Dog Boarding Wingdale

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Over 93
pet parents in Wingdale have booked dog boarding

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.
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Annette G.
Star Sitter
from
$50
per night
5.0 out of 5 stars
336 reviews
130 repeat clients
49 years of experience
Pawling, NY, 12564

Annette is truly a dog/animal lover. After our meet and greet, we felt very comfortable leaving our pups in her hands for our wedding. I did not stress once that they were not being well taken care of. Annette has set up her home to be prepared for all pets’ personalities. When we picked our dogs up, Annette gave us a full and detailed report of how their stay was. They left happy and relaxed! Thank you, Annette!

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Elissa C.
Sitter Profile Image: Saori A.
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Saori A.
Star Sitter
from
$62
per night
5.0 out of 5 stars
66 reviews
19 repeat clients
15 years of experience
Newtown, CT, 06470

Saori was such a great sitter for our pups (1 year old great pyrenees). She took them to the dog park in the morning for a couple of hours, helped continue our invisibile fence training, and sent us so many pics and updates throughout the weekend. I could tell how happy and comfortable our dogs were in her home and under her care. They came home so tired because they had so much fun with her and the other dogs!

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Shantille R.
Sitter Profile Image: Jeff H.
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Jeff H.
from
$64
per night
5.0 out of 5 stars
217 reviews
74 repeat clients
30 years of experience
Poughkeepsie, NY, 12603

Jeff took amazing care of Angus! I’d give 6 stars if I could! He communicates well, we got photos and updates everyday. Angus had a “doggie smile” in every photo. Our flight coming home was very delayed, Jeff was patient and flexible in adjusting our pick up time. Will definitely book again and recommend him to friends! Thank you Jeff!

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Kristin M.
Sitter Profile Image: Sue C.
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Sue C.
Star Sitter
from
$50
per night
5.0 out of 5 stars
9 reviews
4 repeat clients
25 years of experience
Danbury, CT, 06810

Sue was great. Really patient and accommodating. My pup was returned to me happy and healthy. Her husband was also very nice and they both seemed very confident and comfortable with my pup who’s a 48lb pittie. Thank you Sue and Franky. We appreciated your care and attention to our fur baby. Sue also sent regular selfies of the pup and was quick to reply to messages.

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Rachel C.
Sitter Profile Image: Nicole G.
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Nicole G.
Star Sitter
from
$70
per night
5.0 out of 5 stars
130 reviews
30 repeat clients
20 years of experience
Danbury, CT, 06810

Nicole is fantastic! We were nervous about boarding my dog at someone else’s house for the first time and she was reassuring, patient, and attentive to all of Jack’s needs. Great with medication administration and provided daily photos and updates on how Jack was doing. Certainly gave us peace of mind on our trip. We will definitely be using Nicole for our next trip and would recommend her to anyone!

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Cassie R.
Sitter Profile Image: Csaba & Nicole K.
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Csaba & Nicole K.
Star Sitter
from
$69
per night
5.0 out of 5 stars
134 reviews
62 repeat clients
19 years of experience
Pleasant Valley, NY, 12569

Loretta is AMAZING! We left our dog for the first time ever with her & by the time we came back for him to pick him up, he didn’t wanna leave! She sends pics & videos the entire time & it’s just reassurance that your fur baby is doing just fine! It’s never easy to leave our pets but if you ever need to, book Loretta! You will not be disappointed. She is our official dog sitter!

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Tynamarie C.
Sitter Profile Image: Rachael C.
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Rachael C.
Star Sitter
from
$75
per night
5.0 out of 5 stars
61 reviews
19 repeat clients
10 years of experience
Danbury, CT, 06810

My dog Blue stayed with Rachel for almost 10 days and I was honestly sad for him when he had to return to us. He seemed to be living his best life and I was so happy to see him happy via all the pics she would send daily. Will definitely be asking Rachel to watch blue again and again!

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Jane B.
Sitter Profile Image: Dew G.
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Dew G.
Star Sitter
from
$68
per night
5.0 out of 5 stars
54 reviews
23 repeat clients
20 years of experience
North Salem, NY, 10560

Great experience from beginning to end. It was our first time leaving Gigi with a sitter. Dew kept us updated and sent photos, which was a great comfort to us. Will definitely use her again.

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Mindy H.
Sitter Profile Image: Jessica & Ian K.
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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

Jessica and Ian did an amazing job taking care of my pup during my wedding weekend! She has never napped so hard when we brought her home! Will definitely use them in the future of all of my dogs pet sitting needs!

