House Sitting in Winslow

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

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
Which dates do you need?
What size are your dogs (lbs)?
To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

Search Results

Sitter Profile Image: Anna S.
Verified Background Check
Sitter Profile Image: Anna S.
Verified Background Check

1. Anna S.

Veterinary technician
Augusta, ME, 04330
17.7 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
62 reviews
14 repeat clients
from
$45
per night

I am pretty sure my dog is in love with Anna and Oliver, her son! It felt like they just swept her into their family while I was away and that put my mind at ease while being out of town! I would 100% ask for Anna’s help again!

Sitter Profile Image: April M.
Verified Enhanced Background Check
Sitter Profile Image: April M.
Verified Enhanced Background Check

2. April M.

Love my furry friends!
Belgrade, ME, 04917
11.4 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
24 reviews
11 repeat clients
from
$40
per night

This was our first time using April to sit with Aspen…will absolutely be using her in the future. Aspen was happy and content when we got home, house was just as we left it, and April sent us pix while we were gone - great communication as well ??

Sitter Profile Image: Melissa H.
Verified Enhanced Background Check
Sitter Profile Image: Melissa H.
Verified Enhanced Background Check

3. Melissa H.

Passionate Animal Whisperer
Winslow, ME, 04901
0.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
25 reviews
9 repeat clients
from
$40
per night

Melissa was a great house and pet sitter for a long weekend. Excellent communication in advance. Treated both our house and pets with great care. Will definitely use her again for future get-aways.

Sitter Profile Image: Cleo L.
Verified Enhanced Background Check
Sitter Profile Image: Cleo L.
Verified Enhanced Background Check

4. Cleo L.

Life long experience with all pets
West Gardiner, ME, 04345
23.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
21 reviews
7 repeat clients
from
$47
per night

Cleo went out of her way to make sure my Kota man was well taken care of over the weekend while I was out of town! She checked in with me every day on how he was doing and took him on fun walks, to the dog park, etc.! If you need someone to watch your pets or even just stop in for a walk, I highly recommend!

Sitter Profile Image: Alyssa C.
Verified Enhanced Background Check
Sitter Profile Image: Alyssa C.
Verified Enhanced Background Check

5. Alyssa C.

Expert Canine Handler & Dog Lover
Sidney, ME, 04330
8.2 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
1 repeat client
from
$55
per night

Alyssa was amazing with my 2 dogs, and they are not the most easy-going. They had a great time and I would absolutely recommend Alyssa.

Sitter Profile Image: Kelly C.
Verified Background Check
Sitter Profile Image: Kelly C.
Verified Background Check

6. Kelly C.

Peaceful Country Home
Sidney, ME, 04330
7.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
28 reviews
10 repeat clients
from
$70
per night

Kelly watched our two dogs in her home while we went away for a long weekend and she was amazing! I really dreaded leaving them, but her regular updates/pictures put my mind at ease right away. I could see that they were staying busy, getting lots of love and overall, in great hands with Kelly. I'm so glad to have found her!

Sitter Profile Image: Madelyn S.
Verified Background Check
Sitter Profile Image: Madelyn S.
Verified Background Check

7. Madelyn S.

Short, descriptive, and genuine
Fairfield, ME, 04989
6.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
29 reviews
11 repeat clients
from
$120
per night

Madelyn watched our 3 dogs for 2 nights at our house. Our dogs loved staying with her and got lots of exercise while we were gone and our house was clean upon our return.

Sitter Profile Image: Grace B.
Verified Enhanced Background Check
Sitter Profile Image: Grace B.
Verified Enhanced Background Check

8. Grace B.

Hello my name is Gracie :)
Waterville, ME, 04901
0.6 mi. away
House Sitting, Dog Walking
5.0 out of 5 stars
11 reviews
3 repeat clients
from
$30
per night

Grace was so wonderful with Annie and Ollie and our home! She gave us daily updates and pics. We also appreciated how well she communicated with us. We will definitely book her again!!

Sitter Profile Image: Jason F.
Verified Background Check
Sitter Profile Image: Jason F.
Verified Background Check

9. Jason F.

Best care anywhere!!!!
Oakland, ME, 04963
6.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
9 reviews
2 repeat clients
from
$60
per night

Jason was fantastic. He helped me in a pinch and was prompt, communicative and generally happy to spend time with Chloe (my dog). Received photos and updates. Very good experience, will certainly book again. Thank you Jason!

