House Sitting in Winchendon

Find a loving house sitter to watch over your pets and your home.

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Top rated Winchendon house sitters

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: Jorden A.
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Jorden A.
Star Sitter
$73
total per night
5.0 out of 5.0 stars
66 reviews
13 repeat clients
15 years of experience
Rindge, NH, 03461

Jordan was incredible and gave us complete comfort during our time away from our fur baby. She sent pictures often to let us see how happy and content he was. When we got home he was all brushed and looked and felt amazing. We will definitely request Jordan again to take care of him again when we are away.

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A P.
Sitter Profile Image: Amanda P.
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Amanda P.
$39
total per night
4.9 out of 5.0 stars
29 reviews
8 repeat clients
20 years of experience
Winchendon, MA, 01475

Amanda was great! She was very responsive and responsible, and even jumped in during a pinch when we needed someone on short notice. Our super anxious pups (including our 85lb boxer) warmed up to her very quickly and we could tell they had a great time when we got home. We will definitely have Amanda back at our home to stay with our fur babies and recommend her for your sitting needs.

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Chris G.
Sitter Profile Image: Amber P.
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Amber P.
$45
total per night
5.0 out of 5.0 stars
3 reviews
1 repeat client
8 years of experience
Athol, MA, 01331

Amber was great! She cared for a special-needs elderly cat and a senior dog very well. The house was clean and tidy when I returned. Recommended!

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Debbie W.
Sitter Profile Image: Julisa M.
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Julisa M.
$73
total per night
5.0 out of 5.0 stars
9 reviews
1 repeat client
14 years of experience
Winchendon, MA, 01430

Julisa was wonderful - she stayed in frequent contact, sent pictures and, when our rascal of a dog breached the fence and ran off, she immediately got on the phone with me and we tracked him down at a neighbor’s house. I know what a terrible feeling that is when watching someone else’s furry babies and Julisa handled it so well.

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Carolyn D.
Sitter Profile Image: Margaret & Dawson B.
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Margaret & Dawson B.
$36
total per night
20 years of experience
Rindge, NH, 03461

About: I've been helping take care of dogs since I could walk. My family owned at least one dog at all times and my grandmother owned many more. I have worked with purebreds, rescues, big dogs, small dogs, dogs with behavior issues and anything in between. I also have been a handler for a comfort dog for a police department and have been trained in that field. I have trained puppies and have also cared for senior dogs. I love all dogs and think every single one deserves love and happiness! I work Monday-Friday from 8-4 but am available to come home on my lunch break. My fiance works Thursday-Sunday so would be available all day Monday-Wednesday so we have a lot of availability for focused care for your pets. I have two dogs that are very friendly and love other dogs. If you need your dog to be separated, we own a crate as well as live in a large home where we can easily give the dogs the space they need. We live on 10acres of land and can provide long walks around our house or the neighborhood. When taking care of dogs in their own home, I am very respectful of the house and the animals and can accommodate almost any need you would have for house/dog sitting.

Sitter Profile Image: Nichole S.
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Nichole S.
$56
total per night
5.0 out of 5.0 stars
9 reviews
2 repeat clients
25 years of experience
Orange, MA, 01364

Nichole did an amazing job. She was excellent with communicating with me throughout her time. She took great care of my dog. I strongly recommend Nichole , and will 100% use her services again.

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Judi D.
Sitter Profile Image: Taylor D.
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Taylor D.
$36
total per night
5.0 out of 5.0 stars
3 reviews
17 years of experience
Gardner, MA, 01440

About: I’ve taken care of dogs ever since our first family dog who we got when I was 11. I primarily took care of him with the day to day activities such as feeding, walking, and play time. Since then, I have been entrusted by friends and family to watch their for babies especially for weekend getaways. I am able to stay overnights if needed and if local enough I can come through for extra play time and walks. I work full time during the week from 8-5, but if you’re looking for a weekend getaway or need more play time for your fur baby I’m your girl! I personally don’t have a pup or a big enough space to board your fur baby, but at your home I will ensure that it remains a safe place for your pup while still ensuring they get all the play time needed

Sitter Profile Image: Meaghon R.
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Meaghon R.
$62
total per night
5.0 out of 5.0 stars
7 reviews
1 repeat client
20 years of experience
Princeton, MA, 01541

Meaghon was wonderful to work with! Incredibly responsive and my brood loved spending the weekend with her. We were very fortunate to have found her and can’t wait to book future trips knowing our babies will be in the best of hands!

