Dog Sitting Windham

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Sitter Profile Image: Benjamin A.
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Benjamin A.
from
$25
per visit
2 years of experience
Norwich, CT, 06360

About: I’ve had dogs my whole life and have always loved being around them. My girlfriend and I have an Australian Shepherd of our own who’s a huge part of our family, so I know how important it is to find someone you trust with your pup. I’m the go to dog sitter for friends and family, one of my friends even calls me the “dog whisperer.” I’m comfortable with dogs of all sizes and personalities, whether they love to play or just want someone to hang out with. I’m confident handling dogs on walks and keeping up with leash training and good habits. I’m also happy to feed, administer medication, and take care of any special routines or needs your furry family member has. I’ll treat your dog like they’re one of my own and make sure they get plenty of love, attention, and care while you’re away. I’m here for you and for your fur baby, whatever you need I will do it! With that my dog is on a good routine, 7am-7:30am she goes potty 8:30am-9am breakfast 10:30am-11:00am she goes for her first walk for about 30mins to 1.5hours depending on the day Between 12:30pm-4pm we do about 5-10mins of mental stimulation training 5pm-6:30pm she gets dinner and an after dinner walk 7pm-the rest of the night we chill I have a fenced in backyard with plenty of room to run around! The doggos can run around and play with each other or train.

Sitter Profile Image: Sydney P.
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Sydney P.
from
$20
per visit
5.0 out of 5 stars
• 1 review
18 years of experience
Moosup, CT, 06354

About: I treat every pet like family and make sure they feel safe, loved, and comfortable. I have experience with both playful puppies and senior dogs. I’m reliable, detail-oriented, and always keep you updated! I’m a college student here in South Carolina who really misses my pets back home, so I’m looking for chances to care for other people’s pets while I’m at school. Spending time with animals — whether walking dogs, feeding cats, or just giving them attention — makes me happy, helps me manage stress, and gives me something meaningful to look forward to outside of my classes. In my home, pets enjoy a safe and relaxed environment. I have a friendly golden retriever who’s trained to stay in the yard, and a bunny who’s free to move around the house as he wishes. I make sure everyone stays comfortable and safe, supervise outdoor time, and always follow your care instructions closely—whether your pet is with me or I’m caring for them in your home.

Sitter Profile Image: Tara G.
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Tara G.
from
$20
per visit
3 years of experience
Oakdale, CT, 06370

About: I absolutely love going for walks and runs with dogs! Please see updated photos for some of my previous pet clients. Recently took care of a few hairless cats as well as a big dog! I’ve taken care of pets in many settings, including messier households! (Not a neat freak so messes do not bother me!) I trained my Doberman on Couch to 5k, running through all the trails in RI. I’ve taught my cat how to shuffle cards, play piano, and spin in a circle on command, and my mom’s old cat would always practice Pilates with us at 6 in the morning. Recently I dropped in for a friend’s 2 cats, even the shy one eventually warmed up to me! They required medication in their food so she left detailed, neatly handwritten notes on the table, which helped a lot! Known for my positive and caring energy as a music therapist (who works alongside a pet therapist!) and music teacher, and with a mom with a college degree in animal science, I have a passion for animals in general. She is now dating a farmer and we now have a baby cow named clover who I help take care of occasionally on Sundays. Generally I am available in the middle of the day most days of the week for one-off visits. My boyfriend is a biologist and also has a small dog who I walk frequently in the mornings and at midnight (she’s a night owl like us!) Available to do drop-ins at your home within 45 mins of Montville - please message me at least one week before your trip to solidify the booking! Please be kind, respectful, and professional in your requests - I do not take last minute visits but would love to help you out with your furry friend. Not a veterinarian, just an animal lover with a lot of compassion!! One of my favorite activities is running, I can always walk or run with your pet, or if you prefer us to lounge, I have lots of great pet-friendly shows on our nice TV. I love driving so I’m happy to drive to you if it’s further away - as I am regularly back and forth between Westerly, RI and Uncasville, CT. Outside of teaching in a formal studio, I’ve worked in client’s homes for therapy-related meetings as well as for music lessons - and believe it or not often times there are pets who love to sing along to the music! I usually stay home in the morning so I can easily take care of your pet between 7 am and 2 pm. I used to have an office job but found it too sedentary and draining; I discovered I thrive in outdoor and home environments. I’m excited to enter this new chapter and care for animals! I have a partially fenced yard so I would generally take pets out on a leash but it is a non-busy road and very safe - the lawn is freshly mowed and we have a playground your dog can weave around! I also have a cute little neighborhood that we can circle around that is far from the highway and if your pet loved car rides, we can always go to the park and get ice cream! Occasionally our neighbor’s dog likes to come over unsolicited but he is always very gentle and friendly! My cats are also used to my mom’s boyfriend’s rambunctious dogs coming in and out from time to time and we have plenty of doors and rooms in the house and baby gates if we ever needed to keep pets separate! We also have a spare pet bed if needed that was gifted to us - we always want to make sure your pet is comfortable sleeping at night!

