Dog Boarding Winchendon

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Over 43
pet parents in Winchendon have booked dog boarding

Winchendon, Find top rated dog 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: Emily J.
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Emily J.
Star Sitter
$56
total per night
5.0 out of 5 stars
34 reviews
13 repeat clients
35 years of experience
Gardner, MA, 01440

Have used Emily once again and couldn’t be more happy with her updates and photos of Forest while I was traveling. Highly recommend her services if you need any kind of pet sitting.

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David H.
Sitter Profile Image: Judy B.
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Judy B.
$62
total per night
5.0 out of 5 stars
51 reviews
10 repeat clients
50 years of experience
Leominster, MA, 01453

Judy was an awesome host to our dog in her home. Our dog threw her some curveballs, as he can be a bit of a rascal, and she took everything in stride and was extremely patient with him. She kept us updated and gave us complete ease that she was taking excellent care, allowing us to thoroughly enjoy our vacation without worry. Thank you Judy, we would love to have King stay again!

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Elizabeth C.
Sitter Profile Image: Kourtney S.
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Kourtney S.
Star Sitter
$62
total per night
5.0 out of 5 stars
21 reviews
2 repeat clients
15 years of experience
Fitchburg, MA, 01420

Kourtney was great with our pup, Carl. Carl is an energetic guy and Kourtney provided all that he needed in his 9 day stay. Kourtney’s communication with us before and during his stay was professional and timely. We would use Kourtney’s services again 💯.

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Lindy C.
Sitter Profile Image: Sandra A.
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Sandra A.
$67
total per night
5.0 out of 5 stars
4 reviews
1 repeat client
20 years of experience
Templeton, MA, 01468

Took awesome care of moose! Even gave him a bath! Nothing but great things!

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jeffrey g.
Sitter Profile Image: Luiz B.
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Luiz B.
Star Sitter
$62
total per night
5.0 out of 5 stars
172 reviews
32 repeat clients
40 years of experience
Gardner, MA, 01440

Luiz and his family were so sweet to my pup, Echo, that I don’t think she wanted to come home! They treated her like family and she had a blast exploring their wonderful fenced in backyard and lounging on the couch when she needed a break. She played like crazy with the other pups and came home nice and tired! Luiz kept me up to date with frequent pictures and videos of her having fun. I felt so comfortable leaving her with them and will definitely rebook in the future!

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Lindsey B.
Sitter Profile Image: Rachael L.
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Rachael L.
Star Sitter
$56
total per night
5.0 out of 5 stars
44 reviews
18 repeat clients
25 years of experience
Dublin, NH, 03444

I've never had to board my dogs before and was very nervous. Rachael answered my many questions, explained everything I needed to know. Her family is wonderful with my dogs and I finally feel I've found someone caring and trustworthy. I will definitely rebook in the future!

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Joyce L.
Sitter Profile Image: Michael B.
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Michael B.
Star Sitter
$56
total per night
5.0 out of 5 stars
573 reviews
121 repeat clients
15 years of experience
Rutland, MA, 01543

This is the 2nd time of simba going to michael and his family’s home. Simba is happy and well cared for and treated like one of the family! Definitely makes it much easier to focus on my days at work knowing my dog and best friend is well taken care of and happy! Thank you michael & Martina 💕. We’ll see you soon again!

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lynne g.
Sitter Profile Image: Jie M.
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Jie M.
Star Sitter
$62
total per night
5.0 out of 5 stars
43 reviews
9 repeat clients
10 years of experience
Swanzey, NH, 03446

Lou had a wonderful time with Jie! Great communication all around, and extremely accommodating. I highly recommend Jie to look after anyone’s pups!

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Jessica B.
Sitter Profile Image: Susan B.
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Susan B.
$56
total per night
10 years of experience
Orange, MA, 01364

About: I've been around animals my whole life and currently have two pet goats who we spoil like dogs. We have 30 acres of beautiful land surrounded by woods, which is a perfect haven for running, fetch, and all sorts of outdoor shenanigans. I work remotely from home with a flexible schedule. I typically work a few hours in the morning, and then am outside working on projects and playing with the animals all day. We have a large property (about 30 acres) surrounded by woods with lots of room for your dog to run and explore. We also live near some great hiking trails.

Sitter Profile Image: Jo W.
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Jo W.
$39
total per night
5.0 out of 5 stars
32 reviews
12 repeat clients
40 years of experience
Wilton, NH, 03086

Used Jo twice. Both her and her husband are very kind and welcoming. Finnick seems to enjoy their company too. Jo will maintains communication throughout the stay with photos. Overall we will continue to use Jo as long as she provides her services and her schedule is available for Finnick's stay

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Vito P.
Sitter Profile Image: Megan U.
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Megan U.
$56
total per night
5.0 out of 5 stars
28 reviews
10 repeat clients
11 years of experience
Mont Vernon, NH, 03057

Megan is outstanding. She cared for our dog as if she was her own. Thank you Megan for giving us peace of mind while we were away - you are very appreciated!

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Arice G.
Sitter Profile Image: Nicole S.
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Nicole S.
Star Sitter
$73
total per night
5.0 out of 5 stars
81 reviews
23 repeat clients
25 years of experience
Greenfield, MA, 01301

Nicole provided excellent care for our 3 month old puppy. He had a wonderful day full of playtime and snuggles. She also provided lots of pictures throughout the day which we loved!

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Charlotte P.
Sitter Profile Image: Riven H.
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Riven H.
Star Sitter
$54
total per night
5.0 out of 5 stars
45 reviews
16 repeat clients
30 years of experience
Shirley, MA, 01464

Riven and Matt were great! They were able to take care of my pup, Lula Mae, while I needed to be out of town on short notice. Lu was clearly well cared for and happy with them. Really appreciate it!!

