Dog Sitting in Middlebury

Book a Middlebury dog sitter to watch your dog in your sitter’s home or yours.

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Top rated Middlebury dog sitters

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Vera R.
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Vera R.
from
$25
per visit
5.0 out of 5 stars
19 reviews
10 repeat clients
5 years of experience
Watertown, CT, 06779

Vera stepped in as a last-minute replacement, and I’m so grateful she did! She followed all of my detailed instructions and was very intuitive with my persnickety cat. She also sent very charming and kind updates. Highly recommend!

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Greta B.
Sitter Profile Image: Kaylee B.
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Kaylee B.
from
$35
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
5 years of experience
Watertown, CT, 06795

We couldn’t have asked for a better sitter than Kaylee for our dog Nikko while we were away for two weeks. From the very beginning, she went above and beyond to make sure he was not only cared for, but truly loved and engaged. Kaylee spent extra time with Nikko, took him on car rides (which he loves!), and made sure he had both fun and comfort while we were gone. It was clear from the photos and updates—and even more so when we returned—that he really enjoyed his time with her. She treated Nikko like her own, and that kind of care is priceless. We felt completely at ease knowing he was in such good hands. We highly recommend Kaylee and would absolutely book with her again!

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Dave J.
Sitter Profile Image: Darya H.
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Darya H.
from
$19
per visit
10 years of experience
Prospect, CT, 06712

About: I’ve been around animals my whole life and genuinely love spending time with them, especially dogs and cats. I have a golden retriever and two cats of my own, so I know how important it is to have someone you truly trust caring for your pets while you’re away! I’m very reliable, patient, attentive and I honestly just enjoy being around them. I love being outside, going on walks, and making pets feel comfortable, safe, and cared for. I also have a very flexible schedule, so I’m able to give pets plenty of attention and consistency throughout the day. I’m comfortable with dogs of most sizes and energy levels, as well as cats, kittens, and puppies! Whether your pet is super energetic or more shy and relaxed, I’m happy to work with their routine and make sure they feel happy and comfortable while you’re away. I have a flexible schedule and plenty of time to care for your pets! Whether it’s a walk, a drop-in, or just some attention during the day, I’m happy to help! I don’t care for pets in my own home, but I’m very respectful and reliable when it comes to caring for pets in their own space. I always follow the owner’s instructions closely, make sure everything is secure before I leave, and give plenty of attention and care during my visit! I want your pets to feel safe and comfortable while you’re away.

Sitter Profile Image: Cole O.
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Cole O.
from
$17
per visit
5.0 out of 5 stars
5 reviews
1 repeat client
11 years of experience
Middlebury, CT, 06762

Cole was fantastic. On time and communicative. Dealt with some unexpected snow on the driveway without issue. It was great to know my pets were well cared for!

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Steven H.
Sitter Profile Image: Lucy G.
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Lucy G.
from
$25
per visit
5.0 out of 5 stars
7 reviews
4 repeat clients
12 years of experience
Waterbury, CT, 06708

Lucy is awesome! Always punctual and takes great care of Zeus. Super reliable!

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Keith W.
Sitter Profile Image: Anne S.
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Anne S.
from
$25
per visit
5.0 out of 5 stars
7 reviews
20 years of experience
Southbury, CT, 06488

Anne was super easy to work with and did a great job checking in my cats while I was away! She sent pictures and even managed to coax out my anxious cat which I really did not expect at all. She did some playing with my friendlier girl and made sure all their needs were taken care of. I really appreciate having her stop in and I know that the next time I need a sitter I'll book Anne again! Thank you!

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Brittany S.
Sitter Profile Image: Kaylee R.
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Kaylee R.
from
$15
per visit
14 years of experience
Newtown, CT, 06482

