House Sitting in Pittsfield
Find a loving dog sitter to watch your dog overnight in your home.
Every sitter passes an enhanced background check. Learn about RoverProtect
Top rated Pittsfield house sitters
“Jenniffer was awesome. Our dogs loved her and she took great care of our house. She took them on walks everyday and sent lots of pictures and updates. She coordinated letting people into our house and left it cleaner than we left it. She works from home, so our dogs got to go out whenever they wanted and got to sleep in our bed with her- like they prefer! The dogs were relaxed and happy when we returned. So excited to have a professional, compassionate person to look after our dogs from now on.”
“Emily was amazing! She was so good with my 2 pups. I am so thankful for the care and love she showed for Wallace and Wyatt in my home for 2 days. I love my dogs and it was so refreshing to know they were in such great hands while I was away, i was able to relax for once without worrying about them! I would recommend her to anyone.”
“Samantha was very friendly to us but most importantly to our 2 dogs. She went above any beyond and was very respectful to our home and left our place looking very clean in the process. I will definitely be contacting her first for any of our future needs! I highly recommend her.”
Over 7 pet parents in Pittsfield have booked house sitting
How Rover works
1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per night for house sitting in Pittsfield is $39
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 house 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.
House Sitting FAQs
Frequently asked questions about Rover
House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Pittsfield on Rover as of Jun 2026 was about $39 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.
As of Jun 2026, there are 26 house sitters in Pittsfield. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 75% of Pittsfield house sitters respond in under an hour.
Experience can vary widely from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when comparing house sitters available in Pittsfield.
Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Pittsfield house sitters are great for:
- Dogs who’d prefer to stay on their home turf
- Cats and caged pets
- Pet parents on a tight schedule
- Keeping an eye on your home and plants while you’re away
Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.
Connect anywhere with the Rover app
