House Sitting Oakham

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

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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: Kalliah B.
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Kalliah B.
Star Sitter
$60
total per night
5.0 out of 5 stars
50 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: Sarah M.
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Sarah M.
$63
total per night
5.0 out of 5 stars
43 reviews
16 repeat clients
4 years of experience
Petersham, MA, 01366

Thank you Sarah for taking such great care of our girl. We came home to a very happy girl. We received lots of updates and photos. This was Sarah’s first stay with Sadie, but definitely won’t be the last!

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Beverly C.
Sitter Profile Image: Meaghon R.
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Meaghon R.
$67
total per night
5.0 out of 5 stars
12 reviews
1 repeat client
20 years of experience
Princeton, MA, 01541

We seriously could not have asked for a better dog sitter for Archie. Meaghon took amazing care of him while we were away and gave us complete peace of mind the entire trip. Communication was excellent with updates, photos, and check ins that made it so easy to relax knowing Archie was in such good hands. When we came home we could immediately tell Archie was happy, relaxed, and clearly very well cared for. You can tell Meaghon genuinely loves animals and goes above and beyond to make sure they feel comfortable, loved, and cared for. She was professional, reliable, and incredibly easy to work with. We were so impressed that we have already rebooked with her again. Highly recommend Meaghon to anyone looking for someone trustworthy and amazing to care for their pets!

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

Kayla is an amazing sitter. She took care of our two reactive fur babies for a recent weekend trip out of state. It was our first time entrusting anyone outside of family and close friends with Bark and Hachi and Kayla quickly won over both of them. We are so excited, relieved, and grateful. We will definitely be staying in close touch !

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Peter M.
Sitter Profile Image: Kayla S.
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Kayla S.
$54
total per night
5.0 out of 5 stars
26 reviews
8 repeat clients
20 years of experience
Spencer, MA, 01562

Kayla is absolutely amazing. She is the best dog sitter we've had with our pups, we're always at ease knowing she's with them while we are away. She is great at sending pictures and updates

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Stephanie B.
Sitter Profile Image: Sarah M.
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Sarah M.
$45
total per night
5.0 out of 5 stars
6 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. Although I am brand new to this app, 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 am working part time but I am available every weekday from 10:30am 2pm. Also, 5pm-7pm. I am available all day Saturday and Sunday afternoons. As a dedicated pet sitter, I always start by showering your pets with affection! Following this warm greeting, I tailor our time together to meet their needs, whether that involves taking them outside or going for a walk. Upon our return, I can either feed them or engage in some fun playtime, depending on the schedule and your pet’s preferences. I pride myself on being flexible and collaborative, so I'm here to work with you to ensure that your furry companions receive the exceptional care they deserve!

Sitter Profile Image: Kaitlyn D.
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Kaitlyn D.
$45
total per night
5.0 out of 5 stars
15 reviews
8 repeat clients
3 years of experience
Rutland, MA, 01543

Kaitlyn did an amazing job sitting our Appy! I knew he was in great hands while she was with him. Thank you so much again! Would definitely recommend :)

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Sam G.
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
24 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: 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: Rebecka B.
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Rebecka B.
Star Sitter
$84
total per night
5.0 out of 5 stars
53 reviews
17 repeat clients
40 years of experience
Worcester, MA, 01605

Rebecka took wonderful care of Benny. The updates were greatly appreciated, especially knowing he was eating, resting, and settling in well. It was very reassuring to see how comfortable he was with her. Highly recommend!

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Deepa R.
Sitter Profile Image: Joseph P.
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Joseph P.
$36
total per night
5 years of experience
Rutland, MA, 01543

About: I grew up with dogs and cats and I love animals in general. I am patient, experienced, caring and gentle, Rocky Kanaka is someone I look up to. My top priority is making sure your baby feels safe and cared for as though I am family too. I would love to get to know your baby I am available on weekends primarily. I can be available for visits and care from 12-2 Monday thru Friday provided there's no scheduling conflicts. I can take extra time or increase my availability during the week with advanced notice. I carefully follow any instructions left for me, and having had experience caring for my boy, I know keeping your baby safe is the most important part of care that I provide. I am careful to keep an eye on any animal I care for to make sure they don't have the opportunity to run outside off leash

Sitter Profile Image: Jared V.
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Jared V.
$67
total per night
5.0 out of 5 stars
7 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: Kailin D.
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Kailin D.
$65
total per night
5.0 out of 5 stars
7 reviews
1 repeat client
12 years of experience
Holden, MA, 01520

Kailin was a great companion for our pup! She exercised the dog often and was always available for updates. We definitely plan to use her for walking and house sitting needs in the future.

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Brooke P.
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: Brittany N.
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Brittany N.
$62
total per night
5.0 out of 5 stars
12 reviews
4 repeat clients
20 years of experience
Barre, MA, 01005

I couldn't be happier with Brittany! I felt extremely comfortable leaving my 3 puppies in her care. She was very caring, patient and my dogs loved being there with her.

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Jill L.
Sitter Profile Image: Christina C.
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Christina C.
$45
total per night
20 years of experience
Holden, MA, 01520

About: I have had dogs my whole life. I have raised 5 of my own dogs from 8 weeks old. I have experience with many breeds of all ages as well as cats, reptiles, and other small mammals. I currently work as a retail manager so my schedule varies weekly. I am extremely flexible on the days I have off, so last minute needs are not a problem.I know how important it is for pet parents to be able to rely and trust someone with their babies. I am looking to fill more of my days with being able to help other pet parents in need. I have a fully fenced in yard and a 5 month old, very friendly, puppy to help with socialization and a friend if your furry friend needs one. I have a routine with my animals and will maintain yours as well.

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.
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: lindsey r.
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lindsey r.
Star Sitter
$111
total per night
5.0 out of 5 stars
36 reviews
10 repeat clients
10 years of experience
Paxton, MA, 01612

Lindsey did a great job taking care of our pup and two cats. She was punctual, communicative, and overall great to work with. I know our animals appreciated having her here while we were gone and would definitely recommend her to anyone looking for a dog sitter while away!

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skyler c.
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The median cost per night for house sitting in Oakham is $60

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.

How Rover works

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting
  2. 2. Meet & Greet

    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

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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