About: What sets me apart from other sitters is the level of care, patience, and genuine love I bring to every pet I work with. I don’t just “watch” animals—I build trust with them and treat them like my own. My experience as a caregiver has really shaped how attentive and compassionate I am, especially when it comes to understanding different needs and personalities. I also have fostering experience, which has taught me how to work with pets who may be anxious, shy, or adjusting to new environments. Because of that, I’m very comfortable helping animals feel safe and supported. I have experience caring for both puppies and senior pets. With puppies, I can help reinforce basic training, routines, and positive behaviors. With senior pets, I’m extra gentle, patient, and attentive to things like mobility, medications, and comfort. Overall, I pride myself on being reliable, communicative, and someone you can truly trust with your pet. My goal is always to make sure your pet feels happy, safe, and loved while you’re away. I am unavailable mondays and Wednesdays but available all day on Saturday and Sunday. I can work after 4:30pm on Tuesday Thursday and Friday :) Your pet’s safety, comfort, and routine are always my top priorities. Whether I’m caring for pets in your home or stopping by for visits, I do everything I can to make the experience feel calm, consistent, and stress-free. In your home, I respect your space and follow your pet’s normal routine as closely as possible—including feeding schedules, walks, medications, and playtime. I make sure doors are secure, hazards are avoided, and your pet is always supervised and safe. I also keep you updated with messages and photos so you feel confident while you’re away. I’m very attentive to behavior and body language, which helps me quickly notice if something feels off. My background as a caregiver has made me especially detail-oriented, patient, and calm in any situation. Cleanliness is also very important to me—I keep feeding areas, litter boxes, and living spaces clean and comfortable at all times. Overall, I aim to create a safe, loving environment where your pet feels relaxed and cared for, and where you can have complete peace of mind.

Sitter Profile Image: Laura H.
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Laura H.
from
$20
per visit
5.0 out of 5 stars
2 reviews
2 repeat clients
42 years of experience
Woodbury, CT, 06798

Laura is a delight! I am so glad Ted and I found her on Rover.

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Sherri R.
Sitter Profile Image: Maylynn M.
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Maylynn M.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
6 reviews
5 repeat clients
4 years of experience
Waterbury, CT, 06706

Maylynn was so sweet but most of all I loved how my boys reacted to her. It let me know that she is a good person and that my cats were in good hands while I was away. She was on time for both drop in’s and even made sure to give them some playtime. I’ll definitely be using Maylynn again and recommend her to everyone.

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Jenise D.
Sitter Profile Image: Courtney C.
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Courtney C.
from
$25
per visit
15 years of experience
Southbury, CT, 06488

About: Hi! My name is Courtney, and I’m a registered nurse with a lifelong love for animals. Caring for others is what I do every day—both professionally and personally—and that same level of compassion, attentiveness, and responsibility carries over into how I care for pets. I grew up surrounded by animals of all kinds, including dogs, cats, goats, rabbits, chinchillas, hamsters, and birds. Because of this, I’m comfortable with a wide range of personalities, needs, and care routines. I currently have a one-year-old dog who means everything to me, so I truly understand how important it is to trust someone with your pet. I will treat your animals with the same love, patience, and attention that I give my own. Whether it’s dog walking, drop-in visits, or pet sitting, my goal is to make your pet feel safe, comfortable, and cared for while giving you peace of mind. I’m reliable, detail-oriented, and happy to follow any specific instructions to maintain your pet’s routine.

Sitter Profile Image: DEBORAH B.
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DEBORAH B.
from
$20
per visit
40 years of experience
Oxford, CT, 06478

About: I have always had dogs if my own! I currently have a 3 year old Rescue named Brutus! He is my best friend! I have worked in a dog grooming salon giving baths to all the fur babies! I have also dog sat for family and friends! I absolutely love being around dogs!!!! I am currently working full time! But I am available for walks in the evenings or all day on the weekends! I am also available for drop ins! I have a dog Brutus who absolutely loves making new friends! I also have a 16 year old daughter who loves spending time with the babies to!

Sitter Profile Image: Elizabeth L.
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Elizabeth L.
from
$30
per visit
5.0 out of 5 stars
22 reviews
4 repeat clients
3 years of experience
Naugatuck, CT, 06770

Elizabeth was professional and easy to work with. She went above and beyond at taking care of our three large dogs while we were away. Would definitely recommend!

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Laura B.
Sitter Profile Image: Diana S.
Verified Enhanced Background Check
Diana S.
from
$18
per visit
14 years of experience
Naugatuck, CT, 06770

About: Since I was a kid, I’ve had Guinea pigs, birds, cats, and now the dog mom to two wonderful dogs. Let me help ease your mind during days that are a bit hectic for you. Let me know your pets routine and I will take care of the rest. I look forward to meeting you! I currently work full-time with an hour lunch. I can take care of your pet during my break, after 5pm or anytime on weekends. I will do my best to accommodate your schedule. I do my best to treat your pet as if it was my own and would like to keep the routine as normal as possible for them. Let me know if they have a favorite toy or a walking path they prefer.

