Drop-In Visits in Winchester

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

1. Susan

We love dogs like a family member

Burlington, MA, 01803

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

3 repeat clients

"Thor really enjoyed his time with Susan and her kids, Cohan and Makayla. Their family really love dogs. They took really good care of Thor and was always on... (more)"

2. Kristin

Eager to help your family

Belmont, MA, 02478

Drop-In Visits, Dog Walking

9 repeat clients

"Kristin went above and beyond to be helpful! My cat has never been this calm when I got home, usually she is very anxious for a few days, but she was very ha... (more)"

Available this weekend
3. Abbie

Dog Lover!

Woburn, MA, 01801

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"We have only had the pleasure of having Abbie visit twice but we already love her! She's trust worthy and reliable and super super super nice! Marley loved h... (more)"

4. Euginie

Run & play as much as pup wants!

Winchester, MA, 01890

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"our 2 Frenchies love Euginie! (more)"

5. Gabi

Must Love Dogs

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Gabi was able to watch my cats over the holiday on a last minute request. She sent daily updates, and they seemed to be happy when i returned fron my trip. (more)"

6. Allison

Life long dog owner - experienced

Melrose, MA, 02176

House Sitting, Drop-In Visits, Dog Walking

"Allison watched my dog for a weekend while I was on vacation and she did a great job. My dog, Missy, tends to be a bit of a handful at times because she is s... (more)"

7. Ryan

I am OBSESSED with dogs!

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Ryan is my go-to guy for dog walking and petsitting when I'm out of town. He's absolutely fantastic with my dog! My 11 yr old Chihuahua doesn't usually do we... (more)"

8. Sophia

Loving, Responsible Dog Sitter

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

15 repeat clients

"Sophia was great. She showed up on time and listened to all the directions. She seems very knowledge of animals and the cats and dog seem to really like her.... (more)"

9. Angela

I already love your pet

Woburn, MA, 01801

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Angela is the most compassionate caregiver. She genuinely loves my dogs and they love her too! She is also very patient and truly enjoys spending time with m... (more)"

10. Grace

Fun, friendly, happy animal lover!

Melrose, MA, 02176

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Grace was awesome! My boyfriend and I had her drop in on our two cats over Christmas week and she was great about sending photos and updates, and responding ... (more)"

11. Kate

2 sitters for one price

Melrose, MA, 02176

House Sitting, Drop-In Visits, Dog Walking

"Kate has been a wonderful caregiver for our dog and cat while we are out of the country. She comes and stays in our home a couple weeks at a shot and is no ... (more)"

12. Sara

Playful, Nurturing, Pet Lover

somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

About: I work freelance from home which means I can spend majority of the day with your little friends while you are away on trips or at work. I need to ... (more)

13. Alexis

Pets make the world go round.

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

"Alexis was great and super helpful! I went on a two week trip and needed someone to stop by once a day and care for my older cat while I was gone. She gave h... (more)"

14. Meredith

Combining love of dogs & exercise!!

Arlington, MA, 02476

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Meredith's passion and love for animals has made her a fantastic dog-mama to her to pooches at home and will serve her well in caring for your dogs as well. ... (more)"

15. Julie

Belly rubs & puppy massages

Stoneham, MA, 02180

House Sitting, Drop-In Visits, Dog Walking

"I have known Julie for about 30 years now and I would highly recommend her to be your best friends dog sitter. She is a mom of 2 fur-babies herself and if s... (more)"

16. Tracy

Active and Loving Pet Sitter!

arlington, MA, 02474

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Tracy was a fantastic sitter for my cat, Callisto. She took detailed notes of her care, she was very responsive to texts, and sent me photos every day. I wo... (more)"

17. Ursula

College student who loves dogs!

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

"Ursula is very enthusiastic about dogs and it's obvious that she has a lot of love for them. She always is eager to volunteer to walk dogs, and is very respo... (more)"

18. Cameron

A life without dogs is not a life

Arlington, MA, 02476

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Cam is a total dog lover and has 3 wonderful dogs. He is very responsible and trustworthy, and takes great care of his dogs and also his rabbit. (more)"

19. Colin

I love dogs, walks, and playtime!!!

Medford, MA, 02155

Drop-In Visits, Dog Walking

2 repeat clients

"Colin has be an amazing resource for us and Penny. He is local to our neighborhood (Tufts / South Medford), which has allowed him to be available exactly whe... (more)"

20. Jenna

Indescribable love for dogs!

Woburn, MA, 01801

Drop-In Visits, Dog Walking

"Jenna T has two dogs and treats them like her children! She is great with all pets and would be a great asset to local dog owners. I highly recommend her if ... (more)"

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Learn About Premier

With over 140,000 pet sitters and dog walkers on Rover.com, you can easily find pet sitting near you.

As pet lovers, we understand how difficult it can be to leave your pet when you have to head out of town. Luckily, you can find the perfect pet sitter in seconds on Rover.com. If you're looking for trusted pet sitters while you're away, whether it's for one night or a whole month, you can find a sitter who meets your - and your pet's - needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your pet - including background checks, sitter testimonials, community reviews. We also offer training and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of pet lovers for hire.