House Sitting in Pittsfield
Find a loving house sitter to watch over your pets and your home.

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Top rated Pittsfield house sitters
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Erin was amazing! She answered promptly and took me on very last minute. My two dogs loved her and she made me feel very comfortable: as someone who has never used a sitter before! Will be booking again !!”

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!
About: Since becoming fully remote for my full time job in 2020, I have taken on the roll of “trusted pet-sitter” for over 30 families and almost 50 furry friends. Back home in Maryland, I connected with these families just through word-of-mouth and referrals from happy families. Now that I live here in Maine, I would like to continue my expertise and passion for animals, and connect with some loveable furry friends. I am an attentive, detail-oriented pet-sitter, who also knows the importance of respecting another person’s living space and maintaining routines for pets. After years of taking care of every size, shape and age of dog, no request from the owner is too wacky. From complicated medication directions to particular night time routines, I know your pet is part of your family and deserves to go about life as usual, despite mom/dad not being home. Reach out, I would love to connect! I work full-time fully remote! So while I will need WiFi and a desk to type on my laptop while I watch your pet, there is always time for walks, snuggles and whatever else your pet needs. My goal when I pet sit is to keep the pet in its normal environment and routine as much as possible. I am always very clean and respectful of any house I pet sit in.

About: I love all dogs but am especially fond of the giant breeds.🔅WILLING TO TRAVEL OUTSIDE OF RADIUS SHOWN🔅 I am mid 30s and I've always connected with dogs. I recently lost my dog after 13 years of spoiling her. She was our perfect dog, a bullmastiff boxer and a princess, so I know all about finicky dogs. I trained her as a puppy and we always got complimented on how well behaved she was. I know how stressful it can be to leave your pup and worry about them, I used to leave long lists of instructions for our girl and love it when I got text updates of her, so I will do the same for you. When we spoil them it speaks to the depth of our love for them, and that's something special to not entrust with just anyone. So if you have a "diva" or a "prince" I'm your gal. 😁 I miss being around a dog but I am not able to commit to my own right now, so I'd love to give your dog lots of cuddles and spoil them for you while you are away. I do not offer care in my own home or care for dogs dealing with incontinence because things are too fresh still. I do not offer care for dogs with aggression issues either. I feel it's important to make sure both the dog and I are comfortable, and therefore require a meet and greet to make sure it's a good fit. I work from home so I will be able to care for them and cuddle lots throughout the day. I will need to leave briefly in the evenings, but for the most part will be there with them. If your dog is trained to be off leash, I am comfortable with that as long as we do a meet and greet and you show me their responsiveness when called back. I am also fine with taking them out on a leash or letting them into a fenced yard, whatever is their norm. If hired for dog walking I'd prefer to do a meet and greet and go on a walk with you and the dog so you can show me their route and preferences to ensure we are both comfortable
“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 an absolute delight-our dog Winnie was super comfortable with her from the first meeting. Winnie was in great spirits when we got home. The house was in A+++ condition! Thank you, Liseli! So happy!!”

“As soon as we met Madison we felt so comfortable. She was so kind and loving to our dear dog Angel and was flexible with our unique scheduling needs. I loved the photo updates and reports. I could tell that Angel was happy and well cared for while we were away. We are so grateful for Madison!”

About: I was taking care of dogs since I was maybe 4 or 5 my family has relied on me to feed and watch the dog Every day when I get up I will take my dog for a walk feed them have play time then they them nap and go potty after I offer walking, house sitting and over night sitting I will also offer playtime and I will feed them and take them on another walk
“Kirsten did an amazing job watching our dogs! They loved her and she provided diligent, attentive care to them. Our dogs aren’t easy, from daily meds to allergies, they can be a lot to take care of and Kirsten managed it all perfectly. She kept us very well informed while we were gone, sending lots of photos and updates. She also was very neat and clean while she stayed over. I would recommend Kirsten highly to anyone seeking a trustworthy, reliable pet sitter! We are so grateful to her and can’t wait to use her services 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
Over 3 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 $53
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.
Sitters in Pittsfield average 4 repeat house sitting clients
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 Mar 2026 was about $53 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 Mar 2026, there are 36 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, 81% of Pittsfield house sitters respond in under an hour.
House sitters with repeat customers have an average of 4 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters 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.









