Dog Boarding Winfield Woods
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 1 pet parents in Winfield Woods have booked dog boarding
Winfield Woods, Find top rated dog boarding
“When I dropped off our dog, Roxy, she was shaking for fear of being left behind by me. Stephanie was very kind in her approach to Roxy and she seemed to settle. Stephanie sent me pictures throughout the visit. When we picked Roxy up, she was not shaking or barking, which she typically would be when boarded. If in the area again, we would definitely rebook with Stephanie if we had a need .”
“Samantha is such a great caretaker! She really pays attention to my dog’s needs. My dog really enjoyed her stay with her. She got her one her routine well and her yard is a great sniff spot!”
“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”
“This was our first time using Rover and it was a great experience. Frances was wonderful and very responsive during the entire process from booking the reservation, to the meet and greet and sending pictures and updates during our vacation. She and her family took amazing care of our dog. We will definitely book again with her!”
“I feel that words are far too limited to express the help and support we received from Ellen during such a difficult time! I had to travel to another continent and left my cat at the Kittie Room in Ellen’s home, and out of the blue, he needed emergency eye surgery. Ellen was constantly present through it all—strong, incredibly supportive, and providing post-surgery care filled with love, dedication, and countless medications like I had never seen before. I thank God every single day that when all this happened, my cat was with Ellen. In such a hard moment, Ellen, you were a true beacon for my family, and I will never forget it. You are a living miracle, moving seamlessly between the world of animals and the world of humans, with pure love and success in both. THANK YOU FOR EVERYTHING!”
“Jena B was literally the best, my pup was so happy and well taken care of. If you are looking for a star sitter Jena is it. I would use her again 10 times over . Jena is really nice , great communication and so attentive to the dogs in her care . I felt super comfortable from booking to pick up.”
“Karen was truly AMAZING, and we cannot recommend her highly enough! This was our first time ever leaving our two-year-old pups, Ziggy and Ellie, with anyone, and we were going to be away for a very long trip. Naturally, we were nervous, but from the very beginning, Karen made the entire process feel seamless and immediately helped put our minds at ease. Before our meet and greet, I let Karen know that our schnauzer, Ziggy, can be protective when meeting someone new. Karen knew exactly how to approach the situation and took the time to make him feel comfortable and safe. It was clear right away that she is experienced with dogs and genuinely understands and cares about them. While we were away, Karen treated Ziggy and Ellie as if they were her own. She sent us daily updates, pictures, and videos, which meant more to us than she probably realizes. Being so far away from them for the first time was difficult, and seeing their faces and knowing they were happy, safe, and being loved gave us so much peace of mind. Unfortunately, both of our dogs became sick while we were gone, which meant a lot of extra work, cleanup, and special attention. Karen never hesitated. She went above and beyond to care for them and even had to take Ellie to the veterinarian. At times, we had limited phone service while traveling, and Karen helped communicate with the vet and made sure we stayed informed and Ellie received the care she needed. Having someone we could trust to handle such a stressful situation while we were so far away was absolutely invaluable. Karen exceeded every expectation we had. She wasn't simply a pet sitter—she became someone we completely trusted with two very important members of our family. Knowing that Ziggy and Ellie were being cared for with so much patience, compassion, and love allowed us to enjoy our trip without constantly worrying about them. Words truly cannot express how grateful we are for everything Karen did for Ziggy and Ellie and for us. We came home to two pups who had clearly been very loved and well cared for. We would trust Karen with them again without hesitation and feel incredibly fortunate to have found her. Thank you, Karen, for loving and caring for Ziggy and Ellie like they were your own. ❤️🐾”
“Christa was excited to meet our puppy and took such great care of her. She sent me pictures of her throughout her stay and even sent her home with a toy! We will be using Christa in the future!”
“Kimberly is absolutely amazing! She cared for Rome this weekend and was so accommodating, especially since he wasn’t feeling his best. She went above and beyond to nurse him back to feeling better and kept me updated throughout the entire weekend. Her love, patience, and genuine care for Rome give us such peace of mind. This is exactly why we always book with Kimberly! We couldn’t ask for a better sitter! ❤️🐾”
“Theresa and Lyv were the absolute best watching our baby Misa for the week. Theresa sent so many pictures and updates throughout the week and I could tell Misa was having such a great time with them. She loved curling in bed with Lyv and being the diva that she is! It was really good to be able to relax while away knowing she was in good hands. Last minute, Misa had a skin flare up the weekend before we dropped her off and Theresa was able to medicate her and keep a watchful eye so she was all better by the time we picked her up. Can’t say enough good things about Theresa, will 100% use her again when we need a sitter!”
“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!”
“Thank you again so much Evvery for taking such amazing care of our fussy boy, Kingsley! Every time we go out of town - Evvery brings us such peace of mind because she is absolutely fantastic with Kingsley and knows exactly what he needs and wants at all times. I also know that Kingsley loves her cozy home!! He always comes back peaceful, happy, and refreshed from his "doggie-vacay"! Can't wait to book another wonderful stay with you! :)”
“We are so thankful that Mooch was taken care of with so much love and attention. We also appreciated the updates and video compilations that were shared of him having fun in the yard and with the other pups. :)”
“Sayuri was phenomenal. She and her husband took excellent care of our elderly dog and went above and beyond to make him comfortable. He was totally at ease there. Good communication. We will be happy to use her again.”
“Priscilla is AWESOME! She took great care of our dog - who is demanding and spoiled ? - just like he was at home. We could see in all the photos she sent that he was happy and thoroughly enjoyed his time with her! We’ll definitely be calling on her again the next time we need a sitter.”
“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!”
“This was a first time leaving our 3 year old Irish Terrier with someone outside the family, so we were a bit worried, but Amber was absolutely amazing! We received pictures every day and our dog looked happy and calm in them. We couldn’t be more grateful for the excellent boarding service Amber provided.”
“Carrie is a wonderful dog sitter, responsive, warm and welcoming! She made sure to learn about our dog's routine, kept us updated with pictures and was flexible with drop-off and pick-up! Our dog Juno had a great time at her house and returned happy and tired. I can only recommend Carrie!”
The median cost per night for dog boarding in Winfield Woods is €50
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 - Winfield Woods
Select a filter and find qualifying sitters offering dog boarding.Sitters in Winfield Woods average 11 repeat dog boarding clients
FAQs for Dog Boarding - Winfield Woods
Frequently asked questions about Rover
The average cost of Dog Boarding in Winfield Woods is $67 per night as of November 2026. Most bookings cost between $67 and $67 per night. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of November 2026, there are 4,925 sitters on Rover offering Dog Boarding across Winfield Woods. Enter your ZIP code to see which available sitters are closest to your home.
If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.
The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.
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.
94% of sitters in Winfield Woods can provide daily exercise during dog boarding stays. Depending on the sitter, their home environment, and your dog’s needs, this 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 Winfield Woods 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 Winfield Woods.
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.
Yes, you can find sitters who have experience with handling special pet needs in Winfield Woods. On Rover:
- 86% of sitters can help with special care needs
- 92% can help with giving oral medications or injections
- 94% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.
Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.
You and your Winfield Woods 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.
Adding another pup to the pack? Most sitters and walkers offer a reduced rate for additional dogs. You’ll find these exact rates listed under the "Services" tab on any sitter's profile. Since every dog is unique, final pricing may vary depending on the level of care required.
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