House Sitting Chesterfield

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Chesterfield, Find top rated house sitting

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Amadie C.
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Amadie C.
Star Sitter
from
$60
per night
5.0 out of 5 stars
19 reviews
5 repeat clients
2 years of experience
Swanzey, NH, 03446

I'm so lucky to have found Ami. She was caring, my puppy loves her from the start. I felt very comfortable leaving my dog in her care. She was also very punctual and sent constant updates and great pictures.

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Dan W.
Sitter Profile Image: Elias V.
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Elias V.
Star Sitter
from
$75
per night
5.0 out of 5 stars
21 reviews
11 repeat clients
19 years of experience
Putney, VT, 05346

Elias did a wonderful job with Birdy. We are so happy to have found Elias. The house was neat as a pin. Birdy was well cared for. She had an immediate connection with Elias.

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Marybeth P.
Sitter Profile Image: Stephanie T.
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Stephanie T.
from
$80
per night
5.0 out of 5 stars
26 reviews
6 repeat clients
45 years of experience
Keene, NH, 03431

This was our first time working with Stephanie, and it won’t be our last! She communicated well and took great care of our dogs. Left the house super clean, too. We appreciate you, Stephanie!

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Lauren G.
Sitter Profile Image: Haley C.
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Haley C.
from
$100
per night
5.0 out of 5 stars
93 reviews
36 repeat clients
17 years of experience
Hinsdale, NH, 03451

Haley did a great job taking care of our cats while we are away. One our cats got sick while we were away and she provided us with details updates and pictures to make sure we knew what was going on.

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Myles D.
Sitter Profile Image: Benjamin J.
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Benjamin J.
from
$40
per night
5.0 out of 5 stars
1 review
10 years of experience
Dummerston, VT, 05301

Ben took great care of our sweet but shy Niela-Phyu, a 75lbs female Great Pyrenees for 10 days at our house. We came back to a happy, obviously often brushed dog in a clean house (which is a challenge with a shedding dog in summer and well watered garden). Notes on walks, events (tick removal ;) - thx) etc on top of many updates awaited us on return. Can only highly recommend Ben and thank you again for an amazing job.

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Trudy D.
Sitter Profile Image: Louisa M.
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Louisa M.
from
$63
per night
4.9 out of 5 stars
65 reviews
31 repeat clients
15 years of experience
Brattleboro, VT, 05301

Louisa cared for our dog and cat (and house) for 3 days and 2 nights. She was very prompt, communicative, and shared plenty of photos of the pooch and kitty during her stay. Both Kitty K and MollyMo were quite pleased with all of Louisa's pampering and we are quite grateful.

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Jamuel S.
Sitter Profile Image: Mackenzie G.
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Mackenzie G.
from
$40
per night
5.0 out of 5 stars
4 reviews
20 years of experience
Putney, VT, 05346

Mackenzie was great! She was responsive to my request, informative and clearing caring. She was all I could wish for in a pet sitter! Highly recommend her!

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Christine T.
Sitter Profile Image: Nadine N.
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Nadine N.
Star Sitter
from
$150
per night
5.0 out of 5 stars
12 reviews
4 repeat clients
20 years of experience
Keene, NH, 03431

What a dear person. Nadine is a natural with knowledge and a love of animals. She showed great judgement, and was kind enough to let me know when our cat was in for the night. She was thoughtful, and clearly is great with animals. Our cat was thoroughly in love.

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Victoria F.
Sitter Profile Image: Lori L.
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Lori L.
Star Sitter
from
$120
per night
5.0 out of 5 stars
100 reviews
39 repeat clients
15 years of experience
Greenfield, MA, 01301

We had a great experience with Lori house sitting our American Bully & Pit mix. Lori asked questions ahead of time, reviewed our instructions, and sent us text and photo updates. We couldn't have asked for anything more. We really appreciated all of her communication.

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Courtney B.
Sitter Profile Image: Karen K.
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Karen K.
from
$75
per night
5.0 out of 5 stars
6 reviews
2 repeat clients
15 years of experience
Vernon, VT, 05354

Yes, yes, Karen took great care of our pet, Cinder, and our home while she was here. Easy communicator, responsible, and kind. I am so glad to have found Karen and look forward to calling on her again!

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Sara S.
Sitter Profile Image: Kendra K.
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Kendra K.
from
$70
per night
5.0 out of 5 stars
66 reviews
15 repeat clients
20 years of experience
Warwick, MA, 01378

Kendra was a gem to have take care of our pets. She is a kind and caring person who truly understands the animals. She has a background in animal behavior and immediately understood how to give the time needed for our nervous dog to settle down and become comfortable with her presence. Kendra asked numerous questions regarding the pet's needs and personality. While we were away, she sent lots of photos to keep us up to date on the home front.

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Jaye P.
Sitter Profile Image: Grace Z.
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Grace Z.
from
$90
per night
5.0 out of 5 stars
5 reviews
1 repeat client
10 years of experience
Keene, NH, 03431

Grace was fantastic! She was warm, bubbly, and instantly connected with our dogs—they were snuggling with her before we even left the garage. She was incredibly flexible and kept us updated with pictures throughout the stay. She gave us so much peace of mind, especially with our 14-year-old senior dog. We’d love to have her back anytime!

