Pet Boarding Wingdale

Find a loving Wingdale pet sitter to watch your cat or dog overnight at your sitter’s home.

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Over 93
pet parents in Wingdale have booked pet boarding

Wingdale, Find top rated pet 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: Don H.
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Don H.
from
$60
per night
30 years of experience
Pawling, NY, 12564

About: My name is Don H. I am a professional pet sitter, dog walker and licensed dog trainer for 30+ years. I have been in the pet industry for many years, this is what I do full-time and love every minute of it. I care for all breeds of dogs and cats and also reptiles, fish, rodents, goats, horses I will e-mail/text or phone you updates and photos of your pet while you are away. I would love to help you out whether you need a pet/house sitter, dog training, dog walking, trail walks or your dog to be transported to Vet or Groomer. Your pet will be well cared for whether in your home or ours. I am a call way. Sincerely, Don My clients will give reference to how trustworthy and experienced I am when caring for pets in your home. I have respect for your property and even go the extra mile making sure your home is maintained and your pets are safe. I will take in your mail, water plants, take out your garbage/recyclables at no charge. Overnights include picking up after your pet inside and out. Why I love dog sitting I have been around all animals my whole life, I started my journey when I became a certified dog trainer. I also worked as a Kennel Manager for a medium-size kennel in Greenwich, CT. People tell me that I have great patience and calmness when working with difficult dogs. my goal is to help owners and their pet's to become one. I have over 25 years experience as a dog trainer and pet care provider. About my yard Yes i do have a backyard. Although it is not fenced in but I have tree barriers that keeps them safe. I also am close to a dog friendly park where all dogs are on leashes. I will not take a dog off leash when he/she is in my care. My experience administering medication Yes with my kennel experience, I am very comfortable administering medication. I am also comfortable administering shots for dogs and cats. I am a full time pet care provider and a dog walker and i have been training dogs of all breeds for the last 30 years. I give all my furry guest lots of play time and walks and all of our guest hang out with us we are cage free unless your owner wants your dog to sleep in one

Sitter Profile Image: Claudia H.
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Claudia H.
from
$58
per night
5.0 out of 5 stars
139 reviews
78 repeat clients
20 years of experience
Monroe, CT, 06468

Bosco came home happy & tired !!i knew Claudia took good care of him. She was telling me things about him that only a Mom would know .. I now consider Claudia a trusted guardian :) Thank you !!!

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Betty C.
Sitter Profile Image: ATHENA M.
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ATHENA M.
Star Sitter
from
$65
per night
5.0 out of 5 stars
3 reviews
3 repeat clients
18 years of experience
Carmel Hamlet, NY, 10512

Athena, watched my two pups for 5 days! She was great, she came to pick up and drop the pups. She sent me daily photos and updates of them! Very friendly and my pups spent a great time with her! I highly recommend!

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

Our young dog had a great time with Isabel and her family and will be visiting again in a couple weeks. I love that our dog gets to play with children and other dogs when she is there, and is treated as one of the family.

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Elizabeth K.
Sitter Profile Image: Celina I.
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Celina I.
from
$35
per night
5.0 out of 5 stars
23 reviews
8 repeat clients
6 years of experience
Poughkeepsie, NY, 12603

Thank you so much! I’m glad Toque was able to make some new fury friends. He will definitely be back for a play date or overnight sleepover 🐶

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Myrna T.
Sitter Profile Image: Mary Ann P.
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Mary Ann P.
Star Sitter
from
$75
per night
5.0 out of 5 stars
27 reviews
6 repeat clients
14 years of experience
Cornwall, CT, 06753

Once again Mary Ann lovingly looked after our dog. We are so happy to know our dog is very well cared for and looked after when with May Ann.

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Gary S.
Sitter Profile Image: Tinaclem L.
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Tinaclem L.
Star Sitter
from
$60
per night
4.9 out of 5 stars
61 reviews
12 repeat clients
18 years of experience
Danbury, CT, 06811

Ezzy spent almost 10 days with Clementina and was very well-cared for. Clementina always takes her out for walks, sends me pictures, and I trust her completely.

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Ellen B.
Sitter Profile Image: Kyle K.
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Kyle K.
Star Sitter
from
$62
per night
5.0 out of 5 stars
135 reviews
37 repeat clients
21 years of experience
Danbury, CT, 06810

Kyle was great with our two pups! We were in a last minute bind as our usual boarding place closed. We had never used Rover before, but it was recommended and we are so happy we found Kyle. He asked great questions during our initial meet and greet, showing he was well prepared and he knew what was best for the dogs. He sent pictures while we were away and was very timely on all communication. We will definitely be using Kyle again!

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Samantha C.
Sitter Profile Image: Jennifer & Thomas H.
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Jennifer & Thomas H.
from
$45
per night
5.0 out of 5 stars
5 reviews
1 repeat client
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!

