House Sitting Pittsfield
Find a loving house sitter to watch over your pets and your home.
Pittsfield, 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.
“This was our first time requesting house sitting and Erin was punctual, reliable and sent us multiple pics/updates on our pets. She put our minds at ease being gone over the holidays.”
“Excellent dog sitter- our first time with our older (and slightly finicky dog Zeus). This sitter put us and our dog at ease- offering to come for a meet and great. Zeus even was eating well for her which has not happened with a first time pet sitter in the past. A great communicator. Will use again.”
“We had Alex watch our pups during our wedding weekend, and they loved her. Each picture she sent of them they were clearly having a great time, doggy smiles all around. 10/10 would book again.”
“Kiera is amazing!!! Right away the dogs took to her and loved her. She is professional and returns messages immediately. After our first use of rover she has eased our minds that the dogs are in great hands while we are away. I think they had so much fun that when we got home the dogs were bummed out that Kirra wasent there :) I would highly recommend Kirra and we will be definitely be using her and Rover again.”
“Melissa was very understanding of our very excitable dog and worked great with him. Felt very at ease trusting her with our pets and would absolutely book again if we are in need!”
“Fawn did a great job with Marlo while we were away. She is very responsive to my communication and reached out on the first day with an detailed update. Marlo was happy around her and will definitely hire her again.”
“Bridget was great and Vanessa loved her. I appreciated the daily updates with videos & photos. It was our first time trying in home care while we were away and we are very pleased with Bridget as our choice. We will definitely rebook when we go away in the future.”
“We are so happy we found Eleanor on Rover. We needed to find a less traumatic experience than overnight kenneling for our two boys and found our way to Eleanor. She responded very quickly and soon after we had a great meet and greet. The boys LOVED her from the minute she came in. We visited for a long time and decided it was a match. This was an overnight stay while we traveled, which is a first for us, so we were a little nervous. But from the moment she came in, the boys were all over her. We couldn’t have been happier with the attention she rained on them and the updates and photos she sent to us. We were proud dog parents at the company Christmas Party 🎄☺️ When the next event takes us away overnight, Eleanor will be our #1 choice to stay with our boys.”
“Katie is very responsive. She did an amazing job taking care of my two dogs. She was thoughtful and loving and even provided me with pictures. I would hire her again if I need someone”
“Took wonderful care of our large, spoiled, dog and two cats. Received daily reports and pictures. It was great having a house sitter. I would definitely recommend Melanie to all and would welcome her to again care for our precious pets.”
About: I’ve been surrounded by dogs and cats my entire life, so caring for pets has always come naturally to me. While I’m not able to have any furry companions of my own right now because of my current living situation, I truly miss having them in my life. I’d love the opportunity to give your pet plenty of love, attention, playtime, walks, and, with your permission, a few well-deserved treats! I’ll care for your pet as if they were my own, making sure they feel safe, happy, and loved while you’re away. I currently work full time at home Monday-Friday 8:00am-4:30pm however, my schedule is flexible and I am able to take breaks throughout the day. I can make almost anything work with enough notice. I provide care in my client’s home so pets can stay in the environment where they feel happiest and most comfortable. I understand that keeping their normal routine helps reduce stress while you’re away. I’ll make sure your pet receives plenty of attention, exercise, playtime, fresh food and water, and lots of love. I’ll also follow any specific care instructions you provide to ensure your pet’s routine and needs are met every step of the way.
About: I worked at Petco in Virginia for three Summers me and my wife have had animals since we've been together which is 20 years just looking to take care of other people's animals and get some exercise at the same time. We'll be doing it part time I will not be working at any other job this will be my job that I will be doing have to take it easy I've been working hard for the last 30 years I have a routine we take our dogs out at least four times a day to go potty we do walk them around and our big yard they get fed on a regular basis I do have cats outside which are dogs get along with and all of our animals are potty trained so we work with them on making sure they're potty trained they don't misbehave when people around so I'm pretty much good with animals.
About: I’ve always had a love for animals ever since I was small. I want them to have the best life they can, so I make sure to do things right for them! I’ve had pets of my own (like fish and hamsters) along with the family dog that I’ve cared for, and I have also assisted other family and friends with pet sitting before. I am currently a bridal stylist at David’s Bridal and am busiest on the weekends. I am very flexible during the weekdays, and if timing allows I’d love to help you out on a weekend too! I am committed to following all instructions given to me for your pet. I want everyone to be as comfortable as possible, meaning that I will try and keep their routine as close to normal as possible.
About: I treat every dog like family, providing loving, dependable care. I’m patient with puppies, gentle with senior dogs, and always keep owners updated with photos and messages. Pet care fits naturally into my weekly routine, allowing plenty of time for walks, playtime, feeding, cuddles, and giving each dog personalized attention every day! I will provide personalized care for each pup, following each pet’s routine with feeding, walks, playtime, cuddles, medication if needed, and a safe, comfortable environment
About: I am a resent college graduate from UWEC and just moved back to Green Bay! I’ve had dogs my whole life and throughout college I would foster dogs for a day or two with my roommates to help socialize and make sure they got someone one on one play time! I am currently working part time right now so I have plenty of free time throughout the day. I am primarily free from 12pm-6pm for walks! For my own dog I make sure she has plenty of time outside everyday, she is normally on a long leash but always with supervision. She is getting a little older so I make sure to get her out on at least one walk a day.
“Sasha is so great with our two dogs. They love her energy and have so much fun when she’s around. She takes them on walks, takes excellent care of them, and gives regular updates! She is our go-to dog sitter currently!”
About: I have 2 dogs myself, springer spaniels who are full of personality and energy. My pet sitting experience has been going on for almost more than 6 years now. On many accounts I have stayed for a week at a time to dog sit. I have watched all kinds of dogs from a French Bulldog to a Bernese mountain dog. I love nothing more than to spend time with dogs whether it’s walking them or just hanging out with them! I live in Appleton in the summer and winter for winter break, and in the fall and spring I live in De Pere! I am a sophomore at St. Norbert College and I am on the women's soccer team. On M/W/F I have classes from 9-1, on T/Th I have class from 8-11:30. I can definitely work around those times!! My dogs are home are extremely spoiled, so that carries over to whichever dog I get to pet sit. Little things like making sure they are walked/exercised everyday, water is filled, and a healthy amount of treats :)
The median cost per night for house sitting in Pittsfield is $50
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. Search
Browse profiles of sitters near you who offer house sitting
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
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Popular requests for house sitting - Pittsfield
Select a filter and find qualifying sitters offering house sitting.Sitters in Pittsfield average 4 repeat house sitting clients
FAQs for House Sitting - Pittsfield
Frequently asked questions about Rover
As of September 2026, there are 301 sitters on Rover offering House Sitting across Pittsfield. 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 Pittsfield 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 Pittsfield 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 Pittsfield 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 Pittsfield. On Rover:
- 82% of sitters can help with special care needs
- 95% can help with giving oral medications or injections
- 100% 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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