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Caroline K.
Sitter Profile Image: Nicole F.
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Nicole F.
from
$60
per night
5.0 out of 5 stars
1 review
4 repeat clients
2 years of experience
Hinsdale, NH, 05301

About: Hi! I'm Nicole. I'm a software developer & animal lover. I've been around dogs since I was little and have always wanted to adopt one. Caring for dogs with busy owners is a great compromise! Dog owners will love that I will treat their furry pal as if they were mine. They will also love that I have private outdoor space for playtime, anytime, and am right next to central park so there's alot of ground for your furry friend to explore! I truely care about your pets well being so I am consistent with feeding time and will always make sure your furry friend is comfortable, whether its brushing her or refilling her water bowl. I am available Wednesdays and the Weekends for pet sitting, walking, and house sitting. If you are going away for a weekend and need someone to house & pet sit, I'm your girl!

Sitter Profile Image: Tiffany M.
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Tiffany M.
from
$80
per night
5.0 out of 5 stars
2 reviews
1 repeat client
10 years of experience
Newfane, VT, 05345

About: I grew up with animals my whole life and I’ve helped taken care of friends and families animals. I also used to work at a farm and help with those animals many times. I have two babies at home that I take care of 24/7. I’m a stay at home mom who would have plenty of time on my hands every day. I have a big backyard where pups can go out and walk and have fun. I have a dog crate if needed and I have a dog of my own and cats of my own for your fur babies to love.

Sitter Profile Image: Hannah T.
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Hannah T.
from
$75
per night
5.0 out of 5 stars
1 review
8 years of experience
Swanzey, NH, 03446

About: I’ve taken care of a tons of breeds of pups. I have taken care of dogs from puppies to older dogs as old as 17 years old. I have been taking care of dogs ever since I was little. I am able to walk, feed, play fetch, provide overnight care, and make sure your home is safe and sound while you need assistance. I look forward to meeting your pups! I’m able to provide care for your pups as I have a flexible schedule and am able to work around when you need assistance with your pups! I will care for your pets and give them attention constantly. I wake up early and feed them, and make sure they are all set for the day. I will snuggle with them and make sure they are safe :)

Sitter Profile Image: Brandy V.
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Brandy V.
from
$80
per night
5.0 out of 5 stars
11 reviews
3 repeat clients
18 years of experience
Newfane, VT, 05345

Brandy was fantastic! My dog is not easy due to anxiety and fear (she is a rescue). Elly didn't take that long to warm up and once she did they were able to stick to her regular schedule. Brandy was understanding and compassionate to where Elly was emotionally. She took her for great walks and played with her. Brandy sent pictures and lots of updates. Also Brandy was respectful of our house and left it as she found it. I would highly recommend her to anyone and will definitely ask her back. Thank you!

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Rachel S.
Sitter Profile Image: Tessa H.
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Tessa H.
from
$70
per night
5.0 out of 5 stars
3 reviews
1 repeat client
8 years of experience
Springfield, VT, 05156

Tessa is amazing!! She's very communicative and was punctual. My Fozzie took to her right away and I didn't need to worry he was alone. Thank you SO much!! We'll see you soon!

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Aimee K.
Sitter Profile Image: Leslie M.
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Leslie M.
from
$32
per night
1 year of experience
Brattleboro, VT, 05301

About: hi! I am new to pet care, I have taken care of children my whole life! I am Looking forward to gaining experience and knowledge! I am a college student first so I tend to only sit during the weekends, or after class on weekdays if necessary. I’m slightly flexible though! Feel free to reach out :) In your home, I do my best to keep everything just the way your pet (and you!) like it. I follow your routines, stick to their feeding and potty schedules, and give lots of love and attention so they feel totally at ease while you’re away. I’m tidy, respectful, and treat your space like it’s my own. In my home, your pet will be treated like royalty—with a comfy place to nap, toys to play with, and plenty of one-on-one attention. I only take in pets I know I can fully care for, so your furry friend always gets the time and love they deserve. Whether I’m visiting them or hosting them, I make sure every pet feels safe, special, and very, very loved.

Sitter Profile Image: Elizabeth G.
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Elizabeth G.
from
$28
per night
4.8 out of 5 stars
12 reviews
1 repeat client
5 years of experience
Bellows Falls, VT, 05101

Lizzie was great with the dogs and everyone was happy on our return. Lizzie was on time and dependable. Everyone was loved as one of her own. I would definitely recommend.

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Amy H.
Sitter Profile Image: Amanda P.
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Amanda P.
Star Sitter
from
$35
per night
4.9 out of 5 stars
34 reviews
9 repeat clients
20 years of experience
Winchendon, MA, 01475

Amanda was awesome. My Nani girl who is leery of strangers took to right away upon meeting her the first time. She kept in contact and let me know how the pups were doing and sent pics too. All the dogs seemed very happy and calm when we got home.

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Kelli S.
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The median cost per night for house sitting in Chesterfield is $60

Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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 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.

Meet local sitters who will treat your pets like family

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

Sitters in Chesterfield average 3
repeat house sitting clients

FAQs for House Sitting - Chesterfield

Frequently asked questions about Rover

As of July 2026, there are 255 sitters on Rover offering House Sitting across 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 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 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 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 Chesterfield. On Rover:

  • 82% of sitters can help with special care needs
  • 100% can help with giving oral medications or injections
  • 95% 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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