Dog Boarding in Sleepy Hollow, IL
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Top rated Sleepy Hollow dog boarders

“Derek and his family took excellent care of our dog. He was communicative and gave just enough updates to keep us informed on how things were going. Would highly recommend him. We will most definitely be using his services again.”



“Very happy with your service Jessica! Macie wears a special tracking collar so we don't ever lose her. But we can see she must have had good walks and play time with 30k steps the first day she 31k the 2nd day. The only other time we boarded her was at a professional kennel where she had a max of 800 steps for one day. So huge difference. Thank you! The pics were greatly appreciated as well! Would definitely recommend you.”


“Katie and her family are delightful. Bebe is usually cautious meeting new people. Bebe seemed totally comfortable as this kind family held her, petted her and scratched her tummy. The cute photos they sent looked like Bebe Heaven! We feel very grateful for this sweet family, Thanks Katie !”


“Barb, was absolutely wonderful. Very accommodating and communicative. Our dog is a picky eater and she even went as far as feeding him out of her hand to make sure he was eating enough. We couldn’t have asked for a better care taker for our fur baby. Will definitely book again!”


“Jessica took special care of our dog that tends to be very timid and nervous with new people. She sent pictures and gave updates on how he was doing that make us confident in the care that was being provided. We definitely recommend and trust having Jessica watch our Winston!”


“We had Maverick, our 7 months old Husky, with Shauna & Peter for 10 days..They took such a wonderful care of Maverick and shared many photos and videos every day..They took Maverick for multiple walks and lot of outdoor activities. He was very much loved and enjoyed his stay with Shauna, Peter and their daughters. We are glad we found them on Rover. They are wonderful! I would highly recommend Shauna & Peter and would definitely have them to take care of Maverick next time!”


“Katie was amazing from the get go. My previous Rover accommodations fell through last minute and Katie was able to take on both of our dogs last minute. One is a puppy and the other was going through some medical issues and has some personality quirks. She had no problem navigating it, and I felt very confident leaving our dogs with her. She did a great job administering medication and giving them lots of attention and walks. She also sent tons of updates and we would definitely use her again. She did a great job and you could tell she really cared for our dogs!”


“I was so pleased with how Niratcha took care of my dog. She sent videos and multiple photos. She also took him in with a very short notice. Very pleased..He is sleeping and happy now.”


“Cheryl took a really good care of peanut. He seemed happy. Cheryl sent us a picture and an update everyday and set our mind at ease about leaving Peanut behind. Thank you Cheryl”


“Carolyn , was amazing with my puppy . It was my first time ever using the app and I felt comfortable leaving my puppy with her . She send me updates about my puppy and made him felt at home . ❤️”


“Jennifer is amazing. Our Rhodesian Ridgeback Roxi is very picky about people. I have never seen her so comfortable at someone’s house so quick. Jennifer, pearl, and her daughter made the visit such a nice outing for her. ❤️❤️”


“Ashley took great care of our husky, Cleo. We got so many pictures and videos which was really appreciated! Ashley was very communicative throughout the stay. We would definitely board Cleo with her again and highly recommend her services to anyone looking for doggie daycare and boarding in the area!”


About: In middle school and high school, my brother, sister and I would frequently get to dog sit our cousin's Toy Poodle, Rosie. She was like our own dog and we loved having her over to walk and dress up and cuddle. We got our own family dog around my sophomore year of high school, a Jack Russell Terrier named Chavo. We did so many fun things with him like taking him swimming, taking him to a dog carnival, and countless walks. He gave us the best memories. Even after I moved out for college, I would make sure to bring him to my home to spend time and play in the backyard. He lived a long 13 years and we miss him always. His memories always bring me so much joy. Whether it is someone else's doggy or my own, I will make sure to love them and treat them like family. I can't wait to meet your furry friend! I work from home and I typically start around 12 PM. I typically have a rotating weekend (which you will be able to see based on my calendar of availability). I think this schedule will be great for people who need their dogs taken out late morning. Although I live in an apartment, the area is very dog friendly. There is an enclosed dog park and we are right across the street from Randall Oaks, which has paths for a 35-45 minute walk. I am open to drop in visits, doggy daycare or having your furry friend as a overnight stay.

“We just picked Kiska up and she's all smiles after her vacation at Ashley's house. We were able to enjoy our time away knowing Kiska was in great hands. Kiska will be enjoying more visits with Ashley. Ashley was able to quickly pivot and help us with some last minute travel complications. Thank You!”


“Danielle was nice enough to take our pups in an emergency situation. She was absolutely GREAT with them. They were well taken care of, even during a storm. You can rest assured Danielle will take the best care possible of your pets. We already have two other trips booked with her because she was sooo good”


“Jill is an amazing and professional dog sitter! She picked up my dog right from my house and took wonderful care of him for an extended period of time. I felt completely at ease knowing he was in great hands. I highly recommend Jill to anyone looking for the best dog sitter!”


“Kathleen was amazing and caring! Bunch of photos updated everyday and my pup has gotten used to socializing with other fellow dogs thanks to her! Would definitely recommend!”

Loving dog boarding sitters in your neighborhood
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Jackie W.Star Sitter

“We had our 1year golden doodle kept with Jackie, and Jackie has been amazing!! We loved her, and would love to continue keeping Maggie with Jackie!! Thanks Jackie!!”


June & Wade C.Star Sitter

“June did great with my 14 year old dog and provided daily photos! She made she everything went smoothly and was very flexible with pickup times!”


Derek G.Star Sitter

“Derek and his family took excellent care of our dog. He was communicative and gave just enough updates to keep us informed on how things were going. Would highly recommend him. We will most definitely be using his services again.”




