House Sitting in Chester

Find a loving house sitter to watch over your pets and your home.

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Top rated Chester house sitters

Prices are estimates per night for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.

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Sitter Profile Image: Taylor W.
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Taylor W.
Star Sitter
$76
total per night
5.0 out of 5 stars
17 reviews
5 repeat clients
20 years of experience
Lee, MA, 01238

Taylor took wonderful care of our sweet senior girl (15yo!) who has particular needs and takes meds. Sasha was happy and content when we got home, and our house looked great, too. We’re very grateful for the thoughtful care and would absolutely recommend Taylor.

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MA
Sitter Profile Image: Amy H.
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Amy H.
$36
total per night
5.0 out of 5 stars
4 reviews
1 repeat client
5 years of experience
Blandford, MA, 01008

About: Hello! I am a lifelong pet owner and animal lover with experience with everything from chickens and horses to cats and dogs. I have two canine family members myself: a medium-sized mix named Bonnie and a 10-pound Italian Greyhound/chihuahua named Rio. I know how hard it can be to find loving, reliable, and safe pet setters, which prompted me to open up my own home. My dogs love meeting new friends to play with. They get along well with others (though we always require a meet-and-greet before a sit) and are friendly with cats as well. My work-from-home career and spacious property allows me the flexibility to fully care for your pet without any interruptions such as commutes or 9-5 work hours. I am fortunate to enjoy a fully remote, flexible career, which means I am always present for your canine or feline family members. I can accommodate short or long-term stays, and am home throughout the day to maintain your pet's schedule, so they feel completely at home. I think it's important to a pet's sense of wellbeing to be able to keep to their usual schedule as best as possible while in my care. I live on five acres in a log home in a beautiful hilltown in Western Massachusetts, and have a fully fenced yard. I love taking my own pup on daily walks on our property or on nearby dirt roads, so if you have an active dog who needs exercise, I'm your person! If a less active lifestyle is better for your dog, I can fully accommodate that as well. Pets are allowed on my furniture and can make themselves cozy by my wood stove in winter or on my sunny deck in summer. I am familiar with using crates (if desired, but not required) and have a large finished basement perfect for playtime in the winter months.

Sitter Profile Image: Janet M.
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Janet M.
Star Sitter
$36
total per night
4.9 out of 5 stars
16 reviews
5 repeat clients
53 years of experience
Chesterfield, MA, 01012

Janet did a great job with the pups and with the house. Janet sent photos every day and kept us informed as to how the dogs were fairing. Both the dogs and the house were in perfect condition when we returned home. Thank you so much!

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Allison M.
Sitter Profile Image: Saige G.
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Saige G.
$56
total per night
4.8 out of 5 stars
33 reviews
13 repeat clients
11 years of experience
Easthampton, MA, 01027

I couldn't be happier with the love & care Ziggy gave both my dogs & home while we were away for the weekend. Thank you so much, I will definitely be reaching out again!

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Sarah S.
Sitter Profile Image: Janessa A.
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Janessa A.
$78
total per night
5.0 out of 5 stars
28 reviews
5 repeat clients
16 years of experience
Westfield, MA, 01085

Janessa is amazing and so trustworthy!!! She watched our 2 dogs while we were away and we didn’t have to worry at all. She provided just enough updates and we came home to a clean house! Would highly recommend Janessa

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Jacquelyne D.
Sitter Profile Image: Kelly H.
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Kelly H.
$139
total per night
5.0 out of 5 stars
66 reviews
31 repeat clients
14 years of experience
Otis, MA, 01253

Kelly was organized and attentive to every detail about our three dogs with wide ranging needs. She visited in advance, took copious notes and followed up on everything to double check. We will use her again and are very appreciative of her services.

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Marianne D.
Sitter Profile Image: Fiona B.
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Fiona B.
$62
total per night
15 years of experience
Huntington, MA, 01050

About: My family owns and operates a Labrador breeding business and kennel, located in a small slice of heaven in the hill towns. I have been living, breathing, and loving dogs for my entire life and find immense joy simply being around them! I have several years of experience at a boarding facility where I was able to expand my knowledge on any different breed, size, age, temperament and disabilities! I am comfortable with all dogs at any life stages, ranging from a few hours old to sweet elderlies. I am also able to react quickly to any situation and have a solid history of preventing and intervening real fights safely between several dogs. I am available at you and your pets desire! I am able to stay in home and/or overnight, or simply check in! My car is my main way of travel, and has safely transported many pups to their playdates! Care in my clients home includes purely love and sticking to the routine that your pet knows the best! My client will also receive the utmost amount of reassurance and open communication because I understand on a personal level how difficult it is to leave your baby in someone else's hands.

