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.
“My frenchie had the BEST time with Lindsay and her puppy!!!! Lindsay sent me pics daily, and whenever I asked for one. My baby literally had so much fun at her house, I think he sulked for a few days after ? Lindsay will be our go to for boarding in the future.”
“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.”
“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!”
“Vy provides a safe, loving, and enriching home for our dog to feel comfortable while we are away. We had flight complications while traveling and she was very accommodating alleviating any additional travel stresses related to our dog’s care.”
“Our 8 1/2 year old dog just stayed with Candice. He is very attached to me and does not like to get away from my side! Candice took great care of him and he did very well in her care. Candice sent frequent photos - which reassured me how well he was doing. Highly recommend!!”
“Our first time boarding with Shelby was a great experience! She was flexible, communicative, and followed all care instructions for our dog Loki. Will definitely be calling her up in the future.”
“Very happy with the care of our baby 😁 Jay is really picky on who he takes medications from, and Jasimine was the exception. He was comfortable enough to trust her from the beginning (first time in 3 years since he has been comfortable with anyone right off the back!) Very pleased and happy with the care he received.”
“Angela was so kind and easy to work with! She really took our pup's specific needs into mind and helped her have a wonderful stay! Angela shared pictures and videos with us each day and gave us updates on how things were going. Thank you, Angela, for your attentiveness and kindness. We appreciate your kindness and the peace of mind your updates brought to us while we were on vacation. :)”
“We had a wonderful experience boarding our pup in Carla's home! Our dog was so well cared for, and Carla sent daily updates with pictures and videos. Her dog was incredibly sweet and got along great with ours. She did a great job balancing exercise with being mindful of our older dog's past surgeries and individual needs. We would absolutely book with her again and highly recommend her!”
“Peggy was very understanding and loving with Daisy. Daisy is a senior who at times requires a lot of attention. When I picked Daisy up she looked content. Usually when I board her it takes me a couple of days to settle her down. This was not the case with Peggy!”
“Lori, is wonderful! She cared for my little Sienna as if she were her own. She provided several updates daily including photos. I was always informed of Sienna’s activities. I’ll absolutely book Lori again!”
“Tiffany was very responsive when something was not right with one of our dogs during the boarding and went above and beyond trying to help. Her responsiveness allowed us to address the situation promptly.”
“Theresa was absolutely amazing! She communicated very well & cash loved her. She has an amazing home & cash loved exploring her yard. She was patient & very knowledgeable about all types of dogs. I was definitely recommend & I'll be booking again soon.”
“Beth is simply the best! She has provided loving and professional care to both our late geriatric Shih Tzu who had a number of health issues AND our new 5 month old Havanese puppy. Both dogs loved her! We have such confidence in Beth that whenever we need to go away, we can do so with confidence knowing our pup will enjoy her "vacation" too! We appreciate Beth so much and could not recommend her more highly.”
“They were absolutely amazing with Nellie. We couldn't of have had a better experience. Nellie enjoyed her time with them and they treated her very well. It was our first time leaving Nellie with anyone and the random updates on her with pictures and videos helped ease our minds during our time away. We would definitely recommend them to anyone who is looking for pet care/boarding.”
“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!!”
“Debra and her family were AMAZING! Super patient and understanding with all of my doggies quirks and needs! Holly loved playing with her kids! We will be staying with them again. Thank you so much for taking such good care of my girl!”
“Dana’s house was a perfect spot for our dog! She has a great fenced in yard and sent multiple photo updates reassuring us that our doggo was having a great time. Her location was a perfect stop on our way to the beach. Would definitely recommend!!!”
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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