House Sitting in Oakham

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

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Top rated Oakham house sitters

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

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Sitter Profile Image: lindsey r.
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lindsey r.
Star Sitter
$45
total per night
5.0 out of 5 stars
34 reviews
8 repeat clients
10 years of experience
Paxton, MA, 01612

We left our dogs for a week long trip and booked Lindsey for house sitting/drop in visits. She went above and beyond to care for our boys doing more visits than we asked, taking them on walks and providing them daily stimulation while we were gone. She sent lots of pictures and updates, and was very respectful of our home. I would highly recommend!

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Lauren S.
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 did an amazing job with our pups while we were away. She would send photos and updates daily which was excellent. We highly recommend her services.

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Joel A.
Sitter Profile Image: Kaitlyn D.
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Kaitlyn D.
$45
total per night
5.0 out of 5 stars
15 reviews
7 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: Meaghon R.
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Meaghon R.
$67
total per night
5.0 out of 5 stars
11 reviews
1 repeat client
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: Ella S.
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Ella S.
$28
total per night
10 years of experience
Rutland, MA, 01543

About: I’ve had several pets all growing up, ranging from turtles, to birds, to dogs! I have had 5+ dogs that I’ve owned throughout my life! My friends and family go to me to walk/take care of their pets and/or give them advice about them. I am currently free during all times of the day! I have open availability for all week days, preferably in the mornings and or afternoons! I will walk your dog for however long you need me to. I have no problem with long walks and lots of exercise as I’m usually in the gym about 5 days a week, leading me to be pretty fit and diligent for things that require high stamina. I will make sure your pet uses the bathroom, gets all its energy out, and is happy!

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

My wife and I found Sarah on Rover because we were planning a destination wedding with all of our friends and family. All the people we usually ask to watch our dog, our cat, or take care of our house would be joining us for 10 days in another country. Understandably, we were apprehensive about entrusting all that to a person we did not know. When we connected with Sarah, a few months before, we chatted and discussed organizing a meet and greet and then having Sarah do some regular dog walks in the weeks leading up to the event. At every step of the way, Sarah was prompt, communicative, friendly, honest, and above all, incredibly caring and loving to our animals. Before we left, Sarah checked in once more with a detailed review of all the logistics we had discussed for the stay. Sarah arrived as planned and spent 10 days taking the best care of our dog Mia, our cat Tar, and looking after our entire house. She stayed at the house overnight, took Mia for walks each day, played with Mia in the yard, and spent some quality comfort time in the house with both Mia and Tar. She updated us daily with pictures of the animals as well as information about the day’s activities and how the animals were doing. We were always fully comfortable that our house and animals were in the best of hands. We will continue to hire Sarah in the future for house sitting and pet care needs and give her the highest recommendation.

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CHRISTOPHER D.
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 absolutely great. She communicated promptly, sent pictures frequently and was very accommodating. Pepper felt super comfortable with her.

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Rohan S.
Sitter Profile Image: Kayla S.
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Kayla S.
$54
total per night
5.0 out of 5 stars
25 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: 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: Rebecka B.
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Rebecka B.
Star Sitter
$84
total per night
5.0 out of 5 stars
52 reviews
17 repeat clients
40 years of experience
Worcester, MA, 01605

Rebecka was amazing with my special needs senior dog! She adjusted to best care for her while I was away, was communicative, and went above and beyond. I knew my dogs were well cared for — highly recommend Rebecka.

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Hannah L.
Sitter Profile Image: Taylah F.
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Taylah F.
$73
total per night
5.0 out of 5 stars
15 reviews
4 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: Kayla C.
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Kayla C.
$73
total per night
5.0 out of 5 stars
45 reviews
12 repeat clients
3 years of experience
Spencer, MA, 01562

Kayla took care of my two pups while we were away for a long weekend. She wasn’t fazed by my grumpy old guy…. She just rolled with his moods and communicated to us daily. Made it a bit easier to leave my babies home while we were away.

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Julie J.
Sitter Profile Image: Alexandria R.
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Alexandria R.
$43
total per night
5 years of experience
Millbury, MA, 01527

About: Hi! I’m a dependable and caring dog sitter who truly loves spending time with animals of all sizes and personalities. Whether it’s long walks, playtime, or just keeping your pup company while you’re away, I make sure they feel safe, happy, and loved. i just joined Rover, but I’ve grown up around dogs my entire life and have experience volunteering and caring for animals, so I understand how important routine, attention, and trust are when it comes to pet care. I treat every dog like they’re my own, with patience, structure, and lots of affection. I work full time during the week, but I always make time in my schedule to provide reliable care for pets. I plan ahead to ensure I can give each dog the attention, walks, and care they need, whether that’s early mornings, evenings, or weekends. I’m committed to being dependable and making sure your dog is happy, comfortable, and well cared for while you’re away. When caring for pets in a client’s home, I make it a priority to follow their normal routine as closely as possible so the pet feels comfortable and secure in their familiar environment. I follow all feeding instructions, walk schedules, and any special care needs, including medications if required. I also make sure to give plenty of attention, playtime, and companionship so the pet doesn’t feel alone while their owner is away. I treat each home with respect and keep everything clean and tidy, and I always provide updates with photos so owners can feel confident their pet is safe and happy. My goal is to make the experience as stress-free as possible for both the pet and the owner.

