House Sitting Westwood

Find a loving house sitter to watch over your pets and your home.

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Over 32
pet parents in Westwood have booked house sitting

Westwood, Find top rated house sitting

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: Hailey C.
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Hailey C.
from
$40
per night
5.0 out of 5 stars
• 4 reviews
10 years of experience
Winchester, VA, 22602

“Hailey was reliable, sweet & very communicative. Riley was well cared for, and received updates and photos during the day. This was a good experience for my dog.”

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Carmen C.
Sitter Profile Image: Kristine S.
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Kristine S.
from
$40
per night
5.0 out of 5 stars
• 8 reviews
30 years of experience
Winchester, VA, 22601

“Kristine was very responsible taking care of our dog and home while we were gone for 4 days. In fact, more than we expected. We will definitely want her to take of Boots again when we need a dog sitter.”

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Sharon B.
Sitter Profile Image: Christopher P.
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Christopher P.
from
$55
per night
5.0 out of 5 stars
• 13 reviews
3 repeat clients
13 years of experience
Winchester, VA, 22601

“She was amazing! Came on time, follow all the instructions with my little puppy. Send me the updates and photos of Poet. Puppy was happy and safe when I came back home. Her prices are very affordable. You can feel that she loves the animals. Highly recommend Christopher!”

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Tamara K.
Sitter Profile Image: charlotte g.
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charlotte g.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 5 reviews
3 repeat clients
8 years of experience
Winchester, VA, 22601

“Our 130# Newfoundland and cat were well taken care of. Communication was great, even using a different app since we were in Europe. Would not hesitate to use Charlotte again, she cared for our animals like they were hers.”

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Giovanna C.
Sitter Profile Image: Marianina G.
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Marianina G.
from
$30
per night
14 years of experience
Winchester, VA, 22602

About: Hi, I’m Nina! My passion for animals started when I began volunteering at animal shelters when I was 13. By the time I was 19, I was working full-time at a doggy daycare where I learned puppy / senior care, light training experience, medication administration, exotic pet care, behavioral management, navigating social interactions / introductions, and much more in my 8 years there. I am currently working full time, Monday - Friday 8:30am-4:30pm but am hoping to change that soon to focus on my passion for animal care and socialization. I love hanging out and chilling with the dogs I meet and getting to know them. I will take your pets on walks, sit with them in the shade or outside, play with any toys they love, or just hang out on the couch if that’s their speed. My care is custom to your pet and their needs.

Sitter Profile Image: Caitlin M.
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Caitlin M.
from
$60
per night
5.0 out of 5 stars
• 75 reviews
29 repeat clients
15 years of experience
Winchester, VA, 22601

“Caitlin went above and beyond with our special needs hound. We got plenty of communication and updates, along with lots of photos! We’d absolutely use her services again. Thanks, Caitlin!”

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Rachel W.
Sitter Profile Image: Marian K.
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Marian K.
from
$35
per night
10 years of experience
Winchester, VA, 22601

About: I have been taking care of dogs and cats since high school! I am comfortable and familiar with multiple pets at once and even some more eclectic animals like reptiles (turtles and snakes). I would only be able to come to your house to pet sit or walk, I would not be able to bring pets to my apt. I would only be able to pet sit in your home as I live in an apartment where I am unable to bring animals into my space.

Sitter Profile Image: Kathy G.
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Kathy G.
from
$75
per night
5.0 out of 5 stars
• 58 reviews
18 repeat clients
30 years of experience
Winchester, VA, 22601

“This is the first time I've had a sitter stay in my house instead of boarding my girls. After meeting Kathy and seeing how much my younger dog loved her, I felt confident in leaving for a week. However, she went above and beyond to love on my dogs so they wouldn't be upset that I was gone. She communicated daily, sent pictures, and tailored her schedule around the dog's needs. Kathy was also flexible when the dogfood unexpectedly ran out and I had to order more while out of the country. She offered to get food for them locally and then modified their feeding schedule while waiting for the food shipment. Both dogs were happy and healthy when I got home and its clear they were well loved and taken care of. The house was also cleaner than when I left! I've already asked Kathy if she is available for my next trip!”

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Rachel
Sitter Profile Image: Megan S.
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Megan S.
Star Sitter
from
$75
per night
5.0 out of 5 stars
• 89 reviews
29 repeat clients
10 years of experience
Stephens City, VA, 22655

“Megan is the best. I never have to worry about leaving my baby girl thanks to her. Megan always takes such great care of her and sends me updates consistently. Highly recommend her!”

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Cody F.
Sitter Profile Image: Victoria L.
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Victoria L.
from
$35
per night
4.8 out of 5 stars
• 7 reviews
1 repeat client
23 years of experience
Winchester, VA, 22602

“Victoria provided frequent comms and was very responsive. Great job, we will definitely use her again!”

