Pet Boarding Winchendon

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

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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 15%.

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Sitter Profile Image: Andre D.
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Andre D.
$67
total per night
5.0 out of 5 stars
• 6 reviews
10 years of experience
Worcester, MA, 01606

“Andre and his family are such wonderful and kind people. They were very welcoming when we brought our boys over for their introduction before booking for the weekend stay. The updates throughout the weekend via text were a delight to see. As much as we missed the boys we felt so easy to know they truly were in great hands with Andre and family. We will definitely book again.”

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Leslie L.
Sitter Profile Image: Kimberly P.
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Kimberly P.
$35
total per night
1 year of experience
Paxton, MA, 01612

About: My parents had a one year old dog when I was born so I started life with a canine sibling. A dog, or multiple actually, has always been by my side except between 7th and 9th grade, the loneliest two years ever. I lean towards the Irish Setter but I have raised Golden Retrievers, Boston Terriers, Yorkies and Standard Poodles. I currently have two Setters and one Standard. They speak fluent English and surf the Internet for creative ideas to keep mum busy. I am a retired high school teacher since one month and am looking for commitments on a flexible schedule. I want to be busy but not at the hectic pace that teaching requires. I spent 34 years in secondary education so teaching is natural for me. I have had a canine best friend for almost every of my 58 years and have done countless basic training classes. As a former division 1 athlete, I have an exercise centric lifestyle and thrive on being physically active. Retirement is leaving a void in my routine that I anticipate dog-walking will fill. I have a large property, the majority of which is fenced. The basement has a cage assembled, a cage in the closet and a large wooden pen that my three share when I am out. The furniture is dog friendly and I have enough leashes to walk a football team at once.

Sitter Profile Image: Kimme P.
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Kimme P.
$73
total per night
5.0 out of 5 stars
• 11 reviews
6 repeat clients
8 years of experience
Worcester, MA, 01609

“Kimme took good care of our dog and had fun playing with her two pups.”

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Jill B.
Sitter Profile Image: Michelle C.
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Michelle C.
$73
total per night
4.7 out of 5 stars
• 14 reviews
5 repeat clients
15 years of experience
Mont vernon, NH, 03057

“Michelle took great care of Lucas during his stay and updated us with pictures each day. She was responsive throughout the rover process and pleasant to work with. Lucas and Henrietta made quick acquaintanceship, which is always a pleasure to see.”

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Megan U.
Sitter Profile Image: Bailey D.
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Bailey D.
$45
total per night
10 years of experience
Spencer, MA, 01562

About: I've grown up with pets,and started taking care of friends and family pets 10 years ago. They've come for the day, I've watched them while the family goes on vacation. The owners love that I'm with them all the time. I take them for walks, play with them in my yard and sit with them. I really enjoy being with animals. I'm available all day everyday. I'm building my pet sitting services. I can give your pet my full attention and give them the attention they love. I have a good sized yard that your pet can hang out in. I have great walking routes that your pet will love. I also have a good inside area dedicated to pets with a couch, and recliner that they are welcome to sit on.

Sitter Profile Image: Huanchi W.
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Huanchi W.
Star Sitter
$67
total per night
5.0 out of 5 stars
• 7 reviews
3 repeat clients
13 years of experience
Boxborough, MA, 01719

About: My love for pets started 13 years ago when I got my first Samoyed during my freshman year of college. The following year, I welcomed a Husky into my apartment. After graduating, I became a cat owner as well and have cared for three cats over the years. Having lived with both dogs and cats for so long, I’m comfortable with different personalities, energy levels, and daily routines. I’ll treat your pets with the same care, patience, and attention I give my own. My schedule is very flexible, and I’m home most of the day aside from going to the gym. This gives me plenty of time to care for, play with, and spend time with your pets throughout the day. I have a spacious home with a large yard where dogs have plenty of room to relax and play. Depending on your dog’s preferences and routine, they can spend most of their time comfortably indoors or enjoy more time outside in the yard. I’ll always follow your care instructions and make sure they feel safe and comfortable.

Sitter Profile Image: Angel G.
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Angel G.
$67
total per night
5.0 out of 5 stars
• 10 reviews
1 repeat client
10 years of experience
Amherst, NH, 03031

About: I've loved animals for as long as I can remember. Growing up, they were always a part of my life, and caring for them came naturally. Both of my parents shared that same love for animals, so I was raised in a home where pets were treated like family—with patience, kindness, and lots of affection. That love has stayed with me into adulthood. I understand that every dog and cat has their own personality, routine, and needs, and I enjoy taking the time to help them feel comfortable, safe, and happy. My home has a fully fenced yard where dogs can safely run, play, and explore, and there's always plenty of time for walks, playtime, cuddles, or simply relaxing—whatever makes them feel most at home. When your pet stays with me, they won't just be looked after—they'll be welcomed into a home where they're treated with the same love, care, and respect I'd want for my own pets. My goal is for you to enjoy your time away knowing your furry family member is happy, safe, and genuinely cared for. Pet care is a natural part of my daily routine. My schedule allows me to spend plenty of quality time with the pets in my care, whether that's going for walks, playing in the yard, sticking to their normal routine, or simply giving them the attention and companionship they deserve. I enjoy making sure each pet feels safe, comfortable, and right at home while their family is away. My home is clean, pet-friendly, and has a fully fenced yard where dogs can safely play and explore under my supervision. I never leave pets outside unattended, and I make sure they always have fresh water, a comfortable place to rest, and plenty of love and attention.

