House Sitting in Middlebury

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Loving house sitters in your neighborhood

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Sitter Profile Image: Kira D.
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Sitter Profile Image: Kira D.
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1. Kira D.

Versatile pet sitter in CT
Shelton, CT, 06484
14.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5 out of 4.8 stars
25 reviews
7 repeat clients
Profile image

Kira was great! She stayed in communication and seen hey son be pics while he we were away! This helps when you are missing your pets. Highly recommended Kira for your pet sitting needs

Availability updated 20 days ago
Sitter Profile Image: Jillian G.
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Sitter Profile Image: Jillian G.
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2. Jillian G.

Trusted Pet Sitter & Walker
New Milford, CT, 06776
15.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 5.0 stars
6 reviews
Profile image

Jillian was amazing with my pups!! She communicated through out the stay and sent pics! She left my house neat and clean. Highly recommend her!!

Availability updated yesterday
Sitter Profile Image: Katherine T.
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Sitter Profile Image: Katherine T.
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3. Katherine T.

Worry free pet care!
Milford, CT, 06461
19.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 4.9 stars
26 reviews
9 repeat clients
Profile image

Comfortable leaving our pup on long trips! Thank you Katie for letting us feel comfortable leaving our pup on long trips in our home with you. We loved getting photos and knowing he was well exercised and loved.

Availability updated 6 days ago
Sitter Profile Image: David P.
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Sitter Profile Image: David P.
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4. David P.

Star Sitter
I love dogs and they respect me.
Cheshire, CT, 06410
11.5 mi. away
House Sitting, Drop-In Visits
from
$70
per night
5 out of 5.0 stars
24 reviews
8 repeat clients
Profile image

David, we felt an immediate calm when we met you and saw you with Harry. Our snowboarding trip was a blast and we did not worry about our boy. We hope you will be willing for more stays…we want to snowboard more!

Availability updated 5 days ago
Sitter Profile Image: Madeleine D.
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Sitter Profile Image: Madeleine D.
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5. Madeleine D.

I love all animals, big and small!
Plymouth, CT, 06782
9.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 5.0 stars
11 reviews
1 repeat client
Profile image

Madeline took great care of my babies. She communicated every day, and asked questions when she was unsure of behaviors, which I appreciated. My pups were happy and calm when I came home telling me they were well taken care of and loved. I will definitely have Madeljne stay with my pups again.

Availability updated 9 days ago
Sitter Profile Image: Ian W.
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Sitter Profile Image: Ian W.
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6. Ian W.

Calm and Empathetic House-sitter
Sandy Hook, CT, 06482
11.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$62
per night
5 out of 5.0 stars
26 reviews
11 repeat clients
Profile image

My dogs, especially the standoffish one, of my 3, loved Ian upon meeting him. He is very patient and gentle. He is so considerate and attentive. I cant praise him enough! We are actually stuck where we traveled to, and were able to book him last minute for a few more days. We will be tipping him accordingly upon our retun thanks to his last minute flexibility. HIGHLY RECOMMEND

Availability updated 23 days ago
Sitter Profile Image: Juliann M.
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Sitter Profile Image: Juliann M.
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7. Juliann M.

Trustworthy Dog Walker & Sitter
Shelton, CT, 06484
13.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$65
per night
1 review
1 repeat client

Juliann walks and feeds my dog Melody several times a week while I’m at work. My dog absolutely adores her, and loves playing after walks. Juliann also walks my neighbor’s dog and they are also very happy with the care their dog receives. I know Melody is well taken care of when I’m at work, and I would recommend Juliann to all my friends who have dogs!

Availability updated 6 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Hunter N.
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Sitter Profile Image: Hunter N.
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8. Hunter N.

Animal Lover Since Birth!
Naugatuck, CT, 06770
4.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5 out of 5.0 stars
3 reviews
Profile image

Hunter did a fantastic job watching our pets. Very professional and kind. Hunter was a great choice and we will rebook again for sure!! Thank you again.

Availability updated yesterday
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Ally M.
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Sitter Profile Image: Ally M.
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9. Ally M.

I’ll love your dog like my own!
Middlebury, CT, 06762
2.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 5.0 stars
2 reviews
2 repeat clients

About: I have a dog and two cats of my own. They’re very friendly and love to be around all kinds of animals. I have had dogs all my life and know how to care for them well. I know how important it is for dogs to be active and be in the outdoors. I would love taking your dog on walks or even go hiking. I just graduated college at Clemson University and am hoping to attend veterinary school in 2026. I am back home for now and would love to help out taking care of your pets. I have dog sat before many times for friends and family and have loved every second of it. I hope to get the chance to meet even more loving pets! I just graduated from college and back home now. My schedule is very flexible as I am in the process of applying to veterinary school. I have a dog I just recently adopted that is very friendly and loves being around other dogs. She is leash trained and crate trained.

Availability updated today
Sitter Profile Image: Mayerling B.
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Sitter Profile Image: Mayerling B.
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10. Mayerling B.

Reliable & Loving Dog Sitter 🐾🐾
Naugatuck, CT, 06770
6.5 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5 out of 5.0 stars
3 reviews

May was wonderful with our Ziggy. She treated him like her own and followed all the requests we had. Ziggy has a hard time warming up to new people, but he loves time with May. We will definitely use her services again and I highly recommend her.

Availability updated yesterday
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Nicholas C.
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Sitter Profile Image: Nicholas C.
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11. Nicholas C.

