Dog Boarding Winchester Estates
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Winchester Estates, 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.
“Lindsay is amazing. She took such great care of my dog this weekend. From the moment I met her, she put my mind at ease that Comet would be well taken care of. I got several updates throughout the weekend that confirmed just that. If you need a dog sitter in our area, I highly recommend her and will be using her again in the future when I go away.”
“Elena did an amazing job with our Old English Sheepdog Lady. I could really tell that she loves taking care of animals, and she did a great job. Our dog was pretty nervous as she went to the vet the day before, but Eleana made her feel at home and I thank her for that. I highly recommend her.”
“Another stay with Carlie and we cannot recommend her enough! We always have such peace of mind with her daily updates and photos and knowing that our pup, Indi, is safe and having fun. Indi gets her own vacation when she stays here and we love knowing that our she gets to enjoy herself, too! Between Carlie's loving and kind family, the huge bonus yard, and Carlie's attention and ability to continue medicine (she even notices any behavioral changes!), we just know we've made the right choice. Do yourself a favor, and get on her schedule for your pup sitting needs! :)”
“Brigid took care of my senior girl, Chloe, for 4 nights. She was open to a last minute meet and greet. She accommodated Chloe’s senior needs, sent updates, and gave a nice verbal summary at how Chloe’s time went and included things she will miss about her. Chloe seemed content when I arrived, often going over to Brigid several times while we packed up all of her things into the car. Being a dog sitter myself, I found comfort in that, considering they were strangers just days before. I would recommend Brigid!”
“Kimberly and her family took great care of our dog Winnie while we were away over the holiday break! She sent pictures every day of her enjoying time inside and outside on her walks about the neighborhood. We are so grateful that we found them and will definitely use her in the future! Thank you, Kimberly!”
“Our first visit was so smooth. My dog seemed immediately comfortable with Katie. She sent pictures through the weekend and was flexible with pickup times. We are already looking to rebook her for next month. Thanks Katie?”
“Jeren was able to watch our new pup on short notice and did a great job. She sent daily pictures and descriptive updates. Our pup looked like she had a blast! Additionally, Jeren had no issues giving ear meds and was patient with our pup's shy nature. When we need a petsitter again, we'll be contacting Jeren first!”
“Angela was so very warm, welcoming, and kind to our puppy. Minnie took to her right away, and because of the meet and greet, she knew exactly where we were going when we dropped her off. Angela was very thorough, asking all the important questions, and she even let my daughter visit to say hi to Minnie.”
“Peggy was an amazing host. Was very easy to communicate with and took good care of my pup. She sent daily check ins and was very flexible with times. My dog didn’t want to come back with me by the time I picked him up! I highly recommend her to anyone”
“Becca was great! Levi loved her and had such a fun time with her and her family, and she sent updates and photos every day, which I appreciated. We’ll definitely use Becca again in the future!”
“Diana V has been our trusted pet sitter for over four years, and at this point, she’s truly part of our extended family. From day one, she and her family have been incredibly warm, welcoming, and reliable. They don’t just “watch” Kenzi—they treat her like one of their own. That kind of care is rare, and it shows every single time. Kenzi absolutely adores them. The excitement she shows when she realizes she’s going to see Diana says everything. No hesitation, no stress—just pure joy. If you’re looking for someone who will love and care for your pet like family, Diana is it!”
“Lena was WONDERFUL with a very last minute & difficult request. She was so responsive and communicative. We could not ask for a better or more professional / responsible & respectful Rover sitter. HIGHLY RECOMMENDED!”
About: I grew up with family pets and spent years fostering animals before adopting a pup of my own, Lemonade (aka Lemmy). She is a little under 2 years old and loves making new friends. This is a great opportunity for your dog to come stay and play. For best care, I only take pets from one family at a time in addition to my own. I work from home full time during the weekdays, so your pet will be offered lots of play time, potty breaks, and cuddles. I also spend a lot of time home on the weekends and can provide extra quality care. I have a fully fenced front yard and my puppy Lemonade will be with me to help entertain your pet and keep them company during their stay. **Meet and greet is required before your first booking**
About: I will love and care for your pet as if it were my very own Grand-puppy. Like my Charlie. Charlie is my daughters dog who reminded me that I loved dogs. I am looking forward to building my business in a career that I love so I can retire from my current job but still have work I look forward to doing. I will treat your pet as part of my family. I have a Grand-puppy named Charlie who came into my life and reminded me I loved dogs.
“What can I say?!? Candace is a phenomenal dog sitter and my pup enjoyed getting pampered and taking walks. Look no further, Candace is amazing! She will send you pictures/updates and spend lots of time with your pet.”
“Sabrina and Ryan are amazing. They gave constant photos of Sarge and how he was enjoying himself. They have a great backyard with plenty of room for dogs to run around and play. We also liked that there were plenty of dog beds for him to choose from. They also helped us out when our flight was canceled and totally was fine with watching Sarge a couple more days which was really helpful. We’ll definitely be bringing Sarge back for our next trip. You guys are awesome thanks!”
“I am sooooo happy that I found Ashley! She's amazing with Gracie and I am fully at ease while traveling knowing that she is being well taken care of. She keeps me updated daily and I so appreciate that she does it without me having to ask. Ashley is now my go-to sitter!!”
“Demond is a great pet sitter. He communicated well, and sent lots of great pictures and videos of my furbaby while we were away!!! We will definitely be rebooking with him the next time we go out of town!”
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 - Winchester Estates
Select a filter and find qualifying sitters offering dog boarding.FAQs for Dog Boarding - Winchester Estates
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 Winchester Estates home-away-from-home, 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 Winchester Estates.
<b>Tip:</b> 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 Winchester Estates 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 , 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 .
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 MD 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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