Dog Boarding Cragsmoor

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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: Andrea J.
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Andrea J.
Star Sitter
from
$65
per night
5.0 out of 5 stars
• 27 reviews
12 repeat clients
20 years of experience
ellenville, NY, 12428

“I am super new to Rover, Andrea helped every step of the way. I am very grateful for how kind and thoughtful she was. She was very good with Thor and he seemed like he had a nice time. Thank you so much would trust her again.”

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

“Gab is just great with Harper. This is our second time boarding her at Gab’s. We are so fortunate to have found him and his wife Annie. Now we can go away and feel very relaxed. They even taught her to go up and down a full flight of stairs. Harper loves to socialize with Gab and the other dogs. Great place to leave your pet. Everyone is happy all around.”

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Denise W.
Sitter Profile Image: Alexis A.
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Alexis A.
Star Sitter
from
$70
per night
5.0 out of 5 stars
• 48 reviews
14 repeat clients
25 years of experience
Middletown, NY, 10940

“Alexis took great care of our dogs and provided regular updates. She was thoughtful, accommodating, and considerate with all of our plans. Would absolutely recommend her and would definitely book with her again!”

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Sarah A.
Sitter Profile Image: Kristen Elise S.
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Kristen Elise S.
from
$50
per night
5.0 out of 5 stars
• 5 reviews
2 repeat clients
20 years of experience
Kerhonkson, NY, 12446

“Kristen was very accommodating and my pup seemed very happy in her home. My dog is usually very anxious at first but she calmed down quickly with Kristen and her sweet dog Jackson. Will definitely use her again.”

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Lisa D.
Sitter Profile Image: Beckie M.
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Beckie M.
from
$45
per night
4.6 out of 5 stars
• 12 reviews
4 repeat clients
15 years of experience
Walden, NY, 12586

“Beckie and her family were the perfect home away from home for our high-energy 2yo German Shepherd. She has a beautiful and massive back yard and provided photo updates throughout the stay. We’ll happily trust Beckie with Echo on future trips and highly recommend her!”

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Chelsea M.
Sitter Profile Image: Kenniqua B.
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Kenniqua B.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 19 reviews
4 repeat clients
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: Cherissa P.
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Cherissa P.
Star Sitter
from
$70
per night
5.0 out of 5 stars
• 28 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!”

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Mark P.
Sitter Profile Image: Jordan P.
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Jordan P.
from
$35
per night
5.0 out of 5 stars
• 2 reviews
1 repeat client
12 years of experience
Poughkeepsie, NY, 12601

“Jordan was the best!! I called last minute and she graciously accepted my request! Jasper was so happy and well cared for.. I TOTALLY recommend her!!!”

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

“Volha was great to our dog. She sent me pictures on a regular basis while he was in her care. Her daughter was super sweet to our dog as well, which was awesome. Thanks for everything Volha!”

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Rene C.
Sitter Profile Image: Rebecca D.
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Rebecca D.
from
$45
per night
5.0 out of 5 stars
• 72 reviews
24 repeat clients
26 years of experience
Highland, NY, 12528

“Rebecca watched our Golden Retriever for 10 days while we were away internationally, and she was incredibly trustworthy and communicative. She eased all of our worries about being away from our family member for so long. She sent regular updates and photos, and you could tell how much care and attention she gave during his stay. Our dog seems to miss her now that we have him back, which shows what kind of person she is! I would 100% use Rebecca’s services again.”

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Alexandra H.
Sitter Profile Image: Leslie P.
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Leslie P.
from
$65
per night
5.0 out of 5 stars
• 28 reviews
4 repeat clients
5 years of experience
New paltz, NY, 12561

“Leslie and her lovely family took great care of our dog Newt during a long trip! She provided great communication and updates - including pics of Newt enjoying lots of snuggles. When he ran low on food she very kindly took the effort to seek out a special diet food to meet his needs. We really appreciated knowing he was in great hands!”

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Christina B.
Sitter Profile Image: Hali M.
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Hali M.
from
$80
per night
5.0 out of 5 stars
• 12 reviews
3 repeat clients
25 years of experience
Thompson ridge, NY, 10985

About: Looking for a caring and dependable pet sitter while you're at work or on vacation? I offer up to four drop-in visits a day, making sure your pets stay safe, happy, and stress-free in the comfort of their home! With years of experience caring for pets of all kinds, I know how important it is to give each one the love and attention they deserve! Whether your cat needs a quick check-in while you're at work or your dog needs full-time care while you're away. I provide a variety of pet sitting services, including feeding, walks, playtime, and medication administration as needed. My flexible scheduling means we can create a plan that works perfectly for you and your pets. You'll receive daily updates with potty reports and photos of your pets. I’m also happy to water plants, take out the trash, check the mail, and bring in packages while you're away. I also have years of experience with horses and farm animals, including mucking stalls, turnout, feeding, and grooming. Contact for rates! I have many flexible scheduling options for short walks or check-ins while you're away at work, or long terms pet care while you're away on vacation. As a professional pet sitter, I understand that each pet has its own unique needs and personality. That's why I take the time to get to know each pet I care for in my client's home, so I can provide them with the best possible care. When I arrive at your home, I will first greet your pet and provide them with food and water, as well as any medications or supplements they require. I will also spend time playing with your pet, giving them plenty of attention and affection. During my visit, I will take your dog for a walk, giving them the exercise and fresh air they need to stay healthy and happy. If you have a cat, I will spend time playing with them and keeping their litter box clean. I will also make sure your home is safe and secure, checking that all doors and windows are locked and that your pet has access to any areas they need. Throughout my visit, I will keep you informed of your pet's well-being, sending you updates and photos so you can see how your furry friend is doing. Above all, I will treat your pet with the same care and attention that I would give to my own pets, ensuring they feel loved and well-cared for while you're away.

