Pet Sitting & Drop Ins in Upper Hill, Springfield, MA
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Upper Hill pet sitters
Prices are estimates per visit for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
About: Animals enjoy my dog and I's company. Come unsure, leave longing to return. A visit will sure turn into a playdate and lots of misses and kisses. Your pets will feel right at home because the pets here aren't pets; their family. Whether they become extended cousins, or like brother and sister, your pet will feel like home away from home with us! Your pet has plenty of space to run around and if they're up for it will do so on their walks. Each of us have our own personality and here theirs can shine, grow, and learn to be in and create harmony with the world around them.
“Kaitlen was fabulous. She helped us out during a sudden emergency need we had. She went above and beyond to help take care of our dogs, keep us updated, and communicate everything. Definitely book her if you need care for your animals!”

“Went away for a few days to spend time with family for the holidays. Eryn stop In and checked up on my two dogs (feeding, watering, playing, letting outside and cleaning up after them.. Eryn did an excellent job and would use again and highly recommend!”

“I was lucky to find this wonderful family right before heading out on vacation, and I couldn’t be more grateful. From the very start, communication was clear, prompt, and professional. They were reliable and stuck to the agreed schedule, which I truly appreciated. My dog a 5 month old Standard Poodle who’s a giant ball of mischief connected with them right away. It’s clear they have tons of experience and, most importantly, a genuine love for animals. I had originally booked someone else who canceled last minute with a silly excuse… but honestly, I’m glad it happened because it led me to the right people. They deserve all the stars. Highly recommend!”

“Saktah is an amazing choice for anyone looking for pet care. She's incredibly timely with updates and great pictures to let you know your pets are safe and secure when you are away. We have one older cat with medication requirements and another with a special diet. Saktah took care of everything and then some! Her photos, videos and messages about your pets are second to none. Would use her again and recommend to anyone wanting the best for their pets. A++”
About: Since I was a child I have had pets in my life. I am an animal lover of all types. I have cared for fish, hamsters, gerbals, cats, dogs, even reptiles. I have helped family and friends with there pets, and have a good sense of how to undertand whatvthey need. I can bath, groom, give haircuts, and feed them if and when needed. I am willing to open my home to assist families in need. I do have a full.time job, but also have family who are all wonderful and willing to help where it is needed. I am the main care taker, I make sure to work my schedule around the best interest of the pet I am caring for. Your pet will never truly be alone. I have a fenced in yard, I have a friendly chihuahua and a playful, lovable cat. I have a separate and clean space in my basement if needed giving plenty of room to run and play with plenty of toys for pets. Let me not forget my fun and loving family which includes my husband two teenage kids and my self.
“Tori was the absolute best drop-in sitter we've had through Rover, and we are so sad she is moving. Tori was reliable and truly loved our dog like she was her own. She left detailed notes about how each visit went, including if she ate, drank water, or any odd behavior, and she always included LOTS of cute photos. I'm jealous of whomever gets to hire her next!”

“Thanks so much to Charisma for stopping by to let Indigo out & feed him! My first time using the drop-in option on Rover. Great communication, quick replies, & she kept me updated on Indigo with pictures & followed up with me when she left! I will definitely be using her again in the future! 😊”

About: Compassionate, reliable, and experienced pet lover who ensures safety, comfort, and joy for pets. Provides personalized care, detailed updates, and builds trust with owners. I’ve been pet sitting for 6 years both dogs and cats, in all different sizes. Working a flexible full time job at Allen University so I can adjust my schedule to you and your family’s needs. Will not be here for thanksgiving or Christmas. I prefer caretaking at a client’s home so the pet is more comfortable in their environment, and I can accommodate to their needs and yours. It also gives the opportunity to use their toys at home and keep them entertained.
“We previously used our neighbor for trips but would come home to very upset cats. We hired Adam for a week and could not have been more pleased. He was patient and attentive to our skittish kitties. We looked forward to our silly cat updates and pictures. Adam really but our minds and hearts at ease. He even won over our cats love and affection towards the end. Very exceptional care.”

“Jessiana took amazing care of our cat, Winston, while we were out of town for several days. Her updates and punctuality made us feel at ease. We were able to enjoy our vacation knowing he was in such good hands. Thank you again!”

About: I’ve taken care of dogs and cats ever since I was a child. We had a family kitty and other family members had dogs. I have experience taking care of families and friends dogs and cats, whether that was staying at their house and following their routines, taking the dogs out for walks, or simply popping in for their meal time. I have a soft spot for cats, but I’ve never met a dog I didn’t love! I currently don’t have a full time job and am applying to graduate school, so I am available when you need me! I am flexible and can work my routine around your pets’ needs. If you need me to stay over in your home, I will be sure to follow every instruction given, and treat it with the utmost care and cleanliness. I am a guest in your home, and am more than willing to follow any guidelines set by you. My goal is to be seamless and incorporate myself into your pets’ routines, as well as keep your home safe and secure.
About: Hi, I'm Julissa (joo-lee-sah)! I am 31 years old and have had pet dogs for my entire life. I used to volunteer at a shelter walking dogs and completed the orientation that went over recognizing animal body language. I am basically the designated pet sitter for my family and have experience with dogs of all ages and sizes (and some cats and small animals). Petsitting has become my main work at the