Pet Sitting & Drop In Visits in Oakham, MA

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

1. Dani

I can be your dogs work out buddy!

Holden, MA, 01520

House Sitting, Drop-In Visits, Dog Walking

"Dani is super friendly and gets back to you ASAP. I have used her a couple of times for drop in visits to take care of my 6 month old pup and older lab while... (more)"

2. Jessica

I enjoy long walks

Leiecster, MA, 01524

House Sitting, Drop-In Visits, Dog Walking

"Jess has so much love for all dogs and all animals for that matter. Her compassion for rescued or disabled dogs is particularly inspiring to me. She is punct... (more)"

Confirmed 4th of July Availability
3. Christine

I'll treat your pup like my own!

Rutland, MA, 01543

Drop-In Visits, Dog Walking

"Christine was amazing with my three shih tzus! She wrote a long description of her drop in with them with lots of photos! She took really good care of each o... (more)"

Confirmed 4th of July Availability
4. John

Dogs love me! Dog time is the best

Paxton, MA, 01612

House Sitting, Drop-In Visits, Dog Walking

"John is absolutely a life saver when it comes to my dogs!! I have two dogs and one of them is not very friendly with people, but she loves John!! He is very ... (more)"

Confirmed 4th of July Availability
5. Anastasia

Busy schedule? Allow me to help!

Spencer, MA, 01562

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Anastasia is a very responsible and loving pet owner. She has always made sure her animals were happy and comfortable. I believe that this would be an ideal ... (more)"

6. Rebekha

Please Read My full Profile!!

Paxton, MA, 01612

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

About: I'm a 50 year old woman and a stay at home Homemaker. I have had dogs and cats my entire life! Currently I have a 3 year old rescue from Puerto Ric... (more)

7. Nancy

Animal lover seeking new clients.

Hubbardston, MA, 01452

Drop-In Visits, Dog Walking

"Nancy is a dog whisperer. My dogs lover her the minute they met her. (more)"

8. Christopher

Nice home with 1 acre fenced yard!

Leicester, MA, 01524

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: We are a family of 4 who love dogs. We have two children both boys 6 & 9 years old & love dogs. We recently had to put down our husky. We want t... (more)

Confirmed 4th of July Availability
9. Tonya

I enjoy and love dogs!

Paxton, MA, 01612

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"Tonya's passion for animals is unsurpassed. She is a loving, caring person and enjoys the company of dogs. She has a dog and she feed and loves her dog mo... (more)"

10. Alexandra

Flexible hours & can do overnights

Hubbardston, MA, 01452

House Sitting, Drop-In Visits, Dog Walking

"Alexandra is a true lover of animals. She treats each and every one as if it was her own. She is reliable and most important, the animals love her! (more)"

Confirmed 4th of July Availability
11. Kristal

I will pamper your pet.

Paxton, MA, 01612

House Sitting, Drop-In Visits, Dog Walking

About: I will respond quickly, usually within a day. I am a good communicator, as I Text or leave messages for my clients, so they know what I did with t... (more)

Confirmed 4th of July Availability
12. Sarah

Instagram: @katiesarahdoghouse

East Brookfieldi, MA, 01515

House Sitting, Drop-In Visits, Dog Walking

"Sarah is by far the best dog walker and pet sitter I have ever met. She takes such great care of all animals and loves them so much. She is so caring and kin... (more)"

13. Emmersyn

$20 off first time EMMERM32560

Rutland, MA, 01543

Drop-In Visits, Dog Walking

About: I have owned two Labrador retrievers, a beagle, and currently own a Maltese and a cat. I frequently take my dog to Wachusett mountain or even just ... (more)

14. Jourdyn

Large fenced yard on dead end road

spencer, MA, 01562

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"Jordyn took care of our little toy poodle while we were away on vacation. The house and the beautiful back yard were very clean and safe. Our dog played with... (more)"

15. Mia

providing doggie care est. 2012

Rutland, MA, 01543

House Sitting, Drop-In Visits, Dog Walking

About: Looking for a dog walker or dog sitter? I'm a proud owner of a german shepard, and have had dogs (and other animals) all my life. Trained a service... (more)

16. Kaitlin

Kate's Kennel

East Brookfield, MA, 01515

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"Kaitlin is very responsible and loves dogs and is great with animals. She takes care of our dog whenever we go away and I know he is well taken care of an... (more)"

17. Joe

Dogs who love soccer are a plus!!?

North Brookfield , MA, 02455

House Sitting, Drop-In Visits, Dog Walking

About: I've been helping my sister with her pet care business, Cait's Pet Care since I can remember. She is the main reason I love animals so much. Now th... (more)

18. Abbey

Love is a four legged word

North Brookfield, MA, 01535

House Sitting, Drop-In Visits, Dog Walking

About: I am a 21 year old student with a love for animals. I have grown up with dogs my entire life, and love all animals. I currently am away from home, ... (more)

19. Jason

Open minded, creative, animal frien

Rutland, MA, 01543

House Sitting, Drop-In Visits, Dog Walking

About: I have been working with dogs/pets since 2003 when I turned 18. Just out of high school my famuly was fortunate enough to inherit a pet sitting b... (more)

20. Mary

Caring pet sitter

spencer, MA, 01562

House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: I've had dogs for most of my life and would be willing to walk your dogs and fill other needs you may have. Along with taking care of your animals ... (more)


As pet lovers, we understand how difficult it can be to leave your pet when you have to head out of town. Luckily, you can find the perfect Oakham pet sitter in seconds on Rover.com. If you're looking for trusted pet sitters while you're away, whether it's for one night or a whole month, you can find a pet sitter in Oakham, MA who meets your — and your pet's — needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your pet — including background checks, sitter testimonials, community reviews. We also offer educational opportunities and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of pet sitters and dog walkers.

All stays booked on Rover receive our Rover guarantee, 24/7 support, and our reservation protection.

How it works

Card image cap

1) Browse Sitters

We make it easy to find affordable & reliable sitters near you.

Card image cap

2) Contact Sitters

Chat about your dog and your specific needs. Even meet in person before booking if you really want to.

Card image cap

3) Book & pay

Our platform makes it easy and secure. No cash necessary.

Card image cap

4) Enjoy your trip

Drop off your dog without feeling guilty. Relax with regular photo updates from your sitter.