House Sitting Oakham

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Over 6
pet parents in Oakham have booked house sitting

Oakham, Find top rated house sitting

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

1 / 1
Sitter Profile Image: Meaghon R.
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Meaghon R.
$67
total per night
5.0 out of 5 stars
13 reviews
2 repeat clients
20 years of experience
Princeton, MA, 01541

Meaghon was the best! She went above and beyond to care for all of our pets and our home while we were away for the holidays. She communicated often and sent us a lot of pictures. She made sure our pets had lots of love and attention while we were gone. We were so lucky to find her and would highly recommend her to anyone!

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Stephanie B.
Sitter Profile Image: Kalliah B.
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Kalliah B.
Star Sitter
$60
total per night
5.0 out of 5 stars
51 reviews
15 repeat clients
12 years of experience
Barre, MA, 01074

Kalliah was amazing with all of my animals! She was very communicative and sent updates daily. She was a great house guest and left the house clean at the end of the trip. Overall she was wonderful and I would Highly recommend her!

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Tiffany C.
Sitter Profile Image: April G.
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April G.
$78
total per night
5.0 out of 5 stars
7 reviews
1 repeat client
30 years of experience
North Brookfield, MA, 01535

About: Hi! my name is April, I am new to Rover, as you can probably see. In my bio I am going to be as honest and sincere in this explanation of who I am and why you should choose me to care for your pet(s). I recently moved to North Brookfield and in doing so lost contact with a 9yr. old rescued Rottweiler who I loved and cared for. I would walk her, give her medication and feed her of course. I miss her presence. I’ve been trying to figure out what to do with the excess of free time that I have. This job opportunity seems like it will be the perfect fit. I have had many years of experience living with and caring for multiple breeds of dogs, including Rottweiler, Pitbull, Great Dane and numerous other breeds. I am an energetic woman who thrives on outdoor activities, I love exploring nearby parks, or strolling through neighborhoods I haven’t yet explored. My experience extends beyond dogs; I’ve also shared my home with cats, and I even had a wonderful rabbit who enjoyed our walks together. I recently completed a Red Cross certification in cat and dog, first aid, which enhances my ability to provide safe and responsible care for your pets. My deep fondness and connection with animals drives me to provide the best care possible, ensuring that every pet that I take care of receives the attention and exercise they deserve. If you are looking for a reliable and enthusiastic pet walker, who will treat your beloved animal like a best friend, I would love to connect! I am currently studying for a new profession. My studies work around my schedule so caring for your pet, whenever you need me to is not an issue. I unfortunately cannot bring pets to my residence as I am renting a house right now. If you become my client, I will treat your home and your property with the utmost respect. I also have a vehicle large enough to accommodate most dogs and would be thrilled to take them to parks if that’s what works for all of us.

Sitter Profile Image: Kayla S.
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Kayla S.
$69
total per night
5.0 out of 5 stars
27 reviews
8 repeat clients
20 years of experience
Spencer, MA, 01562

This was our first Rover experience and Kayla was terrific! She updated us daily with pictures and comments of Gracie while we were away for the week. During our meet and greet she was very professional and kind with us and Gracie. We 100% recommend her and will be contacting her again if we go away. She did a great job taking care of our pooch!

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Dave F.
Sitter Profile Image: Ashley L.
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Ashley L.
$56
total per night
5.0 out of 5 stars
1 review
27 years of experience
Spencer, MA, 01562

Ashley was very friendly and thoughtful. She sent updates and pics of our pups.

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Heathrr V.
Sitter Profile Image: Kayla C.
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Kayla C.
$73
total per night
5.0 out of 5 stars
47 reviews
12 repeat clients
3 years of experience
Spencer, MA, 01562

Kayla was great! She sent regular pictures and updates. We came home to happy pooches. We will definitely contact her again for future stays!