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Sarah B.
Sitter Profile Image: matt w.
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matt w.
Star Sitter
$54
total per night
5.0 out of 5 stars
22 reviews
4 repeat clients
30 years of experience
Shirley, MA, 01464

Matt is absolutely amazing. He really took care of my dog during the 40 days we were away. He sent pics and videos daily and he's really responsive to questions and requests. My dog had a good time with Matt. I would definitely recommend Matt to anyone who needs boarding service.

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Ran W.
Sitter Profile Image: Tracy N.
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Tracy N.
Star Sitter
$84
total per night
5.0 out of 5 stars
15 reviews
6 repeat clients
13 years of experience
Leominster, MA, 01453

I recommend her; she's very communicative and loving, and that's how she was with Tonka. She kept me updated throughout his stay, letting me know how Tonka was doing and sharing photos. I always knew how he was doing, and she always answered my messages.

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Migdalia H.
Sitter Profile Image: Phillip G.
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Phillip G.
Star Sitter
$56
total per night
5.0 out of 5 stars
209 reviews
101 repeat clients
28 years of experience
Lunenburg, MA, 01462

Bandit had a great time with Phil and his dogs! We received updates throughout the week that put us at ease. We will definitely be using Phil again in the future!

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Samantha L.
Sitter Profile Image: Emerald J.
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Emerald J.
$78
total per night
5.0 out of 5 stars
10 reviews
45 years of experience
Westminster, MA, 01473

Emerald was amazing. My Sawyer loved being there, which made me feel so much better knowing that someone will give him a one on one attention, even though she has her own dog. She also made me feel like Sawyer was her own and did everything with Sawyer that her dog does. I would absolutely go back again as long as she would have Sawyer back.

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Wendy B.
Sitter Profile Image: Amy P.
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Amy P.
$42
total per night
5.0 out of 5 stars
6 reviews
6 years of experience
Troy, NH, 03465

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!

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Julie B.
Sitter Profile Image: Alexis F.
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Alexis F.
$39
total per night
6 years of experience
Fitchburg, MA, 01420

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.

Sitter Profile Image: Donna T.
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Donna T.
$53
total per night
2 repeat clients
30 years of experience
Shirley, MA, 01464

About: I've owned and cared for animals since high school. In addition to dogs and cats, I've owned horses since I was 16. I have been\am a foster parent for the Animal Rescue League of Boston since 2020. I'm a former puppy foster for service dogs and participated with early puppy training. I have carried those skills over to training other foster puppies and my personal dog. I have a medical background (EMT) and my daughter is a Vet Tech so I am very comfortable working with animals with medical needs and will follow any required medical plan. In addition to dogs and cats, I'd love to meet\care for your backyard farm animals; horses, pot-bellied pigs, chickens, goats, sheep, etc. I have experience with some of these animals through ownership and fostering opportunities. I'm open to meeting and learning about new friends. We currently have 4 dogs, 4 cats, and 2 horses in our home. All our animals are our babies and I'll care for yours as if they were my own. I'm currently unemployed so I'll have plenty of time to spend with your pets. I'm available for petsitting any day of the week and can work around any personal appointments. Boarding in my home is restricted to cats or other small animals. Puppies (under 1 year) may be accomodated, no adult dogs. For cats; we have a dedicated "cat room" to keep your pet separated from our pets. The room has a screen door so they don't feel locked away and can be part of our household while remaining safe. I will follow your pet care plan while in your home. For Puppies; all dogs are fed separately to avoid food aggression situations. All puppies will be crated for meals and sleeping overnight. If your puppy is not crate trained, I will work with them to ensure they are comfortable and not afraid. I can support your potty training schedule to maintain consistency.

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The median cost per night for dog boarding in Winchendon is $55

Dog parents share their Rover experiences - Winchendon

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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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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

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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.

  • 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 dogs like family

  1. 1. Search

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

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Sitters in Winchendon average 10
repeat dog boarding clients

FAQs for Boarding - Winchendon

Frequently asked questions about Rover

The average cost for Dog 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 Dog 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 Dog Boarding. For more information on service fees, click here .

As of July 2026, there are 428 sitters on Rover offering Dog Boarding across Winchendon. Enter your ZIP code to see which available sitters are closest to your home.

Every sitter on Rover has their own rhythm and routine, but most will follow the flow that keeps your dog happiest. Sitters can give meals on your dog's regular schedule, provide a comfortable place for sleep, and plenty of one-on-one attention.

93% of Winchendon sitters also include daily walks in the neighborhood during dog boarding stays. You can also request photo and message updates throughout the stay so you can see which Winchendon landmarks or neighborhoods your dog is enjoying.

If your dog is a little shy, consider booking a one-night trial stay! This practice run can boost your and your dog’s confidence before your trip.

Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Winchendon home-away-from-home, we recommend packing:

  • Health and safety essentials such as their ID tags, vaccination records, medication, and emergency vet or secondary caregiver contacts.
  • Food and gear such as harnesses, collars, food (portioned by day), and an item that smells like you.
  • Special instructions such as a list of training cues, medical administration needs, or favorite hang-out spots in your Winchendon.

Tip: You can upload your dog’s routine and medical info directly onto their profile so your sitter always has the details at their fingertips.

You and your Winchendon sitter can schedule drop-off and pick-up in a way that works best for the both of you—and your dog. Most sitters offer flexible times for drop-off and pick-up but the easiest way to confirm those times will be through in-app messaging. Confirm your arrival time the day of pick-up and drop-off can also help keep the process smooth and organized.

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 .

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.

By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.

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 dog to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your dog 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.

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