House Sitting in Chesterfield

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

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Top rated Chesterfield 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: Janet M.
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Janet M.
Star Sitter
$50
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: Ash T.
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Ash T.
Star Sitter
$62
total per night
5.0 out of 5 stars
119 reviews
50 repeat clients
12 years of experience
Florence, MA, 01062

Ash is GREAT with our pretty demanding standard poodle- i'd recommend Ash 100% except im greedy and i want to make sure they're always available for us when needed!!

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Gordon A.
Sitter Profile Image: Abigail S.
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Abigail S.
Star Sitter
$80
total per night
5.0 out of 5 stars
13 reviews
3 repeat clients
4 years of experience
Conway, MA, 01341

Abigail was a great sitter for our crew (2 dogs and 6 cats). She took thorough notes at our meet and greet, was super responsive and provided plenty of updates for us while we were away. It was clear that all the pets enjoyed her company and trusted that she was there to care for them. She left the house in great shape as well and even left us an adorable memento from her time caring for our pets. Would definitely want her to sit for us again!

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Jamison B.
Sitter Profile Image: Jaclyn P.
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Jaclyn P.
Star Sitter
$117
total per night
5.0 out of 5 stars
17 reviews
5 repeat clients
15 years of experience
South Deerfield, MA, 01373

Jaclyn goes above and beyond for the pets she cares for. We got lots of updates and pictures throughout the weekend, and the house was spotless when we arrived home. It felt like our pets were getting a vacation and not just adequate care. My dog was happy and exhausted on Sunday night. Our cat gave Jaclyn a bit of a hard time and was being protective of his space. Jaclyn was patient and a good sport, and Louie got over it quickly! Everyone was happy and stress-free when we got back. Absolutely nothing but good things to say! We'll be lucky if Jaclyn is available next time we need pet care.

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Natalie R.
Sitter Profile Image: Kristin H.
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Kristin H.
Star Sitter
$84
total per night
4.9 out of 5 stars
26 reviews
9 repeat clients
3 years of experience
Northampton, MA, 01060

Kristin was a wonderful cat sitter who took great care of my two kitties while I was away. She was conscientious and communicative, sending updates and photos keeping me well informed of everything happening back home. Highly recommended!

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Stacey N.
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: 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

Saige was amazing and took such great care of our fur baby. Isla is a 10 yo aussie shephard and full of energy and mischief. Saige was wonderful with her and I would HIGHLY recommend putting Saige's talents to work with your fur baby.

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julie s.
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

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: Annika D.
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Annika D.
$95
total per night
5.0 out of 5 stars
51 reviews
19 repeat clients
6 years of experience
Northampton, MA, 01062

Once again we came home to three happy fur babies!! She took excellent care of our animals and our home! We have used her services before and thankfully able to again for this vacation! I can’t recommend her enough! Thank you again!

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Lillie J.
Sitter Profile Image: Dorjee D.
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Dorjee D.
Star Sitter
$73
total per night
5.0 out of 5 stars
24 reviews
16 repeat clients
15 years of experience
Amherst, MA, 01002

About: I am intuitive and attentive to the animals feelings and needs. I focus on their happiness and well being. I engage constantly, feed them delicious nutrients, exercise them well and try to make our short time as positive as I can. I truly enjoy prioritizing and bonding with them! I have fostered dogs for over a year and have experience with all personalities and breeds. I am a full time student and I take care of pets part-time, but when they’re with me they will be my priority as if they were my own. Lots of outdoor time and playtime. During the academic calender I host one pet at a time. I may have a temporary foster dog, but most likely not simultaneously. During the academic breaks I am available all day. As a result, I may have two dogs at once on breaks, but never more than two. If you would like your pet to be sat alone, please communicate, or if you have any questions or concerns about socialization, feel free to let me know. I can crate train, but I have experience and am comfortable without. I want the animal to be as comfortable as possible, so they are free to treat my home as their own.

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 awesome. She watched our senior dog and our 2-year-old dog in our home for a week-long trip. She communicated very well and sent tons of pictures. She gave medications to our senior dog (who requires a lot of patience) and kept our younger dog well exercised. When our flight home got delayed, Lori was super understanding and flexible during the uncertainty. Our house was spotless when we got home. Lori is a true professional and we'd recommend her without hesitation. Thank you, Lori, for giving us peace of mind while we were away.

