


