House Sitting Chester

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Chester, Find top rated house sitting

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
18 reviews
7 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: Janet M.
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Janet M.
Star Sitter
$62
total per night
4.9 out of 5 stars
16 reviews
6 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: Amy H.
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Amy H.
$84
total per night
5.0 out of 5 stars
5 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 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. PLEASE NOTE: At this time, I am not taking any new clients for boarding, but I AM available to dog or cat sit in YOUR home for both new and existing clients. Please see my profile and rates for in-your-home sitting. Thank you! 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 work easily from your home (WiFi is my only requirement) so I can ben present for your pups or cats. 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. For my clients who come to me: 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: 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: 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: Saige G.
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Saige G.
$56
total per night
4.9 out of 5 stars
34 reviews
13 repeat clients
11 years of experience
Easthampton, MA, 01027

Saige got along great with all our animals and everyone seemed well taken care of when we got back. She also kept our house clean and we could hardly tell we had ever left.

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Marissa T.
Sitter Profile Image: Ashley & Robert D.
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Ashley & Robert D.
Star Sitter
$111
total per night
5.0 out of 5 stars
16 reviews
7 repeat clients
25 years of experience
Austerlitz, NY, 12017

Ashley did a wonderful job with my three pups! She quickly understood their personalities and all they needed. She took great care of the house and everything and we look forward to seeing her again soon! Thanks, Ashley!

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Susie N.
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 a pleasure to communicate with before and during the pet sit. Our dog, Katy, who is a somewhat recent rescue who doesn't love everyone, took to Keri right way and rested at her feet when we reviewed my long and detailed instructions in our orientation. Katy has a weird behavior associated with her anxiety and that didn't phase Keri at all. Our house has some idiosyncrasies and Keri didn't seem to mind managing those things, like our Berkey water filter needs refilling in a specific way and the AC drips into a bucket so has to be on a timer, etc. Katy also takes medication and other supplements and Keri was great with all that too. We felt confident leaving Katy in her care and, according to our friend who took over for the second week we were gone, all was well with the house (tidy and clean) and all was well with Katy (relaxed and easy). Keri sent me daily communications and photos. Keri even took Katy to the river that we left instructionsn for. I was impressed that Keri took the trouble to do that special outing with Katy. Keri included her husband (with our permission) who also seemed great with Katy. I highly recommend Keri for pet-sitting. She's just super!

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Joyce P.
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 the perfect dog (and house) sitter. We came home to a relaxed and happy senior dog and the house just as we had left it. Erin went above and beyond by bringing in mail and trash can, watering plants and even reached out to see when Riley could go on the lawn after it was fertilized. Erin is professional and responsive. We will definitely be booking with Erin again!

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Donna D.
Sitter Profile Image: Alli Z.
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Alli Z.
$56
total per night
25 years of experience
Northampton, MA, 01062

About: I have always had at least 2+ dogs in my house since I was born. I currently have 2 of my own who make life so much better! I know it’s not always easy to work and have pets but I hope I can help some people no matter if it’s letting them out or walking them. I am currently a nurse but looking to also do house sitting, dog walking, drop ins, whatever is needed! I am available to help anytime after 4pm on weekdays and anytime on weekends! I am willing to go late as well! Some days I can also go before 7am I have two pets in my home one is a lab mix and one is a heeler mix. Both love all animals and people. They’re both three years old.

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

Trista took amazing care of our two girls during our long weekend in Pennsylvania - she sent photos regularly so we could see how they were getting along with her and that they were having fun while we were away. We will definitely be booking with her again!

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Jessica M.
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: 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: 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 our go to person for our very anxious yet adorable Beagle. Our pup is so well taken care of by Ace. We have no worries when they are on the job!

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Karen M.
Sitter Profile Image: Hailey P.
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Hailey P.
$56
total per night
5.0 out of 5 stars
3 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: Matt L.
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Matt L.
Star Sitter
$78
total per night
4.9 out of 5 stars
76 reviews
18 repeat clients
32 years of experience
Hadley, MA, 01035

Thank you for taking great care of Chloe for us. It was a unique situation where we were from out of town attending a family gathering so needed someone to stay with our dog at a hotel. Matt was flexible to do this for us, kept us informed with photos. I would highly recommend Matt!!

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

Jessica house sat for our special needs cat for several days. At one point he needed to go to the vet and she arranged everything with them and implemented a new medicine. We were provided with daily photos and had good communication while overseas. She followed directions provided for her and gave our boy lots of love while we were away!

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Glenna D.
Sitter Profile Image: Linda I.
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Linda I.
$67
total per night
5.0 out of 5 stars
3 reviews
20 years of experience
Hatfield, MA, 12057

My husband and I were leaving for our 10-day honeymoon when, just a week before our trip, our dogs virus acted up and he could no longer attend daycare as we had planned. We were so relieved to find Linda! She was incredibly communicative from the start and made herself available to lock everything in quickly, which gave us so much peace of mind before we left. While we were away, Linda sent us daily updates and photos of our pup, which we looked forward to every day. It was so reassuring knowing he was able to stay in the comfort of his own home and maintain his normal routine while Linda took such great care of both him and our house. Our 2.5-year-old Golden Retriever is full of energy, and Linda did an amazing job building a relationship with him and keeping him happy, active, and comfortable while we were gone. We came home to a happy dog and a well-cared-for home. We couldn't have asked for a better experience and would highly recommend Linda to anyone looking for a trustworthy, caring, and reliable dog sitter!

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Marissa N.
Sitter Profile Image: Wendy A.
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Wendy A.
$36
total per night
5.0 out of 5 stars
5 reviews
1 repeat client
30 years of experience
Westfield, MA, 01085

About: My dad taught me at a young age how to care for, and respect all animals. I have turned this into a life long love for all animals, both domestic and wild. I am a vet assistant, and currently studying to be a certified vet tech. For the last two years I have worked at the local animal shelter, and for the last year, at a dog daycare as well. I have volunteered at Dakin for the best part of the last 15 years. This has included transportation of animals, dog walking, animal socialization, and the kitten ICU. I am currently working part time, so I will have plenty of time for your furry family members. I am available during the week, on weekends, and holidays. Whether your dog likes the dog park, or playing in the backyard, we can play using their favorite toys. If they are more of a couch potato, I can accommodate them as well. If you have kitties that need company, we can play in the house, or go out for a stroller ride. I have a fenced in backyard for the dogs to play in. In the summer, a pool and water sprinkler will be available. I am a vet assistant, so I have first aid training for both dogs and cats. My house is air conditioned, perfect for relaxing on a summer day.

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

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  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
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How Rover works

  1. 1. Search

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Sitters in Chester average 4
repeat house sitting clients

FAQs for House Sitting - Chester

Frequently asked questions about Rover

As of July 2026, there are 655 sitters on Rover offering House Sitting across Chester. Enter your ZIP code to see which available sitters are closest to your home.

Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:

  • Mail & deliveries: Collecting letters and packages so they don't pile up.
  • Plant care: Keeping your indoor or outdoor garden hydrated.
  • Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
  • Home security: Sitters can stay overnight to keep your home occupied.

The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Chester walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.

It’s helpful to think of house sitting as a "home base" service. Most sitters in Chester maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:

  • Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
  • Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
  • Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.

Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!

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 Chester 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!

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.

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 .

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

A Meet & Greet is a short introductory meeting between you, your pet, 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.

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.

Yes, you can find sitters who have experience with handling special pet needs in Chester. On Rover:

  • 94% of sitters can help with special care needs
  • 100% can help with giving oral medications or injections
  • 94% 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.

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