House Sitting Winchendon
Find a loving house sitter to watch over your pets and your home.
Over 33 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 conscientious and takes care of business. More to the point, Jorden is one of my dog's favorite people, and the cat came out to look and see Jorden on the 2nd day, which is a lot of friendliness on his part!”
“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!”
“Emily was fantastic and exactly what I needed after my existing plans fell through. She stepped up with little notice and did a great job of taking care of Daisy for me. Thank you again!”
“Amadie was amazing! She cared for two of our dogs on a very hot day for three hours. She was prompt, thoughtful, sent great photos, and communicated very clearly. The pups were happy and tired after the time together. Who can ask for more than that? We will definitely book her again!”
“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.”
“Amanda has been amazing! She’s done a couple of drop-ins for me to give my cat her medication, and did a long weekend stay at my house. She left my place in the same state it was in when I left, and provided updates at the end of each visit.”
“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!”
“Kendra watched our two senior dogs and house sat for us for a little over a week while we traveled out of state to visit family. She sent regular updates with photos and videos, took care of everything, and when we came back dogs were in excellent spirits and the house was as clean as we left it (possibly cleaner). Would use her again in a heartbeat.”
“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.”
“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!”
“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!”
About: Owned and taken care of dogs and cats since I was young. Can’t remember a time without having pets! Currently own two crazy pups and two pretty kitties, and can’t wait to meet yours. Have experience with senior dogs, puppies, and everything in between. I am a full time firefighter/EMT, so I only work two 24hr shifts a week, and the rest of the time I get to play with yours, and my own animals! Love to hike or be outdoors with as many pets as possible! If they’re happy, I’m happy! I will follow all rules set for your pet, and be sure to keep their safety at the top of the list! As a pet owner, I can’t imagine something happening to my own animals, and I would never want to let anything happen to yours!
About: Let me bring your dog on an adventure - my dog walks start at $16 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 Katie, of Little Lyons, for about a year. She is contentious, dedicated, and loving to all the people and pets she comes into contact with. I highly recommend her services and happily look forward to working with her again in the future." - Nicole E. "Katie dogsits for me when I go away on business trips or go into Boston for the weekend, and I could not recommend her more highly! She is caring and attentive to my dog; my dog gets so excited to see her. My dog is medium to high energy and Katie always tires her out. She 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. Katie is punctual, she remembers all sorts of details about every dog, and she 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! LGBT+ friendly I am a chronically ill artist who has kept strange hours for a very long time. I can fit your furry (or scaly or feathered) family into my schedule without issue. 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.
“Kayla was fantastic! She helped me in short notice and stayed at my place. I got updates on my dog and how he was doing, and she was very communicative regarding her schedule in tandem with my dog’s. She also happened to be at my place when there was an issue with a leak, and if it wasn’t for her quick response to me then I would’ve come home to a huge mess. She cares about you and your companion(s)! Thank you for being compassionate and respectful, Kayla!”
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.
About: Having spent my entire around dogs and now a proud dog mom to a 3 year old Australian Shepherd named Willow, I am well acquainted with the responsibility of pet ownership. I can offer security for families and dog parents when traveling away from home. I offer home boarding with a large back yard for play and doggy adventures. As an active person who loves being outside with an active dog partner I provide exercise for your doggy friend while your away. I can supplement daily cares of caring for a pet including basic grooming and medication suspension if necessary. Not afraid of large breed dogs or those with anxiety I welcome dogs of all sizes and temperaments into my life. When we travel we should travel with confidence knowing our furry friends are well taken care of, let me help you travel with confidence.
“We two humans, along with Felix-the Dog, all feel like we made a new friend in Kathleen! Felix, who is not always sure about new people he meets, immediately took to Kathleen when she came to our home for a meet-and-greet. Kathleen sensed Felix’s apprehension and quickly put him at ease with her calm, affectionate, low-key response. On the basis of our visit, we mutually agreed to have Kathleen stay with Felix a few days later while we enjoyed a quick 24-hour getaway. While we were away, we had good, clear communication by text message. Although we were delayed getting home, Kathleen volunteered to stay until we returned so she could give us a verbal report, which we appreciated very much. When she left, Felix’s dejected body-language showed he was sad to see her go; clearly he had enjoyed her company. We look forward with confidence to having Kathleen stay with Felix again.”
The median cost per night for house sitting in Winchendon is $60
Pet parents share their Rover experiences - Winchendon
Amanda did a phenomenal job taking care of our two dogs for a long weekend - we strongly recommend her! She sent regular updates with photos which clearly showed how much our dogs were smitten by her and how much fun they were having - including our young dog who can take a while to warm up to people! Amanda was highly communicative about her schedule. She let us know immediately when she had a family emergency on the last day that would impact how many hours during the day she’d be available to hang out at home with our dogs. We offered to try to find someone else to pop in, but she coordinated everything so that she could be back to spend time taking care of them every couple of hours (well within the limit of how long they can hold it). We were so impressed by her thoughtfulness, professionalism, and care for our pups even when she had something else going on! We would book Amanda again in a heartbeat and highly recommend her for in-home pet care.
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.
Meet local sitters who will treat your pets like family
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 for House Sitting in Winchendon on Rover is $57.08 per night (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of House Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for House Sitting. For more information on service fees, click here .
As of September 2026, there are 702 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 short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter 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. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.
Yes, you can find sitters who have experience with handling special pet needs in Winchendon. On Rover:
- 92% of sitters can help with special care needs
- 98% can help with giving oral medications or injections
- 92% 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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