Pet Boarding in Winchendon

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

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Top rated Winchendon pet boarders

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: Jennifer B.
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Jennifer B.
$62
total per night
5.0 out of 5 stars
3 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: Alberta W.
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Alberta W.
$45
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: Abby C.
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Abby C.
Star Sitter
$62
total per night
5.0 out of 5 stars
31 reviews
10 repeat clients
6 years of experience
Antrim, NH, 03440

Abby was amazing with our golden retriever! She kept us updated with pictures and videos, and our pup had a wonderful time! We will be using her again!

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Karolyn W.
Sitter Profile Image: Kristen M.
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Kristen M.
$45
total per night
5.0 out of 5 stars
8 reviews
2 repeat clients
40 years of experience
Templeton, MA, 01468

Great communications, and I will use her again. Worked with my needs and I worked with her needs of Drop off and Pick up.

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Johnny Robert K.
Sitter Profile Image: Brooke L.
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Brooke L.
Star Sitter
$43
total per night
5.0 out of 5 stars
123 reviews
47 repeat clients
14 years of experience
Merrimack, NH, 03054

Brooke was amazing! Communication was fast and easy, and Scottie had a great stay. She sent pictures and updates every day, which was greatly appreciated. In the future we hope to have Scottie stay with Brooke again!!

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Kathryn Benight L.
Sitter Profile Image: Haley B.
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Haley B.
$56
total per night
5.0 out of 5 stars
25 reviews
3 repeat clients
5 years of experience
Ashburnham, MA, 01430

Haley was amazing!! So kind and flexible with communicating and planning with me, and very responsive! I felt very safe leaving my pup with her and her family on a holiday night☺️

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

I would highly recommend Tamara for your pet boarding needs. Very responsive and caring for our dog. She went out of her way to accommodate changes to our boarding plans which including being able to pick our dog up. Definitely will be booking again with her in the future.

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Christopher L.
Sitter Profile Image: Jacquie A.
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Jacquie A.
Star Sitter
$50
total per night
5.0 out of 5 stars
18 reviews
5 repeat clients
20 years of experience
Holden, MA, 01520

Jacky is literally THE BEST! Our 12-year-old goldendoodle stayed with Jacky for two weeks this spring while we were on an international trip. Jacky took such wonderful care of our dog – multiple walks a day in parks and wooded trails, playtime in the yard, and plenty of hugs. We also received daily updates with photos, which made us feel comfortable and happy that our dog was doing so well. I’ve recommended Jacky to our friends and we will definitely be contacting her again!

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Stace C.
Sitter Profile Image: Melissa O.
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Melissa O.
$67
total per night
5.0 out of 5 stars
238 reviews
80 repeat clients
8 years of experience
Worcester, MA, 01602

Melissa was very sweet and her dog Casper really got along with my dog! She sent me plenty of pictures and videos of my dog having so much fun! Her backyard is a dream come true for Tanner! Will definitely come back! Thank you 😘❤️

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Raissa K.
Sitter Profile Image: paul d.
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paul d.
$56
total per night
5.0 out of 5 stars
86 reviews
34 repeat clients
15 years of experience
Lancaster, MA, 01523

Paul is extremely knowledgeable, well set up for dog boarding/sitting, and was extremely kind to us and our dog. Highly recommend booking with Paul!

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Renee B.
Sitter Profile Image: John M.
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John M.
Star Sitter
$73
total per night
5.0 out of 5 stars
146 reviews
51 repeat clients
15 years of experience
Turners Falls, MA, 01376

John provided Lilly with excellent care. Lilly had been traumatized by a two-day visit last year to a kennel last year. We vowed never to do that again. But her visit with John was just wonderful. Lilly will definitely be hanging out with John in the future!

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Pete M.
Sitter Profile Image: Lee J.
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Lee J.
Star Sitter
$67
total per night
5.0 out of 5 stars
9 reviews
3 repeat clients
57 years of experience
West Boylston, MA, 01583

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 !!

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James C.
Sitter Profile Image: Donna T.
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Donna T.
$53
total per night
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.

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

Riven and Matt are very experienced in dog care. Dexter was well taken care of, he was happy and quite himself when we picked him up. I highly recommend Riven and Matt.

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Ed G.
Sitter Profile Image: Sara C.
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Sara C.
$67
total per night
5.0 out of 5 stars
16 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: Karley G.
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Karley G.
$67
total per night
5.0 out of 5 stars
13 reviews
5 years of experience
Fitchburg, MA, 01420

About: I’ve been working for a company based out of Sudbury Ma for 5 years and I’m just looking for extra work :) I’ve worked with dogs of all sizes, ages etc. I have worked with dogs of all temperaments as well. Would love to get to know your pet :) I work full time walking/ pet sitting for a company Monday - Friday and weekends for sitting. I’m looking to expand to some new clients! I could even bring your dog with me for the day on walks with other dogs if I’m sitting them and they would be up for it I can stay in someone’s home or have someone’s dog/ dogs stay in my home if they are friendly with other dogs as I do have my own dog

Sitter Profile Image: Erica P.
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Erica P.
$67
total per night
5.0 out of 5 stars
281 reviews
112 repeat clients
12 years of experience
Worcester, MA, 01606

Erica did a great job with our high-energy puppy! She sent daily pictures and kept us updated throughout the stay. Would definitely book with her again!

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jennifer b.
Sitter Profile Image: Melissa & Axel W.
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Melissa & Axel W.
Star Sitter
$70
total per night
5.0 out of 5 stars
20 reviews
7 repeat clients
30 years of experience
Boylston, MA, 01505

We were so happy with Melissa and Axel. They took great care of our dog, sent us pictures and updates and their kids gave our dog all the love. We will definitely be rebooking.

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Whitney B.
Sitter Profile Image: Migle O.
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Migle O.
Star Sitter
$67
total per night
4.9 out of 5 stars
9 reviews
6 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: Emily M.
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Emily M.
$62
total per night
5.0 out of 5 stars
15 reviews
4 repeat clients
8 years of experience
Peterborough, NH, 03458

Emily was AMAZING! Our Gus had a great time! It was obvious that Emily not only took VERY good care of him but he was treated to his all-time favorite game of fetch and cooling off in the kiddie pool multiple times! He came home happy and tired. :) We highly recommend Emily, she goes above and beyond expectations, and we will definitely use her again! Thanks Emily!

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Julie M.
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Winchendon pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

We are grateful for Amanda and her family and their kind care of our dog! Her first overnight stay was a success. We received detailed updates throughout the weekend of how she was doing which helped us know she was comfortable and having fun. Thank you!

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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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How Rover works

  1. 1. Search

    Read verified reviews by pet parents like you and choose a boarder who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a boarder to discuss the level of care needed for your pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

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 pet boarding sitter has to cancel, we’ll work with you to find a new pet boarding sitter.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Pet Boarding FAQs

Frequently asked questions about Rover

If you’re searching for a Winchendon pet boarding sitter for the first time, visit the sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a sitter before, learn more about how to do this in the Rover app or on your computer.

Typically, pet boarding sitters on Rover respond in under an hour, so you should be matched with the perfect sitter for you and your pet in no time!

Experience can vary widely from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when comparing sitters available in Winchendon.

Rover makes it easy to find Winchendon pet boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet boarding is great for:

  • Dogs and cats of all ages and abilities, including puppies and kittens
  • Pet parents looking for a safe, loving alternative to a kennel or hotel
  • Pets who’d love to socialize with their sitter’s pets

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet boarding sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your pet boarding sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your pet boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.