Sitter Profile Image: Noelani R.
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Noelani R.
from
$15
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
10 years of experience
Waterbury, CT, 06708

We are so so happy to have found Lani!!! She is great with our hyper/crazy large dog. She is always available the days we need her and Callie truly loves when she visits. We can’t be more happy, thanks Lani!!!!!

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Kelsey A.
Sitter Profile Image: Zachary C.
Verified Enhanced Background Check
Zachary C.
from
$15
per visit
5.0 out of 5 stars
3 reviews
1 year of experience
Naugatuck, CT, 06770

About: I’ve been around animals my entire life, growing up with pets and continuing that today with animals of my own. That experience has helped me understand different personalities, energy levels, and the importance of consistency and routine—especially when it comes to dogs and their daily walks. As a full-time art teacher, I’m used to being dependable, attentive, and organized, and I bring that same level of responsibility to every walk. Whether your dog needs a quick outing or a longer walk to burn off energy, I’ll treat them with the same care, patience, and respect that I give my own pets, making sure they’re safe, happy, and well cared for. As a full time teacher, I am usually home by 3pm and off on the weekends. I am available for afternoon and evening care as well as weekends. During July and August my schedule is far more flexible and would be available at all times of the day, 7 days a week. When caring for pets in a client’s home, the goal is to keep their routine as normal, calm, and stress-free as possible. I follow all instructions closely, including feeding schedules, walk times, medication needs, and any specific habits or preferences the pet is used to. I treat every home with respect by keeping things clean, secure, and exactly as I found them. As a full-time art teacher, being responsible, organized, and trustworthy is a big part of my daily life, and I bring that same mindset into every pet sitting visit.

Sitter Profile Image: Amber B.
Verified Enhanced Background Check
Amber B.
from
$30
per visit
5.0 out of 5 stars
11 reviews
1 repeat client
30 years of experience
Bethlehem, CT, 06751

Amber was a pleasure, Hudson was immediately comfortable with her. Her love care and concern for dogs was easy to feel. The pictures she provided say it all Hudson was very happy! Thanks so much!

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Annette L.
Sitter Profile Image: Katie N.
Verified Background Check
Katie N.
from
$25
per visit
4.7 out of 5 stars
12 reviews
7 repeat clients
22 years of experience
Middlebury, CT, 06762

Katie is absolutely amazing! She went above and beyond in caring for my dog. From the moment we connected, her communication was outstanding—she kept me updated with regular messages and photos, which gave me complete peace of mind while I was away. It was clear that she genuinely cared about my dog’s well-being and happiness. I couldn’t have asked for a better experience. I will 100% be using her again and highly recommend her to anyone looking for a trustworthy, compassionate, and attentive pet caregiver!

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Megan R.
Sitter Profile Image: Kathryn A.
Verified Enhanced Background Check
Kathryn A.
from
$18
per visit
5.0 out of 5 stars
5 reviews
5 years of experience
Monroe, CT, 06468

About: I've loved to cat and dog sit for my neighbors, friends, and extended family since I was young. I'm sensitive to different pets' needs and have always had a way of connecting with more timid and distrustful animals. I also have over 10 years of experience caring for and working with horses, so I'm comfortable with handling larger animals. I’m super outdoorsy so I’m always happy to take your pets out on a hike or little adventure. I used to take my aunt’s dog out to hike, camp, and swim in rivers! I’ve just graduated from college, so I have a completely open schedule! I’ll be able to go on walks multiple times a day, hang out and play in the house, and give them all the attention they need. I won’t be having your pets stay in my house, but I’m comfortable coming into your living space and accommodating your pets in their home environment. I can stay overnight in my own house or yours, whatever’s easiest!

