House Sitting West Chesterfield

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West Chesterfield, 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: Janet M.
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Janet M.
Star Sitter
$62
total per night
4.9 out of 5 stars
17 reviews
7 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: Ash T.
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Ash T.
Star Sitter
$62
total per night
5.0 out of 5 stars
127 reviews
54 repeat clients
12 years of experience
Florence, MA, 01062

Ash has been amazing! Our pets love him and he does an amazing job with our animals. Our dog remembers him and loves the walks and cuddles 💕 we will always use Ash

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Becky S.
Sitter Profile Image: Lori L.
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Lori L.
Star Sitter
$134
total per night
5.0 out of 5 stars
100 reviews
39 repeat clients
15 years of experience
Greenfield, MA, 01301

Lori is great! She totally understands our dog's temperament and took him on many adventures while we were away. We think he had more fun than we did!

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Matthew H.
Sitter Profile Image: Paul J.
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Paul J.
$40
total per night
5.0 out of 5 stars
3 reviews
12 years of experience
Northampton, MA, 01053

About: I have cared and worked with cats and dogs since a young age. I will take my time to get to know your animals and they will trust and look forward to seeing me! I work as an educator, so my summer is open and super flexible. In July, I will be working from 8:30am - 12pm Monday through Thursday. Either way, I am a morning person. I love waking up and relaxing on the couch with the animals drinking some coffee or tea, and then spending the day on the couch or outside running around depending on their mood. I fully communicate with clients to ensure set boundaries and specific pet care needs. I can be hands on and active, or simply a presence in the room to ease anxiety.

Sitter Profile Image: Deborah K.
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Deborah K.
$56
total per night
40 years of experience
West Hatfield, MA, 01088

About: I have Joyfully shared my entire life with pets for 70 years now!! I speak Fluent Feline and Canine and have been a pet parent to dogs, cats, hamsters, mice, turtles and fish as a child and provided daycare for birds. I am also a Certified Level ll Reiki Energy Practitioner. My services include Housesitting, Drop-ins and both dog and cat walking! My beloved Josie used to love going outside on a harness and leash since she and brother Shadow were feral-born barn kitties and then “indoor only” rescue pets for 15+ years! My “Platinum Spa” Services include pet massage and Reiki sessions for an additional fee for Housesitting and Drop In clients. My Passion to care for other people’s pets as a new career/business stems from the tragic loss of both my feline companions at the end of 2024. I have decided to no longer own pets myself and to get my “Pet Love Fixes” by Pampering My Client’s pets as if they were my own!! I have maximum flexibility with scheduling 24/7 for all services in the 5 Colleges Area of Western MA. I am also available to travel outside my local area to provide pet, plant and housesitting services upon request. I provide a full menu of services at client’s homes including multiple walks daily on leash, outings to local dog parks and hiking trails, specialized diets and medications, senior and disabled pet care, active playtime, basic training reinforcement, photos and text updates on how your pet is doing with each visit. My exclusive pet massage and Reiki treatments can enhance your pet’s health and happiness under my care!!

Sitter Profile Image: Camron Q.
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Camron Q.
$50
total per night
4 years of experience
Northampton, MA, 01062

About: I've worked in multiple areas of animal care including breeding and puppy development, dog daycare, and veterinary care. I have experience caring for all different breeds and ages of dogs! I don't have much professional experience with cats, but I have lived with many cats throughout my life and am a huge cat lover! I do not have any pets myself as I recently lost my dog. So i am in serious need of some dog time! I am available any time after 2:00pm sunday-thursday and all day friday and saturday(: some days i am available earlier than that, typically sundays and mondays im available around 12:30-1:00pm. I am happy to accommodate any of your pet's needs! I can walk, play, just give love, whatever makes your baby feel the most enriched and happy. I know every dog and cat has their own specific needs and I'm very dedicated to that! I live in a small studio apartment. There is plenty of great space to take walks near my house (i live right on the bike trail) but i do not have a fenced in yard. If this sounds like it could be suitable for your pet, i'm more than happy to board them(:

Sitter Profile Image: Alexis K.
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Alexis K.
$89
total per night
5.0 out of 5 stars
101 reviews
41 repeat clients
30 years of experience
Northampton, MA, 01053

I am extremely satisfied with Alexis. I was nervous about leaving max for the weekend but Alexis took great care of him. She sent photos and videos the entire time (which was absolutely adorable). Max is happy and excited when Alexis come. I will definitely use Alexis again.