Sitter Profile Image: Trista S.
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Trista S.
Star Sitter
$34
total per night
5.0 out of 5 stars
17 reviews
6 repeat clients
30 years of experience
Pittsfield, MA, 01201

Trista was wonderful with my two dogs. I appreciated her last minute availability and professionalism. Both dogs warmed up to her very quickly even my shy one.

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Theresa S.
Sitter Profile Image: Keri H.
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Keri H.
Star Sitter
$106
total per night
5.0 out of 5 stars
57 reviews
19 repeat clients
20 years of experience
Lenox, MA, 01240

Keri was great! She was able to jump in at the last minute and stay at our house with our 2 dogs. She communicated regularly and sent lots of pictures of our pups. I think they liked her so much they didn't even realize we were gone!

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lisa M.
Sitter Profile Image: Erin O.
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Erin O.
Star Sitter
$78
total per night
5.0 out of 5 stars
36 reviews
10 repeat clients
20 years of experience
Westfield, MA, 01085

Erin was so great with Banner. She made sure to get him out for a walk or an adventure each day - something no other sitter has done. My boy is very high energy so he needs that stimulation she was able to provide! She updated me with pictures and texts each day which made me feel confident that Banner was in good hands. Thank you Erin for a great first stay with Banner!

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Megan L.
Sitter Profile Image: Matt L.
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Matt L.
Star Sitter
$78
total per night
4.9 out of 5 stars
75 reviews
18 repeat clients
32 years of experience
Hadley, MA, 01035

Matt is great. Max is always happy to see him and well cared for when I get home. He also leaves my home clean and my linens ready to be laundered.

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Kevin M.
Sitter Profile Image: Jessica B.
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Jessica B.
$50
total per night
5.0 out of 5 stars
5 reviews
1 repeat client
10 years of experience
Agawam, MA, 01030

On time, informative dogs love her

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Renee H.
Sitter Profile Image: Caitlin J.
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Caitlin J.
$36
total per night
5.0 out of 5 stars
4 reviews
20 years of experience
Windsor, MA, 01270

About: I've loved animals forever and have cared for everything from a cockatiel to a chameleon, Great Pyrenees to Pekapoo. I currently have 1 Goldendoodle and 1 chocolate tabby cat in my home with fenced area and walking trails. I'm currently homeschooling my children at our 10+ acre home with fenced area and walking trails. We have a light schedule and are home more often than away. We currently walk our Goldendoodle daily and pet care is our love, in addition to our responsibility. I have a fenced area and multiple indoor secure areas where animals can get healthy time in a safe home without overstimulation. I have 1 Goldendoodle and 1 chocolate tabby cat who are the best of friends and are supportive to newcomers.

Sitter Profile Image: Clara M.
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Clara M.
$62
total per night
5.0 out of 5 stars
17 reviews
3 repeat clients
11 years of experience
Tyringham, MA, 01238

I cannot say enough about Claire. She took care of everything. In my opinion, tater ( the dog ) would rather live with Claire than me at this point. That’s how good she is with animals. 100% recommend her!!!

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Robert K.
Sitter Profile Image: Ace G.
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Ace G.
Star Sitter
$73
total per night
5.0 out of 5 stars
68 reviews
22 repeat clients
9 years of experience
Chicopee, MA, 01020

Ace is ABSOLUTELY THE BEST!!! Ace is so caring, compassionate, and dedicated to the happiness of her Adopted Fur Babies.... Which funnels through to the Fur Babies Momma. Ace is in constant communication and asks questions to assist with the Fur Babies happiness. We looked forward to all the pictures that Ace sent us. We could tell from these pictures that our Fur Babies were well taken care of and happy. Ace follows the plan of care so well, of course, Clyde and Bella are there to assist. lol Ace was so respectful of our home and left it in the same neatness as upon arrival. If I could, I would give ACE 10 stars!!!!! 🐾🐾💕

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Michele A.
Sitter Profile Image: Julie G.
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Julie G.
$56
total per night
5.0 out of 5 stars
4 reviews
4 years of experience
Holyoke, MA, 01040

Julie was amazingly flexible, as our schedule was unknown, and was there when we needed her. More importantly, she was good with Ricky, took him out for walks as well as for his sanitary needs, and kept us regularly informed, with pictures. If we are in the area again we will seek her to assist us, and Ricky, again.

