Dog Boarding Windsor
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Windsor, Find top rated dog boarding
“Joseph was an excellent communicator and helped me to feel comfortable leaving my two rescues in his care. Kind and compassionate! When I picked my pups up, they gave Joseph kisses goodbye, so I know they were well cared for.”
“Hannah saved my wedding day!! Our scheduled dog sitter (not from Rover) cancelled on us two days before our out-of-state wedding, and Hannah not only filled in last minute, she might be our pups favorite person💖 She is incredibly warm, they took to her immediately, and we were so grateful 🙏 Got lots of photos of them just relaxing around her and were able to enjoy our wedding day stress free. Thanks so much, Hannah!!”
“Our dog, Mable, had the best time at Emily’s! My husband and I had our pup stay at Emily’s for a long weekend while we were out of town, and we felt so at ease. Emily sent us updates and pictures multiple times a day. Mable was so happy and came back worn out from all the playtime and love! We will certainly be using Emily again in the future! Highly recommend!”
“Kevin and Inez took SUCH great care of my senior dog while we were visiting Woodstock. I am very nervous about leaving him with others as he usually comes everywhere with me and is older but they made sure to update me with tons of photos and videos. I could tell that Gatsby felt right at home and was very comfortable at their house and with their dogs. I would definitely use them recommend them to anyone looking for pet care in Vermont! Thank you!!!!”
“Susan & John are fantastic, they took great care of Oliver. He loved playing with Emily and all her toys. We’ll definitely be back for more doggie play dates!! Thankful for Sue being so flexible with late notice and timing.”
“Meena did a wonderful job watching Rooni! We could tell right away that Rooni had a great time. She got tons of love and attention, not just from Meena but from her friends too, and she came home happy and energized. Rooni clearly felt comfortable and well cared for. We would absolutely book Meena again and recommend her to anyone looking for a sitter who genuinely loves dogs!”
About: I have taken care of pets and have had pets for as long as I can remember. I have two dogs and three cats! My animals are my kids! I have worked hard with my dogs to train them, as well as, one of them being my service dog. I am currently unemployed and have plenty of time to give your pet lots of time, energy and love. I truly enjoy spending as much time with animals as I can My dogs are trained to be on and off leash. I will take care of your pet in whatever way you feel is best for your pet and per your instructions.
“Hope is a wonderful boarder and I will definitely request her services again. She was very responsive on the app and her property is lovely. Heidi had a terrific time with her new friends and looked happy and healthy when we picked her up.”
“Grace and her sweet pup Luddy made it SO comfortable and easy for us to leave our girl for the weekend. She obviously cares a great deal, is very kind and responsive, and clearly enjoys the time with her guests. Her home and property are safe/comfy with lots of space in nature to play and explore. I highly recommend her and will be asking for her help sitting again for sure!”
The median cost per night for dog boarding in Windsor is CA$63
Dog parents share their Rover experiences - Windsor
Cara was amazing with our Saint Berdoodle Lizzie! She was so understanding of her energetic, playful puppy personality! She sent us pictures and videos while we were away, which gave us peace of mind. Lizzie came home happy, and we were so appreciative that Cara took such great care of her, especially on such short notice.
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.
How to book dog boarding
1. Search
Browse profiles of sitters near you who offer dog boarding.
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 dog boarding - Windsor
Select a filter and find qualifying sitters offering dog boarding.Sitters in Windsor average 10 repeat dog boarding clients
FAQs for Dog Boarding - Windsor
Frequently asked questions about Rover
As of November 2026, there are 76 sitters on Rover offering Dog Boarding across Windsor. Enter your ZIP code to see which available sitters are closest to your home.
If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.
The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.
Every sitter on Rover has their own routine. Depending on the arrangements you agree on before the stay, a sitter can follow your dog’s regular feeding schedule, provide a comfortable place to sleep, offer companionship, and support their usual exercise and play needs.
95% of sitters in Windsor can provide daily exercise during dog boarding stays. Depending on the sitter, their home environment, and your dog’s needs, this may include walks, outdoor play, indoor enrichment activities, or supervised play with compatible dogs. These activities are not automatically included with every booking, so ask the sitter what a typical day looks like.
During the Meet & Greet, discuss your dog’s usual exercise and play routine, whether they can safely interact with other dogs, and any activities or restrictions the sitter should follow. You can also ask the sitter to send photo and message updates during the stay so you can see how your dog is spending their time.
Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Windsor home-away-from-home, we recommend packing:
- Health and safety essentials such as their ID tags, vaccination records, medication, and emergency vet or secondary caregiver contacts.
- Food and gear such as harnesses, collars, food (portioned by day), and an item that smells like you.
- Special instructions such as a list of training cues, medical administration needs, or favorite hang-out spots in your Windsor.
Tip: You can upload your dog’s routine and medical info directly onto their profile so your sitter always has the details at their fingertips.
Yes, you can find sitters who have experience with handling special pet needs in Windsor. On Rover:
- 91% of sitters can help with special care needs
- 92% can help with giving oral medications or injections
- 95% 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.
You and your Windsor sitter can schedule drop-off and pick-up in a way that works best for the both of you—and your dog. Most sitters offer flexible times for drop-off and pick-up but the easiest way to confirm those times will be through in-app messaging. Confirm your arrival time the day of pick-up and drop-off can also help keep the process smooth and organized.
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.
While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.
Many sitters in VT ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies.
By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.
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 dog to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your dog 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.
Adding another pup to the pack? Most sitters and walkers offer a reduced rate for additional dogs. You’ll find these exact rates listed under the "Services" tab on any sitter's profile. Since every dog is unique, final pricing may vary depending on the level of care required.
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