Pet Boarding Winchendon
Find a loving Winchendon pet sitter to watch your cat or dog overnight at your sitter’s home.

Over 44 pet parents in Winchendon have booked pet boarding
Winchendon, Find top rated pet boarding
Prices are estimates per night for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“Ashton was amazing!! I could tell my dogs got lots of love and they enjoyed their stay. Not only was Ashton available and accommodating for our last-minute request, but he was communicative and put my mind at ease about leaving my big goof balls for the weekend. Will definitely be using Ashton and family again!”

“I couldn’t have asked for a better experience. Amy was warm, kind, and incredibly attentive while caring for my dog. It gave me real peace of mind knowing my baby was in such good hands. Communication was great, and it was clear she genuinely cared. I would absolutely trust her again and highly recommend her services!”

About: I have spent my entire life around animals so caring for them has always come naturally to me. I grew up in a household with over 40 animals, including dogs, cats, and exotic pets. I have spent years working in a small locally owned pet store in my home town taking care of exotics, before moving into kennel work at a vet’s office. I have experience in giving medications to dogs and cats in different methods, and monitoring their health afterwards. My primary role was offering our boarding pets the comfort of a home away from home. I’m a reptile dad every day, taking care of my own snake and bearded dragon babies. I’m currently home every day with time and love to give to other pets and their people who need an extra hand. I have a big room with a comfy bed that they can lay on in a nice couch that we can sit and watch shows on. I also have a fenced in yard outback that I can take them in to play, but I have a spacious cemetery up and across the street that is great for leash walks as well. I also have various toys and litter boxes as well.
“John took very good care of our pup and sent up plenty of pictures from their adventures. We will be going through him again in the future! 100% recommend him to everyone!”

“I would like to take a minute and say thank you to Mellisa and her family. My dog stayed twice with them and both times I was getting back happy and satisfied pet. Melissa and her family provided everything my dog needed: love, care and attention. They took my dog on regular walks, played fetch, and provided a lots of hugs. Every day during my dog's stay, Melissa sent me pictures and short updates on how my dog was doing. My vacation could not be more enjoyable without knowing that my dog in good hands and happy. I am highly recommending Melissa. If you care and love your dog, she is the right dog sitter for you.”

“Lee was great !!! Always sent picture and video updates throughout his stay . My dog had a great time and I would definitely book Lee whenever I needed him !!! I highly recommend him !!”

“I can’t recommend Abby more! She was so accommodating and welcoming to our dog. She always kept us in the loop and was sending pictures of all the fun he was having. I’m so happy we have found someone that we truly feel comfortable leaving our dog with. Again, she is so so so amazing and I can’t recommend her enough!”

“Christian is great! He is patient, chill, and very good with dogs! I loved that our dog wanted to go back inside with him when we had to leave; that is a great sign!”

“My dog Miko seems to have enjoyed his stay at Sara's place. He came back all relaxed, complete opposite experience of leaving him in a pet hotel where he came back agitated for many days. Sara's place is perfect with a big fenced garden so he could play freely with her dog and others. I can only recommend her.”


“Samantha and her family were amazing with Strider! She worked to figure out the best way to burn his energy and to keep him happy. As a bonus, she lives in an area any dog would love with places to hike and things to smell. I absolutely recommend her!”

“⭐️⭐️⭐️⭐️⭐️ Erica was great to work with from the start. Very responsive and gave me constant updates of my dog while I was away. I plan to use Erica strictly as my dog sitter from here on. Thank you so much for taking such good care of my baby.”

About: I have been around animals of all kinds for as long as I can remember. Growing up, my family had horses, dogs, cats bunnies, guinea pigs, birds - you name it, we probably had at least one! I absolutely love dogs and currently have a very high energy pit bull names Bizzy. He is a total sweetheart and loves all other living creatures, but he does need a lot of exercise. Luckily for both of us, lots of exercise happens to be my favorite thing! I am a marathon runner and love to take dogs for long walks or even runs if that’s what they need. I know that all dogs are individuals, so I want to get to know every dog I care for. If your dog needs a long run - great! If your dog needs cuddles and quiet time - awesome! I look forward to getting to know you and your pups! I work from home and love hanging out with dogs. During work breaks or on the weekends, I love fitting in hikes with dog friends. I’m happy to care for dogs in my home as long as they can get along with my dog and cat. If I’m in their home, I will always try to go above and beyond to keep the dogs happy and comfortable.
“Extremely accommodating, flexible, and knowledgeable about dog care. They were able to accommodate us at short notice, which was greatly appreciated. Their setup with separate enclosures to acclimate dogs slowly is very nice. Provided updates and photos/videos regularly, quick to respond to inquiries. Zuko had a great time and was well taken care of. Calm and happy upon pickup. Paul is now our go-to for dog care!”


