House Sitting in Oakham

Find a loving dog sitter to watch your dog overnight in your home.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
Which dates do you need?
What size are your dogs (lbs)?
To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

Search Results

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Kayla C.
Verified Enhanced Background Check
Sitter Profile Image: Kayla C.
Verified Enhanced Background Check

1. Kayla C.

The greatest care for your pets 💕
Spencer, MA, 01562
7.6 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
16 reviews
7 repeat clients
from
$65
per night
Profile image

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

Calendar Recently Updated
Sitter Profile Image: Lila S.
Verified Background Check
Sitter Profile Image: Lila S.
Verified Background Check

2. Lila S.

Exceeding Expectations daily
Palmer, MA, 01069
17.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
30 reviews
14 repeat clients
from
$52
per night
Profile image

Lila is amazing. She sent pictures and videos, which gave me peace of mind while I was away. I appreciated her knowledge, experience with animals especially older dogs and rescues and her caring but confident manner. Would highly recommend. .

Sitter Profile Image: Lila P.
Verified Enhanced Background Check
Sitter Profile Image: Lila P.
Verified Enhanced Background Check

3. Lila P.

Paws, claws, I love them all!
Brookfield, MA, 01506
10.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
2 repeat clients
from
$35
per night
Profile image

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!!!

Calendar Recently Updated
Sitter Profile Image: Amanda P.
Verified Enhanced Background Check
Sitter Profile Image: Amanda P.
Verified Enhanced Background Check

4. Amanda P.

Will treat your pets like my own
Princeton, MA, 01541
8.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
5 reviews
4 repeat clients
from
$30
per night
Profile image

Amanda was great! She was very responsive and responsible, and even jumped in during a pinch when we needed someone on short notice. Our super anxious pups (including our 85lb boxer) warmed up to her very quickly and we could tell they had a great time when we got home. We will definitely have Amanda back at our home to stay with our fur babies and recommend her for your sitting needs.

Calendar Recently Updated
Sitter Profile Image: Erin M.
Verified Enhanced Background Check
Sitter Profile Image: Erin M.
Verified Enhanced Background Check

5. Erin M.

Young professional who loves pets!
Holden, MA, 01520
12.2 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
1 repeat client
from
$35
per night
Profile image

Erin was great! She house sat for us for almost a week, and we couldn’t have asked for anyone better. Her communication was quick. She paid careful attention to each of our pets feeding routines and made sure to update us on how much they ate each day (a concern of ours due to a new health issue with one of our cats). We got updates each day with how they were doing, what they did that day, and plenty of pictures! We’ll definitely be using Erin again for future trips and can’t recommend her enough!

Calendar Recently Updated
Sitter Profile Image: Dominique S.
Verified Enhanced Background Check
Sitter Profile Image: Dominique S.
Verified Enhanced Background Check

6. Dominique S.

Looking for fun with puppers!
Holden, MA, 01520
9.7 mi. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
42 reviews
10 repeat clients
from
$63
per night
Profile image

Dominique was awesome. A please to work with, she came and did a house visit prior to booking. Got a long well with Gracie. Will definitely use her for future bookings and totally recommend. She watched Gracie for a week and did 2 house visits a day. Trusted her with our Home and had no issues.

Calendar Recently Updated
Sitter Profile Image: Makayla P.
Verified Enhanced Background Check
Sitter Profile Image: Makayla P.
Verified Enhanced Background Check

7. Makayla P.

Fun & intuitive!
Worcester, MA, 01602
10.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
1 review
from
$32
per night

In college, I adopted two sibling kittens from an overcrowded shelter that Makayla and I volunteered at. Makayla was my roommate and we raised them together for four years. I was unable to care for both of them the entire time so Makayla graciously took one of them on over the summers. When we graduated we decided the best choice was for her to fully adopt one of them- and Makayla has been her cat mom ever since! It was an easy decision; Makayla is flexible, caring, attentive, responsible, and loves animals of all shapes and sizes. Makayla was my first choice to entrust the care of my animals and she should be yours too!

