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 11%.

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Sitter Profile Image: Samantha & Brian S.
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Samantha & Brian S.
$56
total per night
5.0 out of 5 stars
• 8 reviews
1 repeat client
18 years of experience
Wendell, MA, 01379

“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!”

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Devon G.
Sitter Profile Image: Alison L.
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Alison L.
$73
total per night
4.9 out of 5 stars
• 211 reviews
102 repeat clients
13 years of experience
Nashua, NH, 03063

“This was our first stay with Allison and she and her husband made us feel immediately comfortable leaving our 5 month old pup, Boka, with them for an overnight. My family had a long theme park day planned and Allison was super flexible and accommodated our next-day late-night pick up. We communicated off and on throughout the day and were given a positve report when we picked Boka up. Our little dog had so much fun at Camp Puggle that she went right to bed that night and even woke up calm the next morning! She was even too tired for zoomies! I am very happy with the service Allison provided and the care Boka received; not to mention the added perk of socializing and play time with other dogs. I recommend Allison and would absolutely ask her to pet sit for us again in the future.”

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Patricia D.
Sitter Profile Image: Riven H.
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Riven H.
$54
total per night
5.0 out of 5 stars
• 56 reviews
17 repeat clients
30 years of experience
Shirley, MA, 01464

“Thank you Riven for taking in Remi on such short notice. I appreciate the help so much!! Remi liked being there so definitely would like to have you sit for her again.”

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Rosalia L.
Sitter Profile Image: Dawn P.
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Dawn P.
Star Sitter
$78
total per night
5.0 out of 5 stars
• 60 reviews
19 repeat clients
15 years of experience
Worcester, MA, 01606

“Absolute gem of a sitter! Bella had a great time with Dawn and her family for two nights. They are incredibly nice caring people. They took great care of Bella and provided updates with photos throughout the stay. I recommend Dawn be everyone’s first choice!”

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Jessica M.
Sitter Profile Image: Robin K.
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Robin K.
$73
total per night
50 years of experience
Athol, MA, 01331

About: I love dogs. I have a rescue her name is Snickers and shes 7 months old. I've had dogs all my life. How anyone can hurt man's best friend is beyond me. She is like my child and makes me smile, keeps me company and I dont know what I would do without her. I love her with all my heart and wouldnt trade her for the world. I would treat anyone's dog like I would my own. They are all special in their own way. I would be honored to take care of your dog, I look forward to meeting you very soon. Thank you, Robin K I work full time at home and I'm able to walk my dog and take her out anytime! I'm available all day. My Snickers would love a play mate. I dont have crate but if yours needs one you'll have to bring it. I'm very diligent in taking my pup out all day long.

Sitter Profile Image: John M.
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John M.
Star Sitter
$78
total per night
5.0 out of 5 stars
• 157 reviews
59 repeat clients
15 years of experience
Turners Falls, MA, 01376

“John took wonderful care of our Golden Retriever! Ruby was very happy with all the attention, care and play time she got and John was very accommodating of our needs.”

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Heather K.
Sitter Profile Image: Claudia M.
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Claudia M.
$35
total per night
7 years of experience
Leominster, MA, 01453

About: I’ve always grown up with dogs, but now that I’ve moved out, I don’t have one. I love having a furry friend to spend time with and play with. Besides taking care of my own pets, I’ve also had experience caring for my elderly grandparents and working with children for over seven years. I always prioritize my pet’s needs. If my pet eats at 6 am, I’m up and feeding it at 6 am. I also like to let my pet out every 2-3 hours, especially when it first wakes up or after eating. I enjoy going on walks, and there’s a rail trail nearby. Cuddles are everything. If this pet wants me to love on them I will be super cuddly. I want to make them feel as at home as possible.

Sitter Profile Image: Vincenzo S.
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Vincenzo S.
$28
total per night
5 years of experience
Winchendon, MA, 01475

About: I’ve always had a genuine love for animals and understand how important it is to have someone you can trust caring for your pets. I’m comfortable with dogs and cats of different sizes, personalities, and energy levels, and I always take the time to make sure each pet feels safe, comfortable, and cared for. Whether it’s walks, playtime, feeding, potty breaks, or simply providing companionship while you’re away, I’ll treat your pet with the same patience, attention, and care I would give my own. I’m dependable, responsible, and happy to follow your pet’s normal routine and any special instructions you provide. My goal is to give you peace of mind knowing your pet is in good hands. Pet care fits perfectly into my daily routine because I’m home throughout the day and able to give the dogs plenty of attention, companionship, and supervision\. Since I’m home, your dog won’t be left alone for long periods of time\. I have plenty of time for regular potty breaks, walks, playtime, feeding, and of course lots of attention and affection\. I enjoy having dogs around and love making them feel like part of the family while they’re in my care\. I can also follow your dog’s normal schedule and routine to help them feel as comfortable and at home as possible\. My home has a large open backyard with 2.12 acres, giving dogs plenty of space to run, play, explore, exercise, and enjoy the outdoors safely.

Sitter Profile Image: Alberta W.
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Alberta W.
$50
total per night
5.0 out of 5 stars
• 42 reviews
32 repeat clients
20 years of experience
Pepperell, MA, 01463

“Alberta is great; she has nice, spacious pens and always takes very good care of our buns, even though some are "high maintenance." She always sends updates and photos during the stay. Five star service!”

