Pet Sitting Oakham

Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Over 1
pet parents in Oakham have booked pet sitting

Oakham, Find top rated pet sitting

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

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Sitter Profile Image: Kalliah B.
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Kalliah B.
Star Sitter
$28
total per visit
5.0 out of 5 stars
• 54 reviews
18 repeat clients
12 years of experience
South barre, MA, 01074

“Kalliah is so kind,responsible, and reliable. We’ve used her twice now and she goes above and beyond to communicate and takes the best care of our beloved fur babies.”

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Kaitlin S.
Sitter Profile Image: Kayla C.
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Kayla C.
$39
total per visit
5.0 out of 5 stars
• 53 reviews
13 repeat clients
3 years of experience
Spencer, MA, 01562

“Kayla visited our furbabies for yard time while we went out on a date. Kayla was communicative, made sure our babes were well taken care of, and sent us pics immediately after the visit. We are very pleased with the first visit with Kayla ! ☺️”

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Peter M.
Sitter Profile Image: Jenna Cathryn D.
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Jenna Cathryn D.
$34
total per visit
5.0 out of 5 stars
• 23 reviews
9 repeat clients
15 years of experience
North Brookfield, MA, 01535

“Thank you so much Jenna….first time leaving these guys with anyone but family. They loved you!!!! I will definitely be calling you again!!!”

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Pam F.
Sitter Profile Image: Julie D.
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Julie D.
$23
total per visit
5.0 out of 5 stars
• 4 reviews
2 repeat clients
20 years of experience
Rutland, MA, 01543

“Extremely prompt. Lots of photos. Very detailed and thorough updates. I could not have been happier with the services. Highly recommend.”

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Brian F.
Sitter Profile Image: Melissa Q.
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Melissa Q.
$34
total per visit
5.0 out of 5 stars
• 32 reviews
13 repeat clients
15 years of experience
North Brookfield, MA, 01535

About: As a child, I had the opportunity to train and show cows in 4-H and various fairs around Worcester County. This was great because it taught me how to be sensitive to and care for animals. In high school I was able to work with horses and then in college I became a member of the equestrian team. I love working with all kinds of animals and currently have chickens, a house bunny and two young labs. Our dogs LOVE making new friends! We have three college aged kids that also love dogs and know how to treat animals. Your dog becomes a part of our family while you’re away. I send lots of pictures and updates so you can see what your best friend’s vacation is like. **We can only host dogs that get along with other dogs.** I'm comfortable administering medication and working with special needs or senior dogs. Please feel free to contact me with any questions! I currently work from home during the day but my job is very flexible. Your pup stays with me and gets potty breaks at least once an hour. We have a small part of our yard fenced and dedicated as the dog area, right off of our back sliding door. We also have a retractable gate for the front porch that stays closed most of the time so no dogs escape out the front door either. Safety is our top priority! I prefer to only take dogs from one family at a time, so we can provide an environment with plenty of attention and care for your pup!

Sitter Profile Image: Shea & Damien W.
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Shea & Damien W.
$34
total per visit
5.0 out of 5 stars
• 74 reviews
21 repeat clients
40 years of experience
Worcester, MA, 01605

“So appreciative of the last minute help and so glad that our pup is so comfortable with them, she takes some warming up but they are easily becoming her favorite. Highly recommend and will absolutely use again and again!”

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Cady M.
Sitter Profile Image: Jacquie A.
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Jacquie A.
Star Sitter
$28
total per visit
5.0 out of 5 stars
• 21 reviews
8 repeat clients
20 years of experience
Holden, MA, 01520

About: My whole life as long as I remember I was the biggest pet lover. I had my own pets and I’ve taken care and walked the dogs of my neighborhood. I just love them. I work part time, which gives me a lot of time to do my favorite thing: pet sitting!!! I work part time and have a lot of time for my favorite hobby which is caring for these lovely creatures. I have a fenced in yard and I love walking in the woods with the doggies. I have a fenced in yard and I walk the dogs three times a day. My 2 lovely dogs will keep your dogs company. I will make sure they are spoiled.

Sitter Profile Image: Olivia P.
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Olivia P.
$23
total per visit
5.0 out of 5 stars
• 9 reviews
2 repeat clients
17 years of experience
Hubbardston, MA, 01452

“Olivia is fantastic ! I didn't have any worries while I was away .”

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Janice F.
Sitter Profile Image: Jeffrey W.
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Jeffrey W.
$23
total per visit
5.0 out of 5 stars
• 45 reviews
22 repeat clients
12 years of experience
Sterling, MA, 01564

“Jeffrey is responsible, loving with dogs, punctual, and careful! I highly recommend him. We will definitely work together again.”