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Stu Y.
Sitter Profile Image: Shannon B.
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Shannon B.
from
$55
per night
5.0 out of 5 stars
• 5 reviews
5 years of experience
Winchester, VA, 22602

“Shannon was amazing. Our little guys loved being with her. Def will be using her again. Her communication about what the dogs were doing was great. Highly recommend”

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Melissa S.
Sitter Profile Image: Liza E.
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Liza E.
from
$50
per night
5.0 out of 5 stars
• 1 review
15 years of experience
Winchester, VA, 22601

“Liza was AMAZING! My prearrange Sitter canceled three hours before I had to leave for a Fourth of July party and Liza was ready to go and eager to help! I am so thankful and grateful! What absolutely be using Liza again!”

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LN C.
Sitter Profile Image: Linda K.
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Linda K.
from
$60
per night
5.0 out of 5 stars
• 115 reviews
46 repeat clients
18 years of experience
Winchester, VA, 22602

About: (Formerly Kamp Kelley) I have been fostering small dogs for a rescue group in No. VA. for the last 9 years (my aching back doesn’t allow me to work with dogs larger than 20 lbs)--prior to that I fostered cats and kittens. I has experience with many types of small dogs—especially Shih Tzu’s and Llasa Apso’s, but also Yorkshire Terriers, Basset Hounds, Pom's, Toy Poodles, etc. My expertise is in rescuing and caring for senior and special need dogs. Since I have a dog-friendly house and a large-fenced yard (1/4 acre) for them to run and play in, I decided to become a dog-sitter 5 years ago. I believe in loving and treating your fur-baby like my own! We keep her home and yard dog proof so your little angel will be in a safe, relaxed, dog-friendly, and loving environment! Because I am retired, my schedule is very flexible. I'm retired and except for occasional trips to the store, bi-weekly Bridge games. monthly book group and a occasional meeting, I'm home ALL THE TIME. At this point, I am accepting only ONE dog at a time EXCEPT if there are 2 dogs from the same household. Same for cats. I have a large, fenced yard that can be separated off. I have lots of dog equipment. For example large crates if your dog is used to being crated, bowls, beds and cushions, a big bed for them to share with me, jackets, leashes, kongs and lots of love and affection. Same for cats--EXCEPT, I let them out only on the back deck (enclosed).

Sitter Profile Image: Kathryn W.
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Kathryn W.
from
$50
per night
5.0 out of 5 stars
• 2 reviews
10 years of experience
Winchester, VA, 22601

“Katherine was absolutely great with Donner and Murphy during the storms we had yesterday. Played with them cuddled with them to comfort them. We’ll definitely have back as needed.”

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Pamela T.
Sitter Profile Image: Haley Z.
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Haley Z.
from
$55
per night
5.0 out of 5 stars
• 139 reviews
45 repeat clients
17 years of experience
Stephens City, VA, 22655

“Our first experience with Haley was absolutely fantastic. She stayed with our 2.5 y/o Great Dane "Thunder" over the Thanksgiving holiday and truly gave us peace of mind throughout. First, she met with us the day before to get acquainted with our home and Thunder and asked lots of insightful questions that showed her interest in doing a great job. Then, while we were away, she kept us updated on the status of her stay throughout - leaving no doubt we will request her services again very soon!”

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Kyle M.
Sitter Profile Image: Autumn G.
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Autumn G.
from
$25
per night
5.0 out of 5 stars
• 3 reviews
12 years of experience
Winchester, VA, 22601

“Autumn did a great job taking care of my babies while I was gone. She was great at communicating and sent me pictures every day. I would recommend.”

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Dorene K.
Sitter Profile Image: Ilona R.
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Ilona R.
from
$50
per night
15 years of experience
Winchester, VA, 22602

About: I’ve been caring for pets since my early teen years and have over 15 years of experience pet sitting for friends, family, neighbors, and long-term clients. I’ve cared for dogs of all ages, from young puppies to senior dogs in their final years, and I’m comfortable giving medications, including pills and daily injections. For several years, I ran my own pet-sitting business throughout Northern Virginia. After recently moving to the Winchester area, I’m joining Rover to connect with new local families and continue doing something I genuinely love. I’ll do my best to keep your dog happy, comfortable, and on their normal routine while you’re away, and I’ll keep you updated with photos and messages along the way. Pet care fits easily into my daily routine because I have a very flexible schedule and am home throughout the day. This allows me to provide consistent attention, including walks, feeding, playtime, and check-ins without needing to work around a fixed job schedule. I have a fenced-in side yard/patio, which allows for secure outdoor time and potty breaks. Pets are always supervised when outside to ensure their safety. I also have a friendly mini Goldendoodle who is social and comfortable around other dogs. In addition, I have a shy cat who is dog-friendly and generally keeps to himself.

Sitter Profile Image: Destiny F.
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Destiny F.
from
$65
per night
5.0 out of 5 stars
• 3 reviews
1 repeat client
12 years of experience
Stephens City, VA, 22655

“Destiny was absolutely fantastic! She took great care of our babies and they all loved her! She was very communicative, gave great updates everyday, and very responsive! Highly recommend her for your pet sitting needs!!”

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Kayla G.
Sitter Profile Image: Ruby K.
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Ruby K.
from
$40
per night
5.0 out of 5 stars
• 2 reviews
10 years of experience
Winchester, VA, 22602

“Ruby was excellent. She was flexible and responsible. She followed instructions and kept us updated. Thank you Ruby!”

