House Sitting Windsor
Find a loving house sitter to watch over your pets and your home.
Over 124 pet parents in Windsor have booked house sitting
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.
“We've had Tina and her son Skylar as sitters for many years and they always do such a good job. Our pets love them and they are always sure to give frequent updates.”
“Tiana was amazing with our dog and the house was well cared for while gone for an extended period of time. She provided regular updates with pictures that were much appreciated when we started to miss our baby girl.”
“I cannot say enough good things about our experience with Elizabeth. She was so diligent about following Gus's routine, so great about keeping us updated on how things were going, and above all SO kind and understanding of our pups needs as a spicy/reactive dog. She left me completely at ease and able to relax on our trip. I am so glad we've found her and that our baby has someone he will not just be comfortable with, but excited to spend time with while we are gone!”
“Mira was great with our dogs. She sent a lot of cute pictures! We came home to happy, tired dogs as well as a clean house. Thank you Mira, we really appreciate all your help.”
About: We have been loving and caring for dogs for a long time. Big and small dogs; young and old. Our son and 7 year old dog are welcoming I am currently working from home and Bryan works part time. Our son is home schooled at this time, therefore, we have time and energy to help other dogs and other families We have a large yard in a quiet neighborhood; part of our yard is fenced and other part is open for additional exercise. We also walk our dog daily.
“Tonisha has taken care of our pups before for drop in visits and walks. This service was for overnight and as usual, she did an outstanding job! My pups love her so we know they are always well cared for:)”
“Emilee was AMAZING while we were gone for the week! We have three rescue pups all with various needs and anxieties and Emilee could not have been more patient, kind, or accommodating for the three of them. She kept us regularly updated and even offered some guidance/ideas from her years of professional work with dogs. We hope she's available next time we're headed out of town - we can't imagine leaving them with anyone else!”
“Cassie was wonderful! We had no worries, as we were gone for 11 days. She stayed at our home, so it didn’t stress out our dog, Zoe. Cassie was very proactive with asking detailed questions about her and just genuinely concerned about all her needs. She even suggested coming over for some visits prior to our vacation, so Zoe could get use to her. Highly recommend!!?”
“Tucker did a great job watching Zoe & Mocha - regularly sent photos, provided updates from each visit, and was very communicative in providing care.”
About: Hi! I’m Laura — a lifelong animal lover and professional dog trainer with years of hands-on experience with dogs and cats of all breeds, ages, and personalities. I specialize in in-home pet sitting where your pets stay relaxed, routine stays consistent, and your home is cared for with absolute respect. I’m calm, responsible, and deeply experienced with everything from confident working breeds to sensitive, anxious, or quirky dogs. Whether your pet needs quiet companionship, structure, adventure, medication, or extra patience, I tailor care to their exact needs. What You Can Expect Gentle, confident handling Reliable communication + photo/video updates A clean home when you return Safe, respectful care for pets and property Professional judgment in all situations Experience Includes Professional dog training background Puppies, seniors, and special-needs pets Large and working breeds Medication and special-care routines Multi-pet households Basic training reinforcement (upon request) Your pets are family — and I treat them like my own. I travel between Polson, MT and Madison Wisconsin frequently. I run my Dog Training company so I keep busy and can do that from anywhere so the pups are always #1 A mixture of all my years of experience combined with the clients desires and needs for their pet. Each dog I meet is my new best friend!
“Jen was great with my dog. Super attentive, sent me pictures and updates every day, and left my apartment in great condition. I would definitely use her services again.”
“Amazing sitter. My fur baby clearly loved her to pieces. I had her housesit for me to keep him company and I received multiple daily updates of how he was doing. Will definitely have her back to watch my mocha again ?”
About: I’ve grown up with dogs my entire life and currently have three dogs of my own, all with very different personalities and needs. I’ve put a lot of time into training and creating a successful multidog household, which has given me experience with everything from basic obedience and leash manners to reactivity, resource guarding and special-needs dogs. I’m comfortable following established routines, using the training methods and equipment your dog is accustomed to, and adjusting my approach based on each individual dog. I understand that not every dog is a social butterfly, and I’m happy to give dogs the space, patience and structure they need to feel comfortable. Most importantly, I know how nerve-wracking it can be to trust someone else with your dog. I’ll care for yours with the same attention and respect I expect for my own. As a registered nurse, I’m dependable, detail-oriented and comfortable following specific care and medication instructions. I’m also used to communicating clearly, so you can expect plenty of updates while your dog is in my care I’m an RN with a rotating schedule, which gives me several days off during the week and plenty of flexibility to care for your pets. On my days off, I’m available for walks, drop-in visits, playtime and plenty of attention! I am home most of the time and my husband works from home so someone will usually be here. With the occasional instances of going out a few hours at a time. We do keep our dogs crated while we are gone and have cameras on the kennel/dog room to keep an eye on them. I know every dog has their own routine, personality and comfort level. I’m happy to follow your established routine and any specific instructions for feeding, walks, medications, crates or training. I have experience with multidog households, reactive dogs and special-needs dogs, so I’m comfortable adjusting my approach to what makes your dog feel safest and most comfortable. I’ll also keep you updated with photos and messages so you can feel confident your pet is well cared for while you’re away
“Samantha was phenomenal! She provided great communication and provided good updates with my dog. She took amazing care of him. I had her housesitting for me and she was extremely respectful of my apartment as well. I would absolutely have Samantha help me out again!”
“Aslyn did a wonderful job, and I highly recommend her. She is great with Roger & Gucci. Gucci loves everyone, and Aslyn made sure he got all the snuggles he wanted. Roger is shy and barky, and Aslyn gave him the space he needs while letting him know she is someone safe if he wants to be friends. She sent very sweet pictures while I was away, and I appreciated the great questions she asked beforehand.”
“This was my first time leaving my dog and cat and Kirsten did an amazing job! She sent tons of pictures and updates while I was gone. She left my house spotless and got the mail while I was gone. I highly recommend Kirsten to watch your fur babies! I’ll definitely ask her to watch mine again in the future!”
“Louisa was excellent! She was so thorough in our meet and greet making sure she was aware of any and all needs Ollie might have. Ollie loved her right away which made me feel very comfortable. Louisa was great at communicating and sent pictures during the sit which I appreciated. Highly recommend her and will certainly have her care for Ollie in the future!”
“Once again, Jesse is incredible with our pets. She cares for them just like we would, and I couldn’t leave them with anything less than that level of love and care. Thank you Jesse for being awesome!”
The median cost per night for house sitting in Windsor is $50
Pet parents share their Rover experiences - Windsor
This was our first time using Rover, and Emilee made the entire experience so easy and reassuring. She was incredibly responsive, patiently answered all of our questions, and even proactively reached out with questions of her own to make sure she understood Harper’s routine and needs. Communication throughout Harper’s overnight stay was top-notch, and we felt very comfortable knowing she was in good hands. We had a great first experience and would absolutely recommend Emilee and use her again!
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
It's that easy! All payments are processed through Rover's secured platform
Popular requests for house sitting - Windsor
Select a filter and find qualifying sitters offering house sitting.Sitters in Windsor average 4 repeat house sitting clients
FAQs for House Sitting - Windsor
Frequently asked questions about Rover
The average cost for House Sitting in Windsor on Rover is $38.59 per night (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of House Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for House Sitting. For more information on service fees, click here .
As of September 2026, there are 806 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:
- 94% of sitters can help with special care needs
- 98% can help with giving oral medications or injections
- 96% 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.
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