House Sitting in Winchester

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

1. Sophia

Loving, Responsible Dog Sitter

Arlington, MA, 02476

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Sophia was confident and calm with our skittish rescue dog, Maisy and we felt good about leaving her in Sophia's capable hands for the weekend. Maisy was hap... (more)"

2. Jeremy

Your Dog Will Say Bow WOW about me!

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Jeremy has stayed at our house several times with our dog while we were traveling. Our dog Maggie absolutely loves spending time with Jeremy. He is great wi... (more)"

3. Mark

Overnight and Weekend Pup Pal!

Everett, MA, 02149

House Sitting

"We were able to enjoy our recent time away from home because we knew we were leaving our pet with a responsible, caring and compassionate individual. Mark w... (more)"

4. Marielle

Exuberant, Adoring, Dependable

Burlington, MA, 01803

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Marielle was amazing taking care of Belle. Her communications were strong and the shared log was outstanding. I plan on using her services again soon! (more)"

5. Grace

Fun, friendly, happy animal lover!

Melrose, MA, 02176

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Grace stayed with our Bichon mix, Wrigley, over the Independence Day holiday weekend. She was great! She was wonderful to work with and easy to communicate w... (more)"

6. Julianne

It's The Simple Things

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Julianne took such good care of my buddy Benson! He was pooped at the end of the weekend. Will definitely be using her again when I go away for the weekend. ... (more)"

Available this weekend
7. Sarah

Playpal/Den Mom/Champion Cuddler

Arlington, MA, 02474

House Sitting, Drop-In Visits, Dog Walking

11 repeat clients

"Sarah has been amazing! She not only kept our pup happy while we were away, gave him many comforts of home, but she also was so great with communicating with... (more)"

Available this weekend
8. Hillary

I LOVE animals and caring for them!

Medford, MA, 02155

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

"I can't say enough about how amazing Hillary is with animals. I truly feel at ease when I know she is looking after my pet. If you spend even five minutes ta... (more)"

9. Sophie

It's a Ruff Life!

Reading , MA, 01867

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

32 repeat clients

"Sophie is great - a fantastic sitter. My pup loves her! This is the second time I've gone away and had Sophie stay at my home to watch her. I will definite... (more)"

10. Abby

A dog-lover looking to help others

Arlington, MA, 02474

House Sitting, Drop-In Visits

About: Dogs are great animals that deserve great care, especially when separated from the ones they love. As a dog owner myself, I understand the importa... (more)

11. Flavia

Active & Reliable...Your Pup's BFF!

Somerville, MA, 02143

House Sitting, Drop-In Visits, Dog Walking

"Flavia is a dedicated and fun dogwalker. You can trust that when your four legged friend is with her they will get the exact attention they need. Flavia has ... (more)"

12. Ashley

Let's keep everyday exciting!

Medford, MA, 02155

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

5 repeat clients

"Ashley was great as a sitter and companion to our dogs, as well being super responsive and reliable and easy to work with. Highly recommended! (more)"

13. Lawrence

Energetic & Responsible

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

"Hello Lawrence loves dogs. He helped raise our Border Collie/ Mix from a 4 month old pup until we lost him at age 15. His sister adopted a puppy shortly... (more)"

14. Kristin

Reliable and caring dog lover!

Medford, MA, 02155

House Sitting

"Kristin has always been a dog lover. She was the one who helped me take care of our rescued greyhounds many years ago. Now when she's home she loves playing ... (more)"

15. Kate

Active and reliable dog sitter

Somerville, MA, 02145

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Kate rocks! she was amazing with our pup Bowie! She is trustworthy and responsible and what we loved best was that she kept us updated (pictures included). T... (more)"

16. Joann

Loving caring patient and generous

Medford , MA, 02155

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

About: You can ask my best friend how Well I took care of her dog. She was a beagle with some health issues , we all loved her and she loved us. Unfortun... (more)

17. Julia

Dogs make our lives whole

Stoneham , MA, 02180

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Julia is great. This was a "trial" weekend for my original weekend request for the following week. Julia spent time with my Shelley shih tzu for the weekend ... (more)"

18. Samantha

BU & Columbia Grad who loves dogs!

Arlington, MA, 02474

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"We booked Samantha about a week or so out for a multiple day pet stay at our house for our two Chinese Shar-Pei. Samantha was wonderful, sent pictures of th... (more)"

19. Veselina

Puppy lover

Woburn, MA, 01801

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Vaselina was fantastic. Very responsive and capable. Will definitely be asking her to dog sit again. (more)"

20. Casey

I will love your dog like my own

Woburn, MA, 01801

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

"My husband and I have used Casey on a number or occasions for dog walking & pet sitting services. She's fantastic. The dogs are exhausted after her walking a... (more)"

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Home owners love Winchester house sitters on Rover. 28 owners have reviewed sitters in Winchester, MA, giving them an average rating of 4.9/5.

Want to be added to this list of sitters in Winchester? Become a pet sitter or dog walker on Rover.

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.