Calendar Recently Updated
Sitter Profile Image: Olivia P.
Verified Enhanced Background Check
Sitter Profile Image: Olivia P.
Verified Enhanced Background Check

8. Olivia P.

Prepared for pretty much anything!
Hubbardston, MA, 01452
8.5 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
1 repeat client
from
$50
per night

She has watched my cat while I went on a three week vacation and was very attentive to his needs and would send me voice memos of his meows from the other room and how he would reply to hers. And then I sent a voice memo and she played it for him. I am very happy with her services and would highly recommend her to anyone who wants to have her pet sit.

Sitter Profile Image: Sky C.
Verified Enhanced Background Check
Sitter Profile Image: Sky C.
Verified Enhanced Background Check

9. Sky C.

Passion for animals and their care
Hardwick, MA, 01031
10.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
56 reviews
18 repeat clients
from
$60
per night
Profile image

Absolutely wonderful, Sky took great care of our two pups and the house while we were gone. Very punctual and professional. Sky kept us up to date with lots of wonderful pictures and videos on walks and playing around. Couldn't have asked for anything more than that!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Elizabeth N.
Verified Enhanced Background Check
Sitter Profile Image: Elizabeth N.
Verified Enhanced Background Check

10. Elizabeth N.

Animal Lover
Rutland, MA, 01543
5.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
29 reviews
18 repeat clients
from
$25
per night
Profile image

Liz was very responsible, attentive and loving towards Cubby. This was our first time using a Rover sitter and we were very pleased with her care. We will rebooked Liz for the next week because Cubby loved her so much:)

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Amber M.
Verified Background Check
Sitter Profile Image: Amber M.
Verified Background Check

11. Amber M.

Flexible/experienced in animal care
Paxton, MA, 01612
6.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
3 reviews
from
$30
per night

I've known Amber, for the majority of my life, as one of my most caring and trustworthy friends. Our whole lives she's loved animals of all kinds. Over the years she's had plenty of experience with small animals as well as dogs of all sizes. Amber takes such pride in training her animals to be obedient, yet also raising them with unconditional love. I've never been so impressed by the way someone could have such well behaved animals and be so dedicated to making sure they get exactly what they need. Even treating mine as if they were her own. Anyone would be lucky to have Amber as their dogs caregiver!

Sitter Profile Image: Kaitlyn D.
Verified Enhanced Background Check
Sitter Profile Image: Kaitlyn D.
Verified Enhanced Background Check

12. Kaitlyn D.

I love all animals!
Rutland, MA, 01543
5.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
4 reviews
4 repeat clients
from
$35
per night

About: I have two dogs and a cat. I’ve been caring for pets since I was little. Walking, feeding, and playing with animals comes second nature to me. I am a very caring person that loves animals. I am home for summer break and have complete availability! Please write me for more information and details on what dates you need care for. I am used to having no fence so recall and watching closely is something I’m used too. I have a small dog, so I am used to smaller breeds. I also have a large golden retriever to walking large dogs is no issue! I’m really good with any environment though. You’re fur baby will be in good hands!

Sitter Profile Image: Erin H.
Verified Enhanced Background Check
Sitter Profile Image: Erin H.
Verified Enhanced Background Check

13. Erin H.

Mother and Pet Lover
Rutland, MA, 01543
3.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
1 review
from
$85
per night

Erin is amazing with animals! She is so caring and knowledgeable. I remember when she drove for days through different states to help transport a rescue dog. She is extremely responsible and loving. She’s one of the only people I would trust with my two energetic dogs.

Sitter Profile Image: Maria G.
Verified Background Check
Sitter Profile Image: Maria G.
Verified Background Check

14. Maria G.

Backyard Lake/Trails + Chill Home
Jefferson, MA, 01522
8.2 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
77 reviews
29 repeat clients
from
$40
per night
Profile image

Maria was terrific with my dog, Boston. Throughout my time away, Maria kept me updated on activities and sent over pictures highlighting how much he was enjoying his time with her. She was very professional, courteous, and responsive so highly recommend Maria as a great fit for your loved one.