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Danielle N.
Sitter Profile Image: Kathleen D.
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Kathleen D.
Star Sitter
from
$40
per night
5.0 out of 5 stars
12 reviews
3 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: Valerie M.
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Valerie M.
from
$66
per night
4.9 out of 5 stars
71 reviews
37 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: Erika N.
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Erika N.
Star Sitter
from
$50
per night
5.0 out of 5 stars
38 reviews
8 repeat clients
20 years of experience
Carmel, NY, 10512

We are so happy to have found Erika! She takes great care of our 19lb doodle and sends lots of photos. She’s super easy to communicate with and is very personable as well.

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Erin P.
Sitter Profile Image: Marie F.
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Marie F.
from
$70
per night
5.0 out of 5 stars
13 reviews
2 repeat clients
15 years of experience
Carmel, NY, 10512

Marie was so wonderful to Madison (!!!!). Although I was far away, they kept me updated with pictures and texts along the way. I appreciate all that Marie does and couldn't ask for a better sitter.

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Jasmyn J.
Sitter Profile Image: Kenniqua B.
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Kenniqua B.
from
$45
per night
5.0 out of 5 stars
14 reviews
1 repeat client
10 years of experience
Marlboro, NY, 12542

Kenniqua was incredible! She took my request last minute due to a family emergency, and she really eased the stress of that weekend. Our dog was happy, got to sleep on the bed, and got walks. Her space was calm and her dog Honey was a sweetie. Kenniqua provided updates and wonderful communication. Will definitely ask Kenniqua to care for my pup again. Thank you for helping us out, Kenniqua!!

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Ashanti S.
Sitter Profile Image: Jonhnattan Jose C.
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Jonhnattan Jose C.
from
$50
per night
4.7 out of 5 stars
9 reviews
3 repeat clients
10 years of experience
Danbury, CT, 06811

I can't say enough great things about Jonathan and the care he provides for my two babies Louie and Chase. Like many pet owners, my babies mean the world to me and it takes a lot for me to trust someone with them. Jonathan cares for my dogs as if they were his own. He is extremely professional, responsible, and caring. His scheduling system is very easy to use and he provides very personalized care easy to reach and gives updates after her visits. He is very flexible and reliable and has made my life much easier. I highly recommend Jonathan to anyone looking for a dog sitting service.

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Gina D.
Sitter Profile Image: Katlyn & Stephen B.
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Katlyn & Stephen B.
from
$50
per night
5.0 out of 5 stars
2 reviews
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: Judy & Steven C.
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Judy & Steven C.
Star Sitter
from
$50
per night
5.0 out of 5 stars
11 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: Thalya V.
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Thalya V.
Star Sitter
from
$57
per night
5.0 out of 5 stars
27 reviews
9 repeat clients
6 years of experience
Poughkeepsie, NY, 12603

Thalya did great with my pup Apollo! She took him out for long walks to get his energy out and sent frequent updates and pictures letting me know how things were going. Highly recommended! I felt at ease knowing my pup was in good hands.

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Alex C.
Sitter Profile Image: Matthew H.
Verified Enhanced Background Check
Matthew H.
Star Sitter
from
$60
per night
4.9 out of 5 stars
13 reviews
4 repeat clients
20 years of experience
Poughkeepsie, NY, 12603

Matthew and his family are excellent dog caregivers! They have a very large fenced yard for the dogs to play. They are very attentive and sent many photos! I have an older newly adopted dog, they were so sweet and gentle with her. I highly recommend them!!!

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Kim F.
Sitter Profile Image: Christine A.
Verified Background Check
Christine A.
Star Sitter
from
$97
per night
4.9 out of 5 stars
98 reviews
32 repeat clients
33 years of experience
Stanfordville, Stanfordville, NY, 12581

Christine is awesome!!! She’s a dog whisperer and a cat lover whose house is totally pet friendly. Our puppy was so happy with Christine and we will definitely book again whenever we need dogsitting. She’s so comfortable with animals and makes them feel loved. She took amazing care of our baby ❤️ Highly recommend!!!

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MG G.
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The median cost per night for pet 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 pets like family

  1. 1. Search

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

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Sitters in Wingdale average 10
repeat pet boarding clients

FAQs for Dog Boarding - Wingdale

Frequently asked questions about Rover

The average cost for Pet 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 Pet 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 Pet Boarding. For more information on service fees, click here .

There are 757 sitters on Rover for Pet Boarding in Wingdale. About 91% of Wingdale sitters can respond to requests in under 60 minutes. Whether you’re planning ahead for holidays, need last-minute care, or need same-day coverage for an urgent trip, you can message multiple sitters at once to find available care.

Once you find the right match, you can arrange a Meet & Greet to ensure they are a perfect fit for your pet’s personality before confirming.

If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.

The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.

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.

A Meet & Greet is a short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

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. Cats may be required to have Feline Viral Rhinotracheitis and Rabies up to date.

By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.

Emergency support is available by phone or email in English 24/7. When an incident occurs, we recommend that sitters contact our Trust & Safety team immediately so that they can connect your sitter with a board-certified veterinarian or offer other resources to help.

If a sitter needs to cancel at the last minute, Rover’s reservation protection means our team will work with you to find a suitable replacement as quickly as possible.

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