Dog Boarding Wingdale

Find a loving dog sitter to watch your dog overnight at your sitter's home.

Pick-Up
Search

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.

1 / 1
Sitter Profile Image: Annette G.
Verified Background Check
Annette G.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 347 reviews
131 repeat clients
49 years of experience
Pawling, NY, 12564

“Well things could not have been better!! Annette sent text messages and pictures to keep me up to date which keeps anxiety to a minimum. She was great!”

Profile image
KEVIN H.
Sitter Profile Image: Pam R.
Verified Background Check
Pam R.
from
$55
per night
5.0 out of 5 stars
• 69 reviews
31 repeat clients
30 years of experience
Bethel, CT, 06801

“Pam was great. She posted a lot of pictures to let us know Luna was having fun and communicated daily. You could tell she had a lot of experience with dogs and with petting sitting/boarding. We would definitely use Pam again for the next time we go out of town.”

Profile image
Trevor G.
Sitter Profile Image: Jeff H.
Verified Enhanced Background Check
Jeff H.
Star Sitter
from
$70
per night
5.0 out of 5 stars
• 257 reviews
88 repeat clients
30 years of experience
Poughkeepsie, NY, 12603

“Our dog had an amazing stay with Jeff! We are always nervous leaving her with someone new, but Jeff is so responsive and great about sending photos and updates. She had a lot of fun and we were able to relax and enjoy the wedding we were attending in the area. Highly recommend!!”

Profile image
Amy A.
Sitter Profile Image: Cherissa P.
Verified Enhanced Background Check
Cherissa P.
from
$60
per night
5.0 out of 5 stars
• 26 reviews
15 repeat clients
20 years of experience
Poughkeepsie, NY, 12603

“I recently had Cherissa watch over my mini Goldendoodle, Sofia, and I couldn’t be happier with the experience. From the very first interaction, she was professional, kind, and clearly passionate about animals. Cherissa and her family took the time to get to know Sofia’s routine, preferences, and any special needs, which made me feel totally at ease. While I was away, she provided regular updates—including photos and messages—which really reassured me that my pet was happy and well cared for. I highly recommend Cherissa and her family to anyone looking for reliable and compassionate pet care. I’ll definitely be booking with them again in the future!”

Profile image
Mark P.
Sitter Profile Image: Saori A.
Verified Enhanced Background Check
Saori A.
Star Sitter
from
$63
per night
5.0 out of 5 stars
• 101 reviews
30 repeat clients
15 years of experience
Newtown, CT, 06470

“Saori was great. Our one year old lab was in heaven at their place. We received a puppy that was well cared for and had gotten a lot of socialization and exercise is a safe environment.”

Profile image
Matthew H.
Sitter Profile Image: Donna w.
Verified Enhanced Background Check
Donna w.
Star Sitter
from
$35
per night
5.0 out of 5 stars
• 54 reviews
23 repeat clients
50 years of experience
Poughkeepsie, NY, 12603

“Donna was great. She treated my dog like he was her own. I felt extremely confident that Guinness was being very well taken care of. Guinness came home very happy but tired from all the fun he had playing with Donna's dogs. I will definitely use Donna and her services again. I'm very happy. I found her thank you so much.”

Profile image
Briana H.
Sitter Profile Image: Rich U.
Verified Enhanced Background Check
Rich U.
Star Sitter
from
$62
per night
5.0 out of 5 stars
• 399 reviews
100 repeat clients
20 years of experience
Danbury, CT, 06811

“Rich is great with communication and making sure our dogs are safe and having fun. He even prepared a special holiday meal over Christmas for all of them. So happy he was available to care for our two dogs.”

Profile image
Annette F.
Sitter Profile Image: Corrie F.
Verified Enhanced Background Check
Corrie F.
from
$75
per night
18 years of experience
Sherman, CT, 06784

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.

Sitter Profile Image: Stephen N.
Verified Enhanced Background Check
Stephen N.
Star Sitter
from
$110
per night
5.0 out of 5 stars
• 37 reviews
13 repeat clients
25 years of experience
Beekman, NY, 12533

“I cannot recommend Stephen enough. He took amazing care of our Buddy while we were away. He communicated and sent us videos and updates every day. He was cautious when introducing Buddy to the other dogs in his care and we had a meet and greet prior to the stay which I appreciate, he goes above and beyond to make sure the dogs in his care are compatible to keep all dogs safe. I look forward to using him in the future and I know Buddy will too. You can see that dogs in Stephens care are treated as his own and that is so comforting when leaving your dog in his care.”

Profile image
Linda P.
Sitter Profile Image: Erika N.
Verified Enhanced Background Check
Erika N.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 40 reviews
10 repeat clients
20 years of experience
Carmel, NY, 10512

“We couldn’t have asked for a better dog sitter! From the moment we met, it was clear that Erika genuinely loves animals and takes the responsibility seriously. She treated Bowie like a member of her own family, making sure that he was not only well cared for but also happy, comfortable, and loved while we were away. Communication was outstanding throughout our trip. We received regular updates, photos, and videos that gave us complete peace of mind. It was obvious that Bowie was getting plenty of attention, exercise, and affection. It’s such a relief to know we have someone we can trust completely with Bowie. Her professionalism, kindness, and attention to detail exceeded every expectation. We wholeheartedly recommend Erika to anyone looking for a reliable, compassionate, and exceptional dog sitter. We will absolutely be booking with her again, and we know Bowie can’t wait for the next visit!”

