House Sitting in Winchester

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Sitter Profile Image: Mary B.
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Sitter Profile Image: Mary B.
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1. Mary B.

Star Sitter
Dog Lover & Dog Sitting
Neighborhood 9, Cambridge, MA, 02138
5.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
8 repeat clients
from
$50
per night
Profile image

Mary did an excellent job taking care of our two dogs and apartment while we were out of town! She was very communicative and stayed on top of the details. Our two dogs clearly bonded with her. We are planning to book with her again for our next trip!

Sitter Profile Image: Andrew T.
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Sitter Profile Image: Andrew T.
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2. Andrew T.

Star Sitter
Friendly, convenient sitter/walker
Medford, MA, 02155
3.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
68 reviews
25 repeat clients
from
$75
per night
Profile image

Andrew was terrific! He communicated with us regularly to let us know how things were going. He clearly enjoyed Bernie & the feeling was mutual. The house was immaculate upon our return. He was just wonderful to deal with, and we'd most definitely ask him again to take care of Bernie!

Sitter Profile Image: Annette G.
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Sitter Profile Image: Annette G.
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3. Annette G.

Star Sitter
Let me love your babies like you do
Waltham, MA, 02452
5.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
31 reviews
15 repeat clients
from
$60
per night
Profile image

100% recommend. Best, best friend ever! Annette was delightful to work with. She was punctual, attentive and organized. She stayed with our pups for full 4 days and she was always in touch and feeding the animals the right medications and meals. On top of that she was organized and clean. Lastly, what we enjoyed the most is that our dogs seemed very happy and relaxed with her. She is a true find and look forward to working with her in the near future.

Sitter Profile Image: Renee R.
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Sitter Profile Image: Renee R.
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4. Renee R.

Star Sitter
My Best Friend, Dog sitting
Arlington, MA, 02474
2.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
14 reviews
6 repeat clients
from
$75
per night
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Renee was the best! She was so patient with our special needs dog and despite him being a handful she was able to keep him happy and well cared for.

Sitter Profile Image: Caleigh I.
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Sitter Profile Image: Caleigh I.
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5. Caleigh I.

Star Sitter
I love all animals like family.
Cambridge, MA
5.6 mi. away
House Sitting
5.0 out of 5 stars
14 reviews
6 repeat clients
from
$75
per night
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Caleigh was so wonderful!! Not only was she super understanding of me being late to pick up Jackson, she was also super responsive when I asked for updates on Jackson’s condition since he was recently put on new medications. I would recommend her to anyone!

Sitter Profile Image: Kelcee G.
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Sitter Profile Image: Kelcee G.
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6. Kelcee G.

Patient, trustworthy, animal lover!
Somerville, MA, 02145
5.1 mi. away
House Sitting
5.0 out of 5 stars
14 reviews
4 repeat clients
from
$80
per night
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Kelcee was fantastic! She took amazing care of Asya and sent the best pictures and kept me updated on how things were going. She made being away from my fur baby more calming for her momma!

Sitter Profile Image: Makayla K.
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Sitter Profile Image: Makayla K.
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7. Makayla K.

Star Sitter
Lots of flexibility, energy, + time
Woburn, MA, 01801
3.8 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
62 reviews
30 repeat clients
from
$50
per night
Profile image

Makayla was great with our two beagles! I was a little worried about leaving them over the 4th of July weekend because of the fireworks, but Makayla handled their anxiety meds and sent photo updates. The dogs seemed happy and unphased when we returned. Thanks, Makayla.

Sitter Profile Image: Annika H.
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Sitter Profile Image: Annika H.
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8. Annika H.

Vet tech assist@SVC
Lexington, MA, 02421
4.4 mi. away
House Sitting
5.0 out of 5 stars
34 reviews
15 repeat clients
from
$55
per night
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Annika was great with our dog! She watched him for 16 days while we were on vacation. We are so thankful for all she did for our fur baby!!! We loved all the pictures she sent to us while we were on vacation !

Sitter Profile Image: Frances & Julia H.
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Sitter Profile Image: Frances & Julia H.
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9. Frances & Julia H.

Star Sitter
Kind, Loving & Trustworthy Tag Team
Reading, MA, 01867
4.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
26 reviews
8 repeat clients
from
$96
per night
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I am beyond happy with the quality of care Julia and Fran provided. They are so nice and accommodating, and it eased my worries knowing that my pups were in good hands while I was away. I would give 10 stars if I could! Thank you so much :)

Sitter Profile Image: Ella C.
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Sitter Profile Image: Ella C.
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10. Ella C.

Star Sitter
Pet lover with a flexible schedule
Somerville, MA, 02144
4.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
32 reviews
13 repeat clients
from
$75
per night
Profile image

Ella was excellent with our somewhat rambunctious 1 year old cat. She asked great questions, gave her plenty of play time, and was an excellent communicator. It was so nice to know our young cat was in good hands. Would definitely recommend Ella and have her back to catsit again!

Sitter Profile Image: Claire H.
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Sitter Profile Image: Claire H.
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11. Claire H.