Sitter Profile Image: Sarah O.
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Sarah O.
$56
total per night
5.0 out of 5 stars
• 2 reviews
3 years of experience
Nashua, NH, 03063

About: I have grown up with dogs, and I have been taking care of other people’s fur babies for three years! I love cats, dogs, and every animal in between. While I do have a 9-5 job, I am flexible in the evenings and mornings. I have open availability on weekends and a lot of flexibility on Fridays. I can board dogs at my house currently, and I am happy to come and care for them while you are away this holiday season.

Sitter Profile Image: Melissa N.
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Melissa N.
$35
total per night
20 years of experience
Milford, NH, 03055

About: I have been taking care of various animals and pets for my entire life. Over the course of 20 years, I have cared for a myriad of animals ranging from large dogs, small dogs, horses, cats, and many other farm animals for friends, family, and co-workers. I have also been hired for pet care that involved overnight home visits, dog-walks, and hosting pets in my home to care for over two weeks of time as needed. I am a teacher with my summers off, so I have plenty of time to care for your pets. I available for pet care during the week throughout various hours in the day time. I have a means of transportation and am able to safely transport your animals if needed. I have extra supplies of safety items possible needed for animals that is kept in my car as needed.

Sitter Profile Image: Stephanie M.
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Stephanie M.
$84
total per night
5.0 out of 5 stars
• 5 reviews
1 repeat client
40 years of experience
Greenfield, MA, 01301

“Stephanie took great care of our two dogs - took them on long walks, treated them with love, and they had a great time. Will definitely be in touch with her again when we're back in the area!”

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David C.
Sitter Profile Image: Melissa Q.
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Melissa Q.
$55
total per night
5.0 out of 5 stars
• 32 reviews
13 repeat clients
15 years of experience
North Brookfield, MA, 01535

“Our two pugs came home happy as could be from Melissa’s after spending a week over the Thanksgiving holiday. We received feedback and photos throughout the week showing they were enjoying themselves as welcomed guests in her home. We are already planning to rebook for our next vacation.”

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Raeann C.
Sitter Profile Image: Lydia N.
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Lydia N.
$89
total per night
4.8 out of 5 stars
• 22 reviews
7 repeat clients
25 years of experience
Clinton, MA, 01510

“Lydia was great taking care of our dog Ollie while we had our wedding events!! She gave us a reasonable amount of updates as well as pictures, which we loved seeing during some stressful times! She was very friendly and Ollie loved her! We will definitely be using Lydia again! Thank you Lydia!!”

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Brian A.
Sitter Profile Image: Ben R.
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Ben R.
Star Sitter
$114
total per night
5.0 out of 5 stars
• 96 reviews
38 repeat clients
33 years of experience
Lancaster, MA, 01523

“Ben watched my two ridgebacks for me while I was out of town for a night. They looked happy in their pictures. Freshly tuckered out from a walk they both took a nap in the car on our way home.”

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Paula E.
Sitter Profile Image: Kelsey H.
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Kelsey H.
$67
total per night
5.0 out of 5 stars
• 2 reviews
1 repeat client
35 years of experience
devens, MA, 01434

“Kelsey took great care of Rufus. They went on many walks / hikes and she sent me lots of photos. Rufus did great with her dogs and had a great time.”

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Molly C.
Sitter Profile Image: Zachary P.
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Zachary P.
$45
total per night
26 years of experience
Keene, NH, 03431

About: I've been around dogs my entire life. At about 5 years old, my father adopted my grandfather's two Beagles and they quickly became my best friends. Today, I have 2 dogs at home, one that's 17 and one that's 7. And still they're my best friends. For as much as I love dogs, it really does feel like they love me back. Whenever I go over anyone's house I hear " Wow he never behaves this well around people normally." Each dog is so unique and the most fun thing for me is learning what makes them wag their little tails! I work from home from my apartment and only have one roommate so I'm incredibly flexible when it comes to scheduling. I'm sure that I could make just about anything work given a small notice. I have a two room apartment and a kitchen. Playing and feeding is easy for me in the apartment, but I also have a park right near me, about a 5 minute walk away.

Sitter Profile Image: Layton H.
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Layton H.
$67
total per night
5.0 out of 5 stars
• 9 reviews
3 repeat clients
22 years of experience
Brattleboro, VT, 05301

About: Hi, my name is Layton and I've been an animal lover my whole life. I've had furry family members since I was five years old and multiple re-occuring caretaking jobs, so I know how to care for your baby. From 2018 to 2020 I worked as a dog groomer and had the privilege to work with pups of all kind - big, small, young, old, excitable and laid-back. I especially love to provide YOU with a sense of comfort knowing that your pet is in wonderful hands. I am available for overnight sittings, drop-in visits, walks, trips to the dog park and even transports to the vet and groomer. Just let me know what kind of care your pet(s) need and I'll be there! I currently have a pretty flexible schedule for the time being. I am willing to take on weekly walks, occasional overnight sittings and longer term stays. I do not offer care at my home (I live with two cats that are not too fond of other animals). But, I can provide meals, walks, play and love for your pet in their own home!

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The median cost per night for pet boarding in Winchendon is €55

Pet parents share their Rover experiences - Winchendon

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5.0 out of 5 stars

Amanda was so communicative while Stelly was in her care. She provided photos and updates every day. It was clear that Stelly enjoyed her stay and felt very comfortable and welcome with Amanda and her family! I would absolutely rebook!

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Cate K.
Boarding
5.0 out of 5 stars

We are so grateful for Amanda and her family for the love and care they give our dog! We were able to enjoy our longest time away from her yet knowing she was well cared for and really appreciated the daily photo and updates.

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Jillian D.
Boarding
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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. 1. Search

    Browse profiles of sitters near you who offer pet boarding.
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit.
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform.

Popular requests for pet boarding - Winchendon

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Sitters in Winchendon average 10
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 November 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 423 sitters on Rover for Pet Boarding in Winchendon. About 90% 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 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.

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.

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