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Joshua C.
Sitter Profile Image: Jennifer B.
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Jennifer B.
$69
total per night
5.0 out of 5 stars
• 6 reviews
15 years of experience
Troy, NH, 03465

“Chief seemed properly pooped and happy when I picked him up. I got updates and pictures all throughout the stay, which always is appreciated! Thanks for doing an amazing job!”

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Sean J.
Sitter Profile Image: Alexandra D.
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Alexandra D.
Star Sitter
$73
total per night
5.0 out of 5 stars
• 18 reviews
10 repeat clients
10 years of experience
Nashua, NH, 03062

“Tilly seemed to enjoy her overnight stay and interacted well with Alexandra’s dog. There was excellent communication between us with several great status photos provided. Will certainly use her services again!”

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William L.
Sitter Profile Image: Mariia G.
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Mariia G.
$78
total per night
5.0 out of 5 stars
• 7 reviews
1 repeat client
24 years of experience
Ayer, MA, 01432

“Mariia was more than great, she was awesome! She was very accommodating for our trip. My dog Layla was well taken care of. I would highly recommend Mariia.”

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Stephanie V.
Sitter Profile Image: Ana M.
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Ana M.
$67
total per night
3 years of experience
Fitchburg, MA, 01420

About: Dogs have always been a huge part of my life. I grew up surrounded by them and have always loved caring for them. For the past 3 years, I’ve worked full-time with dogs, and I truly treat every pup like my own!! I currently work with a pet care company in another city, and I’m now looking to meet new local clients and pups! Feel free to reach out—I’d love to connect! I live in a home with a large, fully fenced yard and a park nearby, giving pups plenty of space to play and explore. I’m happy to use a crate if preferred, and when your pup stays with me, my home becomes their home too!

Sitter Profile Image: Alison M.
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Alison M.
$84
total per night
5.0 out of 5 stars
• 12 reviews
5 repeat clients
7 years of experience
Littleton, MA, 01460

“Alison was responsive and thoughtful. She agreed to sit our utterly over-exuberant 14-month-old black Lab and we were so concerned that Alison’s family would be overwhelmed. Instead, she sent encouraging notes and exercised our dog extensively, so that she returned home relaxed. We really could not have asked for a better situation. Great people, a terrific fenced back yard, and good communication. Hard to beat that.”

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jane h.
Sitter Profile Image: Sara C.
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Sara C.
$67
total per night
5.0 out of 5 stars
• 18 reviews
5 repeat clients
21 years of experience
Harvard, MA, 01451

“Excellent experience. Sara seemed professional, friendly, and very on top of things. She stayed in close touch about our little guy, and Kiwi seemed in good spirits both during his visit and after. I'd also specifically flag her location as a bonus—the house has a good yard and it's on a small, low-traffic side street, which always makes me feel better.”

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Matthew H.
Sitter Profile Image: Erica H.
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Erica H.
$50
total per night
4.8 out of 5 stars
• 18 reviews
7 repeat clients
23 years of experience
Lunenburg, MA, 01462

“I highly recommend Erica. She was able to watch our 16 year old Polly at a last minute booking. She sent me updates and pictures everyday. Polly is old and does not like being alone and she came home happy. Thank you Erica for taking such good care of our baby.”

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Michelle M.
Sitter Profile Image: Migle O.
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Migle O.
Star Sitter
$56
total per night
4.9 out of 5 stars
• 9 reviews
7 repeat clients
15 years of experience
Worcester, MA, 01606

“Migle was absolutely wonderful with Zoë. She went above and beyond-carrying her up and down the stairs because Zoë couldn't manage them, sending regular photo updates, and treating her like her own. I felt completely at ease knowing Zoë was so well cared for. Truly exceptional.”

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Jen B.
Sitter Profile Image: Tamara J.
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Tamara J.
Star Sitter
$84
total per night
5.0 out of 5 stars
• 17 reviews
14 repeat clients
7 years of experience
Worcester, MA, 01606

“Tamara and family are loving and caring dog sitters for my two yellow labs. I’d give them 6 stars if I could. Your dogs are going to love them!”

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Andrea A.
Sitter Profile Image: Shea & Damien W.
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Shea & Damien W.
$56
total per night
5.0 out of 5 stars
• 73 reviews
21 repeat clients
40 years of experience
Worcester, MA, 01605

“During the stay I received updates throughout the day about what Mipha was doing which I always appreciate. Unfortunately my sweet little brat decided she didn't like their crate at night, and they accommodated to her needs. I would definitely recommend Shea and Damien for boarding!”

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Giselle
Sitter Profile Image: Kaitlyn B.
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Kaitlyn B.
$60
total per night
5.0 out of 5 stars
• 2 reviews
1 repeat client
10 years of experience
Ashby, MA, 01431

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.

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The median cost per night for pet boarding in Winchendon is $56

Pet parents share their Rover experiences - Winchendon

1 / 1
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
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

Amanda was amazing. Accommodating, responsive, flexible and genuinely felt my pups were well cared for....great experience!

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Jeanine D.
Boarding
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  • 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?

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  • Reservation protection

    It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.

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    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

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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 for Pet Boarding in Winchendon on Rover is $66.6 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 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 422 sitters on Rover for Pet Boarding in Winchendon. About 89% 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.

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