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Abby B.
Sitter Profile Image: Cherissa P.
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Cherissa P.
from
$60
per night
5.0 out of 5 stars
23 reviews
15 repeat clients
20 years of experience
Poughkeepsie, NY, 12603

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!

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Donna T.
Sitter Profile Image: Donna w.
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Donna w.
Star Sitter
from
$35
per night
5.0 out of 5 stars
34 reviews
13 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.

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Briana H.
Sitter Profile Image: Rich U.
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Rich U.
Star Sitter
from
$62
per night
5.0 out of 5 stars
377 reviews
96 repeat clients
20 years of experience
Danbury, CT, 06811

Rich was an amazing, caring, and wonderful sitter for my pup. He took wonderful pictures and videos throughout her stay. 10/10 would recommend for any owner!

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Catherine G.
Sitter Profile Image: Mildred P.
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Mildred P.
Star Sitter
from
$50
per night
4.9 out of 5 stars
75 reviews
23 repeat clients
15 years of experience
Poughkeepsie, NY, 12603

I had an exceptional experience. Mildred was so kind and responsive to all my inquiries. I was a little nervous leaving my Max since he's only been with my daughter and I for a few months. but he was well taken care of! I will definitely recommend Mildred for boarding services, and I will be definitely using her in the future. Thanks again Mildred :-)

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Tiffany W.
Sitter Profile Image: Veronica C.
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Veronica C.
from
$50
per night
5.0 out of 5 stars
20 reviews
8 repeat clients
10 years of experience
New Fairfield, CT, 06812

I've used Veronica at least a couple times at this point and she has been nothing less thank fantastic. She has been fantastic at communication, great at scheduling room, and took amazing care of my Mika! Definitely bwill contact her again and I would encourage anyone to do the same.

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sam b.
Sitter Profile Image: Stephen N.
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Stephen N.
Star Sitter
from
$110
per night
5.0 out of 5 stars
33 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.

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Linda P.
Sitter Profile Image: Maria V.
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Maria V.
Star Sitter
from
$45
per night
5.0 out of 5 stars
60 reviews
25 repeat clients
20 years of experience
Milton, NY, 12547

she was an excellent nanny for Pluto .. she was always in contact with me, she sent me photos and videos, she looked after Pluto for 5 days ... 100% recommended, she has a lot of love and responsibility for pets

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Sol N.
Sitter Profile Image: Volha P.
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Volha P.
Star Sitter
from
$65
per night
5.0 out of 5 stars
217 reviews
85 repeat clients
12 years of experience
Poughkeepsie, NY, 12601

We always have a hard time leaving our dog,who is diagnosed with severe skin and food allergies. It is such a relief to have such a caring, warm family as Vohla who take care of our dog as if he is there own. They are our go to caregivers should we need to leave. Above ans beyond communication, with a plethora of extra services should you need. It felt as though our pup was on a holiday as well! Cannot recommend a better Rover caregiver. Thank you!

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Candace F.
Sitter Profile Image: Ryan F.
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Ryan F.
from
$55
per night
5.0 out of 5 stars
8 reviews
15 years of experience
Redding, CT, 06896

We were extremely happy with our experience! Ryan was knowledgeable and attentive to our dog. We received many updates and pictures while we were away which we really appreciated. He was even willing to bathe him after a run in with a mud puddle. 😅 We’ll definitely be repeat customers.

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Hulme F.
Sitter Profile Image: Brittany L.
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Brittany L.
from
$45
per night
5.0 out of 5 stars
35 reviews
11 repeat clients
37 years of experience
Wappingers Falls, NY, 12590

I would definitely recommend Brittany to anyone that needs boarding for their pets. She treated our puppy Storm like she was one of her own. She sent us pictures of Storm having a great time and assured us that she was playing the entire time she was there. When we picked her up she was clearly happy and exhausted. We will definitely be using Brittany again in the future.

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Michael C.
Sitter Profile Image: Michele L.
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Michele L.
from
$70
per night
5.0 out of 5 stars
42 reviews
24 repeat clients
40 years of experience
Bethel, CT, 06801

Michele was awesome. She’s super friendly and made me feel very comfortable about caring for Hershey. When she was watching him she sent me pictures periodically to let me know that all was well. We will definitely reach out to Michele in the future!!

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Elizabeth L.
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The median cost per night for dog boarding in Wingdale is $60

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

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Sitters in Wingdale average 10
repeat dog boarding clients

FAQs for Dog Boarding - Wingdale

Frequently asked questions about Rover

The average cost for Dog Boarding in Wingdale on Rover is $61.05 per night (as of July 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 July 2026, there are 742 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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