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Marsha R.
Sitter Profile Image: Lila P.
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Lila P.
$39
total per night
5.0 out of 5 stars
11 reviews
3 repeat clients
15 years of experience
Brookfield, MA, 01506

Lila was a great sitter for Minnie. My very anxious “baby” took to Lila very quickly and that is not her norm, so I felt very comfortable leaving them together. Lila communicated and kept in touch well. She was very respectful of my home and even left a cute doggie thank you note. Minnie seemed to love her and I know this because often when I get home Minnie us sitting by the door waiting. She was sleeping in the living room and much calmer than my usual returns. I recommend Lila as responsive, responsible, and respectful. Thank you!!!

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Brenda B.
Sitter Profile Image: Fiorella B.
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Fiorella B.
$78
total per night
4.8 out of 5 stars
26 reviews
6 repeat clients
17 years of experience
Worcester, MA, 01604

Fiorella was a wonderful caretaker for our three dogs and home while we were away. She sent regular photos and followed all instructions thoroughly. Also left the house nice and clean!

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Kailey M.
Sitter Profile Image: Tosya F.
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Tosya F.
$56
total per night
5.0 out of 5 stars
6 reviews
1 repeat client
22 years of experience
Holden, MA, 01522

About: I like to watch it’s me or the dog every night. And my cat from hell. I’m interested in getting my dog training certificate in the nearest future. My cat brings me such joy. He is a 16 year old black cat and such a good boy! He can even go on walks with us. I work for the Worcester Public schools and have all school vacations off. I am able to come and do house calls in the evening time (4-late night) or house sit overnight on weekdays or weekends. Also during school vacations including the summer. We have an indoor house cat. He’s declawed and very friendly. We also have a fenced in area in the backyard with very high fences. There is possibility that borders could be segregated from the cat if necessary. We are in a good neighborhood for walking and very near some good trails.

Sitter Profile Image: Sarah M.
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Sarah M.
$78
total per night
5.0 out of 5 stars
7 reviews
1 repeat client
5 years of experience
Rutland, MA, 01543

About: Hi there!😊 My name is Sarah and I currently reside in Rutland MA. I am very excited and looking forward to meeting your pets, and sharing this experience with them! My personal experience in caring for dogs has been pet sitting/walking for family, friends, and coworkers. I have also worked in doggy daycare, and so I am very comfortable with many different types, sizes and breeds of dogs. I understand every dog is different, and unique in there own ways. So my priority is making sure your pets needs are met, with the attention, care and love they deserve! I currently work part-time, so my availability is: Monday–Thursday: 8 AM–12 PM and 3 PM–8:30 PM Friday–Saturday: Available for drop-in visits and overnight stays My schedule can vary depending on existing bookings and plans, so feel free to message me with the dates and times you need. Even if your requested time isn't within my listed availability, go ahead and reach out—I may still be able to make something work! Your pets’ comfort and safety are my top priorities. I always follow care instructions and am attentive to each pet’s individual needs, routine, and comfort. I respect your home and privacy, keeping it tidy and secure while you’re away. My goal is to provide responsible, loving care for your pets during drop-in visits or house sitting.

Sitter Profile Image: Emma G.
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Emma G.
$73
total per night
5.0 out of 5 stars
36 reviews
9 repeat clients
2 years of experience
Ware, MA, 01082

Emma was an excellent pet sitter! She sent pictures and updates and made friends with our sweet dog and our somewhat skittish kitty! I can’t recommend her enough!

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Gina V.
Sitter Profile Image: Kristen M.
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Kristen M.
$56
total per night
5.0 out of 5 stars
8 reviews
2 repeat clients
40 years of experience
Templeton, MA, 01468

About: I’m a very responsible and loving pet owner. Have rescued many pets and now have found myself with some free time and would love to help new pets and people! With notice, I am completely free on Wednesdays, Thursdays, Saturdays & Sundays. (Monday, Tuesday & Friday I can be available for a few hours in the am) I have a fenced in yard with plenty of space to play and a kiddie pool to cool off in! I have three very friendly doggos myself but plenty of space so they can be kept separate if you desire.

