Dog Sitting Middlebury

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

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Over 31
pet parents in Middlebury have booked dog sitting

Middlebury, Find top rated dog sitting

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: 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: Lindsay D.
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Lindsay D.
from
$25
per visit
4.9 out of 5 stars
15 reviews
4 repeat clients
10 years of experience
Watertown, CT, 06795

Overall, I would rate Lindsay as a good pet-sitter. Prior to our vacation, she was very timely in responding to my messages and she also modified the Rover.com charges to a very reasonable rate for her visits with our 2 cats. It was while we were gone that I felt she fell short. My first issue was with her inconsistency in providing updates on the visits - there was a photo and thorough recap on the 1st day, but on subsequent days there was less detail and on one day there was no update at all. My second issue was with the timing of her visits. I had made it very clear that it was important to check in during the early afternoon, but at least twice she didn't visit until the evening. My third issue was with attention to detail - I had left very specific notes about the cats' food/water/litter and it didn't seem that she had followed them. Lastly, my greatest concern was with the well-being of our female cat and her being bullied by the male cat in our absence. We came back to find that she had a facial injury and had urinated in a chair out of fear. All-in-all our pets were reasonably cared for, but I was definitely disappointed. Lindsay is a very nice girl and I'm sure she had the best intentions. I think the issues may have been due to lack of experience or perhaps I wasn't clear enough on stressing the importance of certain things. (To those reading this review, please note that I have very high expectations for the care of my pets and I think Lindsay is absolutely capable of meeting the needs of a less demanding client.)

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Jessica M.
Sitter Profile Image: Sarah M.
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Sarah M.
from
$21
per visit
7 years of experience
Naugatuck, CT, 06770

About: "I have a deep love for animals and years of experience caring for pets. Family and friends have always trusted me to watch, feed, walk, and love their dogs. I specialize in providing a calm, structured, and incredibly safe environment for small and medium adult dogs. Your pup will receive constant attention, plenty of playtime, and treated just like family while staying with me." "I currently work part-time, which gives me a very steady routine and plenty of open flexibility to be home with your dog. I am always mindful of my time management to ensure your pet gets consistent supervision, frequent potty breaks, and lots of individual attention. I have plenty of dedicated time to play, go for walks, and make sure your pup feels completely safe, happy, and pampered while you are away." Safety is my highest priority when caring for your pet. My home is a clean, calm, and smoke-free environment with plenty of open space for small and medium dogs to feel entirely at ease. I maintain a secure setup to ensure no escapes, provide constant direct supervision, and strictly follow any specific care, feeding, or routine instructions you provide to keep your pup happy and safe."

Sitter Profile Image: Priscilla W.
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Priscilla W.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
117 reviews
28 repeat clients
45 years of experience
Plymouth, CT, 06782

Priscilla was absolutely fantastic with our boys. They're prone to mischief, and not surprisingly Priscilla found some. She handled it by first letting us know immediately, and then even cleaned up the mess the boys made by tipping over one of our plants. Communication was excellent, and the boys were clearly comfortable with her caring for them. I recommend Priscilla unconditionally.

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Terri G.
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: Melony S.
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Melony S.
from
$25
per visit
5.0 out of 5 stars
18 reviews
5 repeat clients
15 years of experience
Naugatuck, CT, 06770

Melony was perhaps the best sitter I have hired. She was super responsive anytime I contacted her. She went above and beyond in her duties, even taking out the trash and ensuring everything was tidy before we returned. She was patient and kind to our less than friendly cat and never lost hope that they will eventually become friends, while also respecting her boundaries. I will absolutely be a return customer.

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Brenda D.
Sitter Profile Image: Alexis T.
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Alexis T.
from
$25
per visit
4 years of experience
Naugatuck, CT, 06770

About: My friends, family, and many others have given me opportunities to care for their puppies and dogs! The owners and dogs are always left very happy! I’m currently on summer break from my teaching job. My schedule is very open and flexible to whatever you may need! I love going for walks and hikes and would love a buddy to come with me. I do not have any other pets or children living in my home. My complex is very safe to walk in and I have an awesome hiking trail right next to my place!

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: Laura S.
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Laura S.
from
$25
per visit
5.0 out of 5 stars
36 reviews
9 repeat clients
22 years of experience
Naugatuck, CT, 06770

Laura took great care of our anti-social kitties; she provided daily feedback and excellent communication pre and post care. Will use her again, no question!

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Bazil G.
Sitter Profile Image: Alison K.
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Alison K.
from
$25
per visit
5.0 out of 5 stars
6 reviews
1 repeat client
25 years of experience
Southbury, CT, 06488

About: Hi! I’m a lifelong animal lover and have had dogs and cats of my own my whole life. My family currently has two rescue cats, Henry and Willow. I’m available to sit for your pet in your home, for either daily walks and exercise or overnight! I’m very flexible with my schedule and would love to help care for your pet as if they were my own. I am experienced in administering medication, and I’m comfortable with dogs and cats of any age. I’ve also taken care of rabbits, fish, hamsters, birds and guinea pigs. I have excellent references and welcome the opportunity to help you! I’d love to speak with you, feel free to call or text any time! I have a flexible schedule, so I’m ready to help when needed. I’m available on weekends. I am available most holidays with some advanced notice. I’ve had pets my whole life and I know how important it is to trust someone in your home. I pride my self on being respectful of your space and privacy.