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Patricia R.
Sitter Profile Image: Kaylee S.
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Kaylee S.
$23
total per visit
5.0 out of 5 stars
• 2 reviews
29 years of experience
Worcester, MA, 01602

“It was great having Kaylee look after our cats while we were out of town. We had special requirements as we have two young kitties who were needed to keep separated in a different part of the house from an older cat as the kittens had not yet been fully vaccinated. The kittens got into mischief and made a mess. Kaylee cleaned it up. She vacuumed up stray cat litter too. The older cat is an indoor/outdoor cat who loves to be outside during warmer months and can be very demanding requesting to go out. No escape artists were witnessed. :-) I would not hesitate in book her again when needs arise.”

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Matthew S.
Sitter Profile Image: Katherine A.
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Katherine A.
$23
total per visit
4.9 out of 5 stars
• 66 reviews
40 repeat clients
20 years of experience
Charlton, MA, 01507

“Katherine is always super great to work with and she was willing to go above and beyond while we were out of town during the storm! Highly recommend Katherine for your pet sitting needs!”

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Katy S.
Sitter Profile Image: Alondra R.
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Alondra R.
$18
total per visit
15 years of experience
Holden, MA, 01610

About: I’ve cared for my own dogs since I was young. Responsible, patient, and attentive, I love connecting with dogs beyond the bare minimum, giving them real love and attention. I am a full time student, my classes end around noon time, the latest being 1:45 on Fridays. I have a part time job as well, but my work schedule is very flexible as I can pick the days I work in advance. My home is a safe and welcoming space for dogs. I have a large, fenced backyard where they can play and explore. I live with my parents, which just means even more love for the future pups! I have a small Chihuahua who mostly keeps to herself, but if any issues arise, there’s enough space in the house to separate them. If your dog needs a crate, I can accommodate for that too!

Sitter Profile Image: Patricia H.
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Patricia H.
$28
total per visit
5.0 out of 5 stars
• 3 reviews
1 repeat client
40 years of experience
Princeton, MA, 01541

About: I’ve owned pets since my daughter was young and brought her first kitten home. I’ve been helping her to walk dogs for a couple years now. I’m retired so my schedule is fairly open. It gets me walking and outside, two things I enjoy. It helps my health and makes me feel good. Happy to walk your dog! Cannot have pets stay at my house as I have a kitty cat of my own. His name is Toby and he’s a real pain in the butt! 😂

Sitter Profile Image: Brittany N.
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Brittany N.
$45
total per visit
5.0 out of 5 stars
• 12 reviews
4 repeat clients
20 years of experience
Barre, MA, 01005

About: I have worked with dogs all my life. I use to work/help my mom at a kennel at the young age of 7 and our household was always full of dogs! I have had experience with many breeds. I've owned a wide range of dogs: pit bulls, labs, huskies, dash hound, terriers, rottie and pugs. I love to go for long walks, hikes, play fetch, take them swimming. I love to take my dogs out in the field so they can get rid of their energy and run free. If your dog isn’t a runner I would to take them too. I have a very flexible schedule so I could work the times around your needs and times. Dogs are my passion and I can’t wait to babysit yours!

Sitter Profile Image: Ashley B.
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Ashley B.
$23
total per visit
5.0 out of 5 stars
• 2 reviews
5 years of experience
Worcester, MA, 01605

“Ashley did a wonderful job caring for our 2 kitties and administering meds while we were away. Very much appreciated the updates while we were away. The house was also spotless when we returned.”

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Julie R.
Sitter Profile Image: Jared V.
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Jared V.
$45
total per visit
5.0 out of 5 stars
• 8 reviews
1 repeat client
11 years of experience
Auburn, MA, 01501

About: *MY AVAILABILITY HAS BEEN UPDATED THROUGH THE END OF 2026!* Hi there, my name is Jared and I currently reside in central MA, Worcester area. I have been working with dogs for 11 years now, starting off as a groomer at Petsmart which was a 9 year career, a full time dog walker for a private business for a year and now dog sitting/walking on my own time. My full time job is a singer/dancer for Carnival Cruise Lines and when I'm home in between contracts, I am looking to make extra cash by lending my services and experience to whatever you may need. Along with grooming and dog walking experience, I have also house sat for numerous dogs ranging from puppy to senior. I'm comfortable with handling medications or special treatments that your pup might need. I hope you consider me and I can't wait to meet you guys! When I am home in between contracts with my full time job as a cruise ship singer/dancer, I have complete open availability. My schedule is set now until the end of 2026! I am vigilant, reliable, trustworthy and confident. I will make sure that your pet isn't out of my sight while I am taking care of it and treat it like my own!

