House Sitting Winchendon
Find a loving house sitter to watch over your pets and your home.
Over 34 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%.
“Jorden is always so responsive! When my return flight was delayed, Jorden went back and fed my guys and walked my dog one more time... so grateful to have such a caring, trustworthy person to watch them!”
“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!”
“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!”
About: Let me bring your dog on an adventure - my dog walks start at $20 but I do hikes on a sliding scale. I have group play experience, I can bring your dog to a dog park without any fear that your dog will get into any sort of trouble. I'm a quiet, clean, petsitter, I will likely leave your house cleaner than it was when you let me in. "I have worked with Kae, of Little Lyons, for about a year. He is contentious, dedicated, and loving to all the people and pets he comes into contact with. I highly recommend his services and happily look forward to working with him again in the future." - Nicole E. "Kae dogsits for me when I go away on business trips or go into Boston for the weekend, and I could not recommend him more highly! He is caring and attentive to my dog; my dog gets so excited to see him. My dog is medium to high energy and Kae always tires her out. He is extremely knowledgable about dogs and dog behavior and has given me several tools to help keep my dog more mentally engaged and less stressed. Kae is punctual, he remembers all sorts of details about every dog, and he is my go-to whenever I need someone. Best dog sitter/walker in the Providence area!" - Kate R. I have worked with a doggy daycare, where I learnt dog behavior, and positive reinforcement training. I have worked in home pet sitting for dogs, cats, rabbits, snakes, tortoises, geckos, bearded lizards, salt and fresh water fish, for over a decade. Schedule a meet and greet with your pets! LGBTQIA+ friendly, Disability and Sensory Friendly I have kept strange hours for a very long time. I can fit your furry (or scaly or feathered) family into my schedule without issue. As a pet service professional, I like to make sure your pet is well attended to, and you feel as safe and comfortable as they do. I enjoy waking up to walk a client's dog, or making sure your cat feels safe before it's time to turn the lights off. You can rest assured while I am with your pets that they will be well attended to. A typical visit includes 15-20 minutes of play with your pet depending on energy levels, lots of positive attention and love, feeding and making sure they have access to water and making sure any business is done. As an overnight visitor, often for pets with anxiety or special needs/senior pets, I am with your pet in your home from 10pm-8am, plus visits during any of their usual scheduled feedings. As a dog walker, you can expect me to arrive and provide a full 30 minute walk to your pet. If you book through rover, you can also get a map of the walk we did, how long it took, and I provide pictures along the way. When it's time to go home, I make sure they and your home are safe and secure.
“Amanda was super prompt and responsive while we were out of town! She stayed at our home with our clingy border collie and gave great updates and pictures - they got out and about as much as possible during a heatwave but had plenty of snuggles and scritches inside in the AC. She left the house in perfect order. We would love to have her stay again in the future!”
“Jay stepped in at very short notice to help us out when another sitter fell through. We really appreciated her quick response and regular communication during the transition as well as throughout the sitting. She is very reliable and sends lots of photos and updates. Our pets are in good hands with Jay! We’ve been able to have her house sit two times and would love to have her again.”
“What a dear person. Nadine is a natural with knowledge and a love of animals. She showed great judgement, and was kind enough to let me know when our cat was in for the night. She was thoughtful, and clearly is great with animals. Our cat was thoroughly in love.”
“Jeffrey is trustworthy and supportive. My fur babies love him. He will be back to babysit at the end of the month. We can’t wait to have him again. Thank you so much for your love and kindness to Bella and Coco.”
“Lauren is great. I have three big dogs that can be a little overwhelming but from start to finish Lauren handled them well and I felt very comfortable leaving them under her supervision. Lauren is tuned in and asks all the right questions, cares about the dogs and is a very capable, responsible and common sense person. I would definitely hire her again.”
