Dog Boarding in Windemere, MD
Find a loving dog sitter to watch your dog overnight at your sitter's home.
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Top rated Windemere dog boarders
“Theresa was great with my beagle-mix and was very understanding regarding all of my concerns as a dog-mom. She sent pictures and updates which put my mind at ease. My dog seemed very comfortable with her and I believe he truly enjoyed his stay with her and her chihuahua-mix, Lois.”
“Goose had a fantastic time for several days with Liz, Eric, and their pup as well as other visiting dogs. We loved receiving lots of photos of him each day, and it was good to know he was getting plenty of play and exercise. Goose will definitely be back!”
“Rodney & Marissa watched my two 85 lb. Labradoodles for 10 days while I was on vacation. With other dog sitters my dogs had diarrhea for days after but not this time. They were in great shape! I really appreciated the pictures sent every other day. Thank you! I’ll definitely use you again.”
“I can’t say enough about Gisel and her family that gave us a warm welcome the moment we connected. At our meet and greet, I knew she was the one to host our #furbaby Cody. Even her children were loving towards him. They are a wonderful family and far exceeded our expectations of caring for our Cody with pics and videos the whole seven days. Our neighbor uses her as well for their Yorkie and are very pleased with the care they’ve received. The bonus for us, she’s a stay at home mom and Cody was not left alone all day. She has small dogs as well and he was able to meet new friends. This was our first time leaving Cody without family and Gisel eased all of my anxiety because of her love for animals. We’ll be using her again soon.😊”
“It was a pleasure having Lingli care for my fur baby while I was away. She was always very responsive and sent a lot of pics during my pup's stay. I will definitely be booking again.”
“Carla was great and accommodating as I booked last minute for an overnight stay for Oreo. Great communication and she sent lots of photos and videos of Oreo during his stay. Carla will be my go-to dog sitter!”
“She had done greet with our dog lili she is about a year and six months old no issues at all very knowledgeable of dogs in their situations as well as understanding their behavior with no issues she took care of my dog and my dog played with her dog so now my dog has a friend they went to the park together and everything and she bought my dog back, clean safe and sound no issues Thank you very much once again for watching her for the five days. It’s been great. We definitely use her again just for dog play dates. Also she’s amazing. Don’t hesitate.”
“Gina took great care of Izzy! She sent me plenty of videos and updates and I could tell my baby was happy there. She was flexible with pickup and drop offs as well. Will book again!”
“Linda is absolutely wonderful. She has taken care of my senior dog twice and we are happily repeat customers with three more stays scheduled. She is so patient and loving to my senior dog, who can be a bit challenging.”
“Steph is absolutely AMAZING! First off it was short notice maybe 4 hours before I had to leave and everyone kept turning me down until this wonderful woman was kind enough to take her in . My baby had a blast with her and Jax. She sent me pictures and you could see the happiness in my baby’s eyes . Anytime I go out of town Valkyrie will be hanging out with her new bestfriend Jax . Definitely 10 out 10”
“Ceil took care of my dog for a few overnights and I could not be more happy with the care he gave. From the time I dropped him over I knew right away my dog was in good hands. He kept me updated with pictures and videos which was very warming. If there were 10 stars I woukd of gave all 10”
“Ariel was awesome! She was very welcoming and friendly. She kept me updated with pics and took phenomenal care of Polo. This was his first time being left with a stranger so I was nervous but I can tell he loved Ariel. He will definitely be a frequent flyer with Ariel.”
“We always leave Bruno to Esi whenever we are going out of town because we are confident that our furry baby is in good hands. Thank you Esi for taking good care of Bruno! 😊”
“Whitney took great care of our boy Hokie! He got along great with their dog Alfred who is a sweet gentle dog. I received pictures and updates while we were gone. We will definitely use her again.”
“Melissa was a fantastic sitter for our dog, Blue, while we were away on vacation. We received pictures/videos everyday reassuring us. I would highly recommend Melissa (& her dog, Daisy) to anyone considering this.”
“Andrew was great at providing pictures of my little guy, Bailey, and giving me updates on how he was doing during his stay. I felt at ease leaving Bailey in Andrew’s care.”
Loving dog boarding sitters in your neighborhood
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Theresa C.Star Sitter
“Theresa was great with my beagle-mix and was very understanding regarding all of my concerns as a dog-mom. She sent pictures and updates which put my mind at ease. My dog seemed very comfortable with her and I believe he truly enjoyed his stay with her and her chihuahua-mix, Lois.”
Liz & Eric F.Star Sitter
“Goose had a fantastic time for several days with Liz, Eric, and their pup as well as other visiting dogs. We loved receiving lots of photos of him each day, and it was good to know he was getting plenty of play and exercise. Goose will definitely be back!”
Rodney & Marissa O.
Star Sitter
“Rodney & Marissa watched my two 85 lb. Labradoodles for 10 days while I was on vacation. With other dog sitters my dogs had diarrhea for days after but not this time. They were in great shape! I really appreciated the pictures sent every other day. Thank you! I’ll definitely use you again.”