Sitter Profile Image: Rylee D.
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Rylee D.
$23
total per visit
5.0 out of 5 stars
• 7 reviews
2 repeat clients
8 years of experience
Worcester, MA, 01608

About: Hello! My name is Rylee, i currently own two cats but have been a previous owner to a pitbull adopted from my local shelter. My dog was unfortunately abused as a puppy and had some behavioral issues so I am very use to dealing with these types of dogs. Although I have not owned a dog since, I love all my friends and families dogs dearly. I will be more than happy to provide toys or treats your dog enjoys to have fun while away from home! I treat every dog like it’s my own and will always reach out with any questions or concerns while they are in my care. I have frequent experience dog sitting for my aunt’s two dogs, four cats along with taking care of their fish. I also have experience with administering oral and topical medication to dogs that I have pet sat for and following specific feeding routines. Please feel free to message me to talk about caring for your furry friends! I currently work a full time job but that does not stop me from helping out your pets! I will likely do better with an animal that can manage 6-8 hours without being let out during weekdays. Weekends that I have open availability, your pet will get my full attention! I am more than open to staying in the home to help accommodate your pet and make them comfortable while you’re away! I like to stick as close as possible to your average daily routine with your pets to make things easy for you and them! When staying in peoples homes I am very conscious of keeping things clean and tidy and helping out with other things such as watering plants, bringing in the mail, putting out the trash and making sure things are secure as I come and go!

Sitter Profile Image: Chastity N.
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Chastity N.
$18
total per visit
4 years of experience
Gardner, MA, 01440

About: I have had a passion for taking care of animals since a young age. I have experience with all types of animals. I worked as a doggy daycare attendant and a veterinary assistant, as well as shelter experience. I'm available for drop in visits and dog walking. I do not have a set schedule at work yet so I will have different availability every week. We do have a backyard which is not fenced in and a porch that I usually block off to let my dogs get outside for some fresh air.

Sitter Profile Image: Danielle C.
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Danielle C.
$45
total per visit
5.0 out of 5 stars
• 40 reviews
7 repeat clients
20 years of experience
Worcester, MA, 01605

“I’ve used Danielle several times and would recommend her to anyone. She spends a lot of time with my dog/at my house, provides frequent updates, and leaves the house in equal or better shape then when I left it. She follows all instructions related to medicines and anything else. I know my dog is in good hands.”

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Natasha D.
Sitter Profile Image: Anghelo A.
Verified Enhanced Background Check
Anghelo A.
$28
total per visit
2 years of experience
Worcester, MA, 01610

About: I’ve had experience caring for dogs, cats and birds ranging from new born to senior age. I am willing to attend to any of your pets’ unique needs. I am available for boarding on the weekends and caring for your pets in the mornings and the evening most days. We can work out any days you may need. I am willing to travel to your home and carry out any care plans you already have with your pet. Also, I am available for dog walking.

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The median cost per visit for pet sitting in Oakham is $25

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  • 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 pet sitting

  1. 1. Search

    Browse profiles of sitters near you who offer pet sitting.
  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 pet sitting - Oakham

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Sitters in Oakham average 6
repeat pet sitting clients

FAQs for Pet Sitting - Oakham

Frequently asked questions about Rover

As of October 2026, there are 2,103 sitters on Rover offering Pet Sitting across Oakham. Enter your ZIP code to see which available sitters are closest to your home.

You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.

Before booking, confirm:

  • the timing, length, and frequency of visits;
  • the care instructions the sitter should follow;
  • which parts of your pet’s usual routine should be prioritized;
  • how often you would like to receive messages, photos, or other updates.

Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.

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.

Many pet parents provide a spare key or arrange a lockbox. You can also exchange keys during the Meet & Greet and show your walker how to use digital fobs or personalized codes. It helps to arrange access to your home, from spare keys to concierge introductions, before pet care begins.

If you live in an apartment or condo, don’t forget to discuss details like buzzer access, codes, or elevator etiquette. These details can help a pet sitter feel more comfortable going in and out of your building.

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 .

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.

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

  • 88% of sitters can help with special care needs
  • 92% can help with giving oral medications or injections
  • 94% 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.

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 .

sitters on Rover set their own , 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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