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Top rated Cheshire house sitters

“Olivia was amazing! She was so great with our big guy and sent lots of updates so we were aware of what was going on without feeling overwhelmed. Absolutely will be booking with her again!”


“McKenna was incredible! My picky dog loved her right away, and she navigated his separation anxiety so lovingly and effectively. Her knack and intuition with animals shows. She was extremely communicative, clear and thoughtful at every step. Can't wait to book her again!”


“Caitlin was amazing! It was obvious that Ollie and Daisy loved her. She was very accommodating and took care of our pups with love and kindness. I would ask Caitlin to watch Ollie and Daisy again in a heartbeat! Thank you Caitlin!!”


“Liz met us at our campsite right on time and she immediately got along with our Catahoula, Annie. They were quick friends. Liz did a great job keeping her safe and entertained while me and my family attended a concert, and Annie was safe and relaxed when we got back to our site. Liz did great and I'll recommend her to anyone who needs help watching their fur baby for a few hours.”


About: Hello! My name is Skylar; I am 26 years old, my family has owned dogs my whole life, I own a dog and two cats! I currently work at a daytrain facility for dogs and am on my way to eventually becoming a dog trainer! I am relatively flexible as I work around my jobs schedule but I always provide the upmost care for animals. As a dog lover, I’m here to ensure that your family members stay happy and safe while you’re away! I currently work part time at a daytrain facility for dogs, typically in the afternoons - So I am available mostly in the mornings and evenings ( after 6 pm)! I am able to provide walks if needed (or if there is no fenced in yard), as well as special diets and medications as needed!

About: I have been in the dog world for about 6 years now. I have experience in kennel work, grooming, protection training, and also breeding. I love my dogs just as family and would love to be that loving uncle for you pet when the busy schedule of life is happening. I currently working full time as a dog groomer but can always find the time to take care of you beloved pet family member. Im very flexible around my work schedule. For boarding I will stay at the client's home because its a little better for the dog to be in an environment that he/she knows.

“Sally is amazing! She took great care of our dog and two cats - she clearly loves animals. Additionally, she did a wonderful job looking after our home. She left everything looking tidy, and went the extra mile by washing sheets and towels before she left. She also left good notes about how it all went. She made the weekend easy and stress free! And she sent wonderful photos, too. This was our first time having her in our home and I would have her back in a second. A+ petsitter!”


“Bella was terrific! She stayed over in my home to care for my dog and cat. I appreciated her proactive communications including text with pictures of my dog out on walks with her. She was respectful of my home and I will definitely be in touch with her again to help in the future. I highly recommend her services.”


About: I’ve interned at my local vet clinic for two years now and have recently moved to a paid position as an assistant! through this internship i have not only learned substantial knowledge regarding pet care, such as how to most effectively administer medications, but also discovered my love for pet sitting, as i have become one of the veterinarian’s permanent pet sitter! i also plan to go to vet school after i earn my bachelors degree! i am currently working various part time jobs, so i will need at least two weeks notice for a majority of the services i provide. i will try my best to arrange my schedule for your convenience! i’ll treat your furry family like my own! i come with treats ready (with permission of course) and never leave without a game of fetch or whatever else your babies might enjoy! they’ll definitely be the highlight of my day, so i’ll try to be there’s too!

About: Compassionate and experienced pet caregiver with a proven track record of providing top-notch care for dogs with special needs. Skilled in managing medical conditions such as convulsions and cancer, with a gentle and loving approach. Also well-versed in supervising curious eaters who love to snack on anything they can find! Above all, I shower my furry friends with love, attention, and affection, ensuring they feel safe, happy, and adored in my care. As a dog walker, pet care is a regular part of my morning routine. I typically schedule dog walks Monday through Saturday, usually between , 8am-12pm. This allows me to provide a fun and energizing start to the day for the dogs in my care. I provide fun and safe dog walking services, giving your furry friend the exercise and attention they deserve. Here's how I care for your dog: - 30-minute to 1-hour walks tailored to your dog's individual needs and energy level - Safe and secure walks on a leash, with regular checks for comfort and happiness - Plenty of praise, affection, and treats to keep your dog happy and engaged - Regular updates and photos so you can stay connected with your dog's adventure Your dog's safety, comfort, and happiness are my top priority. I'll work with you to understand their unique needs and personality, ensuring a fun and enjoyable experience for both of us!

