House Sitting in Winchendon
Find a loving house sitter to watch over your pets and your home.

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Top rated Winchendon house sitters
Prices are estimates per night for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“Jordan has been with us for awhile, and we are very pleased with the way completes the job and making sure to communicate with us with any concerns or just to share funny photos of our fur pets. Keep up the good work 👍”

“Amanda was awesome. My Nani girl who is leery of strangers took to right away upon meeting her the first time. She kept in contact and let me know how the pups were doing and sent pics too. All the dogs seemed very happy and calm when we got home.”

“Another wonderful stay with Taylor! Teddy seemed very happy when we returned but also very comfortable with Taylor. This was the first time we had a non family member stay with him overnight and I believe it went very well. Taylor kept us informed of her plans and how Teddy was doing throughout the stay. She kept his routine the same and took great care of our boy and our house. So glad we found her. Such a relief to have someone we trust and Teddy loves.”

“We had a great experience with Rachael! She was able to accommodate our last-minute request, was incredibly flexible with timing, and made the entire process stress-free. Most importantly, we felt completely confident that our puppy, Zeke, and cat, Ophie, were in excellent hands. It gave us so much peace of mind knowing they were being well cared for while we were away. We would happily book with her again and highly recommend her to anyone looking for a reliable and caring pet sitter.”

“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!”

“Sarah was fantastic with our chihuahua. He can be a little fussy until he gets to know you and Sarah bonded with him right away. She did a fantastic job of house sitting and pet care while we were away. We would hire her again in a heartbeat. Highly recommend!”

“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.”
“Kendra was wonderfully communicative and took great care of Cookie and Bean whole house sitting this weekend - I know they are excited for the next time she is over, thank you!”
“We loved Kayla and so did Bella! Kayla gave us great updates/pictures on Bella and things going on at our house. When we arrived home everything was in place and she even took out the trash!! Don’t want to recommend Kayla, because we want to save her for ourselves!! No, Only kidding we highly recommend her, she was fantastic!! ;)”

“Tatyana was wonderful! So kind and sweet with Millie. We were in a new location which made my dog a little nervous, but she did a great job keeping her calm and sending updates and being on time. Highly recommend!”


About: Hi all! I am a stay at home mommy of two adorable and sweet teens . We are a family of animal lovers. I am a pet owner through all my life. I currently have 5 cats.. and one gentle husky/Collie sweetest Puppy ever who craves for companionship <3 I have a nice area for my cats (also a nice fenced cat patio) and a decent size back yard. I live on quiet dead end st. If your dog is boarding with us. At night time, He will have three options. Have its own crate, Or it can be free (as long as it is house trained and won't chase after my other fur-babies -cats- ??) Orrr Sleep in my bed with all my other fur-babies. If you need me to come to your house. I could also do that as well and provide kisses, hugs, playtime, food, water and cleaning. (Special instructions welcome) Oh and please I could also take care of and board Cats or other pets too!!! I love them all and it’s going to be my pleasure! ( I do have a separate area for all my cats and it’s full of fun stuff and catnip ??. But they do have full access of the house at all time) No outdoor cats please. Please come visit me and my fur babies! I am a stay at home mom. And I have plenty of free time in my hands. It would be a pleasure for me and my teens to take care of your pet. It will depend on the client's preference. I could do crating, or free run of the house. (If pet is house trained). Nice decent yard and safe neighborhood.
“Amanda was AMAZING for our house sitting booking. She took such good care of our pitbull and cat. She really connects with animals and they absolutely love her. Our cat, who normally hates strangers and always hides, was curled up on her lap by the first night. We will definitely be booking her again!”

About: Dog mom for the past 8 years and recently lost my girl to cancer. I'd be happy to love on your pup while you're away! I'm a full time teacher so only available for pet care on weekends and breaks during the school year but have full availability in summer. I love having dogs in my house where they can have their own bedroom space or share my room. 1.9 acres next to the rail trail means lots of walks and time spent outside. I also love helping pets work on their manners and good training habits and am happy to help dogs with specific behavior challenges or needs.
“Collin was great with our dog, Remy! He was very nice, professional, and followed all our directions. Remy is 85 pounds of pure muscle and can be a bit rough, especially with pulling on walks, but Collin handled her like a pro from day one. Super responsive and clearly experienced—highly recommend!”

About: I've been helping take care of dogs since I could walk. My family owned at least one dog at all times and my grandmother owned many more. I have worked with purebreds, rescues, big dogs, small dogs, dogs with behavior issues and anything in between. I also have been a handler for a comfort dog for a police department and have been trained in that field. I have trained puppies and have also cared for senior dogs. I love all dogs and think every single one deserves love and happiness! I work Monday-Friday from 8-4 but am available to come home on my lunch break. My fiance works Thursday-Sunday so would be available all day Monday-Wednesday so we have a lot of availability for focused care for your pets. I have two dogs that are very friendly and love other dogs. If you need your dog to be separated, we own a crate as well as live in a large home where we can easily give the dogs the space they need. We live on 10acres of land and can provide long walks around our house or the neighborhood. When taking care of dogs in their own home, I am very respectful of the house and the animals and can accommodate almost any need you would have for house/dog sitting.

About: I’ve been working for a company based out of Sudbury Ma for 5 years and I’m just looking for extra work :) I’ve worked with dogs of all sizes, ages etc. I have worked with dogs of all temperaments as well. Would love to get to know your pet :) I work full time walking/ pet sitting for a company Monday - Friday and weekends for sitting. I’m looking to expand to some new clients! I could even bring your dog with me for the day on walks with other dogs if I’m sitting them and they would be up for it I can stay in someone’s home or have someone’s dog/ dogs stay in my home if they are friendly with other dogs as I do have my own dog
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.
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.
Over 37 pet parents in Winchendon have booked house sitting
Winchendon pet parents share their Rover experiences
This is the 3rd time we have used Jorden. Jorden is amazing with Sam. Sam gets sad everytime Jorden leaves because he is spoiled rotten. Its nice to have someone watch Sam and take such great care of him. Jorden sends great updates daily to keep us updated on how things are going on. Its nice to know that Sam is being taken care of and in good hands. Thank Jorden..and we will definitely keep booking you whenever we need help with Sam!!

Amanda did an amazing job taking care of our large breed dog, Klaus, while we were away. She was incredibly patient with him, kept us updated throughout the stay, and took great care of both Klaus and our home. It gave us so much peace of mind knowing he was in such good hands. We will absolutely be booking with her again for our next vacation!

Maggie went above and beyond when my dog got sick while she was petsitting for us. She cleaned up after him, took him to an emergency Veterinary Hospital and administered the meds that were prescribed. I would highly recommend Maggie and would definitely have her watch.my pets again.

How Rover works

1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets
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. 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 Winchendon is CA$60
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 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 Winchendon 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 Winchendon on Rover as of Jun 2026 was about CA$60 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.
As of Jun 2026, there are 224 house sitters in Winchendon. 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, 85% of Winchendon house sitters respond in under an hour.
House sitters in Winchendon have an average of 18 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 Winchendon.
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. Winchendon 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.




