Dog Boarding Sleepy Hollow
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 79 pet parents in Sleepy Hollow have booked dog boarding
Sleepy Hollow, 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.
“Jackie is awesome with my dog, Corey! He is always so excited to be there were he is treated like one of the family. Jackie has a lovely home and a beautiful fenced in backyard, where Corey can run, run, run.”
“Dorothy is amazing and we couldn’t recommend her enough. She took the time to get to know my pup and her needs, and sent many updates while we were away. We are happy to have found someone we trust so much!”
“Our small dog Marty had an overnight stay here, and we're thrilled with how well she was cared for. We received updates and photos during the stay, which always puts me at ease. My dog seemed happy and relaxed.”
“Leaving my dogs is never easy to do, however, Katey and her family immediately made me feel at ease. Katey was very welcoming to the dogs and receptive to learning their needs. Throughout the weekend, she kept me updated on how the dogs were doing and included supporting pictures. Not only was Katey great at caring for our dogs, but also her family and personal pets. The large fenced in yard was a bonus on top of the great service. We will definitely return to Katey for our future dog watching needs!”
“Patricia took great care of Tess for us! She was very communicative and send lots of updates. Tess came home happy and healthy! We would definitely ask Patricia to help us with Tess again”
“Jeannie is terrific! She really took the time to get to know our dog and asked many questions about his needs & care before the stay. Our dog can be a little challenging at times but Jeannie handled everything like a true professional! So many updates and great pictures throughout our Cooper’s stay made us feel relieved and comfortable knowing he was in great hands! We would definitely recommend her, and will use her again!”
“We left all 3 of our dogs with Jessica for 12 days and they had a blast! She is extremely caring and sent videos to us while we were gone. She treats them like they are her own. They now have a new second home when we travel and we're so grateful to have found her!”
“Holly's second extended stay with Jackie was another great experience. Daily updates and photos, lots of attention and treats, and Holly even received a little holiday gift! Absolutely recommend.”
“Eliza took such great care of our George! She sent updates and photos which we really appreciated! Thank you Eliza! George loved his stay with you and his new friend Lola :)”
About: I know how to make dogs comfortable and make them feel like they’re being taken care of well. Lots of treats they get from me I am free to watch dogs a lot during each day of the week. Any time of the day works for me as well to watch them I have a fenced in yard. I keep my basement closed so no dogs can go down there. Mostly on the main floor with me.
“River enjoyed her stay again and the drop off pick up was super easy and Justine was ready to go. They gave us photos each and kept us up to date. We will be back again. River enjoyed being able to hangout with the kiddos as she's a social people loving dog.”
“Gavin was very patient , kind and understanding of my crazy schedule for this weekend and also my first time pet parent anxiety, and my dog loved being in his carelol I would gladly book with him again!”
“Steph was awesome! This was my first experience with Rover and I have a Boykin Spaniel, which is a 16 month old 40lb high energy hunting machine. She excepted the challenge and treated Kola like he was her own. Very pleased with the whole experience and Steph. I took a fly-in fishing to the northern woods of Canada and due to fires and bad weather in the area had to extend my stay for an additional two days up there because the float plane couldn't come get us. Steph rearranged her schedule to accommodate me. I didn't expect her to do that but greatly appreciate her for doing so. I highly recommend Steph, will use her again in the future (that is if she'll let me LOL).”
“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 . ❤️”
“Taylor and Samuel were amazing and took very good care of our dog. They made sure to send pictures and give updates and clearly enjoyed having him around. I would definitely recommend and book with them again!”
The median cost per night for dog boarding in Sleepy Hollow is $50
Dog parents share their Rover experiences - Sleepy Hollow
Once again, Derek and his family took really good care of my dog Bear for two weeks while we were in Europe.. He made sure to send me pictures almost every day, and I could tell when I picked him up that he was very well cared for. Finding Derek on Rover has been so good for us, as we know, we can travel knowing that Bear is happy and loved.
Amazing sitters! Our first time boarding and they were extremely communicative and sent a lot of pictures to put us at ease! They were great with our older/reactive dog and provided tips as well to help with training! Great quiet neighborhood which was perfect for our dogs. They were great at following the feeding/walking schedule and my dogs had a great time!
Absolutely amazing, my dog has stayed with and friends anx family before and usually for at least a few days she wont eat, she wont come out from under a bed, she was out and eating before the first day was up. I was absolutely stunned and so was my family. Will 100% use again for my next trip!
Brian is a great host. He reached out quickly upon my request and the provided information so I was able to book within about 30 minutes. He was proactive and reached out the night before to confirm arrival time and it was very responsive to all my requests and inquiries over text message. He was able to accommodate my daytime doggy daycare request His neighborhood is great and they even have a small dog area that’s fenced in for some off leash time. Basically, the best experience you could ask for when handing off your fur baby.
We had a great experience boarding our dog with Jackie! She was very thorough and respectful of all of our dog's needs and preferences. We received updates and pictures a few times a day, which gave us so much peace of mind while we were away. It was clear our dog was having a wonderful time—especially having Jackie's dogs as playmates. She was very capable and attentive, and we felt very comfortable leaving our dog in her care. Marty is looking forward to staying at Jackie's again!
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 - Sleepy Hollow
Select a filter and find qualifying sitters offering dog boarding.Sitters in Sleepy Hollow average 12 repeat dog boarding clients
FAQs for Dog Boarding - Sleepy Hollow
Frequently asked questions about Rover
The average cost of Dog Boarding in Sleepy Hollow is $52 per night as of October 2026. Most bookings cost between $32 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 October 2026, there are 2,719 sitters on Rover offering Dog Boarding across Sleepy Hollow. Enter your ZIP code to see which available sitters are closest to your home.
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 Sleepy Hollow 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 Sleepy Hollow home-away-from-home, 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 Sleepy Hollow.
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 Sleepy Hollow 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 , 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 .
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 IL 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.
Connect anywhere with the Rover app
