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%.
“Kendra was absolutely amazing. From the moment I walked in I knew Scout would be well cared for and would also have a fun furry companion to play with. Kendra is very attentive to details, warm, welcoming to cuddle a sometimes shy dog and my pup enjoyed lots of exercise and play. Thank you Kendra!”
“Our dog, Molly, had a great time at Mandy's place! Mandy took her on several walks every day and gave her lots of love and attention that all little dogs need. She kept in touch with us each day by sending us lots of cute and funny photos. It's very clear that Mandy loves dogs and really enjoys caring for them. She definitely gets 5 Stars from us!!! ”
About: I’ve had dogs my whole life and currently have five of my own, so caring for them comes naturally to me. As a stay-at-home mom to four kids, I’m home and available throughout the day—meaning your pup will always have company, love, and attention. Caring for pets is second nature in my home. Between my five dogs and four kids, there’s always love, play, and activity to go around. Whether it’s morning walks, midday playtime, or cozy evening cuddles, pets easily become part of our family rhythm and daily routine. When caring for pets in a client’s home, I follow their routine closely to keep things comfortable and familiar. I make sure they’re well-fed, walked, and given plenty of love and attention—just as if they were my own. I also keep homes tidy and respect any specific instructions, so you can feel at ease while you’re away.
About: I have experience caring for dogs of all ages and sizes, having owned and been with many dogs throughout my life. I provide a safe environment with a large yard, stay home full-time during care, administer medications when needed, and have personally trained each of my dogs, including my French bulldog, Rodolfo. I have flexible schedule, working from home and can provide flexible pick up and drop off times. Playing with the dogs gives me multiple opportunities to step away from work during the day. I live on more than 2 acres on a quiet road. I have a friendly 2 year old French Bulldog that loves to play with other dogs.
About: I have 14+ years experience in the veterinary field. Learning about animal behaviors, preventative care and physical health is a passion of mine. I am a very well rounded animal enthusiast that loves to stay busy. Some of my extracurriculars include training my Australian shepherd, whether it’s dock diving, agility or overall obedience. I will hold each pet to standards that support good manners, so some training may be associated with my services. I strive to exercise your fur babies intellectually as well as physically. I am very detailed oriented, and consider myself very observant. I’m not afraid to communicate and ask questions regarding your pets’ needs. I would be caring for your pet around my typical work schedule, which is M-F ~8-6pm, but I can always drop in mid day during lunch. Communicating your expectations so I may practice proper time management is important for a successful and stress free pet sitting job. I have a very well socialized 5yo male, 50lb, Australian shepherd, Oshie and he loves to play. Additionally I can provide walks, and play sessions. Hikes are also supported.
“Lauren's family is top notch for dog sitting. Right away I felt at ease leaving our pup Olive, with Lauren and Brian. Lauren has a way with dogs, she is knowledgeable and has a caring demeanor about her. I loved the fact that my dog was able to have some extra exposure to children (as I do not have any), so this was a bonus for us. The environment was comfortable and cozy, Olive being a shy, timid soul felt right at home in no time! :)”
“I can’t say enough! Eden and her husband did a terrific job with our Benny, 14 year old dog. Eden was so responsive, sent photos each day, let us know how Ben was doing. It was just wonderful to know he was well taken care of! Eden has 2 older dogs also and I think Ben really enjoyed hanging with his buddies! Thanks Eden!!!”
“I feel so comfortable leaving the dogs with Stephanie. I feel so lucky to have found her and her family. When I pick up the dogs they seem calm and happy. I hope to rebook with Stephanie next time I travel!”
“Ben was communicative with us and attentive to our little dog. She had a an excellent stay with Ben for several nights. Ben was terrific with her, giving her affection and long walks.”
About: Hello, I’m Jayliana! I’m pet CPR and first aid certified, and insured :) I have 10+ years of experience taking care of dogs, cats, birds, and other small animals! Along with a background working with animals at Petco and running my own pet sitting business. I have experience handling anxious pets and large breed dogs (including high-energy and strong breeds), and I’m able to administer medication (injection+oral). A day with me includes: -Full time presence in your home -Walks, playtime, and their structured routine -Light upkeep while you're away - Regular picture and video updates to keep you conncted to your pets :) Feel free to reach out with any questions, thank you! I’m a full-time pet sitter, so my schedule is very flexible and open! 🐾 I’ve been doing this full-time for over a year, which means your pets are always my top priority. My bookings are first-come, first-serve — so once you’re on my calendar, you can count on dedicated care and attention Safety is my top priority. Im insured and completing CPR & First Aid for pets, follow every pet’s routine and medication schedule, and never give anything they shouldn’t have. Whether in your home or mine, I keep a close eye on them so they’re safe, comfortable, and happy!
About: Been a dog lover my whole life. Did dog walking for over 3 years and have taken care of dogs in home. They are my best buddies and give me so much joy love and best medicine to my life. I'd never hurt or neglect animal. The more the merrier. Being a dog mom had always taught me more patience and kindness toward animals. And I wanna make you feel that way when you bring your baby or babies to me I'd love dogs around more. The more I can help others the better this world is. Dogs bring out the best in humans it why they belong to good people who truly love them and care for them I have small back area but my home is open and loved by all. I will walk as much as needed and always take care of them. They are my world!
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.
How to book pet boarding
1. Search
Browse profiles of sitters near you who offer pet boarding.
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 pet boarding - Winchendon
Select a filter and find qualifying sitters offering pet boarding.Sitters in Winchendon average 9 repeat pet boarding clients
FAQs for Pet Boarding - Winchendon
Frequently asked questions about Rover
The average cost of Pet Boarding in Winchendon is $67 per night as of October 2026. Most bookings cost between $48 and $76 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.
There are 416 sitters on Rover for Pet Boarding in Winchendon. About 88% 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 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 , which provides up to 25,000 in eligible veterinary care reimbursement.
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 .
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 .
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.
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, means our team will work with you to find a suitable replacement as quickly as possible.
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