Dog Boarding in Winchester Estates, MD
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Top rated Winchester Estates dog boarders
“My family and I were in town for a couple of days and we needed a last minute dog sitter. Cait had some good reviews and so we decided to move forward and have her dog sit. She was awesome! Our dog had a great time and Cait said she enjoyed playing with her dogs. If we’re in town again, we would definitely reach out!!”
“Michele is now our go-to caretaker for Lucy. She’s so good with Lucy, providing lots of love and playtime, and followed special instructions regarding her eating schedule. I appreciate that she’s a great communicator and sent photos each day:). Will be calling on her again soon!”
“Lindsay was amazing! She sent photos everyday, loved io Pepper while my daughter and I were away, and was always quick to respond if I had a question. Her home was lovely and Pepper enjoyed Lindsay’s backyard and her sweet dog, Coco!”
“Shuling was amazing! She sent us pictures and videos the whole time and made it easier to be apart from our pup. Bailey had a great time playing with the host’s dog and family. Honestly, it looked like a summer camp for the doggies :) 100% recommend her and will use her services again. Jake and Ana”
“Best sitter I could have ever asked for. I received pictures and updates on CJ the entire time. Stacey provided the care and attention my dog needed. Will always look to use her first anytime we may be away. Thank you Stacey!! ❤️?”
“We’re so grateful for the great care Katelyn took of Hank! And appreciate all the communication - receiving pictures, videos, and updates on how well it was going. It was our first time entrusting Hank to a dog sitter so I was nervous but it went perfectly!”
“Before this booking, we had never left our dog with anyone outside of family, and we were really nervous about it. But after meeting Jessica, all our worries disappeared. She made the entire experience AMAZING! She kept us constantly updated, and our dog looked so happy in every photo. I would wholeheartedly recommend her and her family to anyone. She treats your dog with the same love and care you’d expect from family. Thank you so much, Jessica! 100/100”
“Being a first time user of Rover this experience couldn’t have gone any better! After meeting Robin I was at ease. She sent pictures/videos. I’d definitely use Robin again!!”
“This was the second time Andy watched my pup. He was very flexible with drop off timing and sent me photos and updates throughout the stay. I know my girl had a great time staying with him.”
“I cannot complain! I feel my dogs enjoyed their stay and was exhausted when they came home two days later. I also feel that my nuggets picked up a few commands that I was struggling with the last four years. Ryan has a beautiful and a very clean home. They have three beautiful bigger dogs of their own and I liked that my dogs had to learn to be around others. Thank you for the experience, will definitely use Ryan’s service again in the future.”
“Elizabeth was absolutely amazing with my dog Lucy! She updated me with a video and kept in contact with me. She was also absolutely wonderful at helping with my puppy’s socialization skills. I absolutely recommend and will be using her services again.”
“Korra had an amazing time with Jennifer and her family. Plenty of exercise and play time all around. Great communication and photo updates every day. 11/10 would book again and again!”
“I was so nervous boarding our two dogs with a Rover sitter vs a facility, but both Amy and her husband took SUCH good care of our babies. I had a family emergency and had to leave them for five days. They went on tons of walks, got ample amounts of snuggles, and I was updated with pictures every step of the way. I could focus on family knowing they were in excellent hands, and we will certainly be using them again!”
“Great care, flexibility, and plenty of photo updates. Megan took care of my 3 sweet baby angels (cats) for the better part of a week. She did provide some flexibility with my atypical schedule as I was between houses. I’ve since moved out of the area, but I wouldn’t hesitate to use her services again.”
“Leticia was wonderful with Jerry. He is a rescue and this was our first time leaving him while on vacation. Leticia shared multiple videos and photos so we could see that he was in good hands while we were away. It really did allow us to enjoy our vacation without worrying about how our dog was doing. Certainly hope to use her service again in the future.”
About: I’ve lived with dogs and cats my entire life and have over 15 years of hands-on experience caring for pets. Growing up, my mom had five dogs—some of which had puppies—and I helped raise and care for them. I’ve also cared for cats in multi-pet households, including feeding, litter box maintenance, and creating calm, safe environments for shy or senior cats. Neighbors, friends, and family have trusted me for years to walk, feed, bathe, and care for their pets while they’re away. I now have a black Yorkie of my own, and I treat every animal I care for like part of the family—whether they bark or purr! I currently work part time- and have lots of free time! I will send out a daily schedule of what I’ll be doing with the pets! I will take your dog out on walks on our neighborhood trail outside! I also have a few ring cameras, and will send a lot of pictures/videos throughout the day.
“They took great care of our dog! I appreciated the updates, and he enjoyed playing with their dogs during the week. Thanks for taking great care of our Max!”
Loving dog boarding sitters in your neighborhood
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Cait B.
“My family and I were in town for a couple of days and we needed a last minute dog sitter. Cait had some good reviews and so we decided to move forward and have her dog sit. She was awesome! Our dog had a great time and Cait said she enjoyed playing with her dogs. If we’re in town again, we would definitely reach out!!”
Michelle M.Star Sitter
“Michele is now our go-to caretaker for Lucy. She’s so good with Lucy, providing lots of love and playtime, and followed special instructions regarding her eating schedule. I appreciate that she’s a great communicator and sent photos each day:). Will be calling on her again soon!”
Lindsay G.Star Sitter
“Lindsay was amazing! She sent photos everyday, loved io Pepper while my daughter and I were away, and was always quick to respond if I had a question. Her home was lovely and Pepper enjoyed Lindsay’s backyard and her sweet dog, Coco!”
