Dog Boarding Pleasantville

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Pleasantville, Find top rated dog boarding

Prices are estimates per night for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.

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Sitter Profile Image: Christine N.
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Christine N.
Star Sitter
$56
total per night
5.0 out of 5 stars
• 12 reviews
2 repeat clients
21 years of experience
Newmarket, ON, L3Y

“Christine was great with my dog! My dog is on a special diet, and Christine was very careful and responsible about following all my instructions. She got along with my dog really well, and I’m so happy I finally found someone I feel comfortable trusting with her. Highly recommend Christine!”

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Lana F.
Sitter Profile Image: Tsz K.
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Tsz K.
Star Sitter
$58
total per night
5.0 out of 5 stars
• 19 reviews
3 repeat clients
5 years of experience
Aurora, ON, L4G

“We absolutely loved having Tsz take care of Billa! This was our second time using her, and once again, she went above and beyond. She sent us such detailed and frequent updates, which gave us so much peace of mind while we were away. It was clear that she cared for Billa as if he were her own. She even went the extra mile and bought Billa a toy, which was such a sweet and thoughtful surprise! 🥹 You can truly tell how much she cares about the pets she looks after. We will absolutely be using her again and highly recommend her to anyone looking for someone trustworthy, caring, and attentive. Billa clearly had an amazing time!”

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Ranusha P.
Sitter Profile Image: Xi S.
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Xi S.
Star Sitter
$56
total per night
5.0 out of 5 stars
• 7 reviews
3 repeat clients
5 years of experience
East Gwillimbury, ON, L9N

“Xi always takes care of Lemon as if he were her own dog. She is truly amazing—she sends lots of photo and video updates, which always gives me peace of mind. Lemon always comes home happy, relaxed, and well cared for. It really feels like a second home because of all the love, attention, and care he receives. Thank you so much, Xi! We appreciate everything you do.”

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Samia B.
Sitter Profile Image: Jiayi Z.
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Jiayi Z.
$50
total per night
4.9 out of 5 stars
• 26 reviews
6 repeat clients
15 years of experience
Newmarket, ON, L3X

“We are very grateful to Jiayi for taking such wonderful care of our dog, Tileh. She sent us photos and videos every day, which made us feel connected and reassured while we were away. Tileh looked happy, relaxed, and well cared for throughout his stay. Jiayi was responsive, professional, and clearly loves dogs. We would not hesitate to leave Tileh with her again and highly recommend her to other pet owners.”

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Payman J.
Sitter Profile Image: Matthew M.
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Matthew M.
Star Sitter
$54
total per night
5.0 out of 5 stars
• 59 reviews
26 repeat clients
20 years of experience
Aurora, ON, L4G

“Matthew took wonderful care of our sweet golden retriever, giving her lots of love and exercise while we were away. We appreciated the frequent updates and pictures he provided and would highly recommend him. Thank you!”

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Andrea B.
Sitter Profile Image: Dommond N.
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Dommond N.
Star Sitter
$56
total per night
5.0 out of 5 stars
• 182 reviews
36 repeat clients
30 years of experience
Richmond Hill, ON, L4E

“Maple and Nono really enjoy their stay at Dommond’s place. We got photos and videos from them daily and they keep us posted for everything. Will definitely recommend”

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Shannon Q.
Sitter Profile Image: JUN X.
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JUN X.
Star Sitter
$45
total per night
5.0 out of 5 stars
• 14 reviews
9 repeat clients
3 years of experience
RICHMOND HILL, ON, L4E

“I am so grateful for the amazing job Jun did for Cooper. He went beyond my expectations to make Cooper welcome and care for him with love. For dogs owners in the area, look no farther. Jun is absolutely the best. I will always trust him with my dog and I am sure that Cooper is looking forward to his next visit! Amazing job. Thanks Jun from the bottom of my heart.”

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Constance P.
Sitter Profile Image: Rae Z.
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Rae Z.
Star Sitter
$56
total per night
4.9 out of 5 stars
• 159 reviews
57 repeat clients
50 years of experience
Aurora, ON, L4G

“Rae is wonderful and our dogs love her! They are always well cared for and happy and excited to return. Thank you Rae for loving our girls so we'll!!”

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Carol S.
Sitter Profile Image: Simone S.
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Simone S.
$62
total per night
5.0 out of 5 stars
• 14 reviews
4 repeat clients
10 years of experience
Newmarket, ON, L3Y

“Our 16 year old Cockapoo was well looked after while we were on holiday. My wife was initially worried as our dog is aging and this was our first time with Simone. Our regular sitter has moved. We won’t hesitate in scheduling our next trip with Simone. Thanks you!!”

