House Sitting in Winchester

Find a loving dog sitter to watch your dog overnight in your home.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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1. Laura Verified Background Check

Vet tech asst. trained, responsible

Bellmont, MA, 02478

House Sitting

"Laura is an excellent pet/house sitter. She immediately embraced our pets as her own and exceeded all my expectations keeping them happy while we were away. ... (more)"

2. Vivian Verified Background Check

Friendly and playful dog-lover!

Somerville, MA, 02143

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Vivian was amazing. She made sure Finnegan got tons of exercise and love. She kept us updated with photos and texts. We felt so at ease while we were away. (more)"

3. Courtney Verified Background CheckRover 101

Professional Dog Snuggler

Lexington, MA, 02420

House Sitting, Drop-In Visits, Dog Walking

"Courtney did a great job watching my very shy dog! She asked lots of great questions ahead of time and provided updates as she watched my dog, putting my min... (more)"

4. Amelia Verified Background Check

Let's play fetch in my backyard!

Medford, MA, 02155

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Amelia watched our one year old, very active rescue dog for 6 days at our home. She was really a delight to work with and took wonderful care of our girl. ... (more)"

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5. Courtney Verified Background Check

I want to take care of your dogs!!!

Medford, MA, 02155

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Courtney was great with our pets. She was responsive and flexible when we had some late changes to tasks. The pups loved her too. (more)"

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6. Elizabeth Verified Background Check

Dog lover looking for walking buddy

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

"Elizabeth is awesome. She agreed to watch both of my pups on very short notice and made herself available for a meet and greet before we left. Elizabeth was... (more)"

7. Carlos Verified Enhanced Background Check

Caring and trustworthy pet sitter

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

"Carlos was amazing and I highly recommend him for any future pet sitting needs. He was very friendly and treated my dog as if she was his own. During my trip... (more)"

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8. Cory Verified Background Check

Love of animals of all kinds!

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

"Cory is a life saver! Our dogs don’t do well with pop ins, so when we need to be out until later in the evenings he comes and hangs out with them for a coupl... (more)"

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9. Kevin Verified Background Check

Lover of all animals

Somerville, MA, 02144

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"Kevin handled my young puppy very well! I have a 3 month old shiba who has limitless energy, and Kevin was able to hold his own. Well done! (more)"

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10. Megan Verified Enhanced Background Check

Caring Vet Tech Assistant

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

"Megan has been a great sitter for our two cavalier pups. She has stayed overnight with them several times in the past few months while we traveled. One of ... (more)"

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11. Zac Verified Background Check

Muttsachussets is for dog lovers

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

"Our little Sweet Pea loves Zac! So glad we have made this connection ... means so much to know that our fur baby is in good hands when we’re away. (more)"

Confirmed availability
Christmas and New Year
12. Tessa Verified Background Check

Will love your fur-friend

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

"Tessa proved to be responsible, showing up on agreed upon times, and taking good care of our dogs and our house. All was well when we returned home. (more)"

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13. Lea Verified Background Check

I love all pets as they're my own.

Woburn, MA, 01801

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"I have seen Lea in action with animal's. She is caring, attentive, loving, and nurturing person that treats each animal she cares for as if it's her own, and... (more)"

Confirmed availability
Christmas and New Year
14. James Verified Background Check

Graduate Student

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

"Jimmy is one of the nicest guys around, he has always been a very caring friend and has always been great around animals. I have had Jimmy take care of my do... (more)"

Confirmed availability
This weekend
15. Gerardo Verified Background Check

Caring and energetic pet sitter

Medford, MA, 02155

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care

"Gerardo has watched my two very picky very anxious puppies on many occasions and has done an incredible job! He is always punctual and attentive to their nee... (more)"

Confirmed availability
Christmas and New Year
16. Erica Verified Background Check

Flexible Schedule to care for pets

Medford, MA, 02155

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: I am a mom of three children and have been a dog owner for over 40 years. I love dogs, they all have their own unique personalities. I have my own ... (more)

Confirmed availability
This weekend
17. Brooke Verified Background Check

I grew up with 9 cats & 3 dogs

Stoneham, MA, 02180

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Brooke was easy going and friendly. She house sat for us for 5 days during Thanksgiving and We came back to a clean house and happy cats. She was even able t... (more)"

18. Amanda Verified Background Check

Love for your pup while you’re away

Arlington, MA, 02476

House Sitting, Drop-In Visits

"I had an excellent experience hiring Amanda to stay at my house and care for my dog and cat. She was quick and thorough with communication and sent frequent ... (more)"

19. Nicolas Verified Enhanced Background Check

Dog Dad - will walk or sit your dog

Arlington, MA, 02474

House Sitting, Drop-In Visits, Dog Walking

"Nicholas is a fantastic dog owner, sitter, walker, etc.! He's very in tune with each animal's needs and knows how to lead them in an effective way so the dog... (more)"

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20. Alexandra Verified Background Check

Pet lover providing great care!

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

"Finding an individual that you put your faith into to watch after your four legged family members isn’t a task that we take lightly! Especially owning a resc... (more)"

Rover.com is the simple, savvy way to find and book house sitting. It's easy to find the perfect house sitter - many sitters on Rover have a long history of house and pet sitting, and 95% of reviewed stays have received a perfect five-star rating. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Every pet sitter on Rover has the option to complete a free background check, so look for their badge that says they've had the check done. Pet and house sitters are booked on Rover every minute of every day, and 92% of the population lives within a short drive of one of the more 40,000 sitters who've listed their services on Rover, so you're sure to find the perfect house sitter on Rover. When you book with one of our trusted house sitters on Rover you get peace of mind that your home and pets are in loving hands.