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 was incredible and gave us complete comfort during our time away from our fur baby. She sent pictures often to let us see how happy and content he was. When we got home he was all brushed and looked and felt amazing. We will definitely request Jordan again to take care of him again when we are away.”

“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.”

“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.”
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.

“Nichole did an amazing job. She was excellent with communicating with me throughout her time. She took great care of my dog. I strongly recommend Nichole , and will 100% use her services again.”

About: I’ve taken care of dogs ever since our first family dog who we got when I was 11. I primarily took care of him with the day to day activities such as feeding, walking, and play time. Since then, I have been entrusted by friends and family to watch their for babies especially for weekend getaways. I am able to stay overnights if needed and if local enough I can come through for extra play time and walks. I work full time during the week from 8-5, but if you’re looking for a weekend getaway or need more play time for your fur baby I’m your girl! I personally don’t have a pup or a big enough space to board your fur baby, but at your home I will ensure that it remains a safe place for your pup while still ensuring they get all the play time needed
“Meaghon was wonderful to work with! Incredibly responsive and my brood loved spending the weekend with her. We were very fortunate to have found her and can’t wait to book future trips knowing our babies will be in the best of hands!”

“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!”

“Misty was great with Teddy and Dora! They quickly warmed up to her and seemed to be very comfortable and well cared for. She took them out for frequent potty breaks as requested and they received their meals and meds on time. Will definitely book with her again!”

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.
“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:)”

About: I worked in animal shelters for over 15 years and have lots of experience taking care of dogs, cats and chickens. I am experienced in giving meds and insulin. I am extremely diligent with my level of care and the pets safety and comfort are my highest priority. I have 3 dogs of my own and understand the worries having someone else care for them. I am dependsble, mature and have a wide open schedule. I’m currently in the slow period of my business. I am currently available any time of the week or time of the day with enough notice. I will follow whatever instructions you leave for your pet and your home including their routine, preferences, meds, structure, etc. my goal is to take care of them just like you!
“I 100% recommend Kathleen! She really saved us! Our pet sitter canceled the morning we were supposed to leave for a seven-day vacation. I posted a job on Rover and she responded immediately, and very kindly stepped in to help, even though she had just finished another pet sitting gig. She took care of our beloved older dog, Dewey and our nine chickens. She was thoughtful, loving, reliable, and responsible. She texted with us almost daily, which we had asked her to do, and which set our minds at ease. She went above and beyond by giving our chickens daily treats and giving our dog LOTS of love. She is warm, respectful, and a good communicator. She also left the house in immaculate condition--in some ways cleaner than we left it. An ideal house and pet sitter in every way!!”

“Hayley is AMAZING!! One of my cats is very social and the other is shy. She got BOTH of them playing, brushed them, and made sure they knew they were loved on top of the bare minimum of feeding them and giving my old lady her meds. She even checked to make sure my hamster was still breathing while I was away since it was always during my hamster’s sleep time that she was there. Highly recommend. Will be using again if I ever am going away and she is available”

Over 30 pet parents in Winchendon have booked house sitting
Winchendon pet parents share their Rover experiences
Amanda was a wonderful pet sitter, and we couldn’t be happier with our experience. She stayed in our home and cared for our cat while we were away, and she regularly checked in to let us know how things were going, which gave us real peace of mind. When we returned, our cat was happy and relaxed, and everything in our house was exactly as we had left it. We initially felt a little uneasy hiring someone we didn’t know to stay in our home and care for our baby for a week, but we’re so glad we put our faith in Amanda. We completely trust her and will absolutely hire her again.

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 $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 Jan 2026 was about $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 Jan 2026, there are 238 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, 83% of Winchendon house sitters respond in under an hour.
House sitters in Winchendon have an average of 19 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.
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.