Sitter Profile Image: Christina C.
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Christina C.
$67
total per night
5.0 out of 5 stars
1 review
20 years of experience
Holden, MA, 01520

About: Animals have always been part of my life. I’ve raised five dogs from puppyhood and have worked with many breeds, ages, and personalities. I also have experience caring for cats, reptiles, and small mammals, making me a reliable choice for families with diverse pets who need patient, knowledgeable support. I offer fully open availability, providing flexible, reliable care whenever your pets need support. My schedule is built around consistency and convenience for pet parents, and every visit reflects my commitment to animal welfare. As I grow my business, I’m also working toward my long‑term dream of opening a multi‑species rescue to help even more animals thrive. I care for pets in the way that keeps them happiest and most comfortable. In your home, I follow your routines exactly—feeding, walks, playtime, enrichment, medication, and any house rules your pet already knows—so their day feels familiar and stress‑free. In my home, pets enjoy a safe, supervised environment with structured potty breaks, cozy rest areas, and plenty of attention. Whether it’s walks, drop‑ins, boarding, or overnights, I make sure every pet gets individualized care, consistent communication, and a calm, loving experience.

Sitter Profile Image: Jared V.
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Jared V.
$67
total per night
5.0 out of 5 stars
8 reviews
1 repeat client
11 years of experience
Auburn, MA, 01501

Jared was great, attentive and communicated well. Was glad to have someone caring for my dog while he was in cone head mode and had to stay behind on Thanksgiving! Would definitely re-book

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Rachel C.
Sitter Profile Image: Julisa M.
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Julisa M.
$73
total per night
5.0 out of 5 stars
11 reviews
1 repeat client
14 years of experience
Gardner, MA, 01440

Julisa was wonderful - she stayed in frequent contact, sent pictures and, when our rascal of a dog breached the fence and ran off, she immediately got on the phone with me and we tracked him down at a neighbor’s house. I know what a terrible feeling that is when watching someone else’s furry babies and Julisa handled it so well.

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Carolyn D.
Sitter Profile Image: Jacquie A.
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Jacquie A.
Star Sitter
$36
total per night
5.0 out of 5 stars
20 reviews
6 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: Taylah F.
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Taylah F.
$73
total per night
5.0 out of 5 stars
18 reviews
5 repeat clients
10 years of experience
worcester, MA, 01604

I was very happy to have Taylah watch my dog Priscilla for a few nights. I got regular updates and pictures. Definitely would recommend and book her again!

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Nicole G.
Sitter Profile Image: Bethany C.
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Bethany C.
$111
total per night
5.0 out of 5 stars
3 reviews
32 years of experience
Oakham, MA, 01068

Bethany took great care of Bailey while I was on vacation in Florida visiting my family! I highly recommend her for overnights as well as anything else required. She is very knowledgeable and caring.

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Patricia L.
Sitter Profile Image: Lila N.
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Lila N.
Star Sitter
$67
total per night
5.0 out of 5 stars
23 reviews
8 repeat clients
8 years of experience
Worcester, MA, 01604

Lila was great, she took excellent care of my dog and sent updates and photos. She was reliable and communicative, I would definitely book her again!

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Caroline P.
Sitter Profile Image: Amber P.
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Amber P.
$34
total per night
5.0 out of 5 stars
6 reviews
1 repeat client
8 years of experience
Athol, MA, 01331

Amber was great! She cared for a special-needs elderly cat and a senior dog very well. The house was clean and tidy when I returned. Recommended!

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Debbie W.
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The median cost per night for house sitting in Oakham is $60

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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?

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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.

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

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Popular requests for house sitting - Oakham

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Sitters in Oakham average 4
repeat house sitting clients

FAQs for House Sitting - Oakham

Frequently asked questions about Rover

The average cost for House Sitting in Oakham on Rover is $53.28 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 1,295 sitters on Rover offering House Sitting across Oakham. 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 Oakham 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 Oakham 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 Oakham 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 Oakham. On Rover:

  • 94% of sitters can help with special care needs
  • 99% can help with giving oral medications or injections
  • 91% 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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