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Cheyenne N.
Sitter Profile Image: Megan F.
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Megan F.
$45
total per night
5.0 out of 5 stars
30 reviews
8 repeat clients
15 years of experience
Whately, MA, 01093

Megan was the best! She was prompt, very responsible, respected our home , & loved on our sweet pup ?! Meagan communicated & sent pictures frequently throughout our trip, which we asked her to do. She cleaned up after herself, as well as our Susie. We will definitely book again!

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Beth D.
Sitter Profile Image: Shawna B.
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Shawna B.
$76
total per night
5.0 out of 5 stars
9 reviews
4 repeat clients
15 years of experience
Westhampton, MA, 01027

Shawna provided wonderful care for our two small dogs who require overnight company. We are very satisfied with Shawna's level of care and would like to rebook her services in the future!

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Ray O.
Sitter Profile Image: Ryan M.
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Ryan M.
$56
total per night
5.0 out of 5 stars
2 reviews
1 repeat client
20 years of experience
Huntington, MA, 01050

About: I am Very experienced in both dog and cat care as I’ve been a dog dad for 13 years to a black lab and a 2 year old French bull dog. Absolutely love all animals, walking and sitting Included. I am available most nights and weekends for dog/cat walking and sitting.very mindful of details and any requests you may have. I love being active and outdoors so looking forward to hearing from you! I have much experience caring for dogs and cats of all ages. I am Reliable and responsible to you and your pets needs and looking forward to meeting your pup/cat🐶💛

Sitter Profile Image: Matt L.
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Matt L.
Star Sitter
$78
total per night
4.9 out of 5 stars
77 reviews
19 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: Saige G.
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Saige G.
$56
total per night
4.9 out of 5 stars
37 reviews
13 repeat clients
11 years of experience
Easthampton, MA, 01027

Saige was super polite, pleasant, and caring for all of my dogs needs. She brought my boy to the dog park, for walks, and kept him entertained. She was a perfect houseguest, and I will absolutely be booking with her again.

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Nicole B.
Sitter Profile Image: Julie G.
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Julie G.
$56
total per night
5.0 out of 5 stars
7 reviews
1 repeat client
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: 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: Katherine N.
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Katherine N.
$67
total per night
5.0 out of 5 stars
7 reviews
15 years of experience
Holyoke, MA, 01040

About: I believe the best care starts with getting to know each dog's unique personality, routine, and comfort level. No two dogs—or pet parents—are exactly alike. Whether your dog thrives on long walks and adventures, enjoys practicing a few training cues (with allll the snackies!), or simply wants someone nearby while they snooze, I adapt my care to what helps both of you feel comfortable and confident while you're apart. My current job, as I work predominantly remotely, has a fairly flexible schedule. Because of this, I'm fortunate to be able to spend much of the day with the dogs in my care—not just the mornings and evenings. For 15 years, I had the privilege of sharing life with my sweet service dog, Brady. Together we learned, trained, explored, and adapted through every stage of life—from first swims to ongoing training and nosework, and later to weekly physical therapy, acupuncture appointments, and our favorite "ba-ba-baloney" song that became part of Brady's nightly medication routine during his senior years. I loved loving my boy. He taught me early on that every moment, no matter how small, is an opportunity to bring comfort, consistency, and so much joy. I've been fortunate to spend time with lots of different types of dogs—from beloved family companions to comfort dogs in higher education and even municipal working dogs. No matter their role or personality, I genuinely enjoy the thoughtful, individualized connection that helps each pup feel confident, secure, and understood. Whether we're heading out on an adventure or relaxing together while I work, I'm happy to adapt each day to what helps your dog feel most at ease. If they thrive on a consistent routine or have a detailed medication schedule, you can count on me to keep things familiar and consistent. The same goes for communication. If you love updates, photos, and the occasional goofy dog selfie throughout the day, I'm all in. If you'd rather unplug and receive one thoughtful update each evening, I'm happy to do that, too. My goal is to tailor not only your dog's care, but your experience as their person. At the end of the day, my goal is simple: to give you peace of mind while you're away, knowing your pup is safe, comfortable, happy, and well-cared for. I work remotely, which means your dog gets promoted to coworker. My favorite colleagues just happen to have four legs. On the occasional day I head into the office for a meeting, I'm only about 15 minutes away from my home and have a full hour for lunch, making midday walks, potty breaks, playtime, and medication schedules easy to accommodate. My goal is to keep your dog's routine as familiar and consistent as possible while you're away My home is on a quiet side street with a fully fenced backyard and is less than a two-minute walk from a park, giving us easy access to open green space, plenty of opportunities to explore, and, for water-loving pups (with your permission, of course!), a splash pad on warm summer days. Whether I'm caring for your dog in my home or yours, my goal is to provide a safe, consistent environment that feels as familiar as possible.

