House Sitting Winchendon
Find a loving house sitter to watch over your pets and your home.
Over 18 pet parents in Winchendon have booked house sitting
Winchendon, 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%.
“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 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: I’ve taken care of my roommates dog for the past 3.5 years whenever he’s occasionally out on trips. I have also been trusted to dog sit for other family and friends in previous years. I’ll make sure that they get a good walk in, feed them based on their dietary requirements given, play with them, clean up any messes they make, and will make sure they feel safe and loved while you’re away. I work about 32-35 hours a week and usually have early shifts where I get out around 2:30-3:30pm, with the occasional 11:30-8 shift once a week. So I’ll be around to care for your pet before and after work! On Wednesdays I am unavailable due to my partner needing my car to travel to his workplace. I make sure that your pets are cared for depending on their needs and will keep a good eye on your dogs while outside in the backyard whether it’s fenced in or not. I love giving them cuddles during the beginning and end of the day and is comfortable with sharing the bed with them as well!
“Kiersten spent the weekend taking the best care of our dog. She made sure all of his medical needs were met and sent photos and updates throughout the day. She’s the absolute best and we will continue to feel like not guilty dog-parents when we have Kiersten by his side!”
“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.”
“Colin took care of my rescue pup, Annie, a black lab mix with special needs, for an extended stay after a previous sitter had to cancel at the last minute. You could tell right off what a pet lover he was. He asked many good questions at the meet and greet, was punctual and handled Annie’s energy well on a leash. Colin sent me pictures and multiple daily updates on how she was doing. Giving her daily meds, tennis ball play times and long walks to help with her anxiety were part of a daily routine. I came home to a tired and happy pup. I would highly recommend Colin to anyone needing pet sitting services! Jain & Annie”
About: My name is Molly, I live in Gardner MA, I work from home so my schedule is flexible. I also have weekends off. I love cats and dogs!! I have experience in walking dogs, doing over nights at homes, and doing drop in visits with cats and dogs. I could help with any other animals you may have also. I have 2 cats of my own and a almost 2 year old dog. I have helped a lot of people that I know personally with their animals And I am looking to branch out! I can help with older animals or new kittens/puppies. Please feel free to reach out to me I would love to help! I work from home so I have time to attend to your animals needs. I get off around normal business hours so I can attend to them any time after work also. I have a lead in my yard- my dog loves playing with other dogs. I have a crate in home already. I can also separate my dog if you prefer!
“Kayla did a great job under difficult circumstances. She was available on short notice, communicated well, took great care of two Huskies in a brutal heat wave. Kayla took great care of the house, and afforded me the peace of mind one needs to have when you leave your dogs with a sitter. Thank Kayla - much appreciated.”
“This was the first time Jay stayed at our house, and she did an amazing job! One of our pugs is quite the diva, but Jay handled her perfectly. She stayed at our home for four nights and five days, following all of my care instructions like a pro. Her communication was excellent, she kept our house just as we left it, and most importantly, she took wonderful care of my babies. There were a few small hiccups and a learning curve, as expected, but Jay quickly adapted and mastered everything. I would absolutely recommend Jay and will definitely be booking her again for future travels. Thank you, Jay, for taking such great care of Googi and Skylar—and for the thoughtful pup reports at the end of your stay!”
“Sofie and Teryn took such great care of my pup, Harry! He can be an anxious boy but he had a great time with them and Sofie provided plenty of updates. I would recommend them to any pet parent and Harry is already looking forward to his next stay!”
About: I’ve always been a huge dog lover! I grew up with two Labrador Retrievers, one of whom has sadly passed away, and currently have a 5-month-old Lab puppy. I have experience caring for dogs of different ages and understand the importance of patience, exercise, and lots of love! I’ll treat your furry family member like my own, making sure they feel safe, happy, and cared for while you’re away! I’m currently training to become a nail technician, which allows me to have a flexible schedule and plenty of time to care for your furry friends! I’m available on Saturdays, Sundays, Tuesdays, and Wednesdays for walks, drop-in visits, and quality time with your pets. I love staying active and making sure every pup gets the attention, exercise, and affection they deserve! 🐾 Your pet’s safety and happiness are my priority! I’ll provide a loving environment, follow their routines, and send updates so you always feel at ease.
“Lauren is amazing! So grateful to have connected with her to take care of our dog. She is communicative, attentive, and caring. We got pics of our pet with each visit, and she kept on top of any concerns. Would definitely book with Lauren again, she's a pro with pets and very easy to work with!”