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Shannon W.
Sitter Profile Image: Amanda E.
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Amanda E.
$73
total per night
5.0 out of 5.0 stars
8 reviews
4 repeat clients
30 years of experience
Winchendon, MA, 01475

Amanda was AMAZING for our house sitting booking. She took such good care of our pitbull and cat. She really connects with animals and they absolutely love her. Our cat, who normally hates strangers and always hides, was curled up on her lap by the first night. We will definitely be booking her again!

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Sara M.
Sitter Profile Image: Melissa M.
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Melissa M.
$73
total per night
5.0 out of 5.0 stars
28 reviews
4 repeat clients
20 years of experience
Gardner, MA, 01440

Misty was great with Teddy and Dora! They quickly warmed up to her and seemed to be very comfortable and well cared for. She took them out for frequent potty breaks as requested and they received their meals and meds on time. Will definitely book with her again!

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Clara L.
Sitter Profile Image: Kristen M.
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Kristen M.
$56
total per night
5.0 out of 5.0 stars
7 reviews
2 repeat clients
40 years of experience
Templeton, MA, 01468

About: I’m a very responsible and loving pet owner. Have rescued many pets and now have found myself with some free time and would love to help new pets and people! With notice, I am completely free on Wednesdays, Thursdays, Saturdays & Sundays. (Monday, Tuesday & Friday I can be available for a few hours in the am) I have a fenced in yard with plenty of space to play and a kiddie pool to cool off in! I have three very friendly doggos myself but plenty of space so they can be kept separate if you desire.

Sitter Profile Image: Mallory G.
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Mallory G.
$36
total per night
4.0 out of 5.0 stars
3 reviews
2 repeat clients
11 years of experience
Gardner, MA, 01440

Mallory was great with both our dog and cat . She sent pics to us. I would highly recommend her to watch your fury friends

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Steven H.
Sitter Profile Image: Tatyana G.
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Tatyana G.
$70
total per night
5.0 out of 5.0 stars
7 reviews
2 repeat clients
10 years of experience
Jaffrey, NH, 03452

Tatyana was great - she was on time, asked good questions about the dogs and our instructions, sent us pictures and videos, and stayed in touch throughout our time away.

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Carolyn D.
Sitter Profile Image: Elizabeth N.
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Elizabeth N.
$89
total per night
4.9 out of 5.0 stars
47 reviews
26 repeat clients
2 years of experience
Barre, MA, 01005

Liz was very responsible, attentive and loving towards Cubby. This was our first time using a Rover sitter and we were very pleased with her care. We will rebooked Liz for the next week because Cubby loved her so much:)

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Michele D.
Sitter Profile Image: Tracey T.
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Tracey T.
$73
total per night
35 years of experience
Temple, NH, 03084

About: I worked in animal shelters for over 15 years and have lots of experience taking care of dogs, cats and chickens. I am experienced in giving meds and insulin. I am extremely diligent with my level of care and the pets safety and comfort are my highest priority. I have 3 dogs of my own and understand the worries having someone else care for them. I am dependsble, mature and have a wide open schedule. I’m currently in the slow period of my business. I am currently available any time of the week or time of the day with enough notice. I will follow whatever instructions you leave for your pet and your home including their routine, preferences, meds, structure, etc. my goal is to take care of them just like you!

