House Sitting Pittsfield
Find a loving house sitter to watch over your pets and your home.
Over 12 pet parents in Pittsfield have booked house sitting
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.
“As always Tim has done a wonderful job with Dunkin. Unfortunately, he will be leaving the area soon and I won't be able to use him anymore. If he ever comes back, I will definitely be using him again.”
“We rebook Erin again and again! She is responsive, always sending updates, and gives us the peace of mind we need when traveling and leaving senior cats at home in her fantastic care.”
“Kim is the most phenomenal person for pets and house and everything in between. Her attention to detail and true genuineness is unmatched. Good people still exist and Kim is one of them. I will definitely continue to seek her out for our family. She loves the animals and really understands each pet and their different needs and adapts to whatever the challenge may be, effortlessly.”
“She did a great job with my two boys. She communicate daily and even took the time to do somethings I told her on how to extra spoil them. I can honestly after a few years of trying I've finally found someone I trust dog/housesit.”
About: I have taken care of family, friends, and neighborhood, pets since I was young! From meeting all of the new pets I have learned that each has their own unique personality-no two pets are the same! With that comes different approaches to earn their trust and create a bond. I am currently on summer break from teaching so my days are pretty available for the next few weeks. Once school starts my availability will change to the later afternoon. I am a very versatile pet sitter! I have spent time with pets where they just need some company and they get all the love, some want all the love and a nice walk outside. My two fur babies are polar opposite energy wise so I know how important it is to meet the needs and play with one of my cats, and how the other just needs someone to give her a lot of love while she naps!
“Maddie watched our dog sugar and turtle Jerome while we were away, she kept us informed by sending daily updates and pictures. We can’t recommend her enough. We will definitely be using her for all future outings. She was great!”
“Kelly watched our two dogs in her home while we went away for a long weekend and she was amazing! I really dreaded leaving them, but her regular updates/pictures put my mind at ease right away. I could see that they were staying busy, getting lots of love and overall, in great hands with Kelly. I'm so glad to have found her!”
“Liseli is one of the nicest people I have met. My dog Jessey absolutely loved her from the moment she stepped in the door. She’s a fabulous communicator and incredibly neat. Perfect dogsitting experience! Thanks, Liseli!”
About: I've been providing neighborhood pet care since I was 11. Short walkies with tiny terriers, long trails with Labrador retrievers, dog parks, training exercises, puzzle feeders, I've done it and enjoyed it all. I like to make friends with our canine companions, and help them feel safe and secure in the absence of their favorite human(s). I have experience giving pills and administering daily shots, like insulin. I work remotely, so my time is freauently on my own schedule and at my own pace. Having an animal to care for is an added bonus that is easy to work around, and forces me to remember my exercise! Dogs staying at my house get 2 longer walks and a shorter walk per day, depending on age, energy, and ability of the dog. I also try to incorporate a special enrichment activity every day. Example: dog park, trail, swimming, long play/training session, suited to the dog's interests and abilities. The dog's space in my house is also where I work, so I spend a lot of time hanging out with your dog. At your house, I'll ask for their favorite toy or play routine, to keep their space consistent until you come back. I love to put on an audiobook and take dogs on a "sniff walk" where they can just sniff to their heart's content, such great enrichment for their strong noses.
“Truly, there is no one better. Andreas knew exactly how to treat our dog like family. So communicative, warm, and he goes above and beyond. We were so grateful to have Andreas watching our dog.”
“Jessica was an exceptional caregiver for my 14 year old Cavalier. She was diligent in giving medicine and made sure he was comfortable at all times. She stayed in my home for a week and kept it spotless. Jessica sent pictures, updates and videos daily, which was greatly appreciated. My dog loved her. I definitely recommend her and hope to have her stay with my dog again.”
About: I have cared for both dogs and cats and I will care for yours like it is my own at all times so I hope you choose to hire me I am retired with plenty of free time for your animals and I would love to care for them like they are mine to care for I have a yard and a lovely home and I will always leash your dog when outside for safety and I like to kennel dogs when they sleep at night
“Ann was a great pet and house sitter. Our pets (Oscar & Lacey) loved her, I actually think they miss her. She was a great communicator and sent us photos while we were away. We would definitely ask Ann to sit again and again!”
About: I am always the first to be called when a friend needs doggy daycare or house sitting with dogs, cats, and often other animals. I’ve fostered and found homes for rescues internationally and domestically. I’ve worked for a doggy daycare where I was responsible for 50-70 dogs with a crew of 2-4 people. I also spent a few months off and on taking care of 10-22 huskies while part of the herd were sled racing. I’m comfortable with dogs of all sizes and enjoy seeing all of their unique personalities. I’ve loved animals since I was small. We always had cats when I was little, as well as ducks, chickens, guinea pigs, rabbits, my turtle boy China B, parakeets, and a Senegal parrot foster. I was surprised with a rescue dog when I was 10, Hemingway. It was an amazing experience and I helped train Hemmy to be a service dog for my grandmother who was visually impaired. Winter rates are now $250/day for basic overnights, includes 3 pets. Will adjust include extra rates accordingly to animals and household needs. I’m self employed and have the flexibility to set my daily schedule around your animals needs and regular routine. Lots of scritches, play time and love are part of my commitment to your pets. I am available for short and long walks (depending on your animals needs and ability), playtime, companionship, love and affection, meals and snacks as well as monitoring medication if needed.
“One of my favorite Rover sitters! Communication was great! Fallowed directions. I came back after a long day to happy tired dogs. Falisity walked and played with my dogs. If you are at Shore Hills campground look for her on Rover”
The median cost per night for house sitting in Pittsfield is $55
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
The average cost for House Sitting in Pittsfield on Rover is $53.96 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 87 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 administering medication or managing dietary requirements. You can also find pet sitters who accept only one pet at a time, which is ideal for anxious puppies 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 request a Meet & Greet to walk your sitter through your expectations.
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