Dog Boarding Westchester

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Over 288
pet parents in Westchester have booked dog boarding

Westchester, 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: DAMACIA J.
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DAMACIA J.
Star Sitter
from
$28
per night
5.0 out of 5 stars
• 339 reviews
94 repeat clients
30 years of experience
North Chesterfield, VA, 23236

“Damacia is was amazing! I found him on Rover after reading through several reviews, and I’m so glad I chose him. He was very responsive and stayed in touch throughout my entire time away, including sending pictures and videos. My dog, Jaxson, has never been around other dogs before, so I know this was a new experience for him but based on the updates I received, he did great. Damacia made me feel completely at ease, and I now have a dog sitter I truly trust to care for Jaxson while I’m away. Highly recommend 🐾✨”

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M T.
Sitter Profile Image: Laura B.
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Laura B.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 74 reviews
16 repeat clients
30 years of experience
Midlothian, VA, 23114

“Dale and Cyrus had a great time with Laura, DJ, and family! Communication was very easy and we were provided photo and text updates during the stay. We could tell they were having a great time and were treated extremely well. We picked up two very happy and healthy dogs! We will definitely book again for future trips.”

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Christian M.
Sitter Profile Image: Doris C.
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Doris C.
from
$40
per night
4.7 out of 5 stars
• 15 reviews
5 repeat clients
3 years of experience
Bon Air, VA, 23235

“Doris was absolutely amazing! She took such great care of my fur baby, and it was clear he adored her. She is kind, attentive, thorough, and very professional. She kept me updated throughout my time away, which gave me so much peace of mind. I will definitely be booking with her again and highly recommend her to anyone looking for a reliable and caring sitter.”

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Cayla B.
Sitter Profile Image: Cindy T.
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Cindy T.
from
$42
per night
5.0 out of 5 stars
• 326 reviews
90 repeat clients
20 years of experience
north chesterfield, VA, 23235

“Exceptional experience! Despite our fragile itinerary, Cindy remained flexible. As soon our dog met Cindy, she immediately felt welcome and willingly followed Cindy. The pictures confirmed how safe and comfortable our dog felt with Cindy. Next trip, Cindy will be our first choice.”

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Jack W.
Sitter Profile Image: Cassandre S.
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Cassandre S.
from
$40
per night
5.0 out of 5 stars
• 329 reviews
73 repeat clients
30 years of experience
Midlothian, VA, 23114

“We’ve used Cassie multiple times, and she is absolutely THE BEST! Sully loves staying at her home and spending time with Cassie and her family. It’s such a relief knowing he’s happy, comfortable, and well cared for while we’re away. She is kind, attentive, and clearly treats him like one of her own. We couldn’t recommend her enough and will definitely continue using her whenever we need a sitter for Sully.”

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Jean P.
Sitter Profile Image: Paula H.
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Paula H.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 128 reviews
46 repeat clients
20 years of experience
N. Chesterfield, VA, 23236

“Paula is my go-to sitter for Jackson. She takes great care of him and sometimes has playmates for him, which he loves. She's a dedicated walker too which Jackson and I both love.”

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Abby G.
Sitter Profile Image: Amanda E.
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Amanda E.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 42 reviews
27 repeat clients
17 years of experience
The Museum District, Richmond, VA, 23221

“Amanda was absolutely incredible. She was super communicative throughout our dog's entire stay. We loved all the updates and pictures. We could tell our dog was being loved and cared for, which put us at ease while we were out of town. Would 100% recommend Amanda.”

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Liz P.
Sitter Profile Image: Amy M.
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Amy M.
Star Sitter
from
$35
per night
5.0 out of 5 stars
• 314 reviews
117 repeat clients
20 years of experience
Richmond, VA, 23228

“Amy was fantastic! We just moved to the area and she took care our fur babies during the craziness. She was so welcoming and took care of them like they were her own. She will definitely be our go to.”

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Nesvi P.
Sitter Profile Image: Aaren & Jordon D.
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Aaren & Jordon D.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 34 reviews
10 repeat clients
6 years of experience
Swansboro, Richmond, VA, 23224

“Grateful to have found Aaren and Jordon. I felt comfortable trusting our boy with them the moment we met. We appreciated the great communication and the pictures/updates we received during Apollo‘s stay. Plus he got plenty of walking in so we know he loved that. Will be rebooking when that time comes. Thanks guys!”

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Kila
Sitter Profile Image: Shannon O.
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Shannon O.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 66 reviews
29 repeat clients
20 years of experience
Chesterfield, VA, 23832

“We were very pleased with the attention that Shannon and her family gave to Sierra. He is a very senior dog and needs a little extra loving and care. Shannon sent pictures every day and was careful to keep him cool during the hot July 4th weather. Her home is really nice and perfect for a large dog. Sierra really enjoyed Shannon's backyard. He didn't want to come home. We would recommend Shannon to anyone who want's a Rover sitter.”