About: I have not been an official sitter before, but I have been a dog owner for 20 years and know how much trust it takes to leave your dog in someone else’s care. Dogs are family, and I understand the importance of making them feel safe, comfortable, and loved. We do not currently have any fur friends at home, so we would be honored to share that love with your dog. I provide a calm environment, pay attention to routines and needs, and communicate clearly so you can feel confident while you’re away. Because we do not currently have pets at home, we have room in our routine to give your dog plenty of love, attention, and companionship. We can be intentional about feeding, walks, potty breaks, playtime, and rest, and we know how important it is to keep dogs on a routine that helps them feel safe and settled. We know dogs are family, so we care for them with patience, attention, and genuine love. Our home is currently without other pets, which allows us to offer a calm environment and focused care. We will follow your instructions closely, pay attention to your dog’s comfort and behavior, and communicate clearly so you know your pet is safe and well cared for.
“We thought we’d feel guilty leaving our dog behind for vacation, but knowing she was having the time of her life with Dawn and her family made all the difference! Their love and attention to her care were evident in every update, and we couldn’t get enough of the adorable photos and videos. We’re so grateful to have found such a wonderful family for her to stay!”

“Alberta was the best match for "Lucky", my very personable and sweet 15- year old Golden Doodle. Before accepting Lucky for a Sunday-to-Sunday December stay, Alberta asked all the right questions from his daily routine to how best to administer his prescription meds. Alberta also required a current veterinarian record as proof that Lucky was up to date on all his shots and also so she could keep an eye on his health. Aside from a very professional, proficient, and friendly onboarding the real magic happened when Alberta cheerfully greeted Lucky and she knew to give him time and space to acclimate to his new B&B and her own three doggies - a greyhound, a lab and a golden mix. Every morning I received a cutie pie photo of my fur baby in a different scenario which showed me just how well he was doing! Snoozing on his bed, hanging with her other dogs in the fenced in yard, or begging for a treat. Normally when I pick up my boy from other sitters he looks a bit frazzled-as if to say- what was that all about!? LOL But after his stay with Alberta and family Lucky came trotting out, happy to see me and and freshly brushed too. I could see in his eyes that he was well-rested and happy. WOW! Thanks Alberta for all the TLC!”


“I can't recommend Craig and Brianna highly enough. They looked after our dog, Oreo, for a week and provided exceptional care. Their frequent updates and photos showed just how comfortable and loved he was. It’s such a relief to find sitters who treat your pet as their own!”

“Roxy had a great time with Jacquie’s pups and another one who was staying with her for the weekend. She clearly takes great care of them, getting outside a lot despite the snow and appreciating Roxy’s affectionate ways <3”

The median cost per night for pet boarding in Winchendon is $55
Pet parents share their Rover experiences - Winchendon
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 pet boarding2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests near you
Select a filter and find qualifying Winchendon sitters!Sitters in Winchendon average 10 repeat pet boarding clients
FAQs for Dog Boarding - Winchendon
Frequently asked questions about Rover
The average cost for Pet Boarding in Winchendon on Rover is $66.6 per night (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Pet Boarding 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 Pet Boarding. For more information on service fees, click here .
There are 435 sitters on Rover for Pet Boarding in Winchendon. About 91% of Winchendon sitters can respond to requests in under 60 minutes. Whether you’re planning ahead for holidays, need last-minute care, or need same-day coverage for an urgent trip, you can message multiple sitters at once to find available care.
Once you find the right match, you can arrange a Meet & Greet to ensure they are a perfect fit for your pet’s personality before confirming.
If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.
The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.
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.
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.
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 .
While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.
Many sitters in MA ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies. Cats may be required to have Feline Viral Rhinotracheitis and Rabies up to date.
By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.
Emergency support is available by phone or email in English 24/7. When an incident occurs, we recommend that sitters contact our Trust & Safety team immediately so that they can connect your sitter with a board-certified veterinarian or offer other resources to help.
If a sitter needs to cancel at the last minute, Rover’s reservation protection means our team will work with you to find a suitable replacement as quickly as possible.