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Angela E.
Sitter Profile Image: Cailey J.
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Cailey J.
from
$45
per night
4.7 out of 5 stars
• 4 reviews
1 repeat client
10 years of experience
Winchester, VA, 22602

“Cailey is great. I was so happy to know that Saylor was in good hands!”

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Susan G.
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The median cost per night for house sitting in Westwood is $50

Pet parents share their Rover experiences - Westwood

1 / 1
5.0 out of 5 stars

Autumn did a great job taking care of my babies while I was gone. She was great at communicating and sent me pictures every day. I would recommend.

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Dorene K.
House Sitting
5.0 out of 5 stars

Liza was AMAZING! My prearrange Sitter canceled three hours before I had to leave for a Fourth of July party and Liza was ready to go and eager to help! I am so thankful and grateful! What absolutely be using Liza again!

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LN C.
House Sitting
5.0 out of 5 stars

Matt was amazing already booked again did a great job with all 4 including our new pup who is not completely house trained yet

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Ricky
House Sitting
5.0 out of 5 stars

Kathryn was great. JT can be be a challenge due to size. But it evident that both he and the house were well cared for. We will use her again.

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Laurie P.
House Sitting
5.0 out of 5 stars

ruby was super communicative and was so kind to our pup! would definitely book her to dogsit again :)

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Claire M.
House Sitting
5.0 out of 5 stars

If you are looking for a pet sitter who will treat your fur baby like absolute royalty, look no further! We needed someone last-minute to watch our dog for an entire week, and she completely saved the day by stepping in with such short notice. From the moment we left, we were at total ease. She sent constant updates and a ton of amazing pictures throughout the week, which we absolutely loved. It was so reassuring to see our pup so happy, relaxed, and well-cared-for while we were away. She is professional, incredibly dependable, and clearly has a huge heart for animals. We are so incredibly grateful for her help and will absolutely be booking her again in the future. Highly, highly recommend!

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Nicoll F.
House Sitting
5.0 out of 5 stars

Haley house sat for me for a full a week. I have a little dog, Jake, who is almost 15, and a 4 year old hound mix, Maui, who was a rescue. As soon as she walked in my house my dogs went right to her and there was an immediate connection. The dogs had a great week with Haley, and my house looked great when I returned. She sent me updates and pictures frequently, and my dogs loved her. I would definitely rebook with Haley.

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Jim G.
House Sitting
5.0 out of 5 stars

Charlotte came for the day to get to know Finn, our little dog, before coming to stay over in a few weeks time. We left for the day and when we returned Finn was sitting next to her on the sofa looking content and happy:) Charlotte is a calm and friendly person who understands pups very well. :)

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Carly G.
House Sitting
5.0 out of 5 stars

Bailey loves when Riona visits! She takes such good care of her and sends pictures that shows she’s comfortable with her. Thank you!

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Cynthia M.
House Sitting
5.0 out of 5 stars

Megan is the best. I never have to worry about leaving my baby girl thanks to her. Megan always takes such great care of her and sends me updates consistently. Highly recommend her!

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Cody F.
House Sitting
5.0 out of 5 stars

Katie had excellent communication throughout our trip and handled everything so well. Our dogs have a large size difference and she took care of them well. Highly recommend.

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Destiny B.
House Sitting
5.0 out of 5 stars

Could not be more pleased with the compassionate care our dogs received while we were out of the country on vacation! I am the animal worrier of the family and felt very much at ease while away. We returned to a home of happy puppies! Thank you so very much for providing top notch care!

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Donna C.
House Sitting
5.0 out of 5 stars

Emily was great, she watched our pups for the evening. She was very responsive, our dogs loved her and we felt quite comfortable and safe with her, would highly recommend.

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Patrick W.
House Sitting
5.0 out of 5 stars

Kathy G was awesome with our pups while we were gone. She sent updates, pictures and more every day which really kept us from worrying about our fur babies! She also left us a clean house and kept up on the dog items that needed washing. We will definitely call Kathy G again!

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Cindy W.
House Sitting
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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.

Meet local sitters who will treat your pets like family

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting
  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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Sitters in Westwood average 3
repeat house sitting clients

FAQs for House Sitting - Westwood

Frequently asked questions about Rover

The average cost for House Sitting in Westwood on Rover is $49.95 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 House Sitting 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 House Sitting. For more information on service fees, click here .

As of July 2026, there are 589 sitters on Rover offering House Sitting across Westwood. Enter your ZIP code to see which available sitters are closest to your home.

Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:

  • Mail & deliveries: Collecting letters and packages so they don't pile up.
  • Plant care: Keeping your indoor or outdoor garden hydrated.
  • Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
  • Home security: Sitters can stay overnight to keep your home occupied.

The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Westwood walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.

It’s helpful to think of house sitting as a "home base" service. Most sitters in Westwood maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:

  • Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
  • Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
  • Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.

Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Westwood choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

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 .

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 pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet 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.

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.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

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

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

  • 98% of sitters can help with special care needs
  • 100% can help with giving oral medications or injections
  • 93% 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.

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