Sitter Profile Image: Joline R.
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Joline R.
from
$25
per visit
2 years of experience
Ashford, CT, 06278

About: I have over 2 years of dog sitting experience and currently work full time at a doggy daycare, caring for dogs of all sizes, temperaments, and energy levels. I’m experienced with feeding routines, exercise, and group play, and I’m attentive to each dog’s behavior to ensure they feel safe, comfortable, and happy. I work full time, five days a week, as an opener at The Mellow Mutt, with typical 6-hour shifts. My schedule can occasionally shift, so a bit of flexibility is helpful, but I do my best to keep things consistent for pet owners. I’m also a full-time online student at SNHU, which allows me to stay flexible and available for house sitting needs. I usually work Wednesday afternoons and most of the day Sunday, and my only consistent day off is Saturday, making me available for extended stays and attentive overnight care. While staying in your home, I focus on keeping your dog’s routine as normal and stress-free as possible. I stick closely to their feeding, walking, and play schedules, and make sure they get plenty of attention, affection, and exercise. I’m very attentive to their behavior and comfort, so I can quickly adjust to their needs and help them feel safe while you’re away. I also keep your home clean and respected, and I’m happy to provide updates so you can feel at ease knowing your dog is well cared for.

Sitter Profile Image: Faith L.
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Faith L.
Star Sitter
from
$20
per visit
4.9 out of 5 stars
• 60 reviews
10 repeat clients
14 years of experience
Groton, CT, 06340

“Faith is quite possibly the best pet sitter of all time! I forgot to leave my pets stuff out as usual and had to improvise, she is always helpful and always takes great care of my dog while I'm away”

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Joe G.
Sitter Profile Image: Ifan F.
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Ifan F.
Star Sitter
from
$30
per visit
4.9 out of 5 stars
• 98 reviews
36 repeat clients
7 years of experience
East Hartford, CT, 06108

“Ifan is truly an exceptional dog handler, and I cannot recommend him highly enough. From the very first time we worked with him, it was clear that he brings both professionalism and genuine care to what he does. He is extremely experienced and knowledgeable about dog behavior, which immediately put me at ease as a pet owner. He takes the time to understand each dog’s personality, needs, and routines, and it really shows in how comfortable and happy the dogs are around him. What stands out the most is how naturally he connects with the pups. My dog can be a bit particular when it comes to new people, but with Ifan, the bond was instant. Over time, that connection has only grown stronger—my pup gets excited every time he sees him, which says everything about the level of trust and comfort Ifan builds. It’s such a relief knowing that my dog is not just being looked after, but genuinely cared for and understood. Ifan is also incredibly polite, respectful, and communicative. He keeps me updated, is always punctual, and is very flexible when it comes to scheduling. I’ve used his services repeatedly, and each experience has been consistently excellent. Whether it’s handling high-energy playtime, maintaining routines, or just giving the dogs attention and affection, he does it all effortlessly. Overall, Ifan goes above and beyond what you would expect from a dog sitter or handler. His dedication, kindness, and expertise make him someone you can fully trust with your pet. I wholeheartedly recommend him to anyone looking for reliable, caring, and professional dog care.”