Gisel D.Star Sitter
“I can’t say enough about Gisel and her family that gave us a warm welcome the moment we connected. At our meet and greet, I knew she was the one to host our #furbaby Cody. Even her children were loving towards him. They are a wonderful family and far exceeded our expectations of caring for our Cody with pics and videos the whole seven days. Our neighbor uses her as well for their Yorkie and are very pleased with the care they’ve received. The bonus for us, she’s a stay at home mom and Cody was not left alone all day. She has small dogs as well and he was able to meet new friends. This was our first time leaving Cody without family and Gisel eased all of my anxiety because of her love for animals. We’ll be using her again soon.😊”
Jacob & Megan W.Star Sitter
“Jacob and Megan are wonderful sitters. Our two beagles have a blast there. They get plenty of attention and walks as well. I highly recommend”
Lingli Y.Star Sitter
“It was a pleasure having Lingli care for my fur baby while I was away. She was always very responsive and sent a lot of pics during my pup's stay. I will definitely be booking again.”
Carla H.Star Sitter
“Carla was great and accommodating as I booked last minute for an overnight stay for Oreo. Great communication and she sent lots of photos and videos of Oreo during his stay. Carla will be my go-to dog sitter!”
Elizabeth F.Star Sitter
“She had done greet with our dog lili she is about a year and six months old no issues at all very knowledgeable of dogs in their situations as well as understanding their behavior with no issues she took care of my dog and my dog played with her dog so now my dog has a friend they went to the park together and everything and she bought my dog back, clean safe and sound no issues Thank you very much once again for watching her for the five days. It’s been great. We definitely use her again just for dog play dates. Also she’s amazing. Don’t hesitate.”
Gina M.Star Sitter
“Gina took great care of Izzy! She sent me plenty of videos and updates and I could tell my baby was happy there. She was flexible with pickup and drop offs as well. Will book again!”
Linda O.
“Linda is absolutely wonderful. She has taken care of my senior dog twice and we are happily repeat customers with three more stays scheduled. She is so patient and loving to my senior dog, who can be a bit challenging.”
Mila B.Star Sitter
“Mila took wonderful care of our dog Izzy! Izzy seemed very relaxed and right at home in Mila’s care. We highly recommend Mila if you’re looking for a dog sitter!”
Jill & Chad H.
“Another amazing time for our Suzie! We got tons of fun videos and photos during her stay. Along with a bunch of great updates. Can’t recommend them enough!”
Steph P.Star Sitter
“Steph is absolutely AMAZING! First off it was short notice maybe 4 hours before I had to leave and everyone kept turning me down until this wonderful woman was kind enough to take her in . My baby had a blast with her and Jax. She sent me pictures and you could see the happiness in my baby’s eyes . Anytime I go out of town Valkyrie will be hanging out with her new bestfriend Jax . Definitely 10 out 10”
Cecil J.Star Sitter
“Ceil took care of my dog for a few overnights and I could not be more happy with the care he gave. From the time I dropped him over I knew right away my dog was in good hands. He kept me updated with pictures and videos which was very warming. If there were 10 stars I woukd of gave all 10”
Nicole T.Star Sitter
“Nicole is such a great sitter! I’ve used her twice and she’s really good with Prince! She always keeps me updated and her communication is great!”
Ariel M.Star Sitter
“Ariel was awesome! She was very welcoming and friendly. She kept me updated with pics and took phenomenal care of Polo. This was his first time being left with a stranger so I was nervous but I can tell he loved Ariel. He will definitely be a frequent flyer with Ariel.”
Esi-Tawanda P.
“We always leave Bruno to Esi whenever we are going out of town because we are confident that our furry baby is in good hands. Thank you Esi for taking good care of Bruno! 😊”
Whitney R.Star Sitter
“Whitney took great care of our boy Hokie! He got along great with their dog Alfred who is a sweet gentle dog. I received pictures and updates while we were gone. We will definitely use her again.”
Melissa H.Star Sitter
“Melissa was a fantastic sitter for our dog, Blue, while we were away on vacation. We received pictures/videos everyday reassuring us. I would highly recommend Melissa (& her dog, Daisy) to anyone considering this.”
Andrew E.Star Sitter
“Andrew was great at providing pictures of my little guy, Bailey, and giving me updates on how he was doing during his stay. I felt at ease leaving Bailey in Andrew’s care.”
How Rover works
1. Search
Read verified reviews by dog parents like you and choose a boarder who’s a great match for you and your dogs
2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs while you’re away
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
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 dog boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Dog Boarding FAQs
Frequently asked questions about Rover
As of Aug 2025, 1,577 sitters provided dog boarding in Windemere. 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, 93% of Windemere dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Windemere have an average of 16 years of experience. Dog boarding sitters with repeat customers have an average of 11 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 Windemere.
Rover makes it easy to find Windemere 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 1,577 dog boarding sitters in Windemere on Rover, so you’re sure to find the perfect match for your dog! In Windemere, 96% of sitters offer daily exercise, 99% offer medication administration, and 93% 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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