Pawsitively perfect pet care !
Middlebury, CT, 06762
2.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
3 reviews

Nicholas has been a great sitter /dog walker for the past 7 years . I have a dachshund and he meets all his needs. Nicholas knows all about the back issues and is very good with following what is best for him ( ramp , no stairs and no jumping ). I totally trust him with my dog and my dog loves being with him . I would recommend him totally.

Availability updated 9 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Ana C.
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Sitter Profile Image: Ana C.
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12. Ana C.

Super energetic, dog lover.
Naugatuck, CT, 06770
4.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$35
per night
5 out of 4.8 stars
50 reviews
12 repeat clients

Ana was AMAZING! Our pups had such a good time with her and her family, we got constant pictures and appreciate responding times when contacted. I was able to enjoy myself knowing my pups were safe and happy with her. Definitely my permanent sitter!

Availability updated 67 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Olivia S.
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Sitter Profile Image: Olivia S.
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13. Olivia S.

I can’t wait to meet your pets!
Woodbury, CT, 06798
3.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$100
per night
2 reviews

Olivia has been taking care of pets her entire life and has proven to be a caring, conscientious and loving caregiver to all pets in her care. She is excellent with older pets including those with special dietary needs. I would highly recommend Olivia as someone you can trust your pet(s) with.

Availability updated 7 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: zofia d.
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Sitter Profile Image: zofia d.
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14. zofia d.

Pawsitive Pet Care & Happy Dogs!
Woodbury, CT, 06798
4.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$70
per night
5 out of 5.0 stars
6 reviews
Profile image

Excellent communications

Availability updated 2 days ago
Sitter Profile Image: Stephanie F.
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Sitter Profile Image: Stephanie F.
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15. Stephanie F.

Star Sitter
RN who loves to pet sit on the side
Middlebury, CT, 06762
2.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$125
per night
5 out of 5.0 stars
58 reviews
25 repeat clients
Profile image

First overnight with Stephanie watching the boys. We had a great experience and came home to a happy dogs! She has great communication and I had complete confidence leaving her in my home with the dogs. What a relief not having to worry!

Availability updated today
Sitter Profile Image: Ayah A.
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Sitter Profile Image: Ayah A.
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16. Ayah A.

Animal Lover!! 🐾
Middlebury, CT, 06762
1.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$90
per night
2 reviews

Ayah is a person of empathy and gentle grace, with a natural ability to create a nurturing environment for all animals she encounters. I have witnessed her care firsthand, with genuine love and warm attentiveness; these actions are nothing short of exceptional. She approaches pet-sitting and walking pets with deep responsibility and sweet devotion, making sure each pet will feel safe, adored, and understood. Ayah has flawless attention to detail alongside her considerate nature. She will offer a sanctuary of care, making her the ideal and correct choice for those seeking out a reliable and heartfelt personal connection.

Availability updated 3 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Jaiyda L.
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Sitter Profile Image: Jaiyda L.
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17. Jaiyda L.

Loving dog sitter
Waterbury, CT, 06708
4.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$38
per night
2 years of experience

About: I have loved animals since I was little, I’ve learned a lot from having many pets myself including senior dogs and animals with physical and mental health issues I’m available for house sitting, hours can be flexible. I do not work on sundays so please contact me before hand if work is needed on sundays and we can sort something out! I own dogs their names are bella (corgi), tiny (chihuahua) and onyx (pug) they are my pride and joy and I hope to own more dogs in the future lol. They are very loved! Don’t mind bringing my pets along as they are dog friendly

Availability updated 3 days ago
Sitter Profile Image: Alison K.
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Sitter Profile Image: Alison K.
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18. Alison K.

Dedicated Pet Care ?
Southbury, CT, 06488
4.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$70
per night
4 reviews

Alison has been taking care of animals for years. She is mature, responsible and trustworthy. I would recommend her to anyone who wants a very qualified lady to watch your pets.

Availability updated 13 days ago
Sitter Profile Image: Erika S.
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Sitter Profile Image: Erika S.
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19. Erika S.

Dedicated Experienced Pet-Sitter
Naugatuck, CT, 06770
2.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$110
per night
5 out of 5.0 stars
11 reviews
5 repeat clients
Profile image

Erika is the best! She stopped over to review any changes since the last time she house sat, pays great attention to detail & followed our requests to make sure our dogs were safe. She made sure meds were given, they had more opportunities to eat when not interested the first time, and went above and beyond to spend extra outside time with them. She sent updates, pictures, and left a clean house. We have no worries when Erika takes care of our dogs and came home to happy and content pups :)

Availability updated 32 days ago
Sitter Profile Image: Katie C.
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Sitter Profile Image: Katie C.
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20. Katie C.

Animal lover, Pet Sitter and Walker
Middlebury, CT, 06762
1.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$63
per night
5 out of 5.0 stars
3 reviews
2 repeat clients
Profile image

Katie is awesome, highly recommend using her for your pet needs. She arrived early, allowed us to have a meet and greet before her scheduled pet sitting. She is extremely intelligent, kind and has more common sense than most people that I know! She is thorough in her pet sitting and in tune with the needs of the pet that she is sitting with.

Availability updated 3 months ago

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  2. 2. Meet & Greet

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    It doesn’t happen often, but if your house sitter has to cancel, we’ll work with you to find a new sitter.

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