Dog Boarding Sleepy Hollow
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 31 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.
“So happy I found Jennifer to care for my 2 dogs while I was away. I have only ever left them with family and was more than a little nervous. However after the meet and greet I was confident they would be in good hands. The daily updates were great and put my mind at ease that they were being well taken care of. Thank you Jennifer!”
“Happy came back in a good mood. She appeared not ready to leave. Videos showed her being energetic and playful especially running free around the yard. . Her adjustment with Doreen and return home was easy. Will highly recommend Doreen.”
“Five-star sitter who treats your dog like her own. We have a small deaf dog that we are too attached to but loved how Brittany took such good care of our dog during a very hot spell and could not take her with us. She is the best!”
“What a great experience. I love getting updates, and being reassured that my pup is having a good time and also getting what he needs. Valerie is conscientious, for example, she walked my dog before I came to make sure that he had his needs met before a long drive with me. Got an along well with her dog, in a family setting with a backyard — really appreciate her care.”
“Robert has taken great care of our 2 dogs a few times now and we couldn’t be more happy we found him to be their sitter! He is easy to work with and communicates well. Our high energy dogs always come back to us relaxed and exhausted with all the play time they get to have while there!”
“Yasmeen was great. She responded very quickly in such short notice and was very accommodating to my 1 year old Pittie Shadow. Yasmeen responded immediately to my messages and sent me photos and videos through out the night while he stayed over. She updated me with how he was doing and if there were any concerns. My puppy did very well with her. I would definitely recommend!!”
“We are very happy to ask Maureen for our Chamonix. Maureen was waiting for us in front of her house to do a first meeting before sitting. She’s very reliable and responsible. She kindly updated how Chamonix’s doing through her stay. We will definitely return to her if we needs someone next time.”
“Kevin and his family were great dog sitters! They had our dog in their house for the weekend and she seemed to love it there. She had a chair she sat in, they took her on great walks and overall followed her routine. We would definitely use them again!”
“This was my first time leaving my dog Pigeon overnight/extended period while I traveled and Pidgie was so happy and tuckered out when I picked him up! He seems like he had an excellent time, maybe even sad to leave his new friends! I had to book an additional extra night last minute due to international travel and they were so so accommodating, always quick to reply, and sent videos and updates along the way.”
“Stephanie was fantastic! Super easy to work with and was very communicative. She was kind enough to bathe our dog sunny after they went outside and had some tics. Sunny seemed to have a very good time and loved Stephanie 😊”
“Diana is friendly, caring, responsible and she is a great dog sitter. She sent photos and videos everyday and went above and beyond to take care of my shiba inu. In addition, her dog Wendy was a wonderdul playmate for my shiba. She provided a safe, clean and fun environment for the care of my dog.”
“Rene always takes great care of Cory. She noticed that he was itchy and has some skin irritation so asked if he could have some Benadryl, and always sends pics and videos of him playing and having a great time.”
“Elizaveta was wonderful with our dog! She is warm, genuinely loves dogs, and was very flexible with scheduling. We especially appreciated the daily photos and videos she sent. Highly recommend her to anyone looking for a caring and reliable dog sitter.”
“William was great and I felt comfortable boarding my dog with him for a week. He has an excellent space including a fenced in yard for the dogs to enjoy. Would definitely rebook in the future!”
“First time boarding with Randi and it was an incredibly smooth experience. Randi is extremely flexible and was a life saver for when we were away on a multi city driving trip. We were watching the weather in case we needed to abandon our plans and come back home mid trip. Randi was extremely flexible and accommodating and I am so grateful for that. Our dog is a picky eater and is also on some tricky meds…and Randi kept in touch with regular updates. She persevered with attempts to get her to eat both food and meds, until our dog did finally start to eat! Our dog came home happy and healthy! We will definitely board with Randi again!”
“Anat is the best! She took great care of Freddie, sent updates and photos, and assisted with pick and drop off. Thanks to Anat we could travel without worry. See you on our next vacation 🙏”
The median cost per night for dog boarding in Sleepy Hollow is $60
Dog parents share their Rover experiences - Sleepy Hollow
Dog Lovers! I was apprehensive about leaving my tiny, 22 month old Maltese for the first time. However, after meeting Jennifer and her family at a meet and greet along with other dogs she was dog sitting, I felt relieved. My Maltese was welcomed into their home like a family member. Jennifer provided a warm and very safe environment. I informed Jennifer of all of her pet peeves and she made sure that my dog was always secure. Jennifer provided daily pictures and videos which enabled me to enjoy our vacation knowing that my dog was having a good time as well. Several of the videos taken from her home and walks were cute and funny. I can only highly rate Jennifer as a professional dog sitter who will treat your dog as her own. Also, thanks to Jennifer’s husband who assisted on walks!
Catherine was amazing with us and our two dogs. We hardy leave them so finding someone who would give them the care, attention, and love they're used to getting always seems daunting. Not with Catherine from our meet and greet, to drop off, pick up, and the time in-between she was fantastic! She sent text, photos, videos, comforting us all along the way. Through those videos we saw wagging tails and smiles, we knew they would in great hands and could relax from worry about them while away. I would highly recommend Catherine, she's professional, kind, knowledgeable about dogs and is highly sought after. We will certainly be using Catherine again. Thank you so much for taking such good care of our little loves ❤️
We left our baby with Stephanie for 2 weeks and we enjoyed how she sent us daily pics & videos. Our dog looked very comfortable and settled in. She walked and played with her. Seeing my 11yo senior dog playing made our hearts smile. She doesnt play in her own home which reminds me that I need to ask her, 'what toy was that'!! We are very happy with Stephanie and will use her services 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 7 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 $48.15 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 13,227 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.
95% 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 NY 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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