Dog Boarding Wingdale

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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.

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Sitter Profile Image: Annette G.
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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

“Little Man had a wonderful vacation with Annette. He adjusted quickly and was very happy. I was quite comfortable leaving him with Annette. We will definitely use her again.”

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Carol S.
Sitter Profile Image: Donna w.
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Donna w.
Star Sitter
from
$35
per night
5.0 out of 5 stars
• 56 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.”

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Briana H.
Sitter Profile Image: Corrie F.
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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.
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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.”

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Linda P.
Sitter Profile Image: Volha P.
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Volha P.
Star Sitter
from
$65
per night
5.0 out of 5 stars
• 224 reviews
88 repeat clients
12 years of experience
Poughkeepsie, NY, 12601

“I wanted to give the highest recommendation to Volha as a dog-sitter! My 1.5 year old pitbull mix stayed with Volha and her family for 3 nights (3.5 days.) I have to admit, this being my first time using the service, I was a bit nervous. Not because I do not trust Rover, but because my dog in particular is very timid, shy, and can be very introverted - so I did not know how she would take to being left for days with strangers (except for meeting Volha in the park for a few minutes a few days before.) It turns out i had nothing to worry about! She immediately took to the family and stayed on a normal behavioral and sleep schedule and seems to have had a great time. For reference, in the past, even when my dog would stay WITH me but I would take her out of town for a couple of days, she would act a bit strange after being knocked out of her normal routine. (Nothing super out of the ordinary - but she would, for example, go hide in the bathroom for a few hours and generally act very despondent.) My point is - whatever Volha and her family are doing is great! My dog came back happy, healthy, and energetic. In terms Volha's communication style, she sent me several pictures and written updates during the days when I was gone, going out of her way to be in touch and asking the extra questions to make sure that everything was okay. Pending availability, I definitely plan to work with Volha again!”

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Charlie P.
Sitter Profile Image: Lucienne T.
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Lucienne T.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 49 reviews
12 repeat clients
30 years of experience
Carmel, NY, 10512

“Lucienne was great! My two Frenchies had so much fun and were right at home with her. She was communicative and sent pics of my pooches living their best lives. Highly recommend!”

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Jessica C.
Sitter Profile Image: Rosemarie F.
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Rosemarie F.
from
$65
per night
5.0 out of 5 stars
• 98 reviews
17 repeat clients
20 years of experience
carmel, NY, 10512

“Marie and her family were incredible with our puppy. He was only 13 weeks at the time so of course we were a little anxious. What a waste of energy! We got texts and pictures every day so we could see how well he was doing. Allowed us to relax and enjoy our time away. Exceeded all of our expectations. Wouldn’t hesitate to use again and would highly recommend Marie to anyone ?❤️”

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Michael R.
Sitter Profile Image: Maria V.
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Maria V.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 71 reviews
30 repeat clients
20 years of experience
Milton, NY, 12547

“110% recommend! Maria was excellent. We are new to NY and were in a rush to find someone to watch our pup. We got very lucky to have found Maria! She showed true passion and love for our pup just with one visit! She also noticed that he had an ear infection and took it upon herself to do something about it- can you say amazing? She ALSO gave him a bath— literally doesn’t get any better! We will certainly be using Maria again! Can’t thank her enough! ??”

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Paige H.
Sitter Profile Image: Cory M.
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Cory M.
from
$55
per night
5.0 out of 5 stars
• 65 reviews
28 repeat clients
25 years of experience
Wappingers falls, NY, 12590

“Cory and her family did a great job with looking after our senior dog for two nights. She provided photos and updates throughout the weekend. Would recommend and book again.”

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Emily B.
Sitter Profile Image: Brittany L.
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Brittany L.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 47 reviews
15 repeat clients
37 years of experience
Wappingers Falls, NY, 12590

“Brittany was reliable and timely in communicating. Our fur babies had a good time with her and they came home feeling good. She was polite to interact with. We will be using her again if we need a sitter!”

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Christine S.
Sitter Profile Image: Valerie M.
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Valerie M.
Star Sitter
from
$66
per night
4.9 out of 5 stars
• 82 reviews
42 repeat clients
54 years of experience
Sandy Hook, CT, 06482

“Our boxer, Daisy, stayed with Valerie while we vacationed for a week in Florida. Valerie and her family were great from the start, not only with Daisy but also entertaining my eight year old son when we arrived for an introductory visit. They had plenty of room for Daisy to run around and two playful but well behaved dogs of their own that accepted Daisy in. Valerie provided updates during the week to let us know how Daisy was adapting and getting along with everyone and how much her family loved having her. She was also extremely flexible with drop off and pick up times knowing our hectic travel schedule. The next time we go away for an extended period, Valerie is definitely my first contact attempt.”

