Dog Boarding in Wingdale, NY

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Top rated Wingdale dog boarders

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
334 reviews
130 repeat clients
49 years of experience
Pawling, NY, 12564

Annette is wonderful with my old girl Kota , and I have also seen how well she treats all her furry guests , Kota gets a toy and treats when she comes home , i do not have the anxiety I use to when we went on a trip ,,, highly recommended ,, Jane

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

Daisy lived her overnight stay with Saori. She came home happy and super relaxed. I loved getting photo updates throughout her stay. I knew Daisy was in good hands and it helped make my trip so much more enjoyable knowing she was safe and well cared for. I’ll be booking again soon.

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Lisa G.
Sitter Profile Image: Erika N.
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Erika N.
Star Sitter
from
$50
per night
5.0 out of 5 stars
37 reviews
8 repeat clients
20 years of experience
Carmel, NY, 10512

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!

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Mike T.
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
3 repeat clients
25 years of experience
Danbury, CT, 06810

This is my second time having my fur baby with Sue. It was a much longer visit this time (a week) amd Sue remained her kind communicative self. Would recommend in a heartbeat. She goes above and beyond. Thank you! 💕

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Rachel C.
Sitter Profile Image: Donna w.
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Donna w.
Star Sitter
from
$35
per night
5.0 out of 5 stars
29 reviews
11 repeat clients
50 years of experience
Poughkeepsie, NY, 12603

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!

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

Mildred and her family provided excellent care for my dog Mochi. She was also very friendly and professional in the way she related to me. I would certainly recommend her as a pet care provider.

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Tom H.
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
133 reviews
62 repeat clients
19 years of experience
Pleasant Valley, NY, 12569

Loretta and her family embraced Sherley right away - so sweet! We got lots of great pics and updates, and really felt comfortable even though we were away from our puppy for so long. When we have another trip, we will definitely contact Loretta again.

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

Volha and her family are incredible dog sitters. Volha goes above and beyond for the pets in her care and is very adaptable to each pet’s individual needs. She is flexible and her pick up and drop off option came in handy for our pets as they are larger dogs and typically can’t ride in Ubers or the subway. Volha communicated with us every day and sent plenty of photos. Her entire family loves animals and it was clear from the photos that our pets had an incredible time in her care. I could tell my two dogs did not want Volha to leave and truly loved their time with her. I will definitely use her again in the future. Thank you Volha for everything!!!

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

I am so happy to have found Clementina. She is lovely and warm and took such very good care of Ezzy. She has a huge backyard and a dogpark nearby and Ezzy got great exercise daily. She sent me lots of pics and was flexible and accommodating when I asked if Ezzy could stay a little longer than I had planned. Her daughter also was there and Ezzy kissed everyone goodbye when we left and wagged furiously. 5 stars.

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Ellen B.
Sitter Profile Image: Stephen N.
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Stephen N.
Star Sitter
from
$110
per night
5.0 out of 5 stars
32 reviews
11 repeat clients
25 years of experience
Beekman, NY, 12533

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.

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Paul F.
Sitter Profile Image: Jessica O.
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Jessica O.
from
$45
per night
5.0 out of 5 stars
19 reviews
2 repeat clients
10 years of experience
Danbury, CT, 06811

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!

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Faye B.
Sitter Profile Image: Maria V.
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Maria V.
Star Sitter
from
$45
per night
5.0 out of 5 stars
59 reviews
24 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: Rachael C.
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Rachael C.
Star Sitter
from
$75
per night
5.0 out of 5 stars
60 reviews
19 repeat clients
10 years of experience
Danbury, CT, 06810

Rachael is the best dogsitter ever! She always seems to have a house full of dogs (some her own, some sittees), and my dog has a wonderful time and even comes home a little more trained! I cannot recommend her enough -- she is warm and kind and clearly just loves dogs.

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Maia H.
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
29 repeat clients
20 years of experience
Danbury, CT, 06810

Once again Nicole took good care of Lulu while we were away, she always check in once a day with a photo to give us a peace of mind. Thx again for watching lulu!

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Angelica H.
Sitter Profile Image: Jeff H.
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Jeff H.
from
$64
per night
5.0 out of 5 stars
208 reviews
70 repeat clients
30 years of experience
Poughkeepsie, NY, 12603

Jeff and Bruce were great about staying in touch with me about my dog and sent pictures as well. They have ample indoor and outdoor space. This was my first time using Rover.com and I am very happy to have found such caring and responsible people to watch my dog.

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

Cherissa was an amazing host. I had a cancellation last minute with a sitter due to an emergency and she was available and so easy to work with. She shared pictures and updates of our puppy multiple times throughout the day of what my fur baby was doing. I will definitely be booking with Cherissa again.

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Jun C.
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: Dew G.
Verified Enhanced Background Check
Dew G.
Star Sitter
from
$68
per night
5.0 out of 5 stars
53 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.
Verified Enhanced Background Check
Jessica & Ian K.
Star Sitter
from
$65
per night
5.0 out of 5 stars
71 reviews
32 repeat clients
25 years of experience
Sandy Hook, CT, 06482

Jessica and Ian were so welcoming and caring for Maya. They were very responsive and did a great job taking care of our little girl. Highly recommended!

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John J.
Sitter Profile Image: Valerie M.
Verified Background Check
Valerie M.
from
$66
per night
4.9 out of 5 stars
69 reviews
37 repeat clients
54 years of experience
Sandy Hook, CT, 06482

Valerie and her family are amazing hosts and extra loving caretakers. Jameson has his second extended stay with Valerie and he had a wonderful time. I take comfort in knowing he loves staying with Valerie, her children, and sweet Shakespeare when we are on vacation. They truly treat him like their own and he clearly loves them all. We will be back :)

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Brittany C.
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Over 37
pet parents in Wingdale have booked dog boarding

How Rover works

  1. 1. Search

    Read verified reviews by dog parents like you and choose a boarder who’s a great match for you and your dogs
  2. 2. Meet & Greet

    Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

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

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 dog boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.

  • World-class support

    We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.

Sitters in Wingdale average 12
repeat dog boarding clients

Dog Boarding FAQs

Frequently asked questions about Rover

As of Jun 2026, the median cost of dog boarding in Wingdale is $63 per night, including service fees. Boarding your dog for one week typically costs $441. Sitters on Rover set their own rates based on their qualifications, your dog's needs, and their space's amenities. As a result, most Wingdale dog boarding rates can be found as low as $43 to as high as $66 per night.

If you’re searching for a Wingdale dog boarding sitter for the first time, visit the sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, 327 sitters provided dog boarding in Wingdale. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, dog boarding sitters joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple sitters about your booking. Typically, 90% of Wingdale dog boarding sitters respond in under an hour.

Sitters who provide dog boarding in Wingdale have an average of 19 years of experience. Dog boarding sitters with repeat customers have an average of 12 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters in Wingdale.

Rover makes it easy to find Wingdale dog boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog boarding is great for:

  • Dogs of all ages and abilities, including puppies
  • Pet parents looking for a safe, loving alternative to a kennel
  • Dogs who’d love to socialize with their sitter’s pets

There are 327 dog boarding sitters in Wingdale on Rover, so you’re sure to find the perfect match for your dog! In Wingdale, 96% of sitters offer daily exercise, 100% offer medication administration, and 96% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog boarding sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog boarding sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your dog boarding sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your dog boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.