Dog Sitting Windham
Book a Windham dog sitter to watch your dog in your sitter’s home or yours.

Windham, 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.
About: I am an animal lover through and through! I’ve been taking care of many different types of dogs and cats since as long as I can remember. I am comfortable around all dogs and cats, and I am more than willing to adapt and learn how to best care for your animal in particular. When I come to care for, play with, and walk your pet, I will dedicate my time to truly loving them. I have experience staying at owners houses to take exceptional full-time care of their pets, and I also have experience keeping pets in my home! I have practiced basic animal training such as teaching dogs and cats to sit, stay, and shake. I truly adore animals and I will enjoy every minute of caring for your fur-babies! I am currently an Elementary Education student at the University of Connecticut, but I have tons of free time to take care of pets, whether that be for drop-ins or for more personal care in my home! Currently I am available full-time and I can accept last minute bookings. While dropping in to care for your pets, I will of course be incredibly respectful of your space, going only in the rooms I am allowed and touching only the items needed to care for your animals :) To care for animals in my own apartment, I have made sure that potentially hazardous items (small items, food, plants, etc.) are all put away/placed at a height that dogs and cats cannot reach. While I do not have a fenced yard, there are several parks around my apartment where I can consistently take your dog out on long walks. In my home, animals are also allowed on beds and couches! Please let me know if your pet requires any specific accommodations or changes to the environment :)

About: I currently own two dogs a mini Australian Shepard and a cocker spaniel. But, my family is a huge dog loving family and I have also owned labs, retrievers, and collies. I have a fenced backyard with a doggy door that holds about an acre of land and I live on a very quiet road with hiking trails across from my house that I bring my dogs into all the time! I’m work 3 times a week at Ridgewood Country Club in Danbury. I can leave during my breaks to tend to your pets. If they are staying at my home I have a doggy door and fenced in backyard. And then the remainder of the week I am free! I have a doggy door inside my home with a fenced in backyard for the 3 days I can’t be at home all day long. All other days I would love to take the dogs hiking and make sure they have a great time! I do own two dogs that are very friendly. But they can also be seperated into my basement if other dog is not friends with them. I also have a lot of experience with cat sitting my neighbors cats.

“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.”


“Madison was reliable, communicative, and took great care of my two cats while I was away. She sent plenty of photos and updates throughout the trip, which gave me peace of mind and showed that my cats were happy and well cared for. I came home to two content kitties, and I would gladly book with Madison again.”

“Lauren was really nice and communicative while watching my 2 cats! She was able to give my kitty his pills while I was gone and checked in and sent photos every time she stopped by. She also answered within a week of when I needed a sitter! Definitely would recommend booking with Lauren :)”

“Thank you for everything, I know we probably put you in a difficult situation but you did a great job under the circumstances. I would definitely highly recommend you to all that needs a dedicated pet caretaker for your caring and professionalism. Thanks again!”
About: Hey! A little bit about me , im born and raised in ct , have a high school degree and planning to major in animal science once I get into college! I’ve worked at dog kennels , and trained my personal dogs as well! I have a senior pup and a younger dog as well both trained by me! In my experience I can do med assist if your furry friend needs it ! Im excited to hear from you :) Right now I just left my work place , and I’d love to continue my care for animals as it’s my passion I couldn’t see myself doing anything else so I’m almost always available! I’m a very active person and don’t mind helping out as much as you need! I can help with any needs your dog may need at home! If that’s needing potty breaks , house sitting , play times , and plenty of walks and or hikes whatever you need plus med administration

About: I have years of experience taking care of many different type of animals. Many of my clients I have had for a long time and they continue to recommend me to more people in need of animal care! My top priority is to ensure the happiness and safety of all animals. I am currently in school and work a part-time job. Most of my availability is on the weekends, but I can be available Wednesdays after 4pm, along with Mondays between 11am-1pm. When caring for pets in client’s homes I can let them out (in a fenced in area or on a leash) for bathroom breaks and play with them for a little bit.
“Mary was so great with my dog, will be using her as my regular dog sitter going forward. Was super attentive and interactive with him from the first meet and greet. Great communication from her and loved the check ins she sent while she came to visit, very glad I found somebody so happy to spend some time with him when I’m at work. 10/10 recommend!”

“Amanda is a kind and caring person. My kitties were well cared for. Therefore, I was able to relax while away and not worry about my precious kitties. I am eternally grateful for ROVER and Amanda and the services that they provided. Thank you! ❣️🐾❣️🐾❣️”

About: Hi, I’m Rae! I’m a pet-obsessed U.S. Navy veteran, professional dog groomer by trade, and lifelong animal person with hands-on experience caring for animals of all types, sizes, breeds, ages, and personalities. Growing up, I had all kinds of animals to learn from, from small pets to much larger ones. Working professionally with dogs has taught me patience, how to read body language, recognize when a dog is stressed or uncomfortable, and adjust my approach to help them feel safe. I’m comfortable with puppies, senior pets, nervous dogs, high-energy breeds, and multi-pet households. At home, I have an Australian Shepherd, a Miniature Schnauzer, and three cats of my own — and I would absolutely have more if I didn’t have a husband to keep me in check. Each of my pets has their own unique quirks and I’m very familiar with managing different personalities, routines, and energy levels. I’ll treat your pets the way I’d want someone to treat mine: with patience, attention, lots of love, and plenty of updates for you! work as a professional dog groomer, so pet care is already a big part of my everyday routine. My schedule varies throughout the week, which gives me flexibility for drop-ins, walks, and overnight care. When I’m caring for your pet, I’ll make sure their normal feeding, potty, exercise, medication, and bedtime routines are kept as consistent as possible. I’m also happy to accommodate pets who need a little more structure, extra exercise, or simply more one-on-one attention. Safety is always my first priority. As a professional groomer, I’m very comfortable reading animal body language and recognizing when a pet is nervous, overwhelmed, or needs space. In my home, I have a securely fenced yard as well as resident dogs and cats, so introductions and interactions are handled carefully rather than assuming every animal will immediately be best friends. Pets can be separated for meals, downtime, or whenever needed, and I’m comfortable using crates or pens when that is already part of their routine. In a client’s home, I’ll follow your normal routine and house rules as closely as possible so your pet can stay comfortable in their own environment.
“Lila was wonderful with Snickers. She was very prompt and did everything I asked with his crazy senior dog behaviors. She’s sweet and loves dogs, it’s obvious with her interaction when she met my dog. It was also quite a last-minute booking, and she really helped us out that way.”

“Shannon took great care of our fur babies while we were away. Litter box was cleared and furballs picked up! Kitties were very happy to have her visits and give pets! Would absolutely use her service again! Great communication 👍🏽”

“My dogs love Shannon! So much so that after a meet-and-greet with her, one of my dogs was ready to go home with her. Something I had never seen him do before. It was adorable! Shannon was responsive, reliable, prompt, and sent me the cutest pictures of my dogs during her drop-in visits. Shannon gave me total peace of mind while I was away from my home. I will be using her in the future for any pet-sitting needs. I highly recommend her to anyone looking for a pet sitter!”

“We couldn't be happier with Amanda! She took great care of our two dogs and three cats while we were in Alaska. We had some initial guilt and worry, but she quickly put our minds at ease. She showed up daily right on time, and beyond feeding, walking, and administering medications, she sent amazing photos and detailed updates with every visit.”

About: The go-to pet sitter for friends, family, and neighbors! I have experience with kittens, puppies, aged and moody feline friends and senior dogs, and loud pups with lots of energy! I do accept some boarding and daycare requests for puppies & dogs, please note the yard is unfenced but is 2 acres and all outside time is supervised or leashed depending on needs. I run a home based business with a lot of flexibility so I'm available during weekdays from early morning, and on most weekends including holidays. I understand the importance of timing when it comes to feeding schedules and potty breaks and demonstrate punctuality that you and your pets can rely on.
About: I grew up in a family that bread, Dalmatians. As I head into retirement, I'd be happy to help other families with job service services or boarding services. I have a very laid-back in well-behaved male Dalmatian that enjoys company. I’m currently retired so I have time to help our other families. I’d be happy to do drop-ins or pup-sit. If you want socialization then my pup would be thrilled to attend Whether it’s squirrel chasing or some basic training, it’s important to get energy out during drop-in visits. Balls and treats are a good way to break the ice!
The median cost per visit for dog sitting in Windham is $25
Dog parents share their Rover experiences - Windham
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?
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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 sitters who will treat your dogs like family

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Popular requests for dog sitting - Windham
Select a filter and find qualifying sitters offering dog sitting.Sitters in Windham average 5 repeat dog sitting clients
FAQs for Dog Sitting - Windham
Frequently asked questions about Rover
As of October 2026, there are 1,951 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 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 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 Meet & Greet .
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:
- 96% of sitters can help with special care needs
- 97% 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 cancellation policy , 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.