Sitter Profile Image: Jourdyn B.
Verified Enhanced Background Check
Jourdyn B.
from
$25
per visit
4.9 out of 5 stars
15 reviews
7 repeat clients
6 years of experience
Downtown, Naugatuck, CT, 06770

About: Hello! My name is Jourdyn and i am a certified canine coach and have worked with animals for over 6 years. I plan on Spending quality time with your pet, maintaining cleanliness, and being prepared for emergencies. I will adapt to your care routines to the specific needs of your pet, and always prioritize their well-being, and always strive for Providing the best care for you and your pet! I'm available around the clock, 24/7, making me a convenient resource for any of your pet care needs! Same day booking for boarding or daycare are accepted! I always Offer pets 24/7 access to fresh drinking water to keep them hydrated and thriving. i will Also Provide a safe and cozy environment to offer them comfort and protection. Last but not least i will make sure your furry friends get the exercise they require to stay active and maintain their physical and mental health. These simple yet essential steps can ensure that my care will be most fulfilling and best stay for your pets.

Sitter Profile Image: Kassidy F.
Verified Enhanced Background Check
Kassidy F.
from
$20
per visit
4.9 out of 5 stars
9 reviews
1 repeat client
12 years of experience
Oxford, CT, 06478

Kassidy was our first experience with a dog sitter and she was a great one! We are so happy to have found her. Our 4 month old puppy Pepper loved her right away and we hope to have many more meetups with her in the future!

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Melanie M.
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Middlebury dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Keleigh always goes above and beyond for our pets. She’s simply amazing and when she’s taking care of your animals, you don’t have to worry about a thing! Our dog adores her and our finicky cat does too! Don’t think twice - book her!!

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Hallie B.
Drop-In Visits
5.0 out of 5 stars

Rachael is fantastic. She took wonderful care of my dog Riggs and kept me in the loop the entire time. Professional, trustworthy, and a true animal lover. I highly recommend her!

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Nicole B.
Drop-In Visits
5.0 out of 5 stars

Cole was fantastic. On time and communicative. Dealt with some unexpected snow on the driveway without issue. It was great to know my pets were well cared for!

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Steven H.
Drop-In Visits
5.0 out of 5 stars

Steph was soo amazing and such a sweetheart with my dogs. My Bella is weary of people but warmed up to Steph extremely fast. Her updates and photos of our dogs during her visits made it all the more heartwarming and comforting knowing they’re in good hands. Definitely highly recommend and will be coming back when needed. Thank you again for being so wonderful! 🤍💕

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Sonia O.
Drop-In Visits
5.0 out of 5 stars

Katie is absolutely amazing! She went above and beyond in caring for my dog. From the moment we connected, her communication was outstanding—she kept me updated with regular messages and photos, which gave me complete peace of mind while I was away. It was clear that she genuinely cared about my dog’s well-being and happiness. I couldn’t have asked for a better experience. I will 100% be using her again and highly recommend her to anyone looking for a trustworthy, compassionate, and attentive pet caregiver!

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Megan R.
Drop-In Visits
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How Rover works

  1. 1. Search

    Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

The median cost per night for dog sitting in Middlebury is $25

Why Choose Rover?

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  • Reservation protection

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

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Sitters in Middlebury average 5
repeat dog sitting clients

Dog Sitting FAQs

Frequently asked questions about Rover

Dog sitters on Rover are free to set their rates. The median cost to hire a dog sitter in Middlebury on Rover as of Jun 2026 was about $25 per night, after factoring in Rover’s service fees. A dog sitter’s rate may also change as you customize your booking to fit your and your dog’s needs.

If you’re searching for a Middlebury dog sitter for the first time, visit the dog sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a dog sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 2,850 dog sitters in Middlebury. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog sitter near you. As a reminder, dog sitters joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple dog sitters about your booking. Typically, 88% of Middlebury dog sitters respond in under an hour.

Dog sitters in Middlebury have an average of 15 years of experience. Dog sitters with repeat customers have an average of 5 repeat clients. Experience can vary from dog sitter to dog sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Middlebury.

Rover makes it easy to find Middlebury dog sitters to provide loving care from their own home. The background-checked, 5-star dog sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog sitting is great for:

  • Dogs of all ages and abilities, including puppies
  • Dog parents looking for a safe, loving alternative to a kennel
  • Dogs who’d love to socialize with their dog sitter’s pets

There are 2,850 dog sitters in Middlebury on Rover, so you’re sure to find the perfect match for your dog! In Middlebury, 96% of dog sitters offer daily exercise, 96% offer medication administration, and 96% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog sitter near you. As a reminder, dog sitters joining Rover must pass background checks for you and your dog’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your dog sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your dog sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog sitter’s cancellation policy.