House Sitting Pittsfield
Find a loving house sitter to watch over your pets and your home.
Over 77 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!”
“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.”
“We couldn't be happier with the incredible care McKenna provided for our beloved dogs, Raynor and Mojo. From the moment she arrived, it was clear she had a genuine love for animals, and our pups took to her instantly. McKenna went above and beyond, ensuring Raynor and Mojo were not just fed and walked, but truly loved and engaged. We received regular updates and photos that put our minds completely at ease, showing our dogs happy, playful, and comfortable in her care. Beyond her exceptional attention to our furry family members, McKenna also left our home in pristine condition. It was such a relief to return to a clean and tidy house, exactly as we had left it. McKenna is reliable, responsible, and truly a gem. We highly recommend her to anyone looking for top-notch dog sitting services. She treated our dogs and our home with the utmost respect and care. We will absolutely be asking her to sit for us again!”
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! 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.
“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.”
“Ashley did a wonderful job with my three pups! She quickly understood their personalities and all they needed. She took great care of the house and everything and we look forward to seeing her again soon! Thanks, Ashley!”
“Sally was wonderful and very patient with our crew who were adjusting to a brand new environment and definitely were testing boundaries. She was compassionate and communicative and I really felt like she appreciated all their unique little behaviors!”
“Keri was great! She was able to jump in at the last minute and stay at our house with our 2 dogs. She communicated regularly and sent lots of pictures of our pups. I think they liked her so much they didn't even realize we were gone!”
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.
“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!!”
“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.”
“Leona was wonderful with Romeo - he was really calm and happy when I returned. She communicated well, sent updates with photos and left my home better than she found it. I’m booking her for another cat/housesit right now!”
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.
“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!”
About: While working as a travel nurse, I had the privilege of staying in many homes with pets of all personalities and needs, giving me experience adapting to different routines and environments. I bring a calm, grounded, and intuitive presence that helps animals feel safe and at ease. I'm naturally nurturing (a mama to my own two kitties), attentive to the little details, and I truly enjoy building trust with every animal. My goal is for your pet to feel loved, comfortable, and well cared for while you're away, and for you to have complete peace of mind. I genuinely enjoy starting and ending my day with walks, playtime, feeding, and quality time with animals. My schedule is flexible, allowing me to provide dependable care while giving pets the attention, exercise, and companionship they deserve. I love being outdoors, so daily walks are something I truly look forward to, and I always make time for cuddles, enrichment, and keeping pets comfortable in their own routine. My parents have an elderly cockapoo who has taught me the importance of patience, gentle care, and paying attention to the little changes that come with aging. My husband and I also have two cats, so I'm familiar with their daily routines, from feeding and litter box care to playtime, affection, and respecting each cat's unique personality. I understand that every pet has different needs, and I strive to make them feel safe, comfortable, and loved every day.
“Julie was amazingly flexible, as our schedule was unknown, and was there when we needed her. More importantly, she was good with Ricky, took him out for walks as well as for his sanitary needs, and kept us regularly informed, with pictures. If we are in the area again we will seek her to assist us, and Ricky, again.”
“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.”
“Ashley was a fantastic sitter. She stepped in when my sitter fell through at the last minute and took great care of my very energetic 11 month old and 60 pound pup. Grace is an energetic pup and Ashley had no problem keeping her entertained; she even took her for car rides. Ashley was able to give Grace her medication and took her on multiple walks a day. She also took great care of my house, took out the garbage, and left everything in perfect condition. Grace was obviously very well looked after and Ashley's attentiveness made me feel comfortable being so far away from home for the first time. i would recommend Ashley for any and all types pet care and sitting. She was a lifesaver on short notice and I will use her any time I travel in the future.”
“Katie was absolutely lovely, and the pets got on with her really well. She sent through updates and photos, and made sure we felt comfortable (all on a holiday, too!) -- thank you Katie!”
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?
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
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
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 August 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 August 2026, there are 431 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.
Connect anywhere with the Rover app