About: Hi! I’m Melinda, a lifelong animal lover who knows how much our pups mean to us. 🐶💜 I’m dependable, patient, and love getting to know every dog’s unique personality. Whether your pup needs a fun walk, a potty break, playtime, a drop-in visit, or some extra cuddles while you’re away, I’m here to make sure they feel happy, safe, and loved. I’ll treat your dog like one of my own and keep you updated with photos and messages along the way. 🐾✨ I’m available for pet care on weekdays after 5:30 PM and have full availability on weekends. I’m happy to provide walks, drop-ins, playtime, feeding, and loving companionship around your schedule. I provide pet care exclusively in your home, where your pets are most comfortable and can stay in their familiar surroundings. I’ll follow your instructions carefully and treat your home and pets with respect, patience, and care.
“Julie is THE VERY BEST! We have three older dogs who can be challenging. She gave them such loving attention and care. Julie always kept us abreast of their status with updates and photos. When we got home, our dogs were happy to see us, but they didn’t seem as jubilant as they normally do. THAT’S A TESTAMENT to Julie. THEY LOVED HER!!! And that’s what every family should want for their pups. Have no reservations about hiring Julie. We will be using her services again in the future. Thank you, Julie!”
About: Vacation with peace of mind knowing your beloved canine family member will be safe and happy; and perhaps, a bit overly loved. There’s always lots of play and pamper time and all walks are free! I’ll gladly keep in direct contact with you providing pictures and videos throughout each. I will lay with your fur babies, play outside, go on walks/adventures, relax and watch movies. I love all animals and believe they deserve to have a good time even when their owner cannot be home. I have always been an animal lover, i never felt like watching them was work, just fun. I respect the owner's wishes for anything they need me to do in order to give their animal the best experience while I am watching them. I am always home since I’m a full time grooming student @ Animal Behavior College. My long term goal is to open up a pet and spa resort one day! 🐾 I believe that daily exercise, games, mental challenges and proper socialization is necessary for your pup to live a long and happy life! We think it’s so important that we do it for our pup and of course yours while you are away. I have a fenced in back area and 2 fur babies myself to keep your pup company. We have extra crated if needed and loads of toys to keep them happy! If alone time is their thing, they are always allowed to cuddle with us on our furniture! If a drop- in, I am very good at following concise instructions to insure happy and safe animals while you’re away! I am always home as I’m a mom of three. Your pet will get lots of one on one attention from me. I can’t wait to meet your fur baby! I have a fenced yard outside area and lots of toys. Also, I have a pool for my fur friends to play and cool off in during the summer! Your fur baby will feel at home and will receive lots of love and cuddles.
“Danielle is always amazing! She’s reliable and excellent with communication. She keeps us updated and send lots of photos and videos which helps to ease any worry. She also leaves the house looking just as clean as we left it. Our kitties were obviously well loved and cared for while we were away!”
“Laura is, without a doubt, the best pet sitter we've ever had. She took exceptional care of our dogs, and we came home to two happy, tired golden retrievers and a house that was even cleaner than when we left. Laura is trustworthy, incredibly kind, thoughtful, and an excellent communicator. She kept us updated with adorable photos of our dogs throughout our trip, which gave us so much peace of mind. As if that weren't enough, we returned home to find two beautifully wrapped, framed photos of our pups—a thoughtful surprise that truly went above and beyond. We can't recommend Laura highly enough. Don't hesitate to book her—you and your pets will be in the best hands.”
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: I have cared for pets for more than 18 yrs in both Fla and New England. Always willing to travel with you or to your home. I am able to schedule pet sits in advance as needed. Always reliable loving and caring and aware of pets needs. I love the pets. I offer care in your home as well as water plants etc. I will do whatever is asked of me to do for the pets and the families.
“Cianna was spectacular, stepping in with very short notice for an extended stay (2 weeks) after some health concerns with one of our dogs made me hesitant to leave him in the kennel for that stretch. She was awesome with the dogs, on top of all their needs and concerns, and was very communicative throughout. The dogs may have been a bit sad to see us come home at the end of the trip as they loved their time with her.”
“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 $57 per night as of October 2026. Most bookings cost between $54 and $83 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 October 2026, there are 684 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.
<b>Tip:</b> 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 , 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 .
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 .
sitters on Rover set their own , 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:
- 89% of sitters can help with special care needs
- 95% can help with giving oral medications or injections
- 95% 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.
Connect anywhere with the Rover app