About: I've had 5 dogs in 25 years. My 7yr old rescue black lab mix Luna is my current forever pup. She's up for anything & everything. I have an open schedule since retirement. I am looking forward to spending more time outdoors and taking care of other dogs and their owners. Our back yard is fenced in. We have large dog crate if needed. There is a park nearby that we bring our dog to often. I can travel in my vehicle with dogs

About: My experience in pet care began during my childhood on my grandparents’ farm, where I was surrounded by a wide variety of animals every day. From an early age, I learned the importance of responsibility, compassion, and attentive care. I gained hands-on experience feeding, grooming, and nurturing animals of all kinds—including dogs, cats, livestock, and small animals—each with their own unique needs and personalities. More than just daily routines, I developed strong, loving bonds with the animals I cared for, treating them as family. That foundation shaped my deep understanding of animal behavior and my commitment to providing patient, personalized, and reliable care for every pet I work with. I bring a deep love and understanding of dogs of all ages, sizes, and personalities. From playful pups to sweet seniors, I tailor each walk to fit their needs. I prioritize safety, communication, and fun—always engaging with your dog and even teaching basic cues like sit, stay, and wait during our adventures. I’m passionate about nature and I believe dogs thrive when they can safely explore their environment —sniffing the breeze, feeling the grass under their paws, and soaking up the world around them. I’m dependable, energetic, and treat every dog like my own. Whether it’s a gentle stroll or a playful outing, your pup will be in great hands and have a tail-wagging good time! Dog walking fits perfectly into my current routine. I’m a part-time healthcare worker with a consistent schedule, working from 8 a.m. to 1 p.m. on Monday, Tuesday, Thursday, and Friday. Outside of those hours, I have a flexible schedule and plenty of availability and plenty of time to dedicate to your pup. I truly enjoy incorporating walks into my day—they keep me active, bring me joy, and let me connect with more wonderful dogs. Your dog will receive dependable, loving care from someone who’s already made this a part of daily life. Safety, trust, and a positive environment are at the heart of every walk I take. I prioritize clean, open, and dog-friendly spaces—like the Rail-Trail, local parks, and secure walking paths—where pups can enjoy fresh air and nature safely. I always use leash control, stay highly observant of their behavior, and make sure every walk is calm, comfortable, and secure. Whether we’re exploring a quiet trail or playing at a safe dog park, your dog’s well-being is my top priority. You can trust that your pup is in caring, capable, and experienced hands every step of the way.

About: I have always cared for, loved & owned dogs for as long as I can remember. I love to walk so why not combine two loves into one lovely hobby! I live close to the Ashuwillticook Trail and the Greylock Glen where we will have great fun. Can’t wait to meet your special pup & make him/her the happiest hound in town. Whatever it takes I aim to please & pamper your PAWSOME pet! ❤️ 🐶😺 ❤️ I've always cared for, loved & owned cats as well. I would love to meet your special friend & build the fondest feline memories. As for all those small critters, I have experience with many different kinds including fish, hamsters, gerbils, parakeets, ferrets, rabbits and more. Volunteered at Animal Dreams shelter for a series of weeks through a service learning program at MCLA. I work part time as a nurse & ski instructor in the winter. I would love to help out with all of your pet care needs. I'm dependable & ready, snow, sleet, wind, rain or shine with references available upon request. I'm looking forward to hearing from you soon to set up a meet & greet with you & your main squeeze 😍 My schedule is moderately flexible. I would love to become a full time Rover girl in the future. I love all animals. I believe they are vulnerable creatures and most rely on humans to care for & protect them. If you are without a vehicle or your work schedule is super rigid I can pick up or drop off your fur-ever-luv if needed. I would love to help out anyway that I can. I own two dog friendly cats & I will look after your pet as if she/he were my own. I will do everything I can to make it the safest, most comfortable and memorable experience for your special pet.

