Dog Boarding Wingdale
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Wingdale, 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.
“Well Ms Annette was WONDERFUL. Can't recommend highly enough. She obviously has an affection and ability with dogs, witnessed from the first second of our in person interactions in her driveway. It made me feel so relieved to have her take care of them, especially since she sent me updates and photos of them every day. She's fantastic and I'm looking for another trip in that vicinity so I can drop the two boys (mini dachshund, cockapoo) off for another visit to Ms Annette's house in Pawling!”
“Pam is so communicative and always shares photos of the pet :) she took such a good care of Tofu that Tofu cried and didn’t want to leave when we had to pick him up 🤭 thank you so much, Pam!”
About: I have been grooming dogs for over 18 years, and boarding clients' pups in my home for 16 years. My 13 yr old homeschooled son and I adore all dogs. We have 2 wonderful medium sized girls (Myla 8, Josie 1.5) who love all dogs and people! My career in grooming means I truly 'speak dog' and understand their quirks and needs. I have extensive experience with all breeds, sizes, and personalities. I'm comfortable administering oral and injectible medications, as well as supplements. Our dogs eat a raw diet, so food & water bowls get sterilized after each meal. Since we homeschool, we spend a lot of time at home or close by with friends. My son often has friends over who love to play with dogs. This means we have a great balance of calm & quiet time, as well as active & fun time. Our lovely property has Invisible Fence for about a acre, so any dogs trained on it get to enjoy lots of untethered play time. Every dog who stays gets a temporary ID tag with my address and phone number in case of accidental 'escape' We love couch cuddles, and both of our girls sleep in bed with my son. We also have dog beds everywhere, and crates & gates available when needed.
“We are so grateful for the amazing care you gave Cloud while we were away! You went above and beyond—keeping us updated the whole time and sending the sweetest pictures that truly put our mind at ease. It was clear he was in great hands. Til next time!”
“Bruce and Jeff were great and we will definitely use them again. They sent photos and responded very quickly when we reached out. Thanks again for looking after our pup, Oggi!”
“Erika was wonderful! Highly recommend (and will to my friends as well). She was extremely responsive in preparation for our trip, and understanding of some special needs for our yellow lab. She sent pictures throughout, and was flexible when a winter storm messed with our plans (she stayed up late so that we could pick up our pooch). Thanks for taking such great care of our dog, and for being such a pleasure throughout this process, Erika!”
“Stephen is a super care taker, for sure. Great and timely communications, friendly and very accommodating for a last minute request. Made the whole experience of looking after my Gracie seamless and easy.”
“Donna is absolutely great, very nice, accommodating and very punctual. She sent many pictures with our dog, who seemed very happy and well taken care of. We are very pleased to have met her and shall definitely contact her again for future bookings. Thank you, Donna!”
“Our dog, Bagel, enjoyed a wonderful vacation of his own with Nicole! This was his second time staying with Nicole. Bagel is pretty social so being able to play with Nicole's own dogs as well as any other boarders was just the best treat for him. Nicole's daily pictures and quick updates gave peace of mind and assured us that we made the right choice for boarding. Thank you and we will definitely be back!”
“My puppy Skye loved her stay with Cory and her family. She made me feel at ease that she was going to be fine and safe as she’s a climber. Skye did great with Cory and is an exceptional caregiver. She sent me updates on and off as well. I highly recommend Cory and will use her again. Thankyou so much.”
“Sue was absolutely wonderful with Ollie! She was kind, attentive, and took great care of him throughout his stay. Communication was effortless, as she was always prompt with her replies and kept us reassured with regular updates. We also really appreciated how flexible she was with her schedule, easily accommodating our drop off and pick up times. Ollie had a fantastic time with her, and we could not have asked for a better experience. We highly recommend Sue to anyone looking for a caring and reliable dog sitter!”
“Jessica was great at watching Gwen! She was able to accommodate our last-minute request after another sitter cancelled. She was very communicative about Gwen’s stay and sent plenty of photos and updates. She took great care of our little pup!”
“We had a wonderful experience with Volha and her family! We really appreciated the regular updates and pictures throughout our travel. She was very thorough and detailed with her questions about our pups to ensure everything went smoothly. Our pups had a great time and were well cared for. We hope Volha can watch them again soon!”
“Jessica and Ian were terrific! We went away to a family wedding and I was so nervous leaving my 17 year old Bo. When interviewing them I told them about Bo being elderly with walking issues and other elderly ailments, and they assured me that they had no problem, loved elderly dogs, and would take great care of him. Well they were right!! He settled right in and looked so happy in the pics they sent. And he was fine and relaxed when we picked him up.”
“Jomini and her family gave our dog Piper a home away from home! She got a lot of affections, walks, and was treated like a member of the family! I was sent daily updates with pictures. Jomini coordinated with me fairly last minute and I appreciate her flexibility! Would absolutely book again.”
“Very pleased to add another glowing review: this was the first stay for our energetic young cat Bella w/ Maria, her caring family, and resident cats and canines. Maria has a particularly good arrangement and process for gradually acclimating guest cats to a residence, especially one with other felines. As the only pet in our household, Bella's very curious about other cats. The updates and photos show that she was enjoying the run of the house within the first couple days and getting along with the other cats and dogs. It says a lot about the family's skill in creating a comfortable atmosphere for their own pets and boarders alike. Highly recommended.”
The median cost per night for dog boarding in Wingdale is $63
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
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Popular requests for dog boarding - Wingdale
Select a filter and find qualifying sitters offering dog boarding.Sitters in Wingdale average 10 repeat dog boarding clients
FAQs for Boarding - Wingdale
Frequently asked questions about Rover
As of September 2026, there are 696 sitters on Rover offering Dog Boarding across Wingdale. 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.
96% of Wingdale 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 Wingdale 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 Wingdale 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 Wingdale.
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 Wingdale 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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