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Susan H.
Sitter Profile Image: Meghan C.
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Meghan C.
$45
total per night
5.0 out of 5 stars
2 reviews
10 years of experience
Northampton, MA, 01062

Meghan was absolutely wonderful with my high energy large dog. She kept constant communication with me and I really apprecaited all of the pictures. Meghan asked clarifying questions about August's pumpkin powder to add to his food. I am weary of having strangers take August for walks because he is very strong and reactive to other dogs but Meghan handled him well. I would recommend Meghan for anyone with a large dog and will definately be booking her again.

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Rachel K.
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: Betsabee T.
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Betsabee T.
$45
total per night
5.0 out of 5 stars
10 reviews
5 repeat clients
20 years of experience
Easthampton, MA, 01027

Betsy was great! She was so kind and communicative throughout the entire stay, sending regular updates and photos that put us completely at ease. Our pups absolutely loved her and it was clear they were in great hands. We came home to happy dogs! We’d book Betsy again in a heartbeat!

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Michael S.
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: Alexis K.
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Alexis K.
$89
total per night
5.0 out of 5 stars
100 reviews
41 repeat clients
30 years of experience
Northampton, MA, 01053

Alexis always takes such amazing care of my cats! She is truly wonderful with animals and I am so grateful for the high level of care she provides. Always happy to have her care for my babies🥰

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Juliana T.
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

We have an elderly and blind jack russel terrior who has a bit of an attitude and can be reluctant to get out and about but needs it. After meeting Bree I felt assured that she would do a great job taking care of our dog and the house. I was not disappointed. She sent me text updates and pictures which reassured me while I was away and asked questions as necessary. Most importantly, my dog was happy and content in the photos and when we got home. I will be a repeat customer.

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Pamela W.
Sitter Profile Image: Colin B.
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Colin B.
$167
total per night
5.0 out of 5 stars
17 reviews
2 repeat clients
26 years of experience
Deerfield, MA, 01342

Colin was amazing and took very good care of our dogs over a weekend while we were out of town. He was very detailed in capturing all the information about our dogs during his first visit before we left. He captured thorough notes and asked lots of questions while getting to know the dogs and took the time to meet them and walk them multiple times before we left. While we were gone, he kept us updated every day, even if it was just a "they are doing great" text and a picture. Colin is very responsive and we will definitely be asking him to watch our dogs again!

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Alex B.
Sitter Profile Image: James M.
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James M.
$67
total per night
5.0 out of 5 stars
69 reviews
19 repeat clients
5 years of experience
Boston Road, Springfield, MA, 01119

James was great. He watched my house for a couple nights at the last minute, which really helped us out in a pinch. He was on time, respectful, and good with our dog ace. He sent us pictures throughout the day. Left the house just as we left it. I would recommend him and will definitely reach out again if we need someone in the future.

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Brenden R.
Sitter Profile Image: Sonya M.
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Sonya M.
$56
total per night
5.0 out of 5 stars
6 reviews
3 years of experience
Northampton, MA, 01060

Sonya cared for our dog and cat for a week in our home. She was easy to communicate with and great with both pets. Both animals and our house were in great shape when we returned from our vacation. I would absolutely hire Sonya again!

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Jane R.
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Over 9
pet parents in Chesterfield have booked house sitting

Chesterfield pet parents share their Rover experiences

1 / 1
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

Sabrina is AMAZING! This was her first time with our dog and Blue took to Sabrina right away. Incredibly thoughtful and kind and I will most definitely be requesting her again. Thank you!

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Dana K.
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
5.0 out of 5 stars

Sabrina was great with our high energy dog, and very communicative. I would definitely have her dogsit Petoskey again!

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Breana O.
House Sitting
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Find pet care near you

How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

The median cost per night for house sitting in Chesterfield is $55

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

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

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Sitters in Chesterfield 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 Chesterfield on Rover as of Jun 2026 was about $55 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.

If you’re searching for a Chesterfield 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 597 house sitters in Chesterfield. 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, 86% of Chesterfield house sitters respond in under an hour.

House sitters in Chesterfield 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 Chesterfield.

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. Chesterfield 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.