House Sitting Cheshire

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

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Over 2
pet parents in Cheshire have booked house sitting

Cheshire, 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: Olivia S.
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Olivia S.
Star Sitter
$36
total per night
5.0 out of 5 stars
• 41 reviews
15 repeat clients
1 year of experience
Adams, MA, 01220

“Olivia was amazing! She was so great with our big guy and sent lots of updates so we were aware of what was going on without feeling overwhelmed. Absolutely will be booking with her again!”

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Kelsey S.
Sitter Profile Image: Sarah & Noah P.
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Sarah & Noah P.
$62
total per night
5.0 out of 5 stars
• 3 reviews
1 repeat client
10 years of experience
Pittsfield, MA, 01201

About: I have years of experience caring for dogs and cats, including feeding, walking, administering basic medications, maintaining routines, and providing lots of love, attention, and companionship. I mostly work from home but when I’m not home, my fiancé (who will love your pets just as much as me) is! I am always available! A Home Away From Home 🐾❤️ Hi! Welcome to our home! We’re a dog-loving family offering a comfortable, loving, home-away-from-home experience for your fur babies. My partner and I both share a genuine love for animals, and we want every dog in our care to feel safe, happy, and right at home. We have a spacious 2,500-square-foot home with a finished basement that provides extra room and flexibility for our furry guests. We also have a half-acre yard for outdoor time (currently unfenced, so all outdoor potty breaks are supervised and on leash). Our two resident dogs are Sophia, our 50-pound mixed breed, and Chowder, our 20-pound French bulldog. We understand that every dog has their own personality, preferences, and comfort level, so we take introductions at the dogs’ pace and make sure everyone has space to relax when needed. In our home, your dog is welcome to be part of the family! 🛋️🐶 We’re not a strict, no-furniture household. If your pup loves curling up on the couch, they’re welcome to join us. And if they’re used to sleeping in bed with their humans, they’re welcome to snuggle up with me, too! We want them to enjoy the familiar comforts they love at home. We aim to keep your dog’s routine as consistent as possible, including meals, potty breaks, playtime, rest, and plenty of affection. We’ll follow your instructions and do our best to make their stay as stress-free as possible. We’re also happy to send photo updates so you can see how your best friend is doing while you’re away. ❤️ We know leaving your pet with someone new takes trust. Our goal is for you to feel confident that your dog is being cared for like one of our own, with patience, attention, and lots of love. We can’t wait to meet you and your furry family member! 🐾

Sitter Profile Image: Caitlin H.
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Caitlin H.
$56
total per night
5.0 out of 5 stars
• 17 reviews
3 repeat clients
4 years of experience
Pittsfield, MA, 01201

“Caitlin was amazing! It was obvious that Ollie and Daisy loved her. She was very accommodating and took care of our pups with love and kindness. I would ask Caitlin to watch Ollie and Daisy again in a heartbeat! Thank you Caitlin!!”

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Kyle W.
Sitter Profile Image: McKenna P.
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McKenna P.
Star Sitter
$84
total per night
5.0 out of 5 stars
• 408 reviews
153 repeat clients
8 years of experience
Lenox, MA, 01240

“This was our first time using Rover and for our wedding weekend at that! McKenna was all-around phenomenal: Coming by early for a meet-and-greet, sending us updates and photos, and most importantly - she was great with our girl Skye ♥ She made both dog and pet parents completely comfortable, and I would one hundred percent recommend her to anyone! S+C”

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Sarah D.
Sitter Profile Image: Jacob B.
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Jacob B.
$56
total per night
20 years of experience
Lanesborough, MA, 01237

About: Hello, my name is Jake. I am a very outgoing guy with lots of energy which makes me the perfect candidate to play with and care for your pets. I’ve had pets my entire life and am very caring with animals. I will make sure that your pets are well maintained and cared for 100% of the time. I can follow instructions very well. I will also make sure that the experience for your pet/pets is as wonderful as I can possibly make it. If there is anything else I can do to make your experience with me as your pet care taker any better I will be right on top of that wholeheartedly. Thank you for taking the time to read my introduction. I look forward to working with you!