Sitter Profile Image: Colin P.
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Colin P.
Star Sitter
$110
total per night
5.0 out of 5.0 stars
69 reviews
14 repeat clients
15 years of experience
Fitchburg, MA, 01420

Colin is wonderful. He treated my pup like the princess she is, sent photos and updates, and is exactly the kind of human that I trust with my fur baby.

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Joann H.
Sitter Profile Image: Daniel P.
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Daniel P.
$134
total per night
5.0 out of 5.0 stars
6 reviews
2 repeat clients
13 years of experience
Ashburnham, MA, 01430

He took incredible care of both my elderly dog and my home. Would highly recommend

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Janelle G.
Sitter Profile Image: Kathleen M.
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Kathleen M.
$84
total per night
5.0 out of 5.0 stars
2 reviews
20 years of experience
Keene, NH, 03431

I 100% recommend Kathleen! She really saved us! Our pet sitter canceled the morning we were supposed to leave for a seven-day vacation. I posted a job on Rover and she responded immediately, and very kindly stepped in to help, even though she had just finished another pet sitting gig. She took care of our beloved older dog, Dewey and our nine chickens. She was thoughtful, loving, reliable, and responsible. She texted with us almost daily, which we had asked her to do, and which set our minds at ease. She went above and beyond by giving our chickens daily treats and giving our dog LOTS of love. She is warm, respectful, and a good communicator. She also left the house in immaculate condition--in some ways cleaner than we left it. An ideal house and pet sitter in every way!!

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Shaylyn Romney G.
Sitter Profile Image: Haley C.
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Haley C.
$73
total per night
5.0 out of 5.0 stars
73 reviews
32 repeat clients
17 years of experience
Hinsdale, NH, 03451

Hayley is AMAZING!! One of my cats is very social and the other is shy. She got BOTH of them playing, brushed them, and made sure they knew they were loved on top of the bare minimum of feeding them and giving my old lady her meds. She even checked to make sure my hamster was still breathing while I was away since it was always during my hamster’s sleep time that she was there. Highly recommend. Will be using again if I ever am going away and she is available

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Erin D.
Sitter Profile Image: Sarah O.
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Sarah O.
$56
total per night
5.0 out of 5.0 stars
2 reviews
4 years of experience
Gardner, MA, 01440

Great communication and appreciate the flexibility!

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Haley B.
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Over 30
pet parents in Winchendon have booked house sitting

Winchendon pet parents share their Rover experiences

1 / 1
5.0 out of 5.0 stars

Amanda was a wonderful pet sitter, and we couldn’t be happier with our experience. She stayed in our home and cared for our cat while we were away, and she regularly checked in to let us know how things were going, which gave us real peace of mind. When we returned, our cat was happy and relaxed, and everything in our house was exactly as we had left it. We initially felt a little uneasy hiring someone we didn’t know to stay in our home and care for our baby for a week, but we’re so glad we put our faith in Amanda. We completely trust her and will absolutely hire her again.

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Becci E.
House Sitting
5.0 out of 5.0 stars

Adrianna is awesome! We love having her stay with our cat Sasha while we are away. She is very professional and we trust her completely.

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John G.
House Sitting
5.0 out of 5.0 stars

Maggie went above and beyond when my dog got sick while she was petsitting for us. She cleaned up after him, took him to an emergency Veterinary Hospital and administered the meds that were prescribed. I would highly recommend Maggie and would definitely have her watch.my pets again.

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David P.
House Sitting
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Find pet care near you

How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and 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!

The median cost per night for house sitting in Winchendon is $60

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 house 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.

Sitters in Winchendon average 3
repeat house sitting clients

House Sitting FAQs

Frequently asked questions about Rover

House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Winchendon on Rover as of Jan 2026 was about $60 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.

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

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

As of Jan 2026, there are 238 house sitters in Winchendon. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 83% of Winchendon house sitters respond in under an hour.

House sitters in Winchendon have an average of 19 years of experience. House sitters with repeat customers have an average of 3 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Winchendon.

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Winchendon house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house 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 house 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 house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.