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.
About: I have over ten years of experience caring for fur babies of every kind! I grew up surrounded by animals, a passion that has blossomed in my adult years. In high school I worked in a veterinary setting where I was able to learn pet CPR & emergency skills. I am now a human mama to one baby boy who I plan to pass my love of animals onto, we practice and model gentle and respectful handling of all furry friends. I am an animal mama to two goldens, some chickens and a few cats. I work from home, so naturally, spend all my days doting on my fur babies and yours too! Your pets will always be treated with love, kindness & patience by me - whether in my home or yours! I work a very relaxed job from home so I am able to be available to your pet 24/7 for medicine breaks, snack breaks, walks, potty breaks, and scritches! I have experience with every pet type, from Great Danes to bottle fed kittens. If your pet is staying in my home - they can enjoy our fenced in backyard or our dedicated dog loft if they need some time to decompress. Otherwise, they’ll get to hangout with my family 24/7 which includes my two golden retrievers, Franklin & Jasper. Franklin & Jasper have never met a dog they didn’t LOVE. For peace of mind, our dogs will never be fed in the same space as your pet(s). We always welcome you to come see our home and meet Franklin & Jasper before your scheduled drop off date so that you can feel confident and stress free while out of town. If I am watching your pet within your home, my visits are extremely flexible. I am able to accommodate feeding and walk schedules seamlessly.

About: I have several years of experience caring for cats, dogs, birds, and snakes. Skills include elderly and disabled care for cats and dogs, grooming, playing, transportation, and some training. I currently work part-time and have a flexible schedule, so I have lots of time to care for your pets! I can do overnight care on weekends, drop-off after 1pm Friday - Sunday. I have a fenced-in pen in my backyard with a dog and a bird. I have treats and shareable dog/cat toys. I tend to spend lots of time outside with dogs. I tend to meet cats where they’re at, using toys and treats for the shy ones.
“Kayla is a friendly, responsible, hardworking pet sitter and a genuine lover of animals. I would 100% book her again. She had vast experience with all sorts of animals, and I trusted her completely with my pets. I wish everyone was as good as Kayla! Book her, you won’t regret it.”

About: Since I was in Middle School, friends, family, and locals ask me take out, feed, play, and stay with their fur babies! I have watched dogs for 2 weeks at a time, a weekend, a night, and even just a drop in. I have experience with puppies, adult, and senior dogs, and will go out of my way to make sure they feel loved while their pawrents are away! I’m currently working full-time, so I have plenty of time after work to play and take care of your pets! Even with a full-time job, your fur baby will be unconditionally loved, as I love my own. I grew up walking and taking care of my own dogs, as well as friend’s and local’s dogs. I’ve never been without a dog. I’m committed to doing everything I can to keep your fur babies happy, as they will be doing the same for me!
About: I have taken care of dogs for a majority of my life. Whether family dogs or my own. I currently have two pitbulls, who are my best friends. Im looking to help others in the community with any pet need they may need. Please reach out and dont hesitate to ask any kind of question! Starting at the end of October I am available Monday - Friday 7am - 4pm. Weekend and after 4pm availability if it works with my family's schedule. Never hesitate to reach out and ask!! I will be your pets best friend. Im full of energy to meet your pups needs or I can enjoy a good relaxing movie day too if thats what your pet needs. I will make sure they get to go out on walks, go potty, clean their poops up, make sure water is full, we can go on rides, to the doggy park if they are friendly with others, grooms, and much more!!

“Lisa and her partner were available last minute to stay at our home with our dog for a couple days. Our dog was immediately at ease with them and we enjoyed getting picture updates of happy snuggles, playtime, and walks. Great with communication and great with our pup - she was well cared for and relaxed and happy when we got home. All around a good experience!”


“Elise watched our pack this weekend and did such a great job! Leading up to the weekend Elise was very proactive in getting information on them and asking important questions. We were kept up to date on a regular basis with pics!! This made for a stress free weekend and allowing us to enjoy the wedding out of town! Highly recommend!!”

“Kelly is who you want to sit your pets and your house. She's so nice, so patient with all my communication, so responsive and responsible... It's obvious she loves animals, she immediately connected with my cat and my puppy, and they with her. And let me tell you, my puppy is not an easy dog to take care of right now. She's 16 weeks old and in full crazy teething, biting, nipping mode. It's definitely a challenge to be with this land shark. But Kelly handled her with grace. She also left our house spotless. I will definitely ask her to watch my babies again!”