Sitter Profile Image: Susan C.
Verified Enhanced Background Check
Sitter Profile Image: Susan C.
Verified Enhanced Background Check

10. Susan C.

your dogs new second best friend
Belgrade, ME, 04106
11.7 mi. away
House Sitting
4 reviews
from
$30
per night

I highly recommend Susan for anyone looking for a trustworthy and reliable dog sitter. Susan has been boarding my dogs for many years anytime we go on vacation and I couldn't be happier with her services. First and foremost, Susan genuinely cares for the well-being of my dogs. She takes the time to understand their individual needs, preferences, and routines, ensuring that they are comfortable and happy while in her care. I can always trust that my dogs are in good hands when they are with Susan. Not only does Susan provide excellent care, but she also goes above and beyond to keep me updated on how my dogs are doing. She sends regular updates, including pictures and videos, which gives me peace of mind knowing that my furry friends are enjoying their time with her. I also love the private property on the lake for my dogs to have the freedom to run around, play and swim.

Sitter Profile Image: Rylee S.
Verified Enhanced Background Check
Sitter Profile Image: Rylee S.
Verified Enhanced Background Check

11. Rylee S.

I love dogs of all sizes and ages!
Sidney, ME, 04330
8.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
2 reviews
from
$80
per night

Rylee is a very attentive pet caregiver. It is clear that she loves animals and our dogs love her. Rylee is very patient but also very energetic. I know of 4 families who have hired her to care for their dogs and they all seem very happy with her!

Sitter Profile Image: Kaitlyn J.
Verified Enhanced Background Check
Sitter Profile Image: Kaitlyn J.
Verified Enhanced Background Check

12. Kaitlyn J.

Experienced animal lover!
Fairfield, ME, 04937
3.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
11 years of experience
from
$30
per night

About: Grew up with animals including lizards, cats, dogs, birds and horses. Volunteered in animal shelters doing all care of cats and dogs! Love animals :) I volunteer at the shelter, so I work short shifts at odd hours but I am fully available at almost any other time of the day! I have three cats currently who are the most spoiled animals, they get lick mats, vitamins, and all sorts of other fun enrichment. They are also some of the kindest cat you will ever meet! I would extend this love for my cats to your animal offering homemade pumpkin puree treats (if allowed) and plenty of attention and play time!

Sitter Profile Image: Olivia S.
Verified Enhanced Background Check
Sitter Profile Image: Olivia S.
Verified Enhanced Background Check

13. Olivia S.

Veterinary Assistant experience
Fairfield, ME, 04937
3.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
from
$35
per night

About: Hi! I’m Olivia, I’m a 23 year old nail tech & military wife! 🇺🇸 I can care for cats, dogs, birds, farm animals, reptiles & rodents! I absolutely love animals, and would love to care for yours! I am a fur mom to 4 cats, 1 guinea pig & multiple fish! I’ve also had dogs and hamsters in the past. Along with working on a family friends farm. Any animal, any shape or size is welcome! I am a nail tech that is on my own schedule! So my availability is very open to fit your needs! No need to worry :) I currently do not offer services in my home, but I’ll be more than happy to watch your fur, scale or hoof baby in/at yours! :)

Sitter Profile Image: Anna Y.
Verified Enhanced Background Check
Sitter Profile Image: Anna Y.
Verified Enhanced Background Check

14. Anna Y.

No pet to big or small!
Albion, ME, 04910
11.6 mi. away
House Sitting, Drop-In Visits
1 review
from
$60
per night

Anna is a lovely person, extremely responsible and detail oriented. I have so appreciated her precision and care for her work over the past four years have have a huge amount of trust in her as a person.

Sitter Profile Image: Nicole W.
Verified Enhanced Background Check
Sitter Profile Image: Nicole W.
Verified Enhanced Background Check

15. Nicole W.

Will treat your babies as my own
China, ME, 04358
10.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
1 review
from
$35
per night

About: Many friends & families have relied on me to care for their fur babies while away. No matter their age, personality or special accommodations, all are welcome! I currently work in Augusta Mon-Thurs so I am able to pet sit for those weekends away or provide drop ins or walks after 5pm during the week! Your pets safety is my TOP priority! I would never intentionally put them in an unsafe situation. Please let me know if there are certain people/pets we should avoid during our activities.