Jessica V.Star Sitter

“Very happy with your service Jessica! Macie wears a special tracking collar so we don't ever lose her. But we can see she must have had good walks and play time with 30k steps the first day she 31k the 2nd day. The only other time we boarded her was at a professional kennel where she had a max of 800 steps for one day. So huge difference. Thank you! The pics were greatly appreciated as well! Would definitely recommend you.”


Katie J.

“Katie and her family are delightful. Bebe is usually cautious meeting new people. Bebe seemed totally comfortable as this kind family held her, petted her and scratched her tummy. The cute photos they sent looked like Bebe Heaven! We feel very grateful for this sweet family, Thanks Katie !”


Barb K.Star Sitter

“Barb, was absolutely wonderful. Very accommodating and communicative. Our dog is a picky eater and she even went as far as feeding him out of her hand to make sure he was eating enough. We couldn’t have asked for a better care taker for our fur baby. Will definitely book again!”


Jessica & Luis A.Star Sitter

“Jessica took special care of our dog that tends to be very timid and nervous with new people. She sent pictures and gave updates on how he was doing that make us confident in the care that was being provided. We definitely recommend and trust having Jessica watch our Winston!”


Shauna & Peter T.

“We had Maverick, our 7 months old Husky, with Shauna & Peter for 10 days..They took such a wonderful care of Maverick and shared many photos and videos every day..They took Maverick for multiple walks and lot of outdoor activities. He was very much loved and enjoyed his stay with Shauna, Peter and their daughters. We are glad we found them on Rover. They are wonderful! I would highly recommend Shauna & Peter and would definitely have them to take care of Maverick next time!”


Katelynn R.

“Katie was amazing from the get go. My previous Rover accommodations fell through last minute and Katie was able to take on both of our dogs last minute. One is a puppy and the other was going through some medical issues and has some personality quirks. She had no problem navigating it, and I felt very confident leaving our dogs with her. She did a great job administering medication and giving them lots of attention and walks. She also sent tons of updates and we would definitely use her again. She did a great job and you could tell she really cared for our dogs!”


Niratcha L.Star Sitter

“I was so pleased with how Niratcha took care of my dog. She sent videos and multiple photos. She also took him in with a very short notice. Very pleased..He is sleeping and happy now.”


Cheryl B.Star Sitter

“Cheryl took a really good care of peanut. He seemed happy. Cheryl sent us a picture and an update everyday and set our mind at ease about leaving Peanut behind. Thank you Cheryl”


Carolyn G.Star Sitter

“Carolyn , was amazing with my puppy . It was my first time ever using the app and I felt comfortable leaving my puppy with her . She send me updates about my puppy and made him felt at home . ❤️”


Jennifer J.Star Sitter

“Jennifer is amazing. Our Rhodesian Ridgeback Roxi is very picky about people. I have never seen her so comfortable at someone’s house so quick. Jennifer, pearl, and her daughter made the visit such a nice outing for her. ❤️❤️”


Ashley H.

“Ashley took great care of our husky, Cleo. We got so many pictures and videos which was really appreciated! Ashley was very communicative throughout the stay. We would definitely board Cleo with her again and highly recommend her services to anyone looking for doggie daycare and boarding in the area!”


Jeannie F.Star Sitter

“Jeannie and her family are amazing. Our little Siena had a great time and she will love to come back to her. We highly recommend Jeannie and we will be back!”


Corina E.
“Corina took amazing care of my dogs, she went above and beyond. She treats my 3 dogs like her own and I’ve never felt safer than with her watching my dogs. She made sure they were walked, fed, and most of all, happy! She makes sure my dogs are entertained, happy, clean, and most of all- loved!! They love when she is with them. 100/10 would recommend to anyone!!!!”


Ashley C.

“We just picked Kiska up and she's all smiles after her vacation at Ashley's house. We were able to enjoy our time away knowing Kiska was in great hands. Kiska will be enjoying more visits with Ashley. Ashley was able to quickly pivot and help us with some last minute travel complications. Thank You!”


danielle w.Star Sitter

“Danielle was nice enough to take our pups in an emergency situation. She was absolutely GREAT with them. They were well taken care of, even during a storm. You can rest assured Danielle will take the best care possible of your pets. We already have two other trips booked with her because she was sooo good”


Jill N.

“Jill is an amazing and professional dog sitter! She picked up my dog right from my house and took wonderful care of him for an extended period of time. I felt completely at ease knowing he was in great hands. I highly recommend Jill to anyone looking for the best dog sitter!”


Kathleen B.Star Sitter

“Kathleen was amazing and caring! Bunch of photos updated everyday and my pup has gotten used to socializing with other fellow dogs thanks to her! Would definitely recommend!”
Sleepy Hollow dog parents share their Rover experiences
Popular requests near you
Select a filter and find qualifying Sleepy Hollow sitters!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 dogs2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs while you’re away3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per night for dog boarding in Sleepy Hollow is $50
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.
Sitters in Sleepy Hollow average 13 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Aug 2025, 1,240 sitters provided dog boarding in Sleepy Hollow. 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 Sleepy Hollow dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Sleepy Hollow have an average of 19 years of experience. Dog boarding sitters with repeat customers have an average of 13 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 Sleepy Hollow.
Rover makes it easy to find Sleepy Hollow 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 1,240 dog boarding sitters in Sleepy Hollow on Rover, so you’re sure to find the perfect match for your dog! In Sleepy Hollow, 93% of sitters offer daily exercise, 98% offer medication administration, and 92% 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.