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Christle O.
Sitter Profile Image: Annie D.
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Annie D.
from
$38
per visit
5.0 out of 5 stars
• 96 reviews
27 repeat clients
10 years of experience
South Windsor, CT, 06074

“Annie was able to meet up and watch Daisy on short notice and did an amazing job. Definitely would recommend her to anyone whose furry friends need looked after.”

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Jerry L.
Sitter Profile Image: Amber S.
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Amber S.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
• 22 reviews
10 repeat clients
3 years of experience
Sturbridge, MA, 01518

“Amber was very professional and communicative. I really appreciated her daily updates about my cat. Additionally, Amber was extremely personable. I highly recommend.”

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Chris C.
Sitter Profile Image: Mandy B.
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Mandy B.
from
$43
per visit
4.9 out of 5 stars
• 11 reviews
1 repeat client
15 years of experience
Manchester, CT, 06042

“Mandy was amazing taking care my babies ? Really appreciate your kindness and support Hope to see you again !”

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Patzy P.
Sitter Profile Image: Jikang & Leong L.
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Jikang & Leong L.
from
$45
per visit
5.0 out of 5 stars
• 11 reviews
3 repeat clients
5 years of experience
Waterford, CT, 06385

About: Having cared for 13 dogs and 4 cats (yes, we keep count), we've seen it all. Daily exercise and even bathing is quite familiar to us. Leo has hands-on experience with animal shelters, and I have biological based experience with both nutritional needs and animal anatomy, and we both can provide basic training. We currently have a year-old golden retriever and a tabby! We've dealt with a couple lovable (but difficult) pets and can deal with issues like stubbornness, biting, and basic potty training. Leo works from home, and I'm a commuter-basically, there's always someone home! We are both the "outdoorsy" type and frequent the devil's hop yard, as well as hike through our property. As STEM majors, animals keep us sane! We can also transport your pets (we have the seating and everything). Our property has a spacious (but secure) 100-acre forest, perfect for supervised walks and exploration! At home, our pets—a friendly Golden Retriever and a sweet Tabby—ensure your furry friend will never feel lonely. We can also provide crate time if needed for safety or comfort, and (given our flexibility) tailor care routines to meet each pet’s needs!

Sitter Profile Image: Bradley W.
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Bradley W.
from
$30
per visit
23 years of experience
Southbridge, MA, 01550

About: I'm single with no kids, so I can give them all the attention they need! Extra long walks pets treats belly rubs and whatever they need! I'm currently doing uber and rover !the more clients i get for rover will be my more preferred job .I'm single with no kids i love dogs i have 13-year-old husky myself I'm available for drop ins walk overnight stays i can also board if you dog gets along with a older husky. I have my dog crate trained hes a goodold boy never had an issue with him. Love dogs more than people! I have my own place I can board and I have my own car so I can go to you as well whatever's better for you and your pet!

Sitter Profile Image: Anna C.
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Anna C.
from
$25
per visit
5.0 out of 5 stars
• 21 reviews
9 repeat clients
20 years of experience
East Longmeadow, MA, 01028

“Anna is absolutely amazing! I was so nervous to hire a “stranger” last minute for my trip but Anna made everything soooo stress free!!! She took perfect care of my pup, sent daily updates & was easily accessible via message! Anna is the best of the best!! ♥️♥️ so happy she is no longer a stranger !”

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Gianna H.
Sitter Profile Image: Tashani H.
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Tashani H.
from
$15
per visit
5.0 out of 5 stars
• 2 reviews
1 repeat client
5 years of experience
Windsor Locks, CT, 06096

“Tashani was great. Punctual and kept me up to date on our pups. Took lots of pictures:) Definitely recommend her:)”

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Carrie P.
Sitter Profile Image: Ewa J.
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Ewa J.
from
$15
per visit
5.0 out of 5 stars
• 1 review
10 years of experience
New Britain, CT, 06052

About: 🐾 Need a Pet Sitter? 🐾 Over 20 years of experience caring for pets – now with my son by my side! 🐶🐱 We love giving pets the attention, walks, and cuddles they deserve. ✔️ Walks ✔️ Weekends ✔️ Vacation care Because your pets deserve care that feels like family. ❤️ We live in New Britain,CT but we don't mind travelling long distances within the state. 🚗 📅 Message me to book! I’m currently looking for weekend/holiday pet sitting jobs if possible for extra income. I am flexible during the weekends and holidays. If it's an emergency I will try my best to be able to take care of pets during the weekdays. I would prefer to take care of pets at my clients home if possible. I would take care of the pets according to specific needs to the best of my ability.

