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.
“Geraldene was so great with our little Sandy. She sent communication and videos the whole time we were on vacation and it was obvious that Sandy was enjoying her time there. We will definitely book with her in the future.”
“Thank you June and Wade for taking good care of our dog for a long week+ vacation. Thank you for daily pics and updates on how she adjusted over the time. Grateful for her being able to relax at your home, giving me peace of mind.”
“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.”
“Our dog’s stay with Michelle was longer than in prior stays but I received the same service - attention and daily detailed updates! My observation- she’s meticulous with the dogs and very detailed with their care. You can tell that she cares for them. Appreciate the help as always and will use her services again in the future!!”
“We had a wonderful experience with JoAnne. Our lab dog, Charlie got very spoiled for the short time we had him stay with JoAnne. She kept us informed oh how he was doing and sent us pics to put us at ease. We will definitely use her again!!! Charlie got a doggie bag to take home with a tennis bag and treats. Very nice of her to make him feel so special.”
“Julie and Mark took very good care of our fur babies. This was our first time leaving them with anyone that was not family. Julie and Mark were great with sending us photos and I could see how happy and well treated my dogs were. I would highly recommend them and will absolutely use them again!”
“Jessica was flexible and reliable. We felt very comfortable leaving Selah in her hands an we would definitely use her again. Selah seemed to love being with Jessica and her daughter. They even took her in the car for an outing which she loves.”
“udith was wonderful with Linny! My biggest concern when using Rover is that Linny tends not to eat when he's in a new environment. Judith treated him like he was her own and made sure he was eating properly. Whenever he wasn't interested in food, she spent extra time playing with him to help build up his appetite. It was clear she genuinely cared about his well-being. I would definitely book with Judith again and highly recommend her to anyone looking for a caring and attentive sitter.”
“Thank you so much for taking such great care of my 2 pups while we were out of town!! I can tell they had a blast and are exhausted from having so much fun with their doggy friends! Jessica and Christian are amazing and my pups will be so excited to go back and see them!!”
“Katey and her family have done a wonderful job taking care of our Goldendoodle puppy during two vacations. Katey sends daily updates and she and her family (and pets) are great with our dog. I recommend 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.”
“Once again, Derek and his family took wonderful care of my dog Bear while we were on vacation. He and his family treat him like part of their family, and that’s what really matters to us. Thank you so much, Derek.”
“Kira took such great care of my little dog. I think my dog is a little disappointed to be home lol! Kira sent regular updates and the cutest pics. I was a little nervous about my dog being with larger dogs, but it all worked out. They even bought my dog a Christmas gift :). Highly recommend and wouldn't hesitate to rebook.”
“Our dog always seems at ease and happy while staying with Valentina! It eases our minds knowing he is well taken care of, and the daily pictures are always appreciated.”
“Beth was so responsive and took great care of Jude! I will definitely be booking with her again as I knew he was in good hands the whole time. She sent updates and pictures and made me feel very comfortable leaving Jude in her care.”
“Angela (and her husband Dave) took such good care of Zoe! This was our first time leaving Zoe with someone else and they really made it easy for us. She sent us pictures often and sent me updates on Zoe. She really made me feel at ease! We’ve already booked another stay over the holidays.”
“My dog, Lucky, had a great time. We were gone for 10 days and he was so happy. Communication and care were top notch. We will definitely book again the next time we are out of town.”
“We had such a great experience with Morgan and Ross! They were wonderful with Beau and truly treated him like their own! They were great about communicating and sending updates the entire time we were gone, which made us feel at ease. Beau also loved hanging out with their pups Griz and Presley :)”
The median cost per night for dog boarding in Sleepy Hollow is $50
Dog parents share their Rover experiences - Sleepy Hollow
He was great! I reached out pretty last minute and had a slightly complicated situation since I was in Ohio and my dog was with my mom in Chicago, so we had to coordinate everything remotely. He was incredibly accommodating and made the whole process easy. My mom felt very comfortable dropping my dog off with someone neither of us had met before, especially given how last minute everything was. He was super nice, communicative, and sent me pictures and updates while I was away, which I really appreciated. I’d definitely feel comfortable leaving my dog with him again!
Derek has been fantastic to work with, so easy to communicate with and incredibly responsive. We left our 7 year old chocolate lab with him for a weekend out of town and he sent me lots of pictures and updates, which really put our mind at ease. My dog came home happy and clearly has a great time. 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
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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 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.
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