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.
“Jon and Mary took great care of our Faye. We haven't left our puppy with anyone before so we were very nervous. They put us at ease by talking to us for a while about their rover experience. They have two adorable, friendly, fun loving labs that played with our little Faye. Their family all pitched in to keep Faye happy and active. We will definitely be using Jon and Mary again. Highly recomend!”
“Lonnie watched our border collie Gruffy while we went on a week vacation. Gruffy had a wonderful time with Lonnie and I am pretty sure he was on vacation too! Lonnie really did make Gruffy part of his pack that week and took the time to send us pictures. The pictures were great! I know Gruffy had a fabulous experience and we highly recommend Lonnie to anyone who has a fur baby.”
“I felt very confident that my dog Asher was well taken care of at Jena's house. She sent pictures daily which showed him having just as much fun as we had on our vacation away! I look forward to using her in the future.”
“Lydia was an exceptional boarder, I would highly recommend her to keep your pet in her home. Her whole family welcomed Sophie like she was their own! Lydia supplied daily updates with pictures and couldn’t have been any more helpful. I will definitely utilize her services again hopefully (I will be boarding Sophie again in April). Thanks again for the stellar job you did Lydia, my wife and I couldn’t be happier with Sophie’s care! Mike & Lisa”
“Jim and Mary were awesome with our pup. They sent me pictures throughout his stay so I could see how he was doing. He was very comfortable with them and when we picked him up, he acted the same as the dog we had left. (we had previous experiences where he was skittish for a few days after staying with a previous dog sitter) Jim and Mary treated our Camden as if he were their dog. I would be comfortable leaving our dog with them anytime and plan to use them again in the future. I highly recommend them!”
“We’ve always had great experiences with Lingli! Our dog is always so happy to see her, which says a lot. She takes great care of her, and I always get plenty of updates while we’re away, which gives me peace of mind. We really appreciate how well she cares for our dog and would definitely recommend her!”
“Thank you photo for watching Bailey on short notice. He looked well rested and had a great time with you. You were quick to respond and sent pictures and updates. I appreciated the consistent communication. Next time Bailey needs a sitter I will call you.”
“We are so grateful for the amazing care that Heather gave to our 1 year old golden (Cobain) over Easter break!! He really enjoyed his stay with her, the walks to the pond and the creek, playing with her daughter and their farm dog, Charles! We loved getting lots of updates and pictures ❤️ We will definitely be booking with Heather again!”
“I had to leave my dog Thenji with Adrienne and Nick at very short notice. They were able to take her. It was so reassuring to know that she was being so lovingly cared for!”
“Ariel is amazing with my dog - Fluffy. Fluffy seems to really like her and is very happy to be dropped off there. I trust Ariel completely and highly recommend her!”
“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!”
“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.”
“Melissa was wonderful! We received great pictures and updates during our stay. Drop off and pick up was very easy. She was able to manage our large dog and small dog with ease! Our dogs enjoyed Melissa, their stay and playing with her two girls. We will definitely use Melissa again!”
“Keyona was great with my 6 year old Shih Tzu. My mind was at ease with knowing he was in good hands, considering he’s never been with anyone other than a family member. She sent pictures and videos each day, which was a plus. I would definitely book with her again.”
“Liz is amazing! This was my first time leaving my dog with someone and I was nervous but she made everything so easy. She took such great care of my dog that I think he misses her now. We will be booking again in a few weeks ☺️☺️☺️”
“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.”
“Milo had a great time at Fran's! He and her dog Cash were well-matched playmates. Fran was flexible, communicative, and very thorough about detailing Milo's stay. Thanks, Fran!”
“Just picked up my pups from staying with Alex for the weekend. They had a great weekend playing with Reese. Alex sent us pics of them and they were so relaxed and happy. They look forward to staying again!!!”
Dog parents share their Rover experiences - Winterberry
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!!!
Naima had a wonderful stay with Michelle! We’re really pleased with the care and attention she gave her. Michelle kept us updated, made sure Naima felt comfortable and treated her like part of the family. It gave us real peace of mind while we were away. We truly appreciate the great service and would absolutely book with her again. Highly 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 - 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.
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 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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