“Jessie was absolutely amazing! She was quick to reply to us and made the whole process stress free! She was on time for our meet and greet and is the nicest! Our dogs absolutely loved her! She sent us some great photos of our dogs! We never had to worry, our dogs were in great hands! I highly recommend her for anyone who is looking for a great dog sitter!!”


About: ive had a couple of dog growing up in my childhood a sweet old black lab and a super crazy dingo.. in my free time after school and during summer i used to walk them, no amount of walking could satisfy my dingo.. id have her pull my bike to get all her energy out since we didnt have any closed in areas she could run off in.. ( i dont do this anymore! i realize its not very safe! she absolutely loved it for sure though) i love pups big and small old and energetic theyre all very unique and id love some new friends to get me out of the house. id ask you beforehand of course if youd be okay with them swimming, theres a pond i can bring them to after walking to cool off at. our backyard is fenced! i have two cats, so id like to know how your dog reacts around small creatures, if they cant be in contact i can always but them into a room while the dog is over. most likely theyd be outside! lots of shade and id keep em well hydrated and happy :3 i currently have been on a job hunt since what feels like forever, my schedule is very. very open.. since i dont have a car, drop off would be ideal, if your close enough to walk to i can do that too! weekends are the only time id be able to pick up your pooch my cats get their waters filled and cleaned almost daily, lots of love of course and are very spoiled. i dont have any dogs at the moment, so of course id love to chat about what youd expect and need for your lovely pup! im good with communication and friendly, special needs id be extra attentive to. im very good at remembering small things, though id still write em down incase!

About: I am an animal lover at heart. I will care for your fur family like they are my own. I am able to provide medications if required, and plenty of love. I currently am a full time care provider to my parents, which allows my schedule to be flexible to fit your needs. Let’s talk about how I can help you and your fur family. I am happy to come to your home and care for your animals while you are away. I can also be available for one hour walks or drop in visits to your home. I believe staying in the environment that they are familiar with and feel comfortable and safe in is what’s important.

About: Retired Military Veteran, 12 years of service. Very reliable and love animals. I love all breeds of dogs regardless of the stereotypes. Can’t wait to start watching your dogs. I have a vast background, military and emergency services. I’m in the process of becoming a nys emt and then will go on for my paramedic hopefully my flight medic. I’ve grown up with dogs and haven’t had a dog in a year. Feel free to look up my information in the military to know that I’m a veteran. I am always available even for a last minute vacation. My husband and I would love to help who ever needs that extra tlc while their owners go away. I’m home all day every day. I work overnights so my hubby could let your little or big pups out to go potty before work. They will have free range of the house unless they are specifically crated then I can put them in the crate and take them out when needed.

About: I’ve been around animals my whole life. I worked on a farm in 2023 and the rest of my experience is from dog sitting at clients homes, dog walking, house sitting, etc, as well as my own pets. I currently work full time but have a flexible schedule and can check on your pet periodically throughout the day, free all night and on weekends I’d be happy to house sit for you while watching your furry loved ones and taking them on walks, feeding, etc. I am also very good at bathing all animals if needed!
Loving house sitters in your neighborhood
Search Results


Olivia S.

“Olivia was amazing! She was so great with our big guy and sent lots of updates so we were aware of what was going on without feeling overwhelmed. Absolutely will be booking with her again!”


McKenna P.
Star Sitter


“McKenna was incredible! My picky dog loved her right away, and she navigated his separation anxiety so lovingly and effectively. Her knack and intuition with animals shows. She was extremely communicative, clear and thoughtful at every step. Can't wait to book her again!”


Lori L.Star Sitter

“Lori was great with Mocha and Ezzy! We just moved into our new place in Worcester and we felt very at ease with Lori watching over them. Thank you again! -M&N”


Caitlin H.

“Caitlin was amazing! It was obvious that Ollie and Daisy loved her. She was very accommodating and took care of our pups with love and kindness. I would ask Caitlin to watch Ollie and Daisy again in a heartbeat! Thank you Caitlin!!”


Elizabeth B.

“Liz met us at our campsite right on time and she immediately got along with our Catahoula, Annie. They were quick friends. Liz did a great job keeping her safe and entertained while me and my family attended a concert, and Annie was safe and relaxed when we got back to our site. Liz did great and I'll recommend her to anyone who needs help watching their fur baby for a few hours.”


