Dog Walking Middlebury

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

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Sitter Profile Image: Sarah W.
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Sarah W.
from
$20
per walk
5.0 out of 5 stars
13 reviews
3 repeat clients
20 years of experience
Southbury, CT, 06488

Sarah was very helpful and communicative! Followed instructions well and Molly loved her!

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Hannah L.
Sitter Profile Image: Evelyn G.
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Evelyn G.
from
$16
per walk
5.0 out of 5 stars
2 reviews
2 repeat clients
1 year of experience
Naugatuck, CT, 06770

I can tell she truly loves animals. Xander usually barks at strangers but he was very calm with her. It was a very smooth experience with her and I will definitely be using her services again. Thank you so much ❤️

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Kirsten L.
Sitter Profile Image: Theresa T.
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Theresa T.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
315 reviews
31 repeat clients
18 years of experience
Naugatuck, CT, 06770

Theresa is truly AMAZING with animals. My dog Molly had love at first sight with Theresa immediately and I can see why. This is the fist time I've ever had a dog sitter/walker so I was a little nervous but as soon as I met Theresa all my fears went away. Theresa is very caring and so knowledgeable about animals and I will highly recommend her. I feel great knowing that my dog has someone I feel confident in and I was continue to always have Theresa come back week after week whenever she's available. Thank you for giving me peace of mind Theresa, making my life so much easier and also Molly a happier pup! ;)

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

Was able to help us out with our puppy last minute! Quick response, kind and sent us cute pictures! I would recommend.

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Jennifer M.
Sitter Profile Image: Bonnie D.
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Bonnie D.
from
$18
per walk
5.0 out of 5 stars
6 reviews
1 repeat client
10 years of experience
Watertown, CT, 06795

About: I have several years of paid and volunteer experience with all animals, including dogs, cats, fish, chickens, rabbits, horses, and goats. Growing up, I had two dogs, one small and one medium. I also used to volunteer at a therapeutic horse-riding center for people with disabilities, where I groomed horses and cleaned their barns. I currently have two guinea pigs who are contained in cages, but are very curious, playful, and friendly with other animals. I'm an incoming Master's student who is currently working part-time this summer. I have a highly flexible schedule and short commute times, which gives me more time to care for your pets! My pricing is extremely flexible and I am open to negotiating. I have spacious front and back yards where your pet can roam. I also have a doggy gate to block off the upstairs of my house if necessary, but our downstairs and upstairs are very dog-proof from years of caring for our previous pets. I live in a 3-bedroom home, providing ample room for your pet to explore and wander inside if they prefer the indoors. I also have dog bowls, leashes, toys, and food, ready for use.

Sitter Profile Image: Emma R.
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Emma R.
from
$17
per walk
5.0 out of 5 stars
5 reviews
6 years of experience
Seymour, CT, 06483

About: I have taken care of cats and dogs my whole life. I have fostered rescue puppies for five years now. I have also worked at a dog daycare and boarding facility for two years. I am just graduated from college so I am available throughout the week or weekends. I can start booking appointments after June 9th! This includes dog or cat pet sitting, dog walking, or overnights! I will come to your house to pet sit, dog walk, or stay for extended periods of time to ensure the happiness and safety for your pet. Whatever you and your pet need I will do. My utmost priority is your fur baby!

Sitter Profile Image: Rachael R.
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Rachael R.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
8 reviews
2 repeat clients
20 years of experience
Middlebury, CT, 06762

Rachael did a great job with my dog Harry today! He came home happy & tired so that's a good thing. He ate his dinner quite heartily too, ha, ha! I'm looking forward to having her come back again hopefully on a regular basis for walks & see if we can get some weight off Harry as he is overweight for his size right at this stage in life. Thanks so much Rachael!

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Bonnie T.
Sitter Profile Image: Darya H.
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Darya H.
from
$18
per walk
5.0 out of 5 stars
8 reviews
1 repeat client
10 years of experience
Prospect, CT, 06712

Darya was amazing! Kept in touch and sent lots of pictures! I will definitely be using her again 😊

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

Excellent walker

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

About: I have had cats since I was a baby and had chow chow dogs since I was 13 years old. I also worked at a kennel off and on for 12.5 years. I learned a little training but not a lot. I have worked with all different breeds of dogs. I love snuggling with cats as I grew up with having them in my household. I currently work full time however, full time is 30 hours for me so it allows me to have 3 to 4 days off towards the end of the week depending on the week. We have a large back yard with a dog run and as far as my cat. He is an indoor cat and gets spoiled indoors.