Star Sitter
Dogs are my best friends fur-ever!
Arlington, MA, 02474
3.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
18 reviews
10 repeat clients
from
$70
per night
Profile image

Claire stayed with our spaniel-mix Roux over the extended weekend, and took great care of her. Roux is a high-energy dog, and needed plenty of time outdoors and a company inside the house. Claire is a very warm and attentive person, and communication was easy while we were away. We already booked another stay with her.

Sitter Profile Image: Sabine G.
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Sitter Profile Image: Sabine G.
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12. Sabine G.

Loving and experienced pet-sitter
Belmont, MA, 02568
4.1 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
9 reviews
3 repeat clients
from
$60
per night
Profile image

Sabine did a great job staying with our dog while we were out of town. She sent regular updates and kept in touch, which we really appreciated while we were so far away!

Sitter Profile Image: Ilyas A.
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Sitter Profile Image: Ilyas A.
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13. Ilyas A.

Rover 101
I had a pet, but I rather pet yours
Somerville, MA, 02145
4.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
70 reviews
30 repeat clients
from
$55
per night
Profile image

Ilyas was fantastic with our sweet boy, Gus! He was communicative, helpful and kind throughout our initial meeting with him until he left our house. He took great care of our house and our pup. We will absolutely be using Ilyas again when we go away. Thank you!

Sitter Profile Image: StacyLynn S.
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Sitter Profile Image: StacyLynn S.
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14. StacyLynn S.

Rover 101
Will Love Your Furbaby Like My Own
Winchester, MA, 01890
0.2 mi. away
House Sitting
5.0 out of 5 stars
88 reviews
43 repeat clients
from
$85
per night
Profile image

First time using Rover. So happy to have chosen StacyLynn to take care of our pups! We have 3 dogs including a1 yo Rottie who still has puppy craziness. We went away knowing they were in good hands without worry. Will definitely call StacyLynn next time we go away!

Sitter Profile Image: Matthew S.
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Sitter Profile Image: Matthew S.
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15. Matthew S.

Walk, play, run and skip, I'm there
Sommerville, MA, 02144
4.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
1 repeat client
from
$70
per night
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Matthew was great with Cooper! He sat for us over the weekend and did a great job caring for our senior dog and taking care of our house. Highly recommended!

Sitter Profile Image: Jacob Z.
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Sitter Profile Image: Jacob Z.
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16. Jacob Z.

Star Sitter
The dog whisperer.
Winchester, MA, 01890
0.5 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
55 reviews
18 repeat clients
from
$80
per night
Profile image

Jacob was a great sitter for Marilyn when we went away for the weekend! He read through all the instructions thoroughly and was very good about updating us with photos. Marilyn is a 70lb German Shepherd mix and can be a stubborn walker at times and he managed to take her on a ton of walks! He even cleaned up before he left and left the house just as it was when we left. Would recommend!

Sitter Profile Image: Nick L.
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Sitter Profile Image: Nick L.
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17. Nick L.

Patient Pet Partner
Winchester, MA, 01890
0.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
12 reviews
2 repeat clients
from
$50
per night
Profile image

Nick was very responsible throughout the duration of his stay at my home and with my pup. Nick communicated with me daily and followed house specific guidelines. The home was immaculately clean when I returned. Would recommend!

Sitter Profile Image: Adrienne A.
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Sitter Profile Image: Adrienne A.
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18. Adrienne A.

Vet Tech & Animal Lover
Medford, MA, 02155
2.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
55 reviews
21 repeat clients
from
$60
per night
Profile image

Adrienne did a great job looking after my senior special needs pup Gloria while I was out of town for a night. She sent me ample photos and videos and I felt like Gloria was in great hands. My dog does have significant mobility challenges so it was reassuring to have Adrienne there and providing updates along the way, as this was my first time leaving my dog since covid!

Sitter Profile Image: Eric S.
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Sitter Profile Image: Eric S.
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19. Eric S.

Professional Toe Bean Lover
Woburn, MA, 01801
2.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
3 reviews
from
$45
per night

Eric is a thoughtful and caring person. When we worked together at a veterinary hospital he was always busy helping others and looking forward to the next task. Eric always completed things with the patients and his fellow staff in mind. Eric is trustworthy, caring, and truly cares for the well being of animals!

Sitter Profile Image: Maria L.
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Sitter Profile Image: Maria L.
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20. Maria L.

Thoughtfully Trained Caregiver
Somerville, MA, 02144
2.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
113 reviews
34 repeat clients
from
$92
per night
Profile image

Maria did such an awesome job watching our 16yo cat and getting him his meds twice a day (anyone who's had to medicate a cat knows how tricky this can be!). She was proactive with communication, sending us lots of cute pics and updates around feeding/meds time. We were actually able to enjoy our vacation worry free knowing our little guy was in good hands. We immediately rebooked Maria for our holiday trip this year and highly recommend her. She definitely has a way with animals and took excellent care of our cat AND our home while we were away. Thank you Maria!

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  1. 1. Search

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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.

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