Calendar Recently Updated
Sitter Profile Image: Sydney L.
Verified Enhanced Background Check
Sitter Profile Image: Sydney L.
Verified Enhanced Background Check

15. Sydney L.

What can I say, I love Animals!
Rutland, MA, 01543
4.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
6 years of experience
from
$50
per night

About: I’ve been taking care of dogs for 6 years now! I have a medium size dog of my own named Remi. I have experience walking dogs, feeding, taking outside, and playing with dogs! I am currently working Part-time. I would love for the opportunity to play with and walk your pups! I’m so excited to meet them all! Unfortunately, I live on the main road so I am unable to do visits in my home, but I am willing to do what is needed to meet your dogs needs on our walk on in home visit!

Sitter Profile Image: Vicki K.
Verified Enhanced Background Check
Sitter Profile Image: Vicki K.
Verified Enhanced Background Check

16. Vicki K.

Pets of all kinds are safe with me!
North Brookfield, MA, 01535
6.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
2 reviews
from
$25
per night
Profile image

Vicki clearly loves critters of all kinds and immediately connected with Riley the dog. Riley is a fairly new rescue and Vicki understood Riley's anxiety and kept her feeling happy and secure while I was away for the first time. Vicki communicated well and sent me photos, reassuring me as a first time dog person that my little fuzz-face was in excellent hands and doing fine. Vicki went above and beyond, also monitoring the house -- and she left it cleaner than I expected. I would recommend Vicki without reservation.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Brittany N.
Verified Background Check
Sitter Profile Image: Brittany N.
Verified Background Check

17. Brittany N.

Flexible and fun pet sitter
Barre, MA, 01005
6.2 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
11 reviews
3 repeat clients
from
$55
per night
Profile image

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.

Sitter Profile Image: Tara M.
Verified Enhanced Background Check
Sitter Profile Image: Tara M.
Verified Enhanced Background Check

18. Tara M.

Responsible adult -no need to worry
Barre, MA, 01005
2.7 mi. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
2 reviews
from
$50
per night
Profile image

Tara is the best! We stumbled upon rover last minute and the stars must have been aligned that day because we found Tara and her son who happened to be available and they are the best. No need to worry about your babies while you’re away! Truly above and beyond

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jon D.
Verified Enhanced Background Check
Sitter Profile Image: Jon D.
Verified Enhanced Background Check

19. Jon D.

Responsible and Caring Pet Lover..
Rutland, MA, 01543
5.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
10 reviews
1 repeat client
from
$100
per night

Jon is great with animals. He has always been around animals so he had quite a bit of experience. Just right now he has two dogs and a cat. He is very responsible and flexible making him a perfect person to trust your pet with.

Sitter Profile Image: Abby B.
Verified Enhanced Background Check
Sitter Profile Image: Abby B.
Verified Enhanced Background Check

20. Abby B.

Looking to pamper your pets
Barre, MA, 01005
4.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
2 repeat clients
from
$32
per night

Abby has taken care of my four horses and cat. She's read my five pages of notes and followed every detail meticulously. She even sends me pictures of all animals so I can feel secure knowing they are happy and cared for. The best part about Abby is that she takes care of each and every animal like they are her own. It's hard to find someone who can trust with your pets, but Abby is one of those people!

Search Map

Rover also offers House Sitting in:

Rover also offers other services in Oakham:


Rover offers the perfect alternative to dog kennels. The next time you head out of town and need someone to take care of your dog — and your home — turn to Rover for your Oakham house sitting needs. On Rover, it's easy to find a loving dog sitter in Oakham who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at home. Search from hundreds of trusted Oakham house sitters near you, read sitter profiles, and reach out to sitters who seem like a good fit for you and your dog. We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your dog's stay all through Rover — it's easy, safe, and cashless. You get free premium insurance, a team of safety experts available 24/7, and cute photo updates throughout the stay. It's the easiest way to find trustworthy house sitters in Oakham for your dog — people who'll treat him like family.

House Sitting