Profile image
Natalia H.
Sitter Profile Image: Jessica O.
Verified Enhanced Background Check
Jessica O.
from
$48
per night
5.0 out of 5 stars
• 23 reviews
2 repeat clients
10 years of experience
Danbury, CT, 06811

“Our dogs had a great time and were well taken care of with Jessica. She was very responsive, sent pictures and made them feel comfortable. We would definitely book her again.”

Profile image
Matthew A.
Sitter Profile Image: Dew G.
Verified Enhanced Background Check
Dew G.
Star Sitter
from
$68
per night
5.0 out of 5 stars
• 63 reviews
27 repeat clients
20 years of experience
North Salem, NY, 10560

“Dew was wonderful! Our sweet girl can be nervous and uneasy in new situations and Dew was endlessly patient and warm putting her at ease while she was staying with her. Dew sent pictures adn updates to keep us in the loop and was super quick in responding to any questions we had! I would absolutely recommend her and hope to have her pet sit Sankaty for us again!”

Profile image
Elizabeth D.
Sitter Profile Image: Nicole G.
Verified Enhanced Background Check
Nicole G.
Star Sitter
from
$70
per night
5.0 out of 5 stars
• 143 reviews
35 repeat clients
20 years of experience
Danbury, CT, 06810

“Nicole did a great job watching Libby! She was reliable, caring, and attentive, and it was clear that Libby was in good hands. I especially appreciated Nicole’s excellent communication throughout the time she was caring for Libby. She kept us updated and made the whole experience easy and worry-free. I would definitely recommend Nicole to anyone looking for someone trustworthy and caring to look after their pet. We would be happy to have her watch Libby again!”

Profile image
Arthur D.
Sitter Profile Image: Mildred P.
Verified Background Check
Mildred P.
Star Sitter
from
$50
per night
4.9 out of 5 stars
• 79 reviews
27 repeat clients
15 years of experience
Poughkeepsie, NY, 12603

“Mildred was a wonderful sitter to work with. Great communication and prompt responses. My boy had a blast in the beautiful big fenced in yard. I definitely would book again in the future”

Profile image
Donna V.
Sitter Profile Image: Sue C.
Verified Enhanced Background Check
Sue C.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 12 reviews
4 repeat clients
25 years of experience
Danbury, CT, 06810

“Sue is a sweetheart. Highly recommended her watching your pets. She sent photos, is reliable, trustworthy and kind. Will definitely be using her in the future. :)”

Profile image
Emily K.
Sitter Profile Image: Cory M.
Verified Enhanced Background Check
Cory M.
from
$55
per night
5.0 out of 5 stars
• 62 reviews
28 repeat clients
25 years of experience
Wappingers falls, NY, 12590

“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.”

Profile image
Ashlee H.
Sitter Profile Image: Jessica & Ian K.
Verified Enhanced Background Check
Jessica & Ian K.
Star Sitter
from
$65
per night
5.0 out of 5 stars
• 72 reviews
32 repeat clients
25 years of experience
Sandy Hook, CT, 06482

“Jess and Ian were wonderful with my two boys. They communicated with me while on vacation and it eased my mind to know they were ok. Wonderful and honest couple”

Profile image
Eileen F.
Sitter Profile Image: Rachael C.
Verified Background Check
Rachael C.
Star Sitter
from
$75
per night
5.0 out of 5 stars
• 63 reviews
22 repeat clients
10 years of experience
Danbury, CT, 06810

“First time using Rachel C’s services and could not be more pleased. Rachel was helpful on the drop off and pick of our lab and she communicates everyday with great updates. Our lab Milo made some friends and seemed to really enjoy his time visiting at Rachel’s. Strong recommendation for your furry friends.”

Profile image
Michael S.
Sitter Profile Image: Maria V.
Verified Background Check
Maria V.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 69 reviews
29 repeat clients
20 years of experience
Milton, NY, 12547

“Maria (and family) were lifesavers and saved our trip by having availability last minute when another sitter canceled on us. Our dogs looked so happy and loved while we were gone. Definetly recommend and look forward to using her again!”

Profile image
Candice G.
Sitter Profile Image: Jennifer & Thomas H.
Verified Enhanced Background Check
Jennifer & Thomas H.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 7 reviews
2 repeat clients
10 years of experience
Kingston, NY, 12401

“Jennifer, Thomas and their girls took such good care of our pup. They sent frequent updates and photos throughout the visit, and we could instantly tell how comfortable our dog was in their home. Cannot recommend them enough!”

Profile image
Danielle N.
1 / 1
View more

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

  1. 1. Search

    Browse profiles of sitters near you who offer dog boarding
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

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 Dog Boarding - Wingdale

Frequently asked questions about Rover

As of October 2026, there are 704 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 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.

96% of sitters in Wingdale 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 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.

<b>Tip:</b> 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.

Connect anywhere with the Rover app

Download on the App Store BadgeGet it on Google Play Badge