Skylar R.
About: Hello! My name is Skylar; I am 26 years old, my family has owned dogs my whole life, I own a dog and two cats! I currently work at a daytrain facility for dogs and am on my way to eventually becoming a dog trainer! I am relatively flexible as I work around my jobs schedule but I always provide the upmost care for animals. As a dog lover, I’m here to ensure that your family members stay happy and safe while you’re away! I currently work part time at a daytrain facility for dogs, typically in the afternoons - So I am available mostly in the mornings and evenings ( after 6 pm)! I am able to provide walks if needed (or if there is no fenced in yard), as well as special diets and medications as needed!


Anthony C.
“Anthony Castagna has been walking and pet sitting for our Nova for years. He is very reliable and friendly and like part of the family. Our Nova loves him so much!”


Eleanor K.

“Eleanor is very responsible and took great care of Remi!! She communicates well and left the house in perfect condition. I would definitely recommend her!”


Sally A.

“Sally is amazing! She took great care of our dog and two cats - she clearly loves animals. Additionally, she did a wonderful job looking after our home. She left everything looking tidy, and went the extra mile by washing sheets and towels before she left. She also left good notes about how it all went. She made the weekend easy and stress free! And she sent wonderful photos, too. This was our first time having her in our home and I would have her back in a second. A+ petsitter!”


Bella G.


“Bella was terrific! She stayed over in my home to care for my dog and cat. I appreciated her proactive communications including text with pictures of my dog out on walks with her. She was respectful of my home and I will definitely be in touch with her again to help in the future. I highly recommend her services.”


Rita M.
About: I’ve interned at my local vet clinic for two years now and have recently moved to a paid position as an assistant! through this internship i have not only learned substantial knowledge regarding pet care, such as how to most effectively administer medications, but also discovered my love for pet sitting, as i have become one of the veterinarian’s permanent pet sitter! i also plan to go to vet school after i earn my bachelors degree! i am currently working various part time jobs, so i will need at least two weeks notice for a majority of the services i provide. i will try my best to arrange my schedule for your convenience! i’ll treat your furry family like my own! i come with treats ready (with permission of course) and never leave without a game of fetch or whatever else your babies might enjoy! they’ll definitely be the highlight of my day, so i’ll try to be there’s too!


Aura G.
About: Compassionate and experienced pet caregiver with a proven track record of providing top-notch care for dogs with special needs. Skilled in managing medical conditions such as convulsions and cancer, with a gentle and loving approach. Also well-versed in supervising curious eaters who love to snack on anything they can find! Above all, I shower my furry friends with love, attention, and affection, ensuring they feel safe, happy, and adored in my care. As a dog walker, pet care is a regular part of my morning routine. I typically schedule dog walks Monday through Saturday, usually between , 8am-12pm. This allows me to provide a fun and energizing start to the day for the dogs in my care. I provide fun and safe dog walking services, giving your furry friend the exercise and attention they deserve. Here's how I care for your dog: - 30-minute to 1-hour walks tailored to your dog's individual needs and energy level - Safe and secure walks on a leash, with regular checks for comfort and happiness - Plenty of praise, affection, and treats to keep your dog happy and engaged - Regular updates and photos so you can stay connected with your dog's adventure Your dog's safety, comfort, and happiness are my top priority. I'll work with you to understand their unique needs and personality, ensuring a fun and enjoyable experience for both of us!


Jason R.
“Jason is our first choice when we need a dog sitter and/or dog walker. He is responsible, caring, courteous, and reliable. Our dog is always well taken care of and enjoys his time with Jason. 10 out of 10 recommend!”


Christina D.
“Pyper loves Christina so much and has walked her numerous times for me and dog sat since she was a puppy. She is one of the only people I trust to take care of her. Pyper adores her and she is so kind, patient, and loving. I highly recommend Christina. She is trustworthy, reliable, and will always be on time. I will continue to use her. Wouldn't want to use anyone else!”


Danielle P.

