Dog Boarding Windsor
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Windsor, Find top rated dog boarding
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Cara is the best dog sitter. Our Goldendoodle loved her stay so much, which I could tell by the daily pictures sent and communication from Cara. We look forward to more visits when/if we travel in the future!”
“Joe was excellent. He was super attentive and caring, sent daily photos and videos and didn’t hesitate to take on a puppy who has extra needs. We are looking forward to having him watch both our dogs in a few days. Highly recommend!!!”
“Goldie had a great stay at Ashley's home! Ashley was very communicative and sent us lots of photos of Goldie. I didn't feel like I needed to worry about Goldie while she was there. I highly recommend Ashley and would definitely use her again!!”
“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!!”
About: I’ve loved dogs my whole life and grew up in a family with them, so caring for them has always been second nature. Over the years, I’ve also looked after dogs for neighbors, giving me experience caring for pets with different personalities, routines, and energy levels. I’m comfortable with both large and small dogs and enjoy adapting my care to each dog’s individual needs—whether that’s an energetic walk, a trip to the dog park, or simply providing a calm, relaxed environment. I believe every dog is unique, so I take the time to get to know what makes them feel comfortable and happy. What sets me apart is the amount of time and attention I can dedicate to each pet. I genuinely enjoy spending time with animals, pay close attention to their behavior and wellbeing, and communicate regularly with owners through updates and photos so they can have peace of mind while they’re away. I’m currently between jobs, which gives me a very flexible schedule and allows me to provide plenty of attention and exercise throughout the day. My wife works from home, so between the two of us there’s always someone around. We live on Farr farm, an enclosed and expansive former farm on Farr road, so named for my family who has farmed this land for over a century. We already take our own friendly dog, Bunny, out on walks two to three times a day, and I’m happy to include guest dogs on frequent walks and park visits based on their personality, energy level, and your preferences. Your dog’s safety and comfort are my priority. During Lebanon’s hotter days, we carefully plan walks around the weather, avoid the hottest parts of the day, provide plenty of water, and monitor for signs of overheating to ensure every outing is enjoyable and safe. I treat every pet as if they were my own. Before caring for a dog, I like to learn about their routine, personality, feeding schedule, medications, favorite activities, and any behaviors or triggers so I can keep their experience as familiar and stress-free as possible. On our property, when dogs are outside they’re either on a leash walking or in our enclosed large yard space, never bring left unsupervised. Dogs always have access to fresh water, and receive regular potty breaks, walks, playtime, and plenty of attention. I keep a clean, pet-friendly environment and pay close attention to how each dog is feeling, especially during hot weather or after exercise. When caring for pets in a client’s home, I respect both the pet’s routine and the owner’s home. I’ll follow all instructions carefully, keep the home clean and secure, and provide regular updates and photos so you know how your pet is doing. My goal is for you to feel completely comfortable knowing your pet is safe, happy, and well cared for while you’re away.
“Michelle was great with our Enzo. She sent lots of updates with pictures and videos and I know he was well loved. The day we picked him up he slept all afternoon and was such a happy dog. Will absolutely use Michelle again.”
“Our 6 year old dog had a great time with Kevin and Inez, hiding and swimming with their other dogs! Kevin and Inez were both highly communicative, flexible and sent updates each day. Would highly recommend — thank you!!!”
“Jessica did a superb job! Can't recommend her highly enough. She was fantastic with our dog, taking her on lots of hikes and other adventures. And she was a very thoughtful and responsive communicator. It was a pleasure working with her from start to finish. We're lucky to have such a wonderful dog sitter in our area!”
“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!”
About: I am an experienced pet sitter and animal lover! I grew up with a childhood dog whom I loved very much. When she passed, I began dog sitting often because I adore dogs so much I am a current Dartmouth senior with a very flexible day-to-day schedule. I have an active lifestyle and would love to add your dog into it! I live right next to several trail systems which I regularly use. I also live next to an extremely large, unfenced green space + a small front yard.
“Needed last minute help with care for my dog and Susan and John were so helpful and accommodating as my needs changed. This was the second time I’ve had them watch my dog and wouldn’t hesitate to leave Sophie with them again.”
“Nora took WONDERFUL care of our two cats Robin and Stu. Frequent updates, direct & thorough communication, and most of all, in the pictures we could tell that they were super happy while under her care :). Planning 100% to reach out to Nora again when we need pet sitting.”
“Diana was absolutely fabulous, I will definitely be using her services again and can’t recommend her enough. She had great communication and was sending me frequent updates and pictures! She took excellent care of my dog!”
“Sarah, Ben, and Bean are awesome- It was such a relief to get updates and see Attie having such a great time! Having the fenced yard where both dogs could run and get all their wiggles out is a huge bonus, and Attie came home exhausted and happy. Highly recommend them both :)”
“Enzo can be a shy guy and a little nervous but Lauren did everything to make him feel comfortable including checking in with me, which I truly appreciate. He came home happy and tired and we would use Lauren again!”
“Greta provided great care for our independent minded and sometimes mischievous husky mix and was willing to meet us elsewhere for the drop off and pickup since we had some challenging transportation logistics. Good to know we have a great option for Moon!”
The median cost per night for dog boarding in Windsor is $65
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.
Meet local sitters who will treat your dogs like family
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
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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 September 2026, there are 73 sitters on Rover offering Dog Boarding across Windsor. Enter your ZIP code to see which available sitters are closest to your home.
Every sitter on Rover has their own rhythm and routine, but most will follow the flow that keeps your dog happiest. Sitters can give meals on your dog's regular schedule, provide a comfortable place for sleep, and plenty of one-on-one attention.
80% of Windsor sitters also include daily walks in the neighborhood during dog boarding stays. You can also request photo and message updates throughout the stay so you can see which Windsor landmarks or neighborhoods your dog is enjoying.
If your dog is a little shy, consider booking a one-night trial stay! This practice run can boost your and your dog’s confidence before your trip.
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.
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.
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