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Christopher J.
Sitter Profile Image: Kyle K.
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Kyle K.
Star Sitter
from
$62
per night
5.0 out of 5 stars
• 147 reviews
42 repeat clients
21 years of experience
Danbury, CT, 06810

“Kyle made us feel very comfortable about leaving our dog with him. He was very responsive and knowledgeable about dogs. He checked in with us morning and night to keep us updated while we were away. We would trust Kyle to take care of our pets in the future.”

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Ali S.
Sitter Profile Image: Kathleen D.
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Kathleen D.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 18 reviews
7 repeat clients
30 years of experience
Watertown, CT, 06795

“We had a great experience with Kate! Our dog, Sampson, stayed in her home and was very well cared for. Communication was easy and consistent, and we felt completely comfortable knowing our pup was in good hands. Sampson is pretty easygoing, but it was clear he was treated with attention and kindness. We will definitely book with them again.”

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Jessica V.
Sitter Profile Image: Don H.
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Don H.
from
$60
per night
5.0 out of 5 stars
• 7 reviews
30 years of experience
Pawling, NY, 12564

“Don was kind and accommodating to our Finn & Fiona. Thanks for keeping our pups safe while we were away.”

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John T.
Sitter Profile Image: Mario C.
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Mario C.
Star Sitter
from
$110
per night
5.0 out of 5 stars
• 117 reviews
38 repeat clients
20 years of experience
Poughkeepsie, NY, 12601

“Mario (and his sweet family) were amazing! Our dog is a bit anxious and specific about who she feels comfortable with, but they were all so attentive and loving that they had her opening up in no time. I would highly recommend Mario to anyone for top-notch pet care.”

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Dylan V.
Sitter Profile Image: Judy & Steven C.
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Judy & Steven C.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 14 reviews
5 repeat clients
40 years of experience
Poughkeepsie, NY, 12603

“Absolute peace of mind through the entire experience. This was only the third time with a sitter and second boarding my Whiskey dog overnight; but never have I felt as content as when he was with Judy, her wonderful family & beautiful home. Was able to completely enjoy my vacation knowing he was cared for as one of her own. I really can’t thank her enough for what that contentment was worth to me. To top it off she’s so nice!! Had pushed the date forward a day at the last minute, she was totally understanding and went with the flow. Just thank you!!!! I know Whiskey dog misses his new friends already =^_^=”

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George M.
Sitter Profile Image: Katlyn & Stephen B.
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Katlyn & Stephen B.
from
$50
per night
5.0 out of 5 stars
• 4 reviews
1 repeat client
15 years of experience
Pleasant Valley, NY, 12569

“Katlyn took great care of my dog over a weekend i was away. I would have her pet sit again in the future”

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William N.
Sitter Profile Image: Gabriel A.
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Gabriel A.
Star Sitter
from
$70
per night
5.0 out of 5 stars
• 182 reviews
63 repeat clients
20 years of experience
Tillson, NY, 12486

“Gabriel and Annie were wonderful hosts and caretakers for our two pups. Our Australian Cattle Dog and Aussie mix are a handful—energetic, high maintenance, and demanding, with daily exercise/stimulation requirements that can be somewhat daunting. But Gabriel and Annie handled the dogs' every need for a week-long stay. They integrated our dogs into their pack and ensured a safe and playful environment for everyone. And they sent regular updates with cute photos to show us how things were going, putting our minds at ease. Recommended!”

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Andy M.
Sitter Profile Image: Isabel S.
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Isabel S.
Star Sitter
from
$65
per night
5.0 out of 5 stars
• 66 reviews
18 repeat clients
18 years of experience
Brookfield, CT, 06804

“We are so pleased with Isabel and her care and concern with our pup. She had great communication with us and sent daily pictures of all the fun our pup had while away. We will definitely be using Isabel for our next vacation!”

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Elizabeth G.
Sitter Profile Image: Liliana Z.
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Liliana Z.
Star Sitter
from
$55
per night
5.0 out of 5 stars
• 31 reviews
14 repeat clients
10 years of experience
Middlebury, CT, 06762

“I had to fly back to Montana and was not able to bring my fur babies. Lilly and her husband took such great care of both my fur babies. I would highly recommend using them. As I will be using them again.”

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Brittany H.
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The median cost per night for dog boarding in Wingdale is $63

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How to book dog boarding

  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.
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Popular requests for dog boarding - Wingdale

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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 698 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.

95% 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, 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 , 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 .

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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