Sitter Profile Image: Lindsey S.
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Lindsey S.
$56
total per night
5.0 out of 5 stars
• 1 review
25 years of experience
Cheshire, MA, 01225

About: I've grown up with dogs & cats. I am very involved in rescuing & fostering & have plenty of experience with all sizes, ages, temperaments & am experienced with most medical issues/medicating regimens. My schedule for work is Monday- Friday 7:30-4 pm. I'm available from 5-10 pm weekdays for drop ins and walks. I have open availability for weekends to house sit, go on walks and do drop in visits. I am currently in the process of relocating to New Hampshire permanently. I work full time Monday through Friday and offer pet care on evenings during the weekday, and full time on weekends :) I'm experienced with providing care for difficult dogs and cats and have no issues being able to give medications.

Sitter Profile Image: Reymon B.
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Reymon B.
$111
total per night
5.0 out of 5 stars
• 4 reviews
1 repeat client
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.

Sitter Profile Image: Zoey L.
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Zoey L.
$89
total per night
5.0 out of 5 stars
• 2 reviews
10 years of experience
North Adams, MA, 01247

“Zoey was great! And our girl Millie is no easy German shepherd dog for just anyone to bond with,or trust. Also can be very difficult to walk, She gained her trust and kept us updated w pictures of her and the cat so we could enjoy a honeymoon family vacation. She went out of her way to even do the dishes. Highly recommend her services!”

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Butch D.
Sitter Profile Image: Nicole S.
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Nicole S.
$39
total per night
5.0 out of 5 stars
• 8 reviews
2 repeat clients
5 years of experience
North adams, MA, 01247

“Nicole and Terrenze took great care of my cats and pup. I will certainly hire them again next time I go out of town!”

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Whitney S.
Sitter Profile Image: Rita M.
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Rita M.
$70
total per night
2 repeat clients
18 years of experience
North Adams, MA, 01247

About: I’ve interned at my local vet clinic for two years now and have recently moved to a paid position as an assistant! through this internship i have not only learned substantial knowledge regarding pet care, such as how to most effectively administer medications, but also discovered my love for pet sitting, as i have become one of the veterinarian’s permanent pet sitter! i also plan to go to vet school after i earn my bachelors degree! i am currently enrolled in college, as well as working various part time jobs so my availability is limited at the moment, but i will try my best to arrange my schedule best for yours ( and your furry friend’s) needs! i’ll treat your furry family like my own! i come with treats ready (with permission of course) and never leave without a game of fetch or whatever else your babies might enjoy! they’ll definitely be the highlight of my day, so i’ll try to be there’s too!

Sitter Profile Image: Michael B.
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Michael B.
$56
total per night
5.0 out of 5 stars
• 5 reviews
24 years of experience
Deerfield, MA, 01342

“Michael was great watching Bonnie while we were out of town! He took great care of her and provided updates each day. The house was perfect when we got back and Bonnie was so chill. Will definitely be reaching out for his help again!”

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Caitlyn B.
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

“You could not find more thoughtful and caring people to genuinely love your pet than Kelly and Nabil. They prioritized Elmer’s health and happiness to the highest degree and made sure we received videos and photos every day. We feel very lucky to have them in Elmer’s life.”

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Joey W.
Sitter Profile Image: Samantha B.
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Samantha B.
$73
total per night
5.0 out of 5 stars
• 8 reviews
2 repeat clients
10 years of experience
Schodack Landing, NY, 12156

“Pets were happy and fed and my house was in great shape when I got home. Thank you for allowing us a worry free getaway!”

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Michelle F.
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: Brian L.
Verified Background Check
Brian L.
$77
total per night
4.9 out of 5 stars
• 159 reviews
84 repeat clients
20 years of experience
Schenectady, NY, 12306

“This was my first experience with Rover. Brian came over to meet our dog and make sure it was a good fit before we decided to use him. Brian sent pics and left our house in perfect condition. I highly recommend Brian!”