Sitter Profile Image: Ileia P.
Verified Background Check
Sitter Profile Image: Ileia P.
Verified Background Check

16. Ileia P.

Experienced Pet caregiver
Winslow, ME, 04901
2.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
4 reviews
from
$30
per night

Ileia loves animals. Her dogs are spoiled worse than children! Her passion goes beyond her pets as she works with animals as well. I would trust her to pet sit my pack anytime.

Sitter Profile Image: Alyx C.
Verified Background Check
Sitter Profile Image: Alyx C.
Verified Background Check

17. Alyx C.

I have paw prints on my heart.
Waterville, ME, 04901
0.8 mi. away
Boarding, House Sitting, Dog Walking
5.0 out of 5 stars
15 reviews
4 repeat clients
from
$38
per night

About: I love being outside and on the go! Pets are my favorite friends, so count on tons of attention and loves. I have a comfy pet friendly home so your furbaby will have l lots of toys and comforts! My working hours are only between 10-6 so I'm never unavailable for more than 8 hours at a time. With a break every shift, I'm able to make it home at least once per shift. I'm up early and love to get out for an early morning walk! I'm also near my phone always and ready to keep you posted with photos or answers to any questions you have for me or about your pet. I'm also extremely flexible with dates and times! I'm so excited to shake a paw and get to know your furry friend! I currently work part time at WHOP. I always have Sunday, Tuesday, and Wednesday off. Otherwise. I only work 10-6 at maximum. I try my best to get home at least twice during that time, but I always make it once. Every situation is unique. I try to keep the routine for your pet as close to what they experience day to day with you as possible. Typically I'll adjust my routine to your pet, I find this keeps them more comfortable and makes the transition both to and from my home easier.

Sitter Profile Image: Emma B.
Verified Enhanced Background Check
Sitter Profile Image: Emma B.
Verified Enhanced Background Check

18. Emma B.

Dedicated & Skilled Pet Caretaker
Fairfield, ME, 04937
4.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
16 reviews
9 repeat clients
from
$156
per night

Emma has been our farm sitter of choice for years. At 16 years old, she was far more responsible than many older adults. She is capable, knowledgeable and willing to work. She clearly loves all animals and can handle difficult situations with a calm, cool head. I have the very highest regard for her!

Sitter Profile Image: Sarah V.
Verified Enhanced Background Check
Sitter Profile Image: Sarah V.
Verified Enhanced Background Check

19. Sarah V.

Wanting to help other dog parents!
Waterville, ME, 04901
2.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
11 years of experience
from
$40
per night

About: I have always grown up with pets including cats dogs ferrets and many others. I have also been fostering cats and dogs through the Waterville Humane Society for about 8 years! I absolutely love animals and I am currently a stay at home dog mom and I have a dog myself. I am comfortable with feeding, walking and bathing. . I am open to different schedules because I am currently working from home and have plenty of time to help another pet parent. I can do check in during vacation, or daily check ins Your home your rules. Pets love structure so I plan to always follow directions for what is being asked when I’m caring for your pet.

Sitter Profile Image: Monte M.
Verified Enhanced Background Check
Sitter Profile Image: Monte M.
Verified Enhanced Background Check

20. Monte M.

Caring for your furry companions
Waterville, ME, 04901
0.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
3 reviews
from
$30
per night

Monte is great with animals. He is very caring and patient and will do whatever it takes to make sure your pets are well taken care of. Your pets will feel very loved in his care.

Search Map

Winslow House Sitting ratings

Overall Rating:
4.9 out of 5 stars

House sitters in Winslow are rated on average 4.9 out of 5 stars based on 12 reviews.

Rover also offers House Sitting in:

Rover also offers other services in Winslow:


Never beg a friend to watch your dog again. With Rover, you can find your the perfect Winslow house sitter in seconds. When you book house sitting on Rover, your dog will enjoy a loving, relaxing stay in their own home. If you're looking for care for pets other than dogs, you can find a pet sitter who offers care for cats, caged pets, and even horses. No matter what, you'll know that your pet is getting loving care. By removing common pet care obstacles, Rover ensures dogs nationwide are happy and well-cared for even when their human is away, and empowers dog lovers to live happy and fulfilling lives. Founded on the belief that everyone should have the opportunity to experience the unconditional love of a dog, Rover makes it easy for you to reach trusted house sitters in Winslow who can provide the care your dog needs, when they need it.

House Sitting