Sitter Profile Image: Sara R.
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Sara R.
from
$18
per walk
5.0 out of 5 stars
12 reviews
5 repeat clients
10 years of experience
Prospect, CT, 06712

Sara was awesome!! She came literally with an hour notice and my dog enjoyed her walk with her. Definitely recommend & will book again in the future. Thank you!

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Lusianna M.
Sitter Profile Image: Aamarrah S.
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Aamarrah S.
from
$17
per walk
3 years of experience
Waterbury, CT, 06708

About: I’ve always had dogs of my own growing up, so I grew up learning how to take care of pets. I always made sure they were clean, feed well, and treated when accomplishments are made! Before I head out to work around 4, I take my dog on daily walks so she can get fresh air, then I give her treats when we head back inside. I care for my pet by spending time with her because she’s very cuddly. I always make sure her water bowl is full especially for the heat we’ve been getting this summer.

Sitter Profile Image: Sarah M.
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Sarah M.
from
$21
per walk
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: Lindsay K.
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Lindsay K.
from
$15
per walk
4 years of experience
Woodbury, CT, 06798

About: I previously co-founded a dog training business, managing client relationships and operations, but I have since stepped away from it. Prior to that, I worked for Coaching for Paws, a renowned dog training business in northern Connecticut. I have been working with dogs for around five years and have experience with training basic obedience, dog walking, dog sitting, and overall care. I currently have most weekdays free to dedicate to your pups’ needs, which allows me to provide consistent attention, care, and companionship throughout the day. Pet care fits very naturally into my daily routine, and I genuinely enjoy spending time with animals, whether that means going on walks, playing, feeding, or simply keeping them company. Because of my flexible schedule, I am able to accommodate different care needs and maintain reliable routines for pets, helping them feel comfortable, safe, and well cared for while their owners are away. I have lots of experience with different dogs and understand the needs of dogs and owners. I am able to meet any needs or criteria.

Sitter Profile Image: Loretta G.
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Loretta G.
from
$30
per walk
5.0 out of 5 stars
2 reviews
1 repeat client
25 years of experience
woodbury, CT, 06798

About: I am a mom to three human children, three dogs, and three horses. When my kids were younger, my "me time" was spent volunteering for various rescues and shelters. I love taking care of animals and found so much satisfaction helping out those poor little creatures who had no home to call their own! I loved it so much that I decided to start my own 501c3 nonprofit animal rescue! I figured that in doing so, I could help on a way bigger scale! Additionally, I could put more efforts in to helping people through the love of animals in need! Making the adoption process easy and fun, and making sure the humans and the pets are a wonderful match have made my rescue quite successful! Over the past 11 years I have rescued thousands of dogs, hundreds of cats, and three horses from shelters and other high risk situations! Throughout my years of taking care of pets, I have care for basically every age, breed, size, and temperament! I have also provided care on just about every level...from administering meds, IV treatments, vaccines, basic grooming, and basic training/behavior modifications. I joined Rover because I want to continue helping animals and support pet owners who need someone they can truly trust. I understand how important it is to know your pet is safe, comfortable, and cared for like family while you’re away. Being able to provide that peace of mind is something I take seriously. Every pet has unique needs, routines, and personalities. My goal is to provide consistent, attentive care while maintaining the structure and comfort your pet is used to. I also prioritize clear communication so you always feel confident and informed while your pet is in my care. My schedule has a lot of flexibility, and I am a full-time caregiver for these sweet babies! I will always do my best to be available for you and your furry family members! Pets in my home have my full supervision, and when I am unable to have my eye on them, they are either crated or in their own safe space! Our yard is fully fenced!

