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Top rated Windham house sitters
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Orion took great care of our two old dogs while we were away. He was able to manage their demanding food and medicine schedule with easy. The dogs seemed rested and happy and I know they were glad to be able to stay in their own house. We will definitely book Orion again for future trips!”
About: I am a trained and certified k9 trainer with experience in basic and advanced obedience, behavior modification, odor tracking and an affinity for stray dogs. I currently foster so the more dogs the merrier. Im in school but my schedule is flexible so I can work around most things as long as I'm informed at least 6 hours in advance. I have multiple sized indoor and outdoor kennels and playpens for your pup. My property is safe and enclosed. I am former military so I tend to stick to strict schedules and have no problem keeping your pup on one if that is what's needed. OR we can hang out on my couch and watch dog training videos...im good with either one. I do training, temperament tests and socialization mostly to make both our time together interesting. Also offer daily pics for your Instagram!
“Palma was great and took good care of the house and our three pets. I would have appreciated a little more day to day communication but I didn't ask for it so it is difficult to fault her there. Otherwise, our pets and house are in perfect health and they were well taken care of”

“Tiffany is wonderful. Very proactive, lots of communication, so attentive with our girls, and she is really fun to talk to. A great added bonus! We will definitely have her with us again.”


About: I’ve been around dogs for most of my life. Since 2013, my family has had a German Shepherd, and I was actively involved in his daily care and training as he grew up. Through that experience, I became comfortable with everything from basic obedience training to managing routines, walks, and general behavior. I’ve also helped care for my brother’s two dogs on multiple occasions, including feeding, walking, and spending extended time with them. I’m confident handling dogs with different personalities and energy levels, and I’m used to adapting to their needs and following specific care instructions closely. I currently work as a Graduate Assistant in the Philosophy Department at UConn. Over the summer, I’ll be continuing my research from home. I may need to be on campus once or twice a week, but otherwise I’m generally available throughout the week. I also spend a lot of time outdoors trail running or going on long walks, so I’m happy to give active dogs plenty of exercise if needed. I’m available for boarding any day of the week and can usually accommodate bookings with very little advance notice. Your dog’s safety, comfort, and routine are my top priorities. I provide a calm, attentive environment where pets are supervised and cared for consistently throughout the day. I follow all owner instructions closely, including feeding schedules, walking routines, training cues, and any special care needs such as medications or behavioral considerations. During walks, I am very mindful of surroundings and keep dogs safely leashed at all times. In my home, dogs are treated as part of the household and given a comfortable, low-stress environment with plenty of attention and exercise as needed. I also make sure to provide regular updates so you can feel confident and informed while you’re away.
“Kelsey did great with our energetic puppy. She was very diligent about listening to all the things we told her about our dog, environment and needs. I would highly recommend.”

About: I have always loved animals. I treat all animals like my own. I learned to care for cats and dogs(and a variety of other animals) when I was young. Taking care of my own and family and friends pets, furry family members, feeding, bathing, walking, playing, snuggling. I have bottle fed, tended to allergic skin irritations, administered oral medications including chemo therapy. I am looking to make caring for your pets and making a worry stress free experience for you and your pet around your routine/schedule. I have a very open schedule, which makes it easier for me to work around your pets needs. It has worked out very well for me and the pets I have been able to spend time caring for. I will care for your pets in your home. I will care for them like they are my own. Loving, petting, snuggling, playing, walking, feeding making them feel stress free. I will listen to your instructions and follow them for the most personal and relaxed experience with your pet.
“Shannon watched our two huskies and stayed in our home while we were away for a weekend. She took excellent care of our home, collected our mail, and took the best care of our Doggos. She sent several picture updates of our dogs which helped immensely. We will definitely use her in the future and highly recommend her to others!”