About: *PRIVATELY INSURED✅ *CPR CERTIFIED/FIRST AID TRAINED 🩹 ***Please be sure to look through my entire profile, photo album and reviews before reaching out, thank you!*** Growing up in a small town in Vermont, where there were more cows than people, I developed a passion for all animals early on. I spent my summers in high school working with horses before working at my first dog daycare and haven’t stopped working with dogs since! Over the last decade, I have worked at well-regarded animal care companies in Vermont and around the Boston area and recently transitioned from a top-rated dog training/off leash hiking company to providing private, full-time dog care services. Fun facts about me: •I love sharks ◡̈ •I went to school for Graphic Design Serving Middlebury and adjacent communities, my mission revolves around the care and enrichment of my furry friends so I will be with your pup at all times! As someone who has worked with countless animals with many different personalities, making each one feel safe and welcome is most important to me. It is my job to create a clean, safe and fun environment. Your dog will have access to my fully fenced in private back yard with my supervision throughout their stay! I understand that every animal has different needs and desires and I will do everything to make sure your furry family member is comfortable!
About: I’ve been caring for pets for over 35 years, and I just love it! I have to travel for work which means I can’t have my own right now, so looking after others is a true joy. I naturally treat every animal as if they were my own — and making sure they feel secure, loved, and happy while their parents are away. With every sit, I bring both reliability and heart. Over the years I’ve cared for dogs, cats, parrots, chickens, and more — each with their own unique personalities and quirks. I’ve played with energetic puppies who needed training and adventure, given gentle support and patience to sweet seniors, reassured nervous or shy animals with steady routines & space, and comforted sick or elderly pets in their final days. One of the most important lesson I learnt came from my own senior dog, who had arthritis. Beyond medication, what mattered most were the little things. I could see from her body language that her favorite time of day was simply sitting together in the sun while I gently massaged her and talked to her. Those quiet moments made her feel safe and deeply loved — and they taught me how much presence and empathy matter in pet care. I work remotely with flexible hours, which means I can spend plenty of time with your pets — for walks, play, belly rubs, or simply quiet companionship so they don’t feel alone. While I’m new to Rover, I’ve been sitting through other platforms where I’ve built excellent reviews and references. Having hosted sitters myself, I also understand the trust (and nerves!) that come with leaving your pets and home in someone else’s care. That’s why I believe clear communication is key, and I’ll always keep you updated with photos, feedback, and check-ins so you can relax knowing your pets are safe, loved, and well cared for. My work is remote so I can be anywhere as long as I have wifi. I only work part-time with flexible hours which gives me the space to adapt to your pets needs & also have the time to for plenty of walks, cuddles & play. When caring for pets in their own home, I make sure their routines stay consistent so they feel secure — from feeding and walks to playtime and rest. I pay close attention to each animal’s signals, balancing structure with the affection, stimulation, or quiet companionship they need. Safety is always a priority. I follow your instructions carefully, ensure food and medications are given correctly, and keep doors, windows, and gates secure. I maintain a calm, clean environment so pets feel relaxed, and I treat every home with the same respect as my own. I’m a naturally tidy person who cleans as I go, so you’ll return to a home that feels just as you left it. Having hosted sitters myself, I fully understand the trust (and nerves!) that come with leaving your pets and home in someone else’s care. That’s why I believe strong communication is key. I’m happy to provide updates, photos, and even video calls as often as you’d like — so you can relax knowing your pets are safe, loved, and well cared for while you’re away.
About: Leave your dog with me and rest assured that they’ll be having the time of their lives; daily walks and hikes, lots of individual attention, cuddles, and love, and someone home with them most of the day to ensure they get what they need. It’s really important to me to create a safe, loving, and fun environment for your pup while they keep here. I strive to make your dogs stay at my farm special; my repeat client pups are always excited to be here when they’re dropped off. I love dogs, and any pup who’s staying on the farm will be treated like one of my own. I work from home, so i’m almost always home with the pups, and we spend a lot of time outside, hiking, walking, running, or working in the yard. I've been dog sitting since I was young, on and off. I'm also a livestock farmer who cares for livestock guardian dogs, cats, goats, pigs, chickens, and other animals on a daily basis at work. I have a pup of my own, 3 year old Luddy, who makes life better in every way! I'm comfortable providing basic veterinary care, based upon my livestock farming professional background, and will make sure your pet gets lots of exercise and play outside as i'm an avid runner and hiker. I work from home, as a farmer, so your dog will almost never be left alone. They can hang out in the house with me or out in the garden while i work, or in a fenced in portion of the yard. We usually go on a long hike, walk, or run every afternoon, and the pups are invited to sleep anywhere they’d like, whether it’s the couch, my bed, or their own bed or crate. I live in a house on a dead end road with 300 acres of wooded trails right outside my back door, where I take my pup Luddy on long hikes or trail runs every day. We’re far away from any car traffic and have a fenced in portion of the yard for pups to run around in. I spend a lot of time at home working in the garden, playing with Luddy, hiking, or running. Luddy is a very friendly pup who loves to play and wrestle with other dogs, and tends to tire his friends out...at which point he loves to fall asleep curled around another pup :)
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!
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
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, house sitters on Rover 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.