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Michael L.
Sitter Profile Image: Nancy K.
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Nancy K.
$43
total per night
5.0 out of 5 stars
• 11 reviews
3 repeat clients
8 years of experience
Aurora, ON, L4G

“I will only trust my cat to Nancy! My cat Simba stayed with Nancy for one week (it is worth mentioning that Simba is a very sensitive and not social cat). Nancy took the best care of him, sent me lots of photos and videos every day, Simba was very comfortable with Nancy and he became a best friends with her cat Pumpkin. Nancy is professional! It was a very good experience. Thank you Nancy!”

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Valentina N.
Sitter Profile Image: Li L.
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Li L.
$56
total per night
5.0 out of 5 stars
• 6 reviews
2 repeat clients
3 years of experience
Markham, ON, L6C

“I’m so grateful for the wonderful care Li provided for Jelly. She is experienced, attentive, and genuinely cares about Jelly. She kept me updated with many photos and videos, which gave me great peace of mind while I was traveling. I could relax knowing my dog was in such loving and capable hands. Highly recommend!”

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Shirley W.
Sitter Profile Image: Yvonne Y.
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Yvonne Y.
Star Sitter
$50
total per night
5.0 out of 5 stars
• 44 reviews
10 repeat clients
7 years of experience
Richmond hill, ON, L4E

“I’ve had the pleasure of knowing the best Rover ever! She was incredibly attentive to my eight-month-old kitten and eight-year-old Chihuahua. My dog and cat are both thriving with her cats. She keeps us updated with lots of pictures and videos daily. My cat even has her own cozy room. Highly recommend!”

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Rui X.
Sitter Profile Image: Mehak A.
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Mehak A.
$50
total per night
5.0 out of 5 stars
• 5 reviews
1 repeat client
8 years of experience
Bradford, ON, L3Z

“Daisy had a great time with Mehak and her family! She was very communicative and great with keeping us updated and sending lots of pictures! We were very pleased with our booking and would love to book with Mehak again!”

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Amber T.
Sitter Profile Image: Shirley B.
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Shirley B.
Star Sitter
$69
total per night
5.0 out of 5 stars
• 54 reviews
16 repeat clients
20 years of experience
Stouffville, ON, L4A

“Shirley was absolutely fantastic! This was our first time leaving our pup Cola with non-family and Shirley was so reassuring. She sent us regular updates with lots of pictures and even slept with Cola on the couch every night to make sure she wasn’t scared in a new place. She took her on lots of walks and gave her so much love. It’s clear that she is very experienced with dogs and really cares. Thank you Shirley!!”

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Lindy S.
Sitter Profile Image: John H.
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John H.
$84
total per night
5.0 out of 5 stars
• 15 reviews
8 repeat clients
30 years of experience
NEWMARKET, ON, L3Y

“After our regular sitter became unexpectedly unavailable, we tried the Rover app for the first time and are beyond grateful for having come across John & Lisa. From initial contact, they were incredibly responsive, communicative and wonderful to deal with. We felt comfortable even before dropping Bella off and confident she was going to be in good hands. Bella is quite timid at first but through the photos/messages we were regularly provided, it was clear that she felt safe and warmed up quickly. So much so that we’re convinced Bella was a little depressed after we picked her up lol John/Lisa - thank you both so much for making our first Rover experience a pleasant one and for taking such great care of our fur baby. We will undoubtedly be booking with you both again!”

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Christina K.
Sitter Profile Image: David G.
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David G.
Star Sitter
$47
total per night
5.0 out of 5 stars
• 81 reviews
29 repeat clients
6 years of experience
Richmond Hill, ON, L4S

“Because of some last-minute changes in our plans, we found David G just one day before our trip to take care of our dog, Mulan. Since Mulan had never been away from us for such a long time, we were quite worried at first. But David took care of her with great attention, sending us photos every day and giving us daily updates on how she was doing, which really put our minds at ease. We will definitely choose David again and highly recommend him!”

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Jason S.
Sitter Profile Image: Parishi Y.
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Parishi Y.
$62
total per night
5.0 out of 5 stars
• 10 reviews
2 repeat clients
20 years of experience
Newmarket, ON, L3Y

“Parishi took wonderful care of Missy! Missy came home happy and tired - a tired dog is a happy dog (it means lots of play time and fun was had). Thank you again!”

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Jess M.
Sitter Profile Image: Megan R.
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Megan R.
$67
total per night
5.0 out of 5 stars
• 169 reviews
73 repeat clients
12 years of experience
Newmarket, ON, L3Y

“my usual sitter wasn’t available and I came across Megan. If she was closer to where I live, she would have been a usual sitter for me! She was amazing and accommodating. Her response time is immaculate and it made the my trip that much smoother! I would recommend Megan as a sitter!”