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John M.
Sitter Profile Image: Katelyn J.
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Katelyn J.
$56
total per night
3 years of experience
Westfield, MA, 01085

About: I’ve grown up around dogs and currently have a 6-month-old chocolate lab, so I’m very comfortable with puppies, high energy dogs, and daily routines like feeding, walking, and playtime. I understand how important it is to keep dogs active, safe, and on schedule. I’m very responsible and attentive, and I treat every dog like my own. I can handle everything from basic care to more active dogs that need extra attention and exercise. I’m also comfortable following specific instructions to make sure your pet stays happy and comfortable while you’re away. I’m currently a college student with a flexible schedule, so I have plenty of time to care for and spend time with your dog. I’m available most weekdays after classes and have more open availability on weekends. I’m used to managing a routine with my own 6-month-old chocolate lab, so I’m consistent with feeding, walks, and playtime. Your dog’s safety and comfort are my top priorities. I treat every dog like my own and make sure they are always supervised, safe, and well cared for. I have experience handling a high-energy puppy, so I’m comfortable with active dogs and different temperaments. I follow any instructions you provide closely to keep your dog on their normal routine and make sure they feel comfortable while you’re away.

Sitter Profile Image: Hailey P.
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Hailey P.
$67
total per night
5.0 out of 5 stars
2 reviews
1 repeat client
7 years of experience
West Springfield, MA, 01089

About: I’m a graduate student with a bachelors of science in Biology and a concentration in pre-vet, working towards a career in veterinary medicine with years of hands-on experience caring for animals. I’ve worked in a clinical hospital and an animal shelter with both cats and dogs, gaining experience with a wide range of temperaments, ages, and needs. I’ve also taken multiple animal-focused college courses that strengthen my understanding of proper care, behavior, and health. In addition, I’ve provided pet sitting and dog walking for friends, family, and neighbors for several years. I’m comfortable caring for pets of all ages and make sure every animal feels safe, loved, and well cared for. I’m currently working part-time, but I have as much time as I can give for your fur baby! I coach softball so I’m away part of July but other than that my schedule is pretty open. I prioritize pet safety by following routines closely, maintaining clean spaces, and respecting your home. I ensure pets are supervised, secure, and comfortable at all times.

Sitter Profile Image: Valentina M.
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Valentina M.
$36
total per night
6 years of experience
Stockbridge, MA, 01262

About: I grew up with 2 dogs and 2 cats. My family was part of helping a farm when i was little, I got to take care of ducks. They were so cute. I love animals and let me know if you had questions. I work at Marshall’s. I will be taking care of the animals during my days off. I will make sure they have everything they need I grew up with cats and dogs. I love all kinds of animals. I will take good care of them. I can bring them to my house as well.

Sitter Profile Image: Reymon B.
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Reymon B.
$89
total per night
20 years of experience
Pittsfield, MA, 01201

About: Working in various Grooming/Training facilities. I'm currently working with Bumblebee Pet Care with 5 of my own clients. My conversations with the pets are amazing. I'm currently walking dogs 2 days out of the week looking for more to work with within the week. I have an open schedule and interested. I have separate spaces available for each animal. In my care at anytime, I will use provided equipment for transportation. Your pet safety is number one.

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The median cost per night for house sitting in Chester is $60

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    It doesn’t happen often, but if your house sitter has to cancel, we’ll work with you to find a new sitter.

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Sitters in Chester average 4
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 Chester on Rover as of Jun 2026 was about $60 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.

If you’re searching for a Chester house sitter for the first time, visit the house sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 309 house sitters in Chester. 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, 83% of Chester house sitters respond in under an hour.

House sitters in Chester have an average of 18 years of experience. House sitters with repeat customers have an average of 4 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 Chester.

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. Chester 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.