Dog Boarding Windemere
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Windemere, 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.
“Casey and Marwa are the BEST! They spoiled our large dog Indiana to no end with multiple long walks every day, playtime, cuddles, and even grooming. There was plenty of space to roam freely in the house. They posted many pictures and videos every day. Their Pug Kevin is so cute and friendly! Indy came home well fed, nicely groomed, happy, and relaxed.”
“Another wonderful stay with Danielle! Coco is always happy and so well cared for when she stays with her. Danielle continues to be our go-to whenever we need a home away from home for Coco!”
“Nicole is very nice, easy to work with. Her updates with pictures gave us peace of mind. She always quickly texted back. Our dog seemed like he had a good time. Thanks!”
“Steph couldn’t have been any more perfect for our dog, Remy! It was the first time we left a pet with a non-family member but I felt completely comfortable. Steph even has a doggie-sofa in her living area. I could tell from our first meet and greet that she was in tune with dog behavior. Her dogs are the sweetest hosts too! When we picked up Remy, I could just tell that she had a wonderful weekend. I really appreciate having a reliable, loving place to take Remy when needed.”
“Elizabeth took great care of my dog. She gave lots of updates and was a pleasure to work with. My dog loves her and seemed so happy while she boarded with her.”
“Teresa was awesome with Royale, he seem so happy and playful. And he made friends which he usually stays away from other dogs.I was able to relax as Teresa kept me updated with pictures and messages of my baby. I randomly chose her on Rover and I m so happy with my choice...”
“We first went to Melissa's for a meet and greet. Later I brought my dogs back to her house for a 4 night stay. They were pulling me towards her gate happy to be there. They liked the fenced yard, being able to explore freely. Melissa sent us a picture and short update everyday. I picked up very happy pups on Monday. Highly recommend Melissa.”
“Great communication and flexibility. They also offered a half price trial overnight which was a great idea. I was uncertain how Riley would do with young children as she’s never had experience with kids younger than middle school age and having this trial before a week long stay made me more comfortable. Riley had a good time with them and Dunkin. We’ve booked that week long stay.”
“Bee and Pat were so great to work with and took great care of Champ! He loved walks, hanging out with their dogs, running in the yard, and chilling on the couch. I loved the morning and evening updates and pics, as well as clear communication the whole way through booking to pickup. Will definitely rebook and highly recommend!”
“My dog is a bit scared of strangers. We tried one day with Rodney and as I picked up Zuri, she was already friendly with Rodney. I got pictures of my dog playing with his dogs. Rodney replies quickly to any question pre booking and during the stay. Thanks for taking care of Zuri!”
“Deanna is such a great dog sitter! She and her lovely family took such great care of Romee. Romee had walks, plenty of playtime—just a perfect situation. Knowing Deanna was taking care of Romee allowed me to truly relax and not worry a bit while I was out of town. I’ll be rebooking with Deanna! Absolutely recommend.”
“My dog Luna seemed to have enjoyed her time at Linda’s home and playing with the other dogs. Linda was communicative and flexible.i appreciated the daily photos and sometimes even videos. I will be booking with her again.”
“As always, Trixie came home tired and, most importantly, happy. Jenn and her husband do a fabulous job welcoming pups into their dog proof home. I also really appreciate the pickup/drop-off amenity. Will definitely use again”
“We had a great experience with Julia & Jacob. They took such s wonderful care of our dog while we were away. It gave us so much peace of mind to receive regular updates, pictures, and videos — it was clear our dog was happy, safe, and well-loved. Communication was easy, and everything went smoothly. They truly went above and beyond by picking up and dropping off our dog, which made everything so much easier for us. Highly recommend and would absolutely book again!”
“Crissy has great patience and is very easy to speak with. She sent me pics of my pupper and answered all questions while I was away. I highly recommend Crissy.”
“Kellyn took great care of our dog! We appreciated the periodic updates. I can tell that she went above and beyond in making sure Mariner was safe and comfortable. We look forward to booking again!”
“Our dog Buddy stayed with Jennifer for a few nights and we were happy with his stay. Jennifer is very responsive and always replied quickly to any questions we had. She also sent pictures of Buddy having a great time at their house. He seemed to get along well with her dog Buster who really loves to play. Buster seems to have a lot of energy! Buddy came back very tired after playing the whole weekend. This would be a great match if you have another energetic pup. I liked their large, fenced in, backyard. She was home with the dogs the entire extended weekend and I could tell she really cared about Buddy.”
“This was my first time using Roover and I can say Jessica surpassed my expectations for a sitter. I was hesitant to leave our puppy with just anyone, but after meeting Jessica I knew he was in good hands. I look forward to using her in the future.”
Dog parents share their Rover experiences - Windemere
Liza took excellent care of our energetic lab puppy Hank. She provided a safe, reliable, clean and caring environment. She sent several pictures a day and was very easy to communicate with throughout. She took him on a hike with her dog and kids, and Hank had a great time. Would definitely recommend her without reservation.
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
It's that easy! All payments are processed through Rover's secured platform
Popular requests for dog boarding - Windemere
Select a filter and find qualifying sitters offering dog boarding.FAQs for Dog Boarding - Windemere
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 Windemere 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 Windemere.
<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 Windemere 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 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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