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: Sarah M.
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Sarah M.
$45
total per night
5.0 out of 5 stars
5 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: Olivia P.
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Olivia P.
$56
total per night
5.0 out of 5 stars
9 reviews
2 repeat clients
17 years of experience
Hubbardston, MA, 01452

Olivia was.great with our animals. I highly recommend!

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Heather S.
Sitter Profile Image: Erinn O.
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Erinn O.
$89
total per night
5.0 out of 5 stars
7 reviews
1 repeat client
20 years of experience
Holden, MA, 01520

Erinn is the best! We have two senior dogs, one with special needs after having IVDD surgery, and when we came back from our little trip they were happy as ever. She’s knowledgeable, professional, and incredibly good with the pups. I’ve never seen them so at ease with a stranger. We’ll be booking her again soon!

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Hannah L.
Sitter Profile Image: Tosya F.
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Tosya F.
$56
total per night
5.0 out of 5 stars
5 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: Rae D.
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Rae D.
$67
total per night
5.0 out of 5 stars
6 reviews
2 repeat clients
25 years of experience
Hubbardston, MA, 01452

About: I've taken care of dogs for as long as I can remember. I've always been a very empathetic person and just love to wave and say hi to dogs going by. I've had dogs of all sizes. My most recent is experience with Chihuahuas. I just love them! I've raised 2 dogs from 8 weeks old. I love all stages of a dogs life, from puppy to senior. I also have experience with senior dogs who need special care and medication. I'm currently working for myself, so I have plenty of time to spend playing, caring, loving and walking with your pets. I'm available M-F 9-6 pm. I like to make sure the pet is comfortable. I want the pet to feel at home with me. The least amount of change from the pets daily activities are important for the pet to feel safe and happy.

Sitter Profile Image: Madeline K.
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Madeline K.
$78
total per night
20 years of experience
East Brookfield, MA, 01515

About: My dogs are my kids and I’m extremely passionate about providing the best life I can for them. I will treat your pets with the same attention to detail and affection as I would my own. From birth I have been around animals of all kinds and am extremely comfortable with them. I have been around animals of various social levels and am more than comfortable adapting to your pet’s needs to ensure they are comfortable, happy, and safe. I have handled all different breeds, sizes and temperments. From the smallest (with the biggest personalities) to the largest couch potatoes, to the athletes and the shy ones I will provide your pet with care tailored to them. I have experience with senior dog care as well as training and socializing puppies (I am not a certified trainer, I have only trained my own over the years and worked along side multiple trainers). I am comfortable administering various medications and ongoing treatments. If you have specific questions regarding a situation or my experience please reach out to me as there are so many different health situations. My current dogs are Kaya (4 yr GSD) and Tallulah (6 month BMD). Kaya is a fantastic big sister showing her little sister the ropes but Tallulah is the typical 2nd child and loves to cause mischief. I currently work full time, however I do work from home part of the week and have variable availability for midday drop ins. Feel free to send me a message for last minute availability. I have set my area close to my home so more than likely I would be able to make it work! Whatever your pets routine is at home, I will do everything possible to keep it as close to routine as I can. If you have any requests of walks or socializing I am more than happy to accommodate! If your dog needs plenty of mental stimulation I have a plethora of party tricks I like to teach my dogs just for fun, such as ‘sit pretty’ ‘weave’ ‘middle’ ‘spin’ etc. :)

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Over 3
pet parents in Oakham have booked house sitting

How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

The median cost per night for house sitting in Oakham is $58

Why Choose Rover?

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  • Reservation protection

    It doesn’t happen often, but if your house 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.

Sitters in Oakham average 3
repeat house sitting clients

House Sitting FAQs

Frequently asked questions about Rover

House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Oakham on Rover as of Jun 2026 was about $58 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.

If you’re searching for a Oakham house sitter for the first time, visit the house sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 516 house sitters in Oakham. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 88% of Oakham house sitters respond in under an hour.

House sitters in Oakham have an average of 16 years of experience. House sitters with repeat customers have an average of 3 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Oakham.

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Oakham house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.