Pet Sitting & Drop In Visits in Chestnut Hill, MA

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

1. Kendall

Dog-loving Cat Dad...Squirrel!!

Allston-Brighton, Allston, MA, 02134

Drop-In Visits, Dog Walking

12 repeat clients

"Kendall is fantastic! He sends tons of great pictures and takes great care of my cat. Best of all, my cat really loves him and he's not as angry when I retur... (more)"

2. Heather

Flexible, responsible, energetic

Newton, MA, 02458

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Heather went above and beyond normal duties when caring for my cat, Jack while I was away for almost 3 weeks. She really cared for him as her own, gave me co... (more)"

3. Jacky

ISO pups to run/ walk with MON-FRI

Allston-Brighton, Brighton, MA, 02135

House Sitting, Drop-In Visits, Dog Walking

23 repeat clients

"Jacky is the best! She has taken such great care of Hannah! (more)"

4. Colleen

Two Rover Dog Walkers live here!

Cambridgeport, Cambridge, MA, 02139

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

1 repeat client

"Colleen would make an excellent dog walker or pet sitter! She has grown up with dogs (and cats) her whole life. Pets are family members in her household. ... (more)"

5. Evalin

Active and playful with all dogs!

Cambridgeport, Cambridge, MA, 02139

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Evalin was nice enough to stop by the day before and meet my pups. They both seemed really comfortable with her and judging by the photos she took, they were... (more)"

6. Bruna

Bark all Day; Play all Night-Sitter

Chestnut Hill, MA, 02467

House Sitting, Drop-In Visits, Dog Walking

"Bruna loves dogs more than almost anyone I know. Even just seeing a dog brightens up her day. She truly loves animals, and is great with them. Whenever I go ... (more)"

7. Lyndsay

Love to play fetch and long walks

Brookline, MA, 02445

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Lyndsay has proven time and time again that she is a responsible and caring person. She is always willing to help friends out when needed and is astute and i... (more)"

8. Paige

Reliable and Trustworthy Sitter

Brookline, MA, 02446

House Sitting, Drop-In Visits

37 repeat clients

"Paige goes above and beyond in caring for our dog while we are away. She texts us frequently with updates and has a great attention to detail that we appreci... (more)"

9. Carly

The perfect activity partner

Jamaica Plain, Jamaica Plain, MA, 02130

House Sitting, Drop-In Visits, Dog Walking

"Carly is an extremely kind and responsible person. You can rest assured that your dog will be fed, petted, and cared for under her watch. (more)"

10. Katie

I will draw you a pet portrait!

Allston-Brighton, Brighton, MA, 02135

House Sitting, Drop-In Visits, Dog Walking

6 repeat clients

"Katie went above and beyond keeping me updated on Mack, making sure to let me know he was in great hands. I would highly recommend her to anyone looking for ... (more)"

11. Violet

Animal lover, former dog trainer

Allston-Brighton, Brighton, MA, 02135

Drop-In Visits

3 repeat clients

"Violet was so wonderful when I was in a pinch to find a sitter last minute. Great communication before and during my trip and I always felt like my pet was i... (more)"

12. Kathryn

Caring and active dog lover

BROOKLINE, MA, 02446

House Sitting, Drop-In Visits, Dog Walking

"Kathryn is one of the best dog sitters I have ever had the pleasure of meeting! She is very active and loving towards not only dogs, but all animals. I would... (more)"

13. Lauren

Personalized walking and training!

Allston-Brighton, Brighton, MA, 02135

House Sitting, Drop-In Visits, Dog Walking

"I have known Lauren for more than twenty years, and she has always been a responsible, caring, and incredibly reliable individual. I have seen her care for s... (more)"

14. Glenna

Excited to care for your dog!

Allston-Brighton, Boston, MA, 02215

House Sitting, Drop-In Visits, Dog Walking

"Glenna is great with animals! She's been watching dogs in our neighborhood for a number of years and my own dog whenever I visit my parents' home and need so... (more)"

15. Klur

I'll run and snuggle with your pup!

Allston-Brighton, Allston, MA, 02134

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

"Claire is a responsible, kind and capable caretaker and is clearly genuinely interested in making sure that the animals enjoy themselves. I honestly have not... (more)"

Available this weekend
16. Brett

Care for your dog the way you do.

Allston-Brighton, Brighton, MA, 02135

Drop-In Visits, Dog Walking

"There really aren't a lot of quality dog sitters anymore. People who genuinely care for your pet the way you do. I have a St. Bernard, Buzz who, to be quite ... (more)"

Confirmed 4th of July Availability
17. Summer

Fun, Loving, Attentive Pet Care

Brookline, MA, 02445

House Sitting, Drop-In Visits, Dog Walking

9 repeat clients

"Summer was super friendly and very accommodating. She gave our girl lots of love and sent us a bunch of pictures while we were gone. She was really flexible ... (more)"

18. Christian

Dog's Best Friend

Allston-Brighton, Brighton, MA, 02135

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

"Christian is a hard working and dependable caregiver. On many occasions Christian has taken care of my dog Frankie. Frankie is a Portuguese hound dog who is ... (more)"

19. Nancy

Engaging, above-&-beyond pet care

Allston-Brighton, Brighton, MA, 02135

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Nancy has walked our young dog Prince for a little over a year, and we have built such a fantastic relationship with her! Nancy is easy going, easy to work ... (more)"

20. Jim

I love dogs & like walks too!!

Allston-Brighton, Brighton, MA, 02135

House Sitting, Drop-In Visits, Dog Walking

"Jim has been a dog lover ever since I can remember. I'm a first time puppy parent as of 1 year ago and Jim has helped me with his knowledge of dogs he learne... (more)"


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 Chestnut Hill 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 pet sitter in Chestnut Hill, MA 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 educational opportunities 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 sitters and dog walkers.