Sitter Profile Image: Lyla A.
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Lyla A.
from
$14
per visit
5.0 out of 5 stars
1 review
1 repeat client
5 years of experience
Naugatuck, CT, 06770

Lyla was very personable and did a great job with our cats while we were gone for a few days.

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Doug M.
Sitter Profile Image: Natasha T.
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Natasha T.
from
$22
per visit
5.0 out of 5 stars
34 reviews
12 repeat clients
25 years of experience
Naugatuck, CT, 06770

Natasha had come for the pre visit with Sadie and seemed like a great fit with her. Sadie is a youthful, large, strong dog, and Natasha seemed to get along great with everyone. The visit seemed to go great, no surprises, even though Natasha went above and beyond.

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John and Deb F.
Sitter Profile Image: Claire Y.
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Claire Y.
from
$15
per visit
5.0 out of 5 stars
10 reviews
2 repeat clients
5 years of experience
Southbury, CT, 06488

Claire was great with my cats and took every measure to ensure they were well cared for. I would recommend her to anyone, especially those with pets who need special attention, and would have her cat sit any time :)

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Laura b.
Sitter Profile Image: Kayla B.
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Kayla B.
from
$20
per visit
10 years of experience
Waterbury, CT, 06704

About: I’ve taken care of animals for my whole life. I have dogs and puppies of my own that I raised, even other types of animals. I have a huge gated backyard for dogs to run around in. I also take care of my moms cat when she’s not around. I’m currently working part-time as a delivery driver. On my free time I take care and play with my dogs making sure they get the exercise they need. I have a fenced yard so dogs have lots of space to run and play. I can work with animals of all sizes. I’m a quick learner. I care about animals all the time.

Sitter Profile Image: Kailah J.
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Kailah J.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
11 reviews
6 repeat clients
3 years of experience
Waterbury, CT, 06706

Kailah has been great with my dogs! I have 2 rescues who are super nervous around new people. This was our 3rd time booking with Kailah, she has been super patient and they are starting to warm up to her. I would recommend Kailah and will definitely be using her services again.

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Molly R.
Sitter Profile Image: Darya H.
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Darya H.
from
$19
per visit
5.0 out of 5 stars
6 reviews
1 repeat client
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: Sara R.
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Sara R.
from
$20
per visit
5.0 out of 5 stars
11 reviews
4 repeat clients
10 years of experience
Prospect, CT, 06712

Sara is amazing. She followed my instructions and she kept in touch with me on how our old lady was doing. She used good judgment with regard to the poor air quality and heat by limiting the time our dog was out. She paid attention to our dog as well. I desperately wish she lived closer to us and am so thankful that she was able to come to our home. I highly recommend her and believe anyone who gets to have her take care of their pets is very lucky. She also has excellent work ethics.

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D G.
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: Sydney M.
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Sydney M.
from
$25
per visit
5.0 out of 5 stars
13 reviews
6 repeat clients
17 years of experience
New Haven, CT, 06770

This is the second time Sydney has cared for my animals, and I couldn’t be happier and feel more at ease. She goes the extra mile with every visit, and I receive detailed info and photos with every drop in. Sydney genuinely cares for the animals, and it shows. Five star care!

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Cassie R.
Sitter Profile Image: Kara S.
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Kara S.
from
$18
per visit
5.0 out of 5 stars
251 reviews
85 repeat clients
10 years of experience
Ansonia, CT, 06401

Kara was excellent and truly put our minds at ease during our trip. She was very communicative throughout the whole process and was prompt and took amazing care of our babies. Highly recommend working with her and would absolutely book again in the future!

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Shannon R.
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The median cost per visit for dog sitting in Middlebury is $25

Dog parents share their Rover experiences - Middlebury

1 / 1
5.0 out of 5 stars

Rachel was prompt and very conscientious. She did everything she could to make sure my dog was well cared for while I was away. She is very patient and I would recommend using her services.

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Kathryn D.
Drop-In Visits
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

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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  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

Why Choose Rover?

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  • Reservation protection

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

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Meet local sitters who will treat your dogs like family

  1. 1. Search

    Browse profiles of sitters near you who offer dog sitting
  2. 2. Meet In Person

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Sitters in Middlebury average 5
repeat dog sitting clients

FAQs for Drop-In Visits - Middlebury

Frequently asked questions about Rover

The average cost for Dog Sitting in Middlebury on Rover is $22.2 per visit (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Sitting. For more information on service fees, click here .

As of July 2026, there are 2,840 sitters on Rover offering Dog Sitting across Middlebury. Enter your ZIP code to see which available sitters are closest to your home.

A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.

Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Middlebury stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.

Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Middlebury choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.

A Meet & Greet is a short introductory meeting between you, your dog, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.

To find sitters in Middlebury with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.

Yes, you can find sitters who have experience with handling special pet needs in Middlebury. On Rover:

  • 96% of sitters can help with special care needs
  • 96% can help with giving oral medications or injections
  • 97% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.

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