Sitter Profile Image: Emma M.
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Emma M.
Star Sitter
from
$35
per visit
5.0 out of 5 stars
• 32 reviews
13 repeat clients
25 years of experience
Elmwood, providence, RI, 02907

“Emma is simply the best. She is responsible and dependable. She’s a great communicator and takes plenty of pet photos and videos. Best of all, my pets love her! With Emma, I always feel like my animals are in good hands”

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Isabel J.
Sitter Profile Image: Gary M.
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Gary M.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
• 227 reviews
50 repeat clients
6 years of experience
North Providence, RI, 02904

“I connected last minute with a Gary after my scheduled petsitter cancelled the day before my vacation. It worked out great. Gary was engaged and provided pictures each day. He took great care of my cats and definitely won them over. I would not hesitate to recommend Gary as well as use his petsitting service again in the future. Thanks Gary!!!”

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Heather M.
Sitter Profile Image: Hayley L.
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Hayley L.
from
$25
per visit
5.0 out of 5 stars
• 69 reviews
25 repeat clients
5 years of experience
Saunderstown, RI, 02874

“Hayley is amazing with our medium hound Marty! Super quick replies to booking requests and very communicative with texts and pictures. She takes such great care or our little guy.”

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Matt J.
Sitter Profile Image: Lilly T.
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Lilly T.
from
$25
per visit
5.0 out of 5 stars
• 10 reviews
3 repeat clients
19 years of experience
Belchertown, MA, 01007

“Lilly did great with our cat, Cranberry. She administered meds, fed her, and sent us photos. We’ll definitely book her again.”

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Karissa V.
Sitter Profile Image: Rosa D.
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Rosa D.
from
$20
per visit
5.0 out of 5 stars
• 12 reviews
5 repeat clients
15 years of experience
Prospect, CT, 06712

“The best!”

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Nathan M.
Sitter Profile Image: Natalie K.
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Natalie K.
from
$25
per visit
3 years of experience
Southold, NY, 11971

About: I live in Southold and I am available for dog walking and dog/cat sitting during the day and overnight in the area. I have taken care of dogs for 7 families so far. I have watched small dogs as well as large dogs. I also have watched two cats. I have a cat at home :) For many of the dogs I watch I take them on walks ranging from 15 mins to an hour. I have done jobs where I check in on a pet/pets during the day to let them out or feed them, but I also do overnight care. I am pretty flexible and available, I am available anytime after 7 am for checking in on pets/walks/etc. During the summer I will be available for pet sitting in the Southold area. During the fall I will also be available in the Southampton area as well. I am available to stay overnight with cats or dogs in my clients home. I am also available to stop in during the day/night to feed and check in on/hangout with pets.

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The median cost per visit for dog sitting in Windham is $25

Dog parents share their Rover experiences - Windham

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5.0 out of 5 stars

Marcos was awesome, took care of my pup very well and checked in constantly if anything were needed or out of place. He also sent in plenty of photos and made sure her area was clean when I got back.

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Aubre S.
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How to book dog sitting

  1. 1. Search

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Popular requests for dog sitting - Windham

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Sitters in Windham average 6
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FAQs for Dog Sitting - Windham

Frequently asked questions about Rover

As of October 2026, there are 1,924 sitters on Rover offering Dog Sitting across Windham. Enter your ZIP code to see which available sitters are closest to your home.

You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.

Before booking, confirm:

  • the timing, length, and frequency of visits;
  • the care instructions the sitter should follow;
  • which parts of your pet’s usual routine should be prioritized;
  • how often you would like to receive messages, photos, or other updates.

Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.

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 Windham 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 .

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 , which provides up to $25,000 in eligible veterinary care reimbursement.

A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first .

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 Windham 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 Windham. On Rover:

  • 90% of sitters can help with special care needs
  • 93% can help with giving oral medications or injections
  • 96% 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 , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

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

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