“I can’t say enough good things about Tessa. Leaving Vader and Jameson can make me a bit nervous, but Tessa sent regular photos and updates that put my mind completely at ease. She took incredible care of our boys, sticking to their routine and giving them all the love and attention that we do. We’ll definitely be rebooking!”
About: Ive been a dog trainer for about 4 years. I specialize in reactive dog handling and went through intense training myself in Maine for 6 months to be able to do what I do & would love to work with your dog/dogs. I have training in working with all type of breeds & temperaments. I currently work part-time as a dog trainer, so pet care fits naturally into my daily routine. I’m available for walks, drop-ins, and training sessions throughout the week, with the most flexibility in the afternoons and evenings. Your dog’s safety and comfort are my top priorities. I create a structured, low-stress environment by sticking to your dog’s routine as closely as possible while also reinforcing calm behavior and good habits. I have experience handling dogs of all temperaments, including reactive and high-energy dogs, and I’m always mindful of body language and triggers to prevent issues before they start.
About: My journey as a pet caretaker began early, with the responsibility of taking care of family and friends' pets. I offer attentive and personalized care, adapting to the individual needs of each pet, including specific diets, medication schedules and exercise routines. I guarantee safety, affection and a lot of fun, keeping tutors informed with regular updates. Your pet will be in an environment of love and trust. My passion for animals allows me to integrate pet care into my daily routine in a very flexible way. Although I have a current commitment, I am looking for more opportunities in the area of pet care and I dedicate myself to it. I can adapt to your pet's schedules for daily visits and walks, with great availability in the afternoons, evenings and every weekend, ensuring that your pet receives constant attention. Each pet is treated with the utmost affection and constant supervision to ensure its safety at all times. In the customer's environment, I focus on maintaining the established routine and creating a calm and fun space. If it's on tours, I use adequate safety equipment. Trust is built through my responsibility, attention to detail and genuine care that always prioritizes the health and happiness of your furry friend.
“Bri was the perfect fit for our energetic dog. She provided updates and pictures while we were away. It put our minds at ease knowing she was taking such great care of our dog. I would definitely book with her again!”
About: I have lifelong experience caring for dogs, from playful puppies to gentle seniors, and I’ve cared for many small dogs with different personalities and routines. I specialize in small dogs, generally 25 lbs and under, and provide patient, attentive, and loving care in a comfortable home environment. I understand that some dogs settle in right away, while others need a little extra time and reassurance. Puppies are welcome too! Since they need extra attention and supervision, I generally accept puppies when I don’t have other boarding dogs, so they can receive plenty of one-on-one care. My goal is simple: a happy, comfortable dog and a worry-free owner. I currently have an open schedule, allowing me plenty of time to care for and play with your furry family member. Whether it’s walks, playtime, or just keeping them company, I’ll make sure they get the attention and love they deserve. Your pet’s safety and comfort are my top priorities. Whether in my home or yours, I provide a clean, pet-friendly environment where they feel secure and loved. I follow any special instructions, maintain a consistent routine, and ensure plenty of supervision, playtime, and care. With patience and attention to detail, I create a stress-free experience so both pets and owners can feel at ease.
“As always our dogs are so happy and love when Amad stays with them, they start wagging their tails when the suitcases come out. Amad is very attentive and walks them frequently throughout the day. He is very easy going and does a great job.”
The median cost per night for house sitting in Winchendon is $60
Pet parents share their Rover experiences - Winchendon
Amanda was fantastic! Not only was she able to take care of our pets on short notice, she took great care of everyone (including our house rooster) and followed our very detailed instructions perfectly. She left our house clean and animals happy! I highly reccomend her!
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 to book house sitting
1. Search
Browse profiles of sitters near you who offer house sitting.
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit.
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform.
Popular requests for house sitting - Winchendon
Select a filter and find qualifying sitters offering house sitting.Sitters in Winchendon average 4 repeat house sitting clients
FAQs for House Sitting - Winchendon
Frequently asked questions about Rover
The average cost of House Sitting in Winchendon is $56 per night as of November 2026. Most bookings cost between $32 and $68 per night. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of November 2026, there are 691 sitters on Rover offering House Sitting across Winchendon. 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 Winchendon 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 Winchendon 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 Winchendon 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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet.
sitters on Rover set their own cancellation policy, which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.
Yes, you can find sitters who have experience with handling special pet needs in Winchendon. On Rover:
- 90% of sitters can help with special care needs
- 95% can help with giving oral medications or injections
- 94% 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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