Shuling J.Star Sitter
“Shuling was amazing! She sent us pictures and videos the whole time and made it easier to be apart from our pup. Bailey had a great time playing with the host’s dog and family. Honestly, it looked like a summer camp for the doggies :) 100% recommend her and will use her services again. Jake and Ana”
Stacey B.
“Best sitter I could have ever asked for. I received pictures and updates on CJ the entire time. Stacey provided the care and attention my dog needed. Will always look to use her first anytime we may be away. Thank you Stacey!! ❤️?”
Katelyn M.Star Sitter
“We’re so grateful for the great care Katelyn took of Hank! And appreciate all the communication - receiving pictures, videos, and updates on how well it was going. It was our first time entrusting Hank to a dog sitter so I was nervous but it went perfectly!”
Jessica W.
Star Sitter
“Before this booking, we had never left our dog with anyone outside of family, and we were really nervous about it. But after meeting Jessica, all our worries disappeared. She made the entire experience AMAZING! She kept us constantly updated, and our dog looked so happy in every photo. I would wholeheartedly recommend her and her family to anyone. She treats your dog with the same love and care you’d expect from family. Thank you so much, Jessica! 100/100”
Robin F.Star Sitter
“Being a first time user of Rover this experience couldn’t have gone any better! After meeting Robin I was at ease. She sent pictures/videos. I’d definitely use Robin again!!”
Andy & Lydia M.Star Sitter
“This was the second time Andy watched my pup. He was very flexible with drop off timing and sent me photos and updates throughout the stay. I know my girl had a great time staying with him.”
Seth G.
“Seth was awesome. He took care of our dogs as if they were his own and he was available for us in a pinch.”
Ryan P.Star Sitter
“I cannot complain! I feel my dogs enjoyed their stay and was exhausted when they came home two days later. I also feel that my nuggets picked up a few commands that I was struggling with the last four years. Ryan has a beautiful and a very clean home. They have three beautiful bigger dogs of their own and I liked that my dogs had to learn to be around others. Thank you for the experience, will definitely use Ryan’s service again in the future.”
Elizabeth N.
“Elizabeth was absolutely amazing with my dog Lucy! She updated me with a video and kept in contact with me. She was also absolutely wonderful at helping with my puppy’s socialization skills. I absolutely recommend and will be using her services again.”
Jennifer D.
“Korra had an amazing time with Jennifer and her family. Plenty of exercise and play time all around. Great communication and photo updates every day. 11/10 would book again and again!”
Candice W.Star Sitter
“Candice was amazing! She sent us frequent updates and pictures on how our dog Daisy was doing. Helped us relax and enjoy our trip knowing she was in great hands.”
Amy D.Star Sitter
“I was so nervous boarding our two dogs with a Rover sitter vs a facility, but both Amy and her husband took SUCH good care of our babies. I had a family emergency and had to leave them for five days. They went on tons of walks, got ample amounts of snuggles, and I was updated with pictures every step of the way. I could focus on family knowing they were in excellent hands, and we will certainly be using them again!”
Elizabeth W.
“I had great peace of mind knowing my dog was in good, kind hands for the day. I got updates that showed he was doing well. Thank you!”
Megan H.Star Sitter
“Great care, flexibility, and plenty of photo updates. Megan took care of my 3 sweet baby angels (cats) for the better part of a week. She did provide some flexibility with my atypical schedule as I was between houses. I’ve since moved out of the area, but I wouldn’t hesitate to use her services again.”
Leticia G.
“Leticia was wonderful with Jerry. He is a rescue and this was our first time leaving him while on vacation. Leticia shared multiple videos and photos so we could see that he was in good hands while we were away. It really did allow us to enjoy our vacation without worrying about how our dog was doing. Certainly hope to use her service again in the future.”
Aliciya M.
About: I’ve lived with dogs and cats my entire life and have over 15 years of hands-on experience caring for pets. Growing up, my mom had five dogs—some of which had puppies—and I helped raise and care for them. I’ve also cared for cats in multi-pet households, including feeding, litter box maintenance, and creating calm, safe environments for shy or senior cats. Neighbors, friends, and family have trusted me for years to walk, feed, bathe, and care for their pets while they’re away. I now have a black Yorkie of my own, and I treat every animal I care for like part of the family—whether they bark or purr! I currently work part time- and have lots of free time! I will send out a daily schedule of what I’ll be doing with the pets! I will take your dog out on walks on our neighborhood trail outside! I also have a few ring cameras, and will send a lot of pictures/videos throughout the day.
Jillian & Richard A.Star Sitter
“They took great care of our dog! I appreciated the updates, and he enjoyed playing with their dogs during the week. Thanks for taking great care of our Max!”
Winchester Estates dog parents share their Rover experiences
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The median cost per night for dog boarding in Winchester Estates is $50
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It doesn’t happen often, but if your dog boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.
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Sitters in Winchester Estates average 12 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Aug 2025, 348 sitters provided dog boarding in Winchester Estates. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, dog boarding sitters joining Rover must pass a background check for you and your dog’s safety.
Rover makes it easy to reach out to multiple sitters about your booking. Typically, 91% of Winchester Estates dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Winchester Estates have an average of 19 years of experience. Dog boarding sitters with repeat customers have an average of 12 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters in Winchester Estates.
Rover makes it easy to find Winchester Estates dog boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog boarding is great for:
- Dogs of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their sitter’s pets
There are 348 dog boarding sitters in Winchester Estates on Rover, so you’re sure to find the perfect match for your dog! In Winchester Estates, 98% of sitters offer daily exercise, 100% offer medication administration, and 84% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog boarding sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog boarding sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your dog boarding sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your dog boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
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