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

Trista stayed overnight with our fur babies. She was so good with our 3 dogs. She put our mind at ease. She sent updates and pictures throughout the day. The pups were happy too :) Will definitely book again.

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Sylvia 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: Bree M.
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Bree M.
Star Sitter
$95
total per night
5.0 out of 5 stars
183 reviews
54 repeat clients
20 years of experience
S Deerfield, MA, 01373

Bree was fantastic! She is definitely an animal person who connected with our dog immediately. She sent fun pictures that reassured us how happy he and our cat were and also let us know she was remembering his meds and walks. She left out place as clean or cleaner than when we left. She was very open to communication. We would recommend her to any and all!

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Heidi A.
Sitter Profile Image: Amanda D.
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Amanda D.
$134
total per night
5.0 out of 5 stars
35 reviews
3 repeat clients
24 years of experience
Whately, MA, 01093

About: When I was growing up, I was always caring for at least two dogs and cats at my family’s house. Neighbors and friends also made me their go-to dog sitter when they went away. I have loved caring for two greyhounds, four loveable slobbering hunting hounds, a giant golden who always thought he was a puppy, and one super sweet bullmastiff. Since my landlords do not allow pets, I am looking to give my attention to someone else's canine. I am comfortable with all sizes of dogs. I especially appreciate dogs that behave well on leashes and like big walks. I would like to help care for dogs in the Pioneer Valley, ideally around Amherst, Deerfield, and Northampton. If you are looking for a trustworthy, reliable, and experienced dog sitter/walker then let's talk! I look forward to meeting you and your dog(s)! Cats are cool too 👍 This winter and spring I have flexible working hours. I would love to break up the working day by visiting your pet and going for a walk. I will always provide gentle and loving care to your pets whether that’s playing outside or inside. Wherever care is given, I will always be mindful about respecting your living space

Sitter Profile Image: Paisley R.
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Paisley R.
$50
total per night
5.0 out of 5 stars
5 reviews
1 repeat client
10 years of experience
West Springfield, MA, 01089

About: Hiya, I’m Paisley! I’m an avid animal lover, and have two four-legged little ladies of my own - Winnie (10), and Stella (4). I love meeting new pups of all different personalities. I’d be thrilled to meet yours and be their friend in need! I’m dedicated to making sure they’re treated as if they were my own. Thank you for considering me! I’m available Monday-Friday with flexible times, so I can work around what schedule is ideal for your best friend’s needs. Whether it’s a walk, a feeding, or play time - I’ve got you covered! I have two very charming little ladies at home. Your fur-baby will be taken care of as if they were my own. I have patience for all animals of any size, and have experience with nervous and anxious animals as well.

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

Pet parents share their Rover experiences - West Chesterfield

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5.0 out of 5 stars

Janet was absolutely wonderful. This was the first time I have had a stranger in my home caring for my dogs. (I usually have friends/family care for them). She was very loving towards my two dogs and sent me pictures daily. She took great care of my home and was tidy and overall a lovely person. I will be using her anytime I need dog care.

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Barra C.
House Sitting
5.0 out of 5 stars

Janet did a GREAT job caring for our girl, tons of walks amd company even with a 2ft snow blizzard during her stay. Kept the house amd took care of everything that came up too! Totally recommended!!

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Gordon A.
House Sitting
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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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Popular requests for house sitting - West Chesterfield

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Sitters in West Chesterfield average 4
repeat house sitting clients

FAQs for House Sitting - West Chesterfield

Frequently asked questions about Rover

As of July 2026, there are 561 sitters on Rover offering House Sitting across West Chesterfield. 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 West Chesterfield 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 West Chesterfield 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 West Chesterfield 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 West Chesterfield. 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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