Sitter Profile Image: Anne S.
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Anne S.
from
$20
per walk
5.0 out of 5 stars
8 reviews
20 years of experience
Southbury, CT, 06488

About: I am a semi retired veterinary assistant with nearly 20 years professional experience and a passion for caring for animals. As a life long pet owner myself, I know how hard and stressful it can be to leave your pets at home. I appreciate and respect the trust that every owner puts in me when they contact me to care for their animal. I can give medications if needed, including injections. Also have worked in shelters and volunteer at rescues. I have taken care of senior dogs and cats. Feeding, walking, playing or if they have any special needs is not a problem. I have a flexible schedule and open to working with you to arrange drop in visits. Mid morning through later afternoons are open for me. If you need another time, just let me know. I'm happy to do whatever your pets need, whether they want to play, walk or just hang out. If they are a little shy and need time to get used to me is totally understandable, I will follow their cues. I will take my time to learn what they need and adapt to them. The goal is always to keep them as stress free as possible.

Sitter Profile Image: Vera R.
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Vera R.
from
$27
per walk
5.0 out of 5 stars
19 reviews
10 repeat clients
5 years of experience
Watertown, CT, 06779

About: I have been a dog enthusiast. I have experience with large breeds. Turtles. Rabbits. I love to walk dogs and work one on one with them. Available to help anytime especially in the VALLEY AREA ;) Have experience with large breed dogs. Especially love mastiffs. Bulldogs. And french bulldogs. Pitbulls and fast moving dogs I have 2 french bulldogs currently with a fenced yard. And access to seperate dogs. I love animals and can relate to them to ease their anxiety.

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

She was great! Came the day before to meet me and my dog to go over everything. Very responsive and obviously caring!

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Mikaela D.
Sitter Profile Image: Keleigh L.
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Keleigh L.
from
$35
per walk
5.0 out of 5 stars
45 reviews
10 repeat clients
8 years of experience
Middlebury, CT, 06762

Keleigh is a star as always! Our dog is anxious, however, she connects really well with Keleigh and is relaxed and happy to see her. We couldn’t ask for a better match.

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Laura B.
Sitter Profile Image: Mair H.
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Mair H.
from
$50
per walk
5.0 out of 5 stars
8 reviews
40 years of experience
Woodbury, CT, 06798

About: I adore pets. I've cared for dogs/cats my entire adult life. I'm an expert in senior animal care as well as puppy/kitten care. Dignity's a must. I can't wait to meet and care for your pet! I'm currently a part-time fitness trainer/nutritionist, sculptor & writer, so I have lots of time to care for your pets. My schedule is flexible. Avail. weekdays, weekends, and holidays. While I'm caring for your pet in your home, I am attentive to their needs. I'm especially compassionate with fearful animals. Always loving & gentle.

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The median cost per walk for dog walking in Middlebury is $23

Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • 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?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • 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 walkers who will treat your dogs like family

  1. 1. Search

    Browse profiles of walkers near you who offer dog walking
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

Popular requests for dog walking - Middlebury

Select a filter and find qualifying sitters offering dog walking.

Sitters in Middlebury average 3
repeat dog walking clients

FAQs for Dog Walking - Middlebury

Frequently asked questions about Rover

The average cost for Dog Walking in Middlebury on Rover is $21.4 per walk (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog Walking 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 Walking. For more information on service fees, click here .

As of July 2026, there are 2,943 sitters on Rover offering Dog Walking across Middlebury. Enter your ZIP code to see which available sitters are closest to your home.

Whether you want a solo or group walk depends on your dog's personality. Solo walks can be beneficial for dog parents with reactive dogs, puppies, or dogs who are anxious around unfamiliar animals. Many dog walkers on Rover offer private, one-on-one walking services.

Group walks are a good fit for social dogs who enjoy structured walks. If your dog prefers the energy of a group stroll, ask your dog walker about group walks in your Middlebury. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.

For dog walking services, you can request a report card update with specifics about your dog’s walk. Report cards require photos and can include a map of the walking route , total walk time, poop and pee breaks, and distance traveled, so you know exactly where your dog has been walking in Middlebury.

Got specific details you'd like the dog walker to include? Message them in the app before your dog’s walk begins.

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.

Every walker 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 .

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

  • 92% of walkers can help with special care needs
  • 95% can help with giving oral medications or injections
  • 98% 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.

A Meet & Greet is a short introductory meeting between you, your dog, and a walker. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your walker 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 walker questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and walkers 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.

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 walker.

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