Sitter Profile Image: Jillian B.
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Jillian B.
from
$68
per night
5.0 out of 5 stars
• 1 review
15 years of experience
Goshen, NY, 10924

“Jillian was great with our dog Rufus! He loved the freedom of the large fenced in backyard that he could freely roam and run around in with Jillian's two dogs! Rufus made new friends! We highly recommend Jillian and will definitely book with Jillan again soon!”

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Mary Ellen H.
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
• 13 reviews
5 repeat clients
40 years of experience
Poughkeepsie, NY, 12603

“Our little guy, Wrigley, had an absolutely wonderful stay with Judy and Steven! I wholeheartedly recommend them to anyone looking for a warm, welcoming environment for their pup. As a beagle, Wrigley usually hates being left behind—but I felt completely at ease knowing he was in such caring hands. He got the royal treatment with pup cups, plenty of love and attention, and he even made a new friend in their sweet dog, Ginger. Thank you, Judy and Steven, for making Wrigley feel so at home and for giving me such peace of mind!”

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Susan & Dave J.
Sitter Profile Image: Diana H.
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Diana H.
from
$75
per night
5.0 out of 5 stars
• 8 reviews
1 repeat client
18 years of experience
Middletown, NY, 10941

“This was our first time leaving our English Bulldog with a stranger. Diana made me feel at ease by providing constant updates and pictures of our dog. You were amazing, thank you! We will definitely be using you again.”

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Paola P.
Sitter Profile Image: Katarzyna R.
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Katarzyna R.
from
$60
per night
4.9 out of 5 stars
• 70 reviews
15 repeat clients
24 years of experience
Bloomingburg, NY, 12721

“Such an amazing experience! This was our first time leaving both our dogs with someone and they can be quite the handful. I had so much anxiety leaving them with someone but Katarzyna put all of my fears to rest as soon as I met her! She has a beautiful yard and sent us picture updates of the dogs. Would recommend her to anyone.”

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Jessica H.
Sitter Profile Image: Monica & Jeremy K.
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Monica & Jeremy K.
from
$70
per night
5.0 out of 5 stars
• 14 reviews
2 repeat clients
30 years of experience
Modena, NY, 12548

“They treated my pup so well. Honestly couldn't have asked for a better sitter. Kept my pup busy with puzzles, and outdoor activities. Made their home feel like his own. So grateful for them. I trust them to watch Cash in the future.”

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Aaron J.
Sitter Profile Image: Lauren S.
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Lauren S.
from
$52
per night
5.0 out of 5 stars
• 5 reviews
15 years of experience
Rock Tavern, NY, 12575

“Highly recommended!! Lauren took great care of my pup while I was away for the weekend. She sent me pictures and regular updates throughout the day to keep my mind at ease. I will definitely use her again!”

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Andrew E.
Sitter Profile Image: Jacqueline V.
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Jacqueline V.
Star Sitter
from
$80
per night
5.0 out of 5 stars
• 29 reviews
7 repeat clients
25 years of experience
Kingston, NY, 12401

“Jacqueline is an absolutely amazing dog sitter! Took fantastic care of my dog, Koda, and took so many pictures, which I really appreciated. He was treated like her own, and I felt completely at ease knowing he was in such good hands. Highly recommend!”

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Lexi M.
Sitter Profile Image: Emily L.
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Emily L.
from
$65
per night
5.0 out of 5 stars
• 4 reviews
10 years of experience
New Paltz, NY, 12561

“Emily is amazing! I live in LA but was visiting my mom in Woodstock and needed a dog sitter last minute for my little senior dog, Rihanna. Emily graciously took her for a house sit in her home for a long weekend. Emily was thorough and asked about Rihanna’s routine, taking care to follow it well. I can tell that Emily has extensive experience with pets and a special love for them. Rihanna required both liquid and pill medicines that Emily took care to give her 2x a day. Emily also sent photo updates in the app and kept me informed about how Rihanna was doing. Rihanna seemed extremely happy with Emily, and I can tell that she got lots of love. She can be anxious when traveling, but Emily’s calm presence was great for her. I would 100% select Emily again!”

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Melissa D.
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Dog parents share their Rover experiences - Cragsmoor

1 / 1
5.0 out of 5 stars

We are so grateful our best girl was so taken care of!! Thank you so much Andrea for loving Lily while we were away, she had a great time!

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Stephen C.
Boarding
5.0 out of 5 stars

Andrea is super reliable and keeps the pup always well taken care of. Second visit here and always very satisfied

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Vikas B.
Boarding
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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.

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.
  3. 3. Book & Pay

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

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FAQs for Dog Boarding - Cragsmoor

Frequently asked questions about Rover

Rover is the largest marketplace for local pet care. Whether you're looking for pet sitters, dog walkers, or house sitters who specialize in pet sitting, you can narrow your search by entering your ZIP code to find sitters within walking distance in your neighborhood.

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.

Depending on the sitter, their home environment, and your dog’s needs, daily exercise 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 Cragsmoor 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 Cragsmoor.

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 Cragsmoor 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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