About: I have always cared for, loved & owned dogs for as long as I can remember. I love to walk so why not combine two loves into one lovely hobby! I live close to the Ashuwillticook Trail and the Greylock Glen where we will have great fun. Can’t wait to meet your special pup & make him/her the happiest hound in town. Whatever it takes I aim to please & pamper your PAWSOME pet! ❤️ 🐶😺 ❤️ I've always cared for, loved & owned cats as well. I would love to meet your special friend & build the fondest feline memories. As for all those small critters, I have experience with many different kinds including fish, hamsters, gerbils, parakeets, ferrets, rabbits and more. Volunteered at Animal Dreams shelter for a series of weeks through a service learning program at MCLA. I work part time as a nurse & ski instructor in the winter. I would love to help out with all of your pet care needs. I'm dependable & ready, snow, sleet, wind, rain or shine with references available upon request. I'm looking forward to hearing from you soon to set up a meet & greet with you & your main squeeze 😍 My schedule is moderately flexible. I would love to become a full time Rover girl in the future. I love all animals. I believe they are vulnerable creatures and most rely on humans to care for & protect them. If you are without a vehicle or your work schedule is super rigid I can pick up or drop off your fur-ever-luv if needed. I would love to help out anyway that I can. I own two dog friendly cats & I will look after your pet as if she/he were my own. I will do everything I can to make it the safest, most comfortable and memorable experience for your special pet.


Jessie L.

“Jessie was absolutely amazing! She was quick to reply to us and made the whole process stress free! She was on time for our meet and greet and is the nicest! Our dogs absolutely loved her! She sent us some great photos of our dogs! We never had to worry, our dogs were in great hands! I highly recommend her for anyone who is looking for a great dog sitter!!”


Mariana F.
About: ive had a couple of dog growing up in my childhood a sweet old black lab and a super crazy dingo.. in my free time after school and during summer i used to walk them, no amount of walking could satisfy my dingo.. id have her pull my bike to get all her energy out since we didnt have any closed in areas she could run off in.. ( i dont do this anymore! i realize its not very safe! she absolutely loved it for sure though) i love pups big and small old and energetic theyre all very unique and id love some new friends to get me out of the house. id ask you beforehand of course if youd be okay with them swimming, theres a pond i can bring them to after walking to cool off at. our backyard is fenced! i have two cats, so id like to know how your dog reacts around small creatures, if they cant be in contact i can always but them into a room while the dog is over. most likely theyd be outside! lots of shade and id keep em well hydrated and happy :3 i currently have been on a job hunt since what feels like forever, my schedule is very. very open.. since i dont have a car, drop off would be ideal, if your close enough to walk to i can do that too! weekends are the only time id be able to pick up your pooch my cats get their waters filled and cleaned almost daily, lots of love of course and are very spoiled. i dont have any dogs at the moment, so of course id love to chat about what youd expect and need for your lovely pup! im good with communication and friendly, special needs id be extra attentive to. im very good at remembering small things, though id still write em down incase!


Lori M.
“We had Lori watch our 2 hundred pound Chesapeake Bay Retrievers as well as my niece’s rescue dog for 2 days while we were in the Berkshires on a family vacation. Lori spoiled them all with cuddles, pets, pool and toy play. When we came home the pups were smiling and wagging there tails. I would highly recommend Lori. She is a punctual, professional and extremely caring person. 5 star review!! Thank you Lori”


Nikki R.
“What I know about Nikki is that she's a kind and caring person and has been around dogs most of her life. When she has been around any of my dogs she has always been attentive.”


Hayleigh J.
About: I’ve been around animals my whole life. I worked on a farm in 2023 and the rest of my experience is from dog sitting at clients homes, dog walking, house sitting, etc, as well as my own pets. I currently work full time but have a flexible schedule and can check on your pet periodically throughout the day, free all night and on weekends I’d be happy to house sit for you while watching your furry loved ones and taking them on walks, feeding, etc. I am also very good at bathing all animals if needed!
How Rover works
1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets2. 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 away3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
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.
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 Cheshire on Rover as of Aug 2025 was about $65 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 Aug 2025, there are 96 house sitters in Cheshire. 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, 95% of Cheshire house sitters respond in under an hour.
House sitters in Cheshire have an average of 15 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 Cheshire.
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. Cheshire 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.
