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 for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“Brooke and her family were kind and loving to Millie! She hasn’t been with anyone but us and she isn’t a very easygoing pup so we were so relieved when Millie was so relaxed and happy in Brooke’s home. Brooke kept us updated and sent many adorable photos! I would absolutely book with Brooke again and will recommend her to anyone needing care for their fur children.”
“Jess was great! She was super flexible on a last-minute booking. My pup has almost boundless energy, but she came home happy and pretty worn out. We'll definitely be sending her to Jess again!”
“I have no words for Mahayla! Couldn't ask for anyone better than you!! She went above and beyond for Chow and Zoe in their stay.We know 100% sure they will be safe and well taken care when they are with her.”
“Patti and her family took such great care of Luka while we were away. She got so much love and Luka was sad to leave when we came to pick her up. She will definitely miss the amazing yard! I know she will be very excited to go back when our family goes away again. Thank you Patti for loving our sweet girl and taking such good care of her.”
About: My family has always had dogs, and I feel that they enhance the family unit. No discrimination against certain breeds. German Shepherd, Rottweiler, American Staffordshire, Boxer, makes no difference to me. I adore all the four-legged kids! I have my own four-legged kid, and truly appreciate the help I’ve received through Rover.com, while being at work or out of town. It’s such a relief to know that the he is taken care of, so I can continue working to provide for him. Updating you on the visit with pictures and/or videos, so you can see your four-legged kid(s) have been cared for, would be my pleasure. Dogs are family, and I would gladly treat yours as part of my pack. I would be happy to perform drop-in visits or walk your dog(s) during the day, or into the night hours, as my schedule allows. Currently, I am unavailable for midday drop-ins and walks Mondays through Thursdays. Updating you on the visit with pictures and/or videos, so you can see your four-legged kid(s) have been cared for, would be my pleasure. I happily treat your fur kids as lovingly as my own. Always checking that food and water bowls filled as needed. Utilizing the crate should they need it upon my leaving.
“My dog was well taken care of and didn't spend my vacation locked up in a kennel, so I didn't have to worry about her. Aura sent pictures and updates every day, and I was very happy with the whole situation.”
“As I write this review I look down at my pup who is exhausted from her stay with Mary and Todd. They took Harper in last minute for an overnight/all day play date with their other dog pepper. Harper was treated as one of their own. Over the course of her stay we had daily updates and shared pictures of the trip to art Omi and for evening/morning walks. I can’t thank them enough so I figured this review would be accepted as my appreciation. I would highly recommend them, you will not be disappointed!!! Thanks again Mary and Todd”
“Ericca is an amazing dog sitter. We heve 3 Bernese Mountain Dogs who have never been to a kennel or anyone's house, but we needed to find someone for a 2 day stint. Ericca is so professional and met our dogs prior to agreeing to take them. Upon meeting her I felt instantly comfortable and knew she would be wonderful. She exceeded our expectations. Her fenced in yard was critical for us and her knowledge and caring of pets was exceptional. I would never hesitate to use Ericca again. She kept in touch with us during the dogs stay and was sure to provide feedback that out us at ease. If you need a caring pet sitter who has loads of experience with dogs, she is the person!”
“We are so fortunate to have found Laura through rover. She takes care of Pepper and we dont have to worry while we are away. She sends me pictures and updates. She is a true gem!”
“Both of our dogs were calm and relaxed after a 4-day stay. James was attentive to all of their needs and was very kind. His roomates were a bonus, because someone was almost always around to hang out with our dogs! Thanks James, we will be back!”
About: Lifelong dog person, I have cared for dozens of furry friends, mine and others. I currently have a 4 year old Shepherd Mix. Former PETCO employee and rescue volunteer I am currently working part-time and unavailable 2pm to 7pm Monday- Friday. There is some flexibility, so please ask about your specific timing needs. Thanks I will follow your instructions as well as your pet's needs, mood, and personality. I do my best to let your fur baby be comfortable and themselves.
About: I’m an active, outdoorsy person who loves getting outside and enjoying some fresh air with a dog by my side. I especially enjoy walks, exploring new trails, and giving dogs plenty of time to play and get their energy out. I’m comfortable caring for dogs with different personalities and energy levels, and I’m happy to follow their normal routines for meals, walks, playtime, and downtime. I want every dog in my care to feel comfortable, safe, and well cared for while their people are away. I’ll also keep you updated with photos and messages along the way! I work remotely 5 days a week and have plenty of time to hang with your pup! Working from home gives me the flexibility to let your dog out for potty breaks as frequently as needed. I live close to a network of trails that your dog will love! My friendly Bernedoodle is always looking for friends and will keep us company!
About: walking service tailored to meet the needs of both you and your furry companion. Whether you're away for work, a vacation, or just need some extra help, I ensure your dog is well cared for, exercised, and happy. My dog sitting service provides your pet with personalized attention, a comfortable environment, and plenty of playtime, while my dog walking service offers a fun, safe, and invigorating walk to keep your dog active and healthy. With a focus on trust, safety, and companionship, I aim to give you peace of mind knowing your dog is in loving, responsible hands. I am a stay at home mom. Me and my son Liam would love to spend time with your doggo. Reach out and we can discuss further what times would work best for you and your furry babies needs. Pets feel secure with predictability, so I maintain their feeding, exercise, and play routines as closely as possible to their normal habits.Understand and respect each pet’s individual needs and preferences, such as their comfort level with strangers, exercise needs, and dietary restrictions.
“I only have great things to say about our experiences with Shawna! She's great at communicating - she was always quick to respond to qurstions and sent daily updates and pictures. She is also just a very nice person who immediately puts you at ease when leaving your pup in her care. She took great care of our guy and we will definitely use her again!”
“Karen and family were awesome with Alibi, our 15 months old Australian Shepherd. Lots of personal attention, and a great large fenced yard for the dogs to chase each other around. Karen’s whole family welcomed Alibi into their home and she really connected with their dog Lily. All in all, the stay was great and we will certainly be using Karen’s services again!”
“Bean had a wonderful time staying with Kristin and Shelly. It was very comforting to know that Bean was in good hands and spending lots of time playing outside with other friendly dogs. Kristin and Shelly were very accommodating with drop-off and pick-up times. Bean will definitely be staying with them all again!”
“We had an absolutely fantastic experience with Danielle and her family! We were looking for a warm, home environment for our dog Tanner rather than a kennel, and we couldn’t have found a better fit. We booked just two days in advance, and Danielle responded immediately. After a quick meet and greet, we knew she was the perfect choice—we had full confidence from the start, and that trust was reinforced throughout Tanner’s entire stay. Her communication, kindness, and genuine care were exceptional. I can’t recommend Danielle highly enough.”
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.FAQs for Dog Boarding - Windsor
Frequently asked questions about Rover
Rover is the largest marketplace for local pet care. Whether you're looking for pet sitters, dog walkers, or house sitters who specialize in pet sitting, you can narrow your search by entering your ZIP code to find sitters within walking distance in your neighborhood.
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.
Depending on the sitter, their home environment, and your dog’s needs, daily exercise 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.
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 MA 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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