House Sitting Pittsfield
Find a loving house sitter to watch over your pets and your home.
Over 76 pet parents in Pittsfield have booked house sitting
Pittsfield, 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%.
“Tara was so amazing with our dog and our cat. She sent us lots of updates while house sitting, took our dog for lots of walks, and gave them both lots of attention 😊 Great job with our pets and great communication. Would book her again in a heartbeat!”
“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!!”
“Rick & Autumn were fantastic. They stayed with our 2 crazy pups in our hotel room during our wedding. They spent over 10 hours with them and went above and beyond transporting them to our reception site for pictures and then bringing them back to the hotel. We would absolutely use Rick & Autumn again when we visit the area.”
“McKenna was incredible! My picky dog loved her right away, and she navigated his separation anxiety so lovingly and effectively. Her knack and intuition with animals shows. She was extremely communicative, clear and thoughtful at every step. Can't wait to book her again!”
About: Hi! My name is Joss, and I’m a passionate animal lover with years of experience caring for pets. I’ve had dogs and other pets throughout my life, so I understand how important they are as members of the family. I’m responsible, patient, trustworthy, and caring, and I always make sure every pet feels safe, comfortable, and loved while they’re in my care. Whether it’s walks, playtime, feeding, administering basic care, or simply keeping them company, I’ll treat your furry friend as if they were my own. I know how much trust it takes to leave your pet with someone else, and my goal is to give you peace of mind while providing your pet with the attention, affection, and care they deserve. If you have any questions or would like to schedule pet care, please don’t hesitate to call or text me . I’d love the opportunity to meet you and your furry friend! I provide loving, attentive, and reliable care for every dog as if they were my own. I take dogs out for potty breaks at least three times a day and make sure they get plenty of exercise, playtime, and attention. I love taking dogs on long walks, visiting dog parks, going on hikes, and enjoying outdoor adventures whenever possible. Since I work part-time, I have a flexible schedule that allows me to spend quality time with your pet instead of rushing through visits. My goal is to make sure your dog stays happy, active, safe, and well cared for while you’re away. I can also keep you updated with messages and photos, so you always know how your furry friend is doing! Your dog’s safety and comfort are my top priorities. I live in a safe, clean, and pet-friendly home where dogs can relax and feel comfortable. I always keep a close eye on the pets in my care and make sure they’re supervised, happy, and well cared for at all times. I understand that every dog has different needs and routines, and I’m happy to follow your instructions to help them feel right at home. My goal is to provide a loving, stress-free environment where your furry friend feels safe, comfortable, and treated like family.
About: I have been loving and caring for dogs my entire life! Nothing makes me happier than spending quality time with a furry friend. I have experience with basic obedience training and grooming (including nail trimming), and I'm more than happy to take your dog on a long-distance walk if needed. I work from home, so your pet will enjoy around-the-clock company! I can board throughout the week and am available for short or long-term stays. I have a very friendly Beagle who will love becoming your pet's next best friend! If needed, I'm able to crate small dogs (below 25 lbs). Though I don't have a backyard, I'm near plenty of green spaces where your pet can enjoy time outside. Your pet can expect multiple daily walks, plenty of play time, and an experienced and caring sitter.
About: I’ve been around all types of dogs my whole life. I love each personality I meet and their uniqueness. The trust being built with your dog(s) is always something i look forward to gaining. I have a flexible job who are all dog owners and understand having more than one job. I live nearby and available if needed help. I am very observing. While my house they can roam fee or In my personal room. I do go outdoors to closed in dog parks or personally walk around the area or nearby park for extra space to explore.
About: I have had pets my whole life. I pride myself on caring for dogs the way you would. Walks, play and snuggles are just a must every day. Our 151/2 year old Wheatlie was given a ride/park adventure every day! My favorite activity of the day is walk-let me help you when you don’t have time to get out-your pet will feel good after a brisk walk! I am currently semi-retired so I am available for walks and care during the day. Our senior dog has passed so my attention is on caring for your pet the way I cared for my Wheatlie. I have a large yard for lots of fun! A typical day would involve play time, walks, treats, snuggles and scratches. Your pet is part of my family.
About: I have many years of experience caring for dogs, cats, bunnies and chickens and am comfortable with feeding, walking, playtime and daily care routines. I understand that every pet has unique needs and will make sure they receive plenty of attention and proper care! I work remotely, providing me with a flexible schedule and plenty of time to care for your pets. I currently work remotely as a paralegal so I have plenty of time to tend to your pets. I do serve some nights but aside from that will be fully available for walks, potty breaks, feeding and all other activities. I have a large house with a big lawn. I also have a large crate and smaller carriers as well. I do have a pet bunny who will stay in my room and away from all pets.
“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.”
About: Hello! I've had animals my whole life and love being around them. I'm available to walk dogs and give them good exercise for those that have a lot of energy. I am also available to stay overnight to take care of your house and animals. My love for animals has pushed me to study to become a veterinarian technician. I also currently work at Berkshire Veterinary Hospital so I'm comfortable bringing them to the vet in an emergency. I am also able to medicate (orally or injected) your animals. I'm also comfortable cutting nails. I have the most experience with cats and dogs but enjoy taking care of all animals whether they are furry, feathered, or scaled. I have a very calm personality so most animals trust me right away and if they don't, I'm very good at earning it. Let me earns yours and you won't regret it.
“Taylor was great to work with. She communicated during her stay at our house about our dog who takes many medication and how he was doing. Even sent us a great picture of him lounging on the couch. I would recommend her highly.”
About: I have been a volunteer at the Berkshire Humane Society for about 6 months now working within the kennel and have been trusted with friends and family's dogs throughout my life! I have personally trained both of my large breed pups and have experience with both puppies and senior dogs! <3 I currently work part-time from Fri-Sun so I have full availability throughout the week to play with your pup(s)! I will always find the best time and place to give your pets what they need. I am not able to bring pets to my apartment, but will gladly give them all the care and attention they need in their home, or out and about!
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.
“Ashley and Bob were great with my 10 year old, nervous & quirky pup! They stayed at the house with her for 3 days and 3 nights and during that time, sent frequent updates and pictures. I was so grateful for their communication and care of my dog.”
About: I’ve been caring for animals most of my life, starting with my own cat who is now 11 years old. I’m very experienced with daily cat care, including feeding, litter box cleaning, playtime, and understanding their behavior. In addition, I’ve helped care for my family members’ dogs, handling walks, feeding, and general care. I’m comfortable with different personalities and make sure every pet feels safe, relaxed, and well cared for. I treat every pet like my own and always follow their routine closely. I work remotely and am a full time student, so during the summer I’m fully available for any dog or cat needs!! I’m happy to help out any time from 9am-10pm :) I their usual routine as closely as possible. This includes feeding, fresh water, walks for dogs, and litter box cleaning for cats. I also spend time with them so they feel comfortable and not alone. I pay attention to each pet’s behavior and needs, and I make sure they are safe, relaxed, and well cared for while their owner is away.
“Sally is amazing. She sent me pics and updates about my boys every day. She took care of my home leaving it cleaner than when we left. I enjoyed my vacation with complete peace of mind.”
About: As a dog and cat owner myself, I’m happy to treat any pets as my own. I have two pets, an elder dog and a cat who both have unfortunately needed medication throughout the years, so I’m experienced in administering medicine to pets. I’ve also fostered dogs and cats with all types of different personalities, and love running along with dogs and cats alike. 😸🐶 I’m a college student and have finished all my classes for the semester, meaning I have plenty of time to help out with fur babies. I’m used to incorporating my own pets into my routine, so any pet schedule works with my own! I’ve fostered both dogs and cats before, so I’m experienced with crating and transporting dogs or cats. Whatever you need for your pets in your home I’m happy to offer!
About: I have years of animal care experience. Starting with watching my GSD and American Husky as a teenager. I personally own a cat and an American Staffordshire Terrier mix. I have experience with large dog breeds, medium, and small. I currently am in school asynchronously, therefore allowing me full time scheduling for pet care needs. I also have a work from home position outside of Rover that allows me to adjust my own hours. 1. As a responsible dog sitter, I prioritize the well-being and happiness of your furry friend by ensuring regular walks, playtime, and affectionate attention throughout the day. 2. Your dog's comfort and safety are my top priorities, maintaining a clean and welcoming environment while following any specific care instructions or dietary needs provided. 3. With frequent updates and photos, I aim to provide peace of mind to pet owners, reassuring them that their beloved companion is in good hands and receiving the care and attention they deserve.
“Brenna was an amazing pet sitter for us. We have two dogs, both seniors, and one with significant health issues. It is always hard to leave him but had our son's wedding in Canada to attend. Brenna sent constant updates and photos to ease our mind while away. They were very well cared for and loved. I would use Brenna again in a heart beat!”
The median cost per night for house sitting in Pittsfield is $60
Pet parents share their Rover experiences - Pittsfield
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?
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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
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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 3 repeat house sitting clients
FAQs for House Sitting - Pittsfield
Frequently asked questions about Rover
The average cost for House Sitting in Pittsfield on Rover is $55.5 per night (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of House Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for House Sitting. For more information on service fees, click here .
As of July 2026, there are 451 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:
- 94% of sitters can help with special care needs
- 100% 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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