Dog Boarding Sleepy Hollow
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 68 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.
“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!”
“Brian was very accommodating, taking care of my dog for two weeks on short notice. He provided updates and photos that gave me piece of mind. Plus, my dog was able to socialize with his dog, which was a bonus! His rates were reasonable; he answered my texts and questions in a timely manner. Overall very happy, and I will check back with him, should we need help with boarding our dog in the future. Thank you Brian!”
“June is a fabulous calm and aware mother hen. I have an anxious 10 pound dog and she took very good care of her. She was worried about her. I knew my dog was doing well when I saw her tail up rather than between her legs. June sent beautiful photos of her relaxibg at her home. It was worth the hour drive to find someone as attentive and caring as June.”
“A very loving family with lots of pet experience. They were able to teach my dog how to “drop” a ball after fetching. Before she would not want to give it up after fetching a toy. They also helped her learn how to get along with other dogs.”
“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.”
“We love these guys! Our puppies feel at home and are well loved, treated as family and always have a great time. The timely updates, lovely artistic pictures and videos and the great care they offer our pups is invaluable.”
“I don't know where to start. They took care of our dog for 8 days and we were able to enjoy our vacation without worrying. I received daily updates with pictures, videos and kind words. They are wonderful! I would highly recommend Shauna & Peter’s family and I will use them again without doubt. Thank You!!”
“Roberto and his family welcomed my dog to his family who are all dog lovers. He was well cared for and enjoyed his time with them. Would confidently recommend Roberto.”
“I feel so lucky to have found niratcha as a dog sitter for my big baby lab she took great care of him She sent pics and updates daily, and our boy came home exhausted and happy. We're so grateful to have found someone who truly cares for our boy the way we do! VERIFIED!”
“Patricia took amazing care of Zoey. She was great with sending us video and photo updates which gave us peace of mind. I highly recommend Patricia and look forward to having her watch Zoey again.”
“Danielle was amazing! Updated me often and truly made this experience wonderful. She reached out without me doing so, sent pics and videos and responded always within minutes. Most importantly understood my bulldogs separation anxiety. Will definitely reach out again for her services.”
“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!”
“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!”
“I was very happy with how things went. Loved that they were around other dogs and could roam the home freely and openly. My 2 dogs are also attached to each other and were able to be with each other throughout. They received their needed meds on time....one being insulin injection 2xs daily...and overall did well as I got video updates on their progress throughout the wk. I will definitely use Jessica and her husband again!”
The median cost per night for dog boarding in Sleepy Hollow is $50
Dog parents share their Rover experiences - Sleepy Hollow
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.
This was our second time leaving our lab, Nola, with Derek and Melissa and she is clearly loving her time with them. She is so settled and well adjusted when we pick her up, there is no doubt the loving care she receives during her stay. Derek sends us daily pictures and a small update and we are able to enjoy our time away without worrying about her. Highly recommend!
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.
Meet local sitters who will treat your dogs like family
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 for Dog Boarding in Sleepy Hollow on Rover is $52.17 per night (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Dog Boarding easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Boarding. For more information on service fees, click here .
As of September 2026, there are 2,728 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 rhythm and routine, but most will follow the flow that keeps your dog happiest. Sitters can give meals on your dog's regular schedule, provide a comfortable place for sleep, and plenty of one-on-one attention.
92% of Sleepy Hollow sitters also include daily walks in the neighborhood during dog boarding stays. You can also request photo and message updates throughout the stay so you can see which Sleepy Hollow landmarks or neighborhoods your dog is enjoying.
If your dog is a little shy, consider booking a one-night trial stay! This practice run can boost your and your dog’s confidence before your trip.
Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Sleepy Hollow 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 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 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 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