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HENRY G.
Sitter Profile Image: Sophie H.
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Sophie H.
$139
total per night
5.0 out of 5 stars
• 31 reviews
10 repeat clients
15 years of experience
Hudson, NY, 12534

“Sophie cared for our very active Australian Shepherd puppy, cat, and our home with love, skill, and the highest level of professionalism. She was very responsive and eased my anxiety over leaving my boys with pictures and prompt communication. I trust her completely.”

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Aimee M.
Sitter Profile Image: Evan N.
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Evan N.
$82
total per night
4.3 out of 5 stars
• 7 reviews
1 repeat client
10 years of experience
Albany, NY, 12203

“This was the second time for Evan to stay with Dale. Once again, it was good to know our older guy was being well cared for. Happy to have Evan stay with our boy.”

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Suzanne P.
Sitter Profile Image: Jeffrey S.
Verified Enhanced Background Check
Jeffrey S.
$173
total per night
30 years of experience
Falls Village, CT, 06031

About: Hi I'm Jeff an experienced and professional pet sitter, dog walker, and provider of overnight pet care, I offer loving, dependable service that brings complete peace of mind. Whether it's daily visits or extended stays, your pets are treated like family every step of the way. I'm fully licensed, insured, and bonded, and certified in Dog and Cat First Aid & CPR—so you can rest easy knowing your furry companions are in safe, experienced, and genuinely caring hands. I have over 25 years of construction experience. I also offer Handyman Services which can be done while I am at your home. 🐾 Licensed, Insured, and Bonded • Certified in Dog & Cat First Aid and CPR Caring for animals isn't just something I do—it's my full-time profession, my livelihood, and my passion. I take great pride in providing dependable, compassionate care for pets of all kinds, including dogs, cats, birds, fish, chickens, goats, rabbits, hamsters, gerbils, and more. When you entrust me with the care of your beloved companions, I go far beyond basic walks and feeding routines. Their happiness, comfort, safety, and well-being are always my highest priorities. While I know I can never replace your presence, I work hard to provide the love, attention, companionship, and personalized care your pets deserve while you're away. To make life easier for my clients, I also offer handyman and home care services. Whether it's watering plants, bringing in mail, managing trash and recycling, hanging pictures, completing small repairs, painting, or helping with other household tasks, I'm happy to assist while caring for your pets and home. By combining professional pet care with reliable home services, my goal is to give you complete peace of mind, knowing your pets are loved, your home is cared for, and everything is being looked after by someone who genuinely cares. 🐾❤️🏡 When you entrust me with the care of your furry companions, I go above and beyond basic dog walking and playtime; I prioritize their happiness and welfare. Understanding that I can never replace your presence, I tirelessly strive to complement your affection and care by providing the attention and love your pets deserve, even in your absence. I also integrated handyman services into my offerings, recognizing the convenience and practicality of addressing tasks while caring for your pets. Whether it's watering your plants, hanging a picture, managing waste or recycling, or even handling small repairs and painting, I am here to help. Through this fusion of pet care and handyman services, my aim is to simplify your life while ensuring the well-being of your cherished pets and your home.

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

Pet parents share their Rover experiences - Cheshire

1 / 1
5.0 out of 5 stars

Zoey was great! And our girl Millie is no easy German shepherd dog for just anyone to bond with,or trust. Also can be very difficult to walk, She gained her trust and kept us updated w pictures of her and the cat so we could enjoy a honeymoon family vacation. She went out of her way to even do the dishes. Highly recommend her services!

Profile image
Butch D.
House Sitting
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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.

How to book house sitting

  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.

Popular requests for house sitting - Cheshire

Select a filter and find qualifying sitters offering house sitting.

Sitters in Cheshire average 4
repeat house sitting clients

FAQs for House Sitting - Cheshire

Frequently asked questions about Rover

As of October 2026, there are 400 sitters on Rover offering House Sitting across Cheshire. 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 Cheshire 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 Cheshire 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.

<b>Tip:</b> 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 Cheshire 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 , 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 .

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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first .

sitters on Rover set their own , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.

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

  • 91% of sitters can help with special care needs
  • 95% can help with giving oral medications or injections
  • 97% 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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