House Sitting in Winthrop

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

Confirmed President's Day Availability
1. Callie

I miss my dog let me love yours!!!

Back Bay-Beacon Hill, Boston, MA, 02114

House Sitting

4 repeat clients

"Callie took excellent care of our puppy. She house-sat for us while we were away for a long weekend, and also walked our pup over the next week after we ret... (more)"

2. Nicole

Best Pup-snuggler In Southie!

South Boston, Boston, MA, 02127

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

"I've known Nicole for a few years now and she's been helping with over night dog sitting for my little pit mix Jackson. Jackson has severe separation anxiet... (more)"

3. Elizabeth

Dogless DogLover

East Boston, Boston, MA, 02128

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Liz was great! One of our pups is quite needy and the other a little standoffish, so we were a little worried leaving them for so long, but they seemed to ha... (more)"

4. Jenna

Responsible and Caring Dogsitter

Revere, MA, 02151

House Sitting, Drop-In Visits

"Jenna is an amazing dog sitter!!! Jenna has dog sat for my fiancé and I multiple times. She has stayed in our house with our dog who is a Chug and 15 pounds.... (more)"

Confirmed President's Day Availability
5. Gabriela

Experienced, reliable, & loving

South Boston, Boston, MA, 02127

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Gabby was outstanding! She stayed overnight at my place for nearly a week walking Layla twice daily and sending me lovely photos and ensuring that she was we... (more)"

6. Sarah

I'll love your pooch like my own!

Central, Boston, MA, 02108

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Sarah is lovely! She house sat Biden (my 2 month goldendoodle) for the day, and she was kind and playful with him. She was a great apartment guest as well. (more)"

7. Nives

Full- time dog lover!

South Boston, Boston, MA, 02127

House Sitting, Drop-In Visits, Dog Walking

"I would like to give my glowing recommendation and praise to Nives. She has been a dog sitter for me several times over the last couple of years. I completel... (more)"

8. Jasline

Dog will be treated like my own

Revere, MA, 02151

House Sitting, Drop-In Visits, Dog Walking

"Jasline has always been an animal person. She has a great vibe to her which dogs seem to really love. In the past Jasline has taken great care of my dog whil... (more)"

9. Jade

I'll care for your dog like my own!

South Boston, Boston, MA, 02127

House Sitting, Drop-In Visits, Dog Walking

"Jade is a very responsible and loving dog caregiver. In the 7+ years I’ve known her, she has always put her own dog’s needs first and made her a priority, wh... (more)"

10. Jasmina

Safe home for your dog

East Boston, East Boston, MA, 02128

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

18 repeat clients

"Jasmina is our go to sitter whenever we need someone to look after our girls (two dogs). She is excellent with dealing with all of the specific instructions ... (more)"

11. Catherine

TLC for your pets while you're away

East Boston, east boston, MA, 02128

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

"Catherine is an amazing dog mom, and dog caregiver! She has a big loving heart and a passion for caring for animals. Whenever she sits my dog, I worry that h... (more)"

12. Melissa

Near city pet sitter!

Winthrop, MA, 02152

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

"Melissa is so good with dogs of all ages. I have a senior dog who can be a "grumpy old man" and is very lame, Melissa is so kind and patient with him. His ... (more)"

13. Laura

Every dog is my dog haha

Revere , MA, 02151

House Sitting, Drop-In Visits, Dog Walking

About: My fur pups and their owners will love all the fun long walks we will have together! I have delt with all sizes and breeds of dogs and have two of ... (more)

14. Felicia

A dog's best friend

East Boston, East Boston, MA, 02128

House Sitting, Dog Walking

"Felicia is a responsible and reliable worker with a caring heart. As her employer I highly recommend her for the position she is applying for. (more)"

15. Hannah

Lifetime dog lover and runner!

East Boston, Boston, MA, 02128

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

2 repeat clients

"Hannah is great! She took care of our large dog at our house for 4 days. She sent pictures of them going for walks/hanging out. Great sitter! (more)"

16. Deanna

Experienced Veterinary Technician

East Boston, Boston, MA, 02128

Dog Boarding, House Sitting

"I've had the pleasure of seeing first-hand how Deanna cares for animals that she boards, treating them like her own. Challenging pets, and animals with spec... (more)"

17. Samantha

I'll run walk play & love your dog!

East Boston, Boston, MA, 02128

House Sitting, Drop-In Visits, Dog Walking

"She has puppy sat a French bulldog as well as puggle. She is responsible and enjoys taking dogs on walks. She often helps her family out with a few of their ... (more)"

18. Elizabeth

I live next to a park!

East Boston, Boston, MA, 02128

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

"Elizabeth has a loveable, bubbly personality that makes it hard not to smile when around her. She is very smart and always excelled in her goals. She loves a... (more)"

19. Jill

Fur babies make the best friends...

Winthrop, MA, 02152

House Sitting, Drop-In Visits, Dog Walking

"Jill is excellent with our dog Sully. Sully is always super excited to see Jill and she always remembers what his favorite toys and treats are. Sully is a bi... (more)"

20. Kristina

I'll run and snuggle with your dog

East Boston, Boston, MA, 02128

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

1 repeat client

"Kristina is a very reliable individual and has been a go-to person when it comes to our friends and neighbors needing a dog sitter. Kristina grew up having c... (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.