About: I grew up owning 2 dogs and I have experience working in shelters as well as pet stores. I’m an animal lover who knows meeting the specific needs of each pet is necessary and important to complete my job. Currently, I work 2nd shift full time and I am able to take short term bookings (up to 2 weeks) for animal care. My availability is varied. I work 2nd shift full time Sun-Thurs, so I am available in the mornings on those days. Fridays & Saturdays I have open availability. I will follow your instructions and care for your pet as if it were my own. As someone who has owned pets with various temperaments and medical conditions, I am flexible to accommodations that are needed.
“Emily was AWESOME. Very communicative upfront and during her stay watching Koby. I came back from vacation to a happy dog and a perfect house. Will 100% rebook the next time I vacation.”

About: Reliable, caring, and attentive pet and house sitter who will treat your pets and home like my own! As the owner of an 8-year-old yellow lab, I understand how important it is to have someone trustworthy and dependable caring for your pets while you’re away. I have experience watching friends’ and family members’ pets and homes, and my hybrid work schedule at Travelers allows me extra flexibility during the week for house sitting, companionship, walks, playtime, and consistent care throughout the day. I currently work full time at Travelers Insurance with a hybrid schedule that allows me to work remotely two days a week. I am in the office Tuesdays, Thursdays, and Fridays, but I am home the majority of weekends and available to stay full time while caring for your home and pets. As the owner of an 8-year-old yellow lab, I understand how important it is to have someone trustworthy, attentive, and compassionate caring for your pets while you’re away. I have experience watching friends’ and family members’ pets and homes, and I always strive to make pets feel safe, comfortable, loved, and well cared for. I’m also very active and would love to take your pets on walks, play with them, and give them as much attention and companionship as they need! Your pets’ safety, comfort, and happiness are always my top priorities. I understand how important it is to trust someone with both your pets and your home, and I will always treat them with the same care and respect I would my own. I strive to maintain your pets’ normal routines as closely as possible, including feeding schedules, walks, playtime, bathroom breaks, and any specific instructions you provide. As a pet owner myself, I know every animal has different needs and personalities, so I focus on creating a calm, safe, and loving environment where they feel comfortable while you’re away. I’m very attentive, communicative, and happy to provide updates and photos for peace of mind. Whether it’s overnight house sitting, companionship during the day, or keeping active pets engaged with walks and playtime, I am committed to making sure your pets feel safe, loved, and well cared for at all times.
“Susan did an excellent job taking care of my cat and home while I was away for two weeks! She and my cat were fast friends and I returned to a clean home. I would definitely recommend her!”

“Savannah was wonderful, I would highly recommend her to watch your pet. She always quickly responded to me and sent pictures of my pet to let me know they were comfortable and happy staying at home. I will definitely use her services again without hesitation.”

“Rebekah took great care of my dog. She took him on daily hikes or walks , sent picture updates while I was away , and gave him lots of tlc. I felt really safe leaving my dog in her care and will definitely use her in the future.”


“Annie was AMAZING! She took such great care of our babies. Patches has anxiety, and unfortunately gets sick sometimes from it, and Annie went above and beyond on making sure she was OK. She also sent us pictures and a video while we were away. Highly recommend this young lady!!”

“Kate was absolutely amazing! We were so worried about our special needs cat while we were out of town but both of our cats and dog loved her!! She was able to get out very shy cat to eat his medicine and play with her in such a short amount of time. We will definitely be using Kate in the future when we’re out of town!”

Windham pet parents share their Rover experiences
Bekka was a terrific companion for my two pugs. She indulged their insatiable appetite for play, and made sure that they got plenty of walks and kept to their feeding schedule. She also did a great job looking after the house and taking care of a few vital upkeep items. Bekka is excellent!

How Rover works

1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per night for house sitting in Windham is $55
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 house 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.
Sitters in Windham average 3 repeat house sitting clients
House Sitting FAQs
Frequently asked questions about Rover
House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Windham on Rover as of Jun 2026 was about $55 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.
As of Jun 2026, there are 1,185 house sitters in Windham. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 87% of Windham house sitters respond in under an hour.
House sitters in Windham have an average of 17 years of experience. House sitters with repeat customers have an average of 3 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Windham.
Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Windham house sitters are great for:
- Dogs who’d prefer to stay on their home turf
- Cats and caged pets
- Pet parents on a tight schedule
- Keeping an eye on your home and plants while you’re away
Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.