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Aurrora G.
Sitter Profile Image: Stuart H.
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Stuart H.
$67
total per night
5.0 out of 5 stars
• 10 reviews
1 repeat client
35 years of experience
Newmarket, ON, L3X

“Our girl has never been left with anyone but my brother before this 2 week vacation and she's been with us for 5 years! Finding Stuart on Rover seemed to good to be true, but Stuart and his wife exceeded our hopes for having the best care possible for our girl. Stuart's connection and genuine care for our dog was instantaneous and obvious. Stuart's extensive experience with dogs results in his calm, accurate understanding of a dog's individual personality. Our girl connected with Stuart immediately. Her positive reaction confirmed my own confidence in Stuart's ability to care for her. Stuart and his wife provided a warm, comfortable, welcoming home where our dog was happy and healthy. All our dog's needs were met and then some: walks, food, play, comfort and companionship. This was clear from the start and was confirmed when we returned to pick up our girl who was calm and had no anxiety at all after spending 2 weeks in the incredible care of Stuart and his wife!”

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Candace S.
Sitter Profile Image: Elizabeth W.
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Elizabeth W.
$35
total per night
10 years of experience
Newmarket, ON, L3Y

About: I grew up with various pets and have always loved animals. I was trusted to walk and feed neighborhood dogs on numerous occasions. My family dog lived 13 years and our cat lived 20. I got my own dog as a puppy 5 years ago and did her training. I also got a kitten last year. I am currently working at home full time I have my own business and have a pretty flexible schedule for morning or afternoon pet care throughout the week I live in a quiet street with lots of green space and parks and trails close by. My dog is friendly and always loves a friend to play with. I also have a crate and baby gate if needed.

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Dog parents share their Rover experiences - Pleasantville

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5.0 out of 5 stars

Christine is amazing! She communicates well, is very pleasant, flexible and I am so happy to have her watch our dog. He had a great time, they walked, played, cuddled and it was nice to get photo updates. I would highly recommend Christine to anyone and will definitely be taking our boy to her in the future.

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Diane P.
Boarding
5.0 out of 5 stars

Simone took really great care of Daisy and treated her like part of the family. We will definitely have her stay with Simone in the future!

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Kerrie C.
Boarding
5.0 out of 5 stars

From all the videos Luna looked like she was having the time of her life! Thank you for looking after her, will definitely have to have her go to you again.

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Sina S.
Boarding
5.0 out of 5 stars

Rena had another great stay with Anna. She enjoyed her time with the other dogs and was well loved. I am so comfortable with leaving her in such good hands.

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Natalie R.
Boarding
5.0 out of 5 stars

What can I say about Kiera? Only that she went over and beyond our expectations! Last minute changes had us scrambling for a dog sitter and no one had availability for us but then Kiera, originally declining us, messaged us back to say she would make an exception in our case! We are so thankful for her being so accommodating and taking care of Rocky as her own! She provided us with regular photos and updates as to how he was coming along. We are extremely happy with the care she took of Rocky. He seemed very comfortable with her, based on the pics she sent us. Thank you again Kiera! We will 100% use her services in the future when needed! 😊

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Josie A.
Boarding
5.0 out of 5 stars

Pivonne is always a great host to Zoey! We get photos and feedback daily which is great. We already repeated the stay 3 times and hope to continue to do so! Highly recommend :)

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Maria B.
Boarding
5.0 out of 5 stars

As first-time Rover users, we were quite stressed about leaving our dog with someone new. Liu made the entire experience so much easier. She is incredibly responsive, caring, and attentive. She provided regular updates and photos, which gave us great peace of mind while we were away. She was also very flexible and accommodating. Most importantly, she took wonderful care of our dog, and we could tell our dog was happy and well looked after. We highly recommend Liu and would not hesitate to book with her again!

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Lorraine A.
Boarding
5.0 out of 5 stars

Jennah took great care of Jimmy over this past weekend, checked in with me and sent pictures. I would definitely recommend Jennah and book again!

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Karen I.
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.

Popular requests for dog boarding - Pleasantville

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FAQs for Dog Boarding - Pleasantville

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 postal code to find sitters within walking distance in your neighbourhood.

Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Pleasantville 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 favourite hang-out spots in your Pleasantville

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.

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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet.

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they do not have any disqualifying offences.

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.

Yes, you can find sitters who have experience administering medication or managing dietary requirements. You can also find pet sitters who accept only one pet at a time, which is ideal for anxious puppies or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and request a Meet & Greet to walk your sitter through your expectations.

sitters on Rover set their own cancellation policy, which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.

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