Dog Boarding Winterberry
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Winterberry, 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.
“I couldn’t have asked for more loving people to keep my fur baby while we were away! They treated Tater as though he was part of the family, and sent frequent photos and updates. I never had to worry about Tater’s happiness or wellbeing. Thank you all so much for taking such wonderful care of my boy! ❤️❤️❤️”
“We needed help with our dog as we moved into a new home so he wouldn’t be under foot. We were so lucky to find Heather D! Her property was right down the road from our new place! She is warm and friendly and her property is huge with all of the makings for a great time for dogs! Spacious and large grassed and fenced areas for playtime! Heather D graciously shared photos of Tucker having the time of his life. Tucker is a friendly dog and gets along with all animals he encounters so we were thrilled he’d have playmates with our visiting dogs. Fantastic photo moments of him running and playing with other dogs and some of the quieter moments like sitting on the couch watching TV with Heather D’s family. Her property was safe and clean and truly ideal for what she provides for boarding. I’d highly recommend Heather D and Tucker looks forward to spending time there again! 5 stars :)”
“Jena is the best!!!! Whenever we are leaving our dog Ellie with Jena, we tell her she is going to camp because she loves it so much! She always makes a new friend and is totally exhausted from playing by the time we bring her home. Jena truly treats her like a pet of her own, and we are so grateful!”
“Rodney and Marissa were absolutely incredible in watching our 6 year old English Bulldog. The communication was open and timely. They even sent pictures during his brief stay. Thank you for taking such good care of Taz.”
“Thank you so much for taking such phenomenal care of Snoopy! You completely put our minds at ease from the start. The daily photo updates were great and put our minds at ease. It was clear that he was in good hands. Snoopy came home happy and relaxed and we will definitely be booking again!”
“Couldn't be more pleased with Ashley and Joshua! We had never boarded our dog Maggie before, so we were a little anxious about how she would do, but she was in great hands. Ashley sent us a few pictures over the weekend and let us know that Maggie was doing well. They have enough room that Maggie was able to keep to her own space (she can be reactive to other dogs) but she got plenty of attention! Highly recommended!”
“Mila was absolutely fantastic and treated Fluffy like her own dog! Our flight was delayed and we couldn't pick him up as scheduled. She was so accommodating and kept him another day. Mila even made him chicken soup for the extra day!! She went above and beyond. Fluffy loves his new grandmother, he barely looked at me when I saw him after a week :)”
“Simon had a great day with Lonnie and the other dogs. He was so tired from playing, he didn't even hop on the couch with us that night. Lonnie was quick to reply, sent pictures and you can really tell he just loves dogs like his own. He also sat with Simon in a quiet space so S could eat his dinner. He has a tendency to not eat when he's busy busy with other doggies, so we really appreciated that. Would definitely recommend!”
“This was our girl Elsie’s first stay and it worked out great! Mary and James are lovely and we could tell that they were spoiling our girl. We loved the funny photos they sent. We look forward to having our dog stay there again”
“Great sitter! She took fantastic care of my dog over the holidays. Her house has a good size yard to roam around. She sent us pictures everyday and responds quickly. She went above and beyond by sanitizing everything when we picked our dog up. I highly recommend Audrey and would use her services again.”
“Candace is amazing at giving updates of my baby and making sure he is comfortable. Being a last minute booking, Candace still took my baby in and she’s very reliable. I will continue booking with her.”
“Phyo took great care of my dog & was very nice. Gave her a bath & updated me with photos while I was away . Has enough space for the dog to roam around . For me using the rover app for the first time I was nervous, but phyo made it very easy . 5 stars ⭐️”
“We had a wonderful experience with Lydia! She and her family took excellent care of our dog while we were away, kept us updated with messages and photos, and gave us complete peace of mind. It was clear our pup was happy, comfortable, and well cared for. We truly appreciated her reliability, kindness, and genuine care for our dog. We wouldn’t hesitate to book her again and highly recommend her to anyone looking for someone trustworthy to care for their dogs!”
“Casey and Marwa are the most accommodating and caring dog sitters, we have ever had. They do their best to keep with the routines that Indiana knows and then add extra long walks, treats, brushing, playing, and lots of love. Their Pug Kevin is so cute and friendly. On top of that, they are super-flexible with drop off and pick up times and took Indy in on very short notice. Will definitely be back”
“We couldn’t have asked for a better sitter with our pups!!!! Daily updates and pictures!!! Was wonderful in making us feel like our babies were in good hands!!!!”
“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.”
“Curtis and Lindsay were great, sharing pictures and communicating the whole time we were away. Our pup appeared content, happy and tired out when we brought her home. Would definitely recommend!”
“Brianna is amazing! I felt like my dog was in safe hands the entire weekend. She was very communicative and always sent us photos of Teddy and her hiking, hanging out and playing. We highly recommend her for watching your fur baby!”
“We recently had to board our dog, Coco, with Joyce on very short notice due to a family emergency. We can’t thank her enough for her incredible care and support during this difficult time. From the moment we dropped Coco off, it was clear she was in good hands. Joyce was attentive, kind, and made sure Coco felt comfortable and loved. We truly appreciate the extra effort Joyce put into making our pup feel at home. We’ll definitely be returning for future boarding needs. Thank you, Joyce, for being such a wonderful host!”
“This was my first time using Rover and it will not be my last. Felice, Ken, and Tyler treated my little girl like a princess. In each photo, she seemed to be having so much fun. Felice, Ken, and Tyler sent me numerous photos and included Riley in all of the family activities. When Ken realized Riley preferred to eat alone, he moved her feeding bowl to a more private area. The family was so attentive, and I will definitely book again.”
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 - Winterberry
Select a filter and find qualifying sitters offering dog boarding.FAQs for Dog Boarding - Winterberry
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 Winterberry 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 Winterberry.
<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 Winterberry 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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