Dog Boarding Winsome Heights
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Winsome Heights, 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.
“Hazel always has a great stay with Jonathan and Jen! We can’t thank them enough for putting up with her puppy energy while we’re away. Heck, she usually sleeps for a day or two after stay she has so much fun.”
“Lonnie was able to take my request with only a few days notice, he really helped me out there. Great yard with plenty room to run and his dogs got along great with mine. Plenty of pictures and videos updating me throughout the day. Definitely will come back”
“Jena was AMAZING! My dog thoroughly enjoyed himself the week he stayed with Jena. She sent lots of pictures throughout his stay and kept in contact with us. I highly recommend her. She also has a very spacious backyard and there was a ton of play time and time outdoors. Cannot recommend her enough. We definitely will be booking with her in the near future.”
“What a wonderful, loving family to leave your fur baby with! Tater had a ball swimming and running around the farm! Heather sent me so many pictures and I could tell he was getting so much love and attention. I can’t thank you enough!! ❤️❤️❤️❤️❤️”
“Kimberly is the best, she took such great care of my Neco. She cared for him for 6 days through the Thanksgiving Holiday. She sent me great pictures and videos of him daily. She is a true dog lover. I will definitely be booking her again to care for my dog.”
“I’m always nervous to leave my dog with someone new but they were great to work with, communicative and always answered any questions I had about how Abbey was doing. They have a lovely home with a sunroom and amazing backyard perfect for curious doggos wanting to stare at birds and chipmunks all day. Thank you for looking over my fur baby!”
“Adrienne took great care of our dog Rosie! She was very responsive and sent us daily updates, pictures and a video. Adrienne's dog Cooper and Rosie had fun playing together. We will definitely book Adrienne again. Simon and Roberta”
“Brittanie and Ryan took wonderful care of our dog and gave her lots of love. Great communication and pictures. We would strongly recommend them to any dog owners.”
“Ebony did a great job with our Rusty. She sent pictures and videos every day. When he had an upset belly and needed a diet modification, she had no problem making adjustments! Thanks, Ebony!”
“Fantastic time was had by all! Brianna is a warm soul who knows dogs, detailed, and observant! I looked forward to her message updates and pictures of the pups while i was away on a trip.”
“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!”
“Oliver was so loved by Svitlana and her family. I had regular updates and photos, and my dog seemed so comfortable and happy while there. Svitlana was very communicative, and I highly recommend her. We will be repeat customers for sure.”
“This was our second time booking and Jessica was once again AMAZING with our Chance. He loves her and vice versa! We will always leave our fur baby with her.”
“Erin was fantastic! My dog is only 5 pounds and can easily slip out of the front door when someone is at the door. Erin was VERY consciences of my concerns and I was very comfortable with her visit even though this was our first time boarding with Erin. You are in good hands with Erin!”
“Wow!! Cannot say enough good things about Robin and her family. Louie had a wonderful time and was pooped when he got home! He met so many new friends. Robins home was clean and she runs a very organized well managed doggy daycare. I cannot recommend her enough.”
“Erika is wonderful!!!! "I can’t recommend her enough! From the moment I booked, communication was excellent — quick responses, regular updates, and the sweetest photo check-ins. My Ocean always comes home happy! I can always tell she is cared for like family. It gave me so much peace of mind knowing my pet was safe, happy, and well taken care of. Not our 1st time, and definitely not the last!!”
“Kaye was amazing with cat, Frankie! She got her a toy and played with her which is the key to Frankies heart. I was in a bind and needed someone to watch Frankie with only a few days notice and She was great!”
Dog parents share their Rover experiences - Winsome Heights
If you're at all apprehension about leaving your pets with a caregiver, message Michelle!!! This was our 1st experience with a stranger caring for our pets and we were extremely happy with Michelle and her family. She often sent photos and videos of our pets playing with her dogs and also her sweet little girls. They have a large fenced in back yard for the dogs to run and play. We would not hesitate to have Michelle care for our pets in the future. Thank you so much!!!
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 - Winsome Heights
Select a filter and find qualifying sitters offering dog boarding.FAQs for Dog Boarding - Winsome Heights
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 Winsome Heights 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 Winsome Heights.
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 Winsome Heights 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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