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Ginny Y.
Sitter Profile Image: Caitlin L.
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Caitlin L.
from
$52
per night
5.0 out of 5 stars
• 23 reviews
10 repeat clients
30 years of experience
North Chesterfield, VA, 23235

“Caitlin was a fantastic dog sitter! I contacted her somewhat last minute to watch my cavalier King Charles for the weekend and she was able to accommodate. I did a meet and greet and saw that she has a perfect place for dogs and a huge fenced-in backyard. Her and her husband are very attentive and I could tell they really care about the animals they watch. Very happy to have found her and will definitely be using her again. She even gave me a write-up report at the end with a little story of Berkeley's adventure!”

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Evan K.
Sitter Profile Image: Jennifer A.
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Jennifer A.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 103 reviews
40 repeat clients
20 years of experience
Richmond, VA, 23233

“Jennifer took phenomenal care of Jedi! He has so many little quirks and she navigated each of them perfectly. Cannot recommend enough and will absolutely continue to use her services for Jedi in the future.”

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Aria C.
Sitter Profile Image: Cyrus S.
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Cyrus S.
Star Sitter
from
$38
per night
5.0 out of 5 stars
• 10 reviews
2 repeat clients
14 years of experience
Henrico, VA, 23238

“Cyrus was phenomenal. He kept us in the loop about how the dogs were doing the whole time we were away & truly felt they were in the best care.”

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Kevin H.
Sitter Profile Image: Joy D.
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Joy D.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 88 reviews
40 repeat clients
7 years of experience
Midlothian, VA, 23112

“Spencer had a great time hanging out with Joy and her family for the night. Spencer was given a lot of affection and cuddles. He left with a sense of complete enjoyment! I appreciate you, Joy, for being so accommodating with my schedule. I am grateful to your family for taking good care of Spencer, and you are so kind-hearted.”

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Katie G.
Sitter Profile Image: Zach K.
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Zach K.
from
$45
per night
5.0 out of 5 stars
• 17 reviews
5 repeat clients
9 years of experience
Reedy Creek, Richmond, VA, 23225

“First time having my dog watched by Zach he did everything I asked of him and more and on top of that was extremely friendly and kind! My dog had an accident or two didn't, cause a issue about it while I was for business I would definitely recommend leaving your dog with him”

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Aatom
Sitter Profile Image: Kendra B.
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Kendra B.
Star Sitter
from
$25
per night
5.0 out of 5 stars
• 56 reviews
13 repeat clients
25 years of experience
North Chesterfield, VA, 23237

“This is our second time having Kendra watch Teddy. He has such a great time when he is in her care and she always makes sure to keep us updated throughout his stay. I love to see him hanging out with her pup Gizmo. They’re such good buddies. Kendra is the best. I cannot recommend her enough!”

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Tya P.
Sitter Profile Image: Ethel & Clayton V.
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Ethel & Clayton V.
from
$39
per night
5.0 out of 5 stars
• 64 reviews
26 repeat clients
12 years of experience
Carver, Richmond, VA, 23220

“Ethel was so accommodating with our last minute request to book. She was flexible and timele responded to any messages. Highly recommend and would definitely re-book!”

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Emaline M.
Sitter Profile Image: angelica s.
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angelica s.
Star Sitter
from
$63
per night
5.0 out of 5 stars
• 13 reviews
2 repeat clients
16 years of experience
Brookhaven Farms, Richmond, VA, 23224

“Killie was so well taken care of with Angelica. I received multiple updates a day which I was happy to share with my daughters about their “brother” while we were away. It appears that his playtime and cuddle time needs were more than adequately met and we hope he’ll get to hang with Angelica again very soon 🩵”

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Avery C.
Sitter Profile Image: Ashley H.
Verified Enhanced Background Check
Ashley H.
Star Sitter
from
$55
per night
5.0 out of 5 stars
• 31 reviews
9 repeat clients
1 year of experience
Chesterfield, VA, 23832

“This was our first time using Ashley, and we couldn’t be happier. We went on a seven-day cruise and she took amazing care of our dog. Ashley sent us pictures and updates throughout the trip and kept us informed as needed, which gave us total peace of mind. When we unexpectedly got stuck on our cruise ship for an extra day, Ashley immediately stepped in and kept Kaja an additional day with zero hesitation. She was easy to contact, flexible, and truly went above and beyond. We highly recommend her and will definitely use her again!”

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Christine M.
Sitter Profile Image: Shanisse P.
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Shanisse P.
from
$40
per night
4.9 out of 5 stars
• 22 reviews
10 repeat clients
10 years of experience
Glen Allen, VA, 23060

“I had the pleasure of leaving my puppy with Shanisse and Kim for 1 week while I went away. I can't lie leaving my puppy that long was extremely hard for me. She sent me pictures and videos of Coco multiple times of the day. They have a really big closed in backyard and she seemed to love running around in it. As far as Coco being in the she house she was in her own space that was sort of "fenced" in with appropriate pet friendly gates. She had her own "condo" space. They did have one dog and a cat that coco got along with but I do not believe they had much interaction. I left food, toys and instructions that I do believe they followed. The communication was very good with Shanisse and Kim. I did not have much communication with Shanisse in person but more with Kim. They seem to work well together one for caring for the pets and one for the online support. Overall my experience was very good and I will be booking again. For reference my puppy is a cavapoo and is an out 15lbs. She did very well in their home. The posting says dogs allowed on furniture but I am not sure if she was in their furniture or not because I left her own bedding and she had her own little condo.”

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Daneil D.
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The median cost per night for dog boarding in Westchester is $45

Dog parents share their Rover experiences - Westchester

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5.0 out of 5 stars

Luther. Is always happy to see Damacia. She is very accommodating when our plans change. Luther loves to play with Bastian, her dog.

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Cindy M.
Boarding
5.0 out of 5 stars

Doris fue muy amable, amorosa y paciente con ally la cuido muy bien la recomiendo y sin duda alguna la volveríamos a elegir; fue muy comunicativa y me envió muchos videos de ally durante su estadía con ella…

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Maryory T.
Boarding
5.0 out of 5 stars

Niko had a great time with Aileen and her family! Her kids were the perfect playmates for Niko. They played fetch, tug of war, and they even covered him with blankets to keep him cozy while resting! Aileen was so kind to send several pictures during the stay and was very communicative. She mimicked our schedule and environment, and when we picked Niko up, he was so calm and happy. We will definitely use Aileen and her family in the future as long as they’ll have us!

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Rachael & Sam M.
Boarding
5.0 out of 5 stars

Dawn is very conscientious and we feel comfortable knowing our dog is well cared for when we are away.

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Susan D.
Boarding
5.0 out of 5 stars

Taryn has been taking care of my pups for years, and I’m so grateful to have someone I trust. She took such great care of them. She sent lots of photos and updates, was incredibly flexible with our travel and flight schedules, and made it so easy for us to actually relax and enjoy our trip knowing they were in great hands. Such a huge relief to have her, and I can’t recommend her enough! ❤️

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Britt N.
Boarding
5.0 out of 5 stars

Sarah was great! Provided alot of updates and photos and gave our dog the best care. We will definitely be using her again.

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Courtney C.
Boarding
5.0 out of 5 stars

Another amazing stay with Ruth and Danny! Torrance had the best time and I always feel so safe leaving him with them! They take such great care of him and I could not recommend them more!!

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Madison P.
Boarding
5.0 out of 5 stars

Adele and Clay are the best! I know my dog is getting lots of care and attention when he is at their place. They play fetch with him in the backyard and snuggle with him in the house. He and Fitz have become little friends. Can’t recommend them enough.

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Anne Marie M.
Boarding
5.0 out of 5 stars

Maggie is the best we’ve ever had with our very senior dog. She and her husband have the most caring touch and gentle demeanor to deal with those eccentricities that older dogs have. They truly do the extra mile!

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Lucy H.
Boarding
5.0 out of 5 stars

Great sitters. They took excellent care of my senior dog, kept me informed, and clearly cared about my pet. Highly recommend.

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shari g.
Boarding
5.0 out of 5 stars

Great experience! Andrew was very communicative and wonderful with my two dogs. The daily photos he sent showed they were well cared for and completely comfortable in his home. I would absolutely book with him again.

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Beth R.
Boarding
5.0 out of 5 stars

Denise was a perfect host for us! Very friendly, attentive and took such good care of Jerry! Would recommend!!

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Kelsie G.
Boarding
5.0 out of 5 stars

Miguel was great. He was very responsive and kept me updated with photos and check ins. If you are in need of a sitter who will treat your pet like you would, book with Miguel

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JQuan J.
Boarding
5.0 out of 5 stars

Josie really enjoyed her time at Caitlin’s. Caitlin kept us updated with photos and Josie seemed to be right at home during her weekend stay. Would definitely use Caitlin again.

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Kristina P.
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

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  • 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

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Popular requests for dog boarding - Westchester

Select a filter and find qualifying sitters offering dog boarding.

Sitters in Westchester average 12
repeat dog boarding clients

FAQs for Dog Boarding - Westchester

Frequently asked questions about Rover

The average cost of Dog Boarding in Westchester is $34 per night as of November 2026. Most bookings cost between $28 and $50 per night. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of November 2026, there are 817 sitters on Rover offering Dog Boarding across Westchester. Enter your ZIP code to see which available sitters are closest to your home.

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.

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.

96% of sitters in Westchester 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 Westchester 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 favorite hang-out spots in your Westchester.

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.

Yes, you can find sitters who have experience with handling special pet needs in Westchester. On Rover:

  • 91% of sitters can help with special care needs
  • 95% can help with giving oral medications or injections
  • 96% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, 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 use the Meet & Greet to walk your sitter through your expectations.

You and your Westchester 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 Rover Guarantee, 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 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 VA 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.

Adding another pup to the pack? Most sitters and walkers offer a reduced rate for additional dogs. You’ll find these exact rates listed under the "Services" tab on any sitter's profile. Since every dog is unique, final pricing may vary depending on the level of care required.

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