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.”
“Tina was amazing staying with my dogs! She’s like an elderly dog whisperer and dealt with an unexpected snow storm and potty accidents with love and care. My dogs were so happy, would book again anytime!”
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
“My dogs love Angelica. They get so excited when they see her. Angelica kept me updated with pictures and texts. My dogs were healthy and happy after a 2 week sitting. While I was gone there was a plumbing problem and she handled it professionally. Keeping me informed daily. I would recommend her for your next trip.”
“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.”
“We couldn’t be happier with the care our dog Walter received. Alex was incredibly attentive, responsible and kept us updated with great communication throughout her two night stay. Walter absolutely loved her and so did we. It’s such a relief to know he was in such loving and capable hands. Highly recommend.”
“I absolutely adore Samantha! I went on vacation for 6 days and felt at ease knowing she was here with all my babies taking good care of them. I received pictures and messages daily letting me know how things were going. She also wasn't afraid to ask me questions which was amazing! I came home to happy animals. If you want a stress free vacation, book with Samantha! Thanks again for everything :)”
“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 give Melissa our HIGHEST RECOMMENDATION! She was a pet sitter for us for 6 days/5 nights! We just moved to the area and needed to find a responsible person to take care of our dog while we were out of town. Melissa was super responsive, highly professional and extremely trustworthy. Our pet has a significant medical condition and Melissa kept us updated and was extremely comfortable handling any special needs. She left our home in better condition that we left it. She went above and beyond to take care of our dog and we so appreciated it! We have used many pet sitters in the past, but Melissa was a step above all others!”
About: I used to work at Bark and Brew and occasionally dog sit! I have three of my own puppies at home so I have plenty of experience as well as also fostering dogs! I’m looking for something to do in my free time as well as making some furry friends 😊 I am currently working two part time jobs but I can help before or after either of the job when need be. I have lots of free time in the middle of the day between 12-4! I love interacting with pets as in playing with them or walking them! I make sure they get everything they need and more hoping to make their day enjoyable!
“Eleanor always goes above and beyond with handling my 3 rowdy young pups!! i’m a helicopter parent and have zero worries when i travel. my dogs love her and she’s been a huge blessing. 10/10 recommend!!!”
“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”
“Madisyn has been an on going and very reliable dog sitter for me. I will continue to book with only her as long as she is available to help. I have had a couple other dog sitters that did not show my Chubby as much love and care as she has.”
About: Animals have always been a huge part of my life. I’ve helped care for pets for friends, family, and neighbors for years, including feeding, walks, playtime, and giving them attention while their owners are away. I’m patient, reliable, and love getting to know every pet’s personality. I’m currently working overnight so I’m usually free during the day, around noon would be perfect but I’m pretty flexible as far as letting your dog out or feeding your cat if needed! As a pet owner living in an apartment with my own dog, I understand how important it is for animals to get exercise, attention, and time outside instead of feeling cooped up indoors. I make it a priority to keep pets active, comfortable, and emotionally cared for through walks, playtime, and quality attention. I always want every animal in my care to feel safe, loved, and comfortable in whatever environment they’re in
“Jane is a fantastic dog sitter! She took great care of our two aussies. They absolutely loved her and they were very relaxed when we got home. Our house was also well taken care of and clean when we got home. We will definitely be repeat customers!”
About: I have not only personal experiance talking care of dogs but also professional experience working at a dog daycare and boarding company. I can manage any size and any number of dogs and you can assure that your animal will be in capable hands. Having experience with a dog of my own that needs to go on at least three walks a day I will be fully committed to making sure your dog is exercised and ready for bed at the end of the day. I am here to make your dogs experiance as stress free as possible while you are away and provide them with the comfort and nessasary needs to keep them happy. There will be no need for you to worry so you can fully enjoy your time away from home.
About: Since I was one month old, I’ve been around animals. I treat them with respect, love, boundaries and instinct. They’re family, and should be treated as such :) I run my own business and make my own schedule, so animal care will be around your schedule. I would ensure your pet’s routines are accommodated. My house and yard are over 3 acres. if there’s a way in which we can care for your pet here, we will and will be quite happy
About: I have had cats since I was born and my whole life have helped take care of them. My life passion is cats and I currently have two of my own. I have experience in administrating oral, topical and injectable medications and have experience with cats with many personalities. I am working full time, so my availability varies, but send me a message and see if I’m available! I’ll do my best to accommodate :) I am always respectful of other people's spaces and act as I would like others to act while they are in my home. I always treat animals with care and respect and do what I can to make sure that they are comfortable.
About: I have lived with dogs my entire life and have always been drawn to them. My Dad jokes that he would love to be one of my dogs because they are treated like royalty! There are always 2 to 3 dogs in my pack at all times along with 1 to 3 fosters. I have been fostering for Happily Ever After Animal Sanctuary for about 15 years now and have been walking dogs at their Sanctuary facility for almost 13. I love to be around any dog of any size, but always have a soft spot for the shy guys or trouble makers:) I feel it's my job to do what I can to restore the animals faith in humanity after it was let down by the person who was trusted to take care of them. If you have a dog or dogs who need someone to come take care of them while you are away, I would love to do so! Or if you have a long day at work and would like them to get a walk, I can do that too:) Looking forward to meeting you and your dog soon! Missy I will do my best to work your needs into my daily routine. In home care is also an option for any day of the week... I have 5 acres with a fenced in yard and 5 dogs currently living with me. There is a heated garage and greenhouse for separation if needed and I also have kennels in all various sizes.
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
3. Book & Pay
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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 July 2026, there are 315 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:
- 90% 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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