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.
“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.”
“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 :)”
“Shannon took care of our kitties while we were away for a few days. They were very well taken care of and loved seeing her again! She is wonderful with them! She communicates very well with us-we get pictures and a nice note on how the kitties were doing! Highly recommend! Thank you!”
“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!”
About: I am an Animal Science student at UConn and have been working as a vet tech at Ipswich Animal Hospital for the past 3 years. I work with many different types of animals, mostly cats and dogs, and I can cater to their needs. I can administer medication, clip nails, certain grooming tasks such as brushing and bathing, and I can also do hair trims if needed (some of these services may require an additional person; if I determine it is needed for that specific pet that would require another person other me entering your home). I am very active and can provide long walks for pets and can also provide photos and videos of your pets. I am a college student so I am available during winter and summer break. I do not usually travel so I am available for holidays and vacation weeks. I have owned dogs all my life and have taken care of many of my friends' cats. I have 2 dogs at home and regularly take care of 4 cats. Each pet obviously has different needs, and I try my best to accommodate them. I often groomed the cats I look after and adjust so that they are comfortable.
“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!”
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 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!
“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.”
“Amanda did a wonderful job caring for our cat Serene while we were on vacation. She was extremely kind, caring and thoughtful, she provided excellent and constant communication about Serene’s well-being. She not only fed Serene and cleaned her litter box every visit like asked, but also played with her and bonded with her, and provided us with cute photos of her to look at while we were away and missing her. I would absolutely recommend Amanda for any pet owner who needs someone to do drop-ins with their pet while they are away, and would definitely book her again! Thank you Amanda 😊”
“Amanda is kind and caring. I trust her to care for my precious pets. We’ve used her services twice and are quite pleased. I highly recommend her. Thank you Amanda/Rover.⭐️⭐️⭐️⭐️⭐️”
About: I have owned dogs throughout my whole life. At one point Our pack totaled 6. I’ve owned 2 horses, a guinea pig, a rabbit, and a cat. I worked as an apprentice vet tech until the veterinarian died unexpectedly of a heart attack. I have recently pursued more education regarding grooming. I have groomed my own dogs and friends dogs over the years. I am conscientious and will never allow a dog to be in pain seeking medical care immediately. I would like it to be part time to start with the option of going full time further down the road. I am working on grooming lessons, and my current part time job. I believe in being observant of their behaviors and to respond accordingly. Our dogs receive much love and play time. They are allowed to be with us and on our furniture. I realize that many owners frown upon that and I will honor their wishes when caring for their pet
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.
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.
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.
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?
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 sitters who will treat your dogs like family
1. Search
Browse profiles of sitters near you who offer dog sitting
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
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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 Drop-In Visits - Windham
Frequently asked questions about Rover
As of September 2026, there are 1,961 sitters on Rover offering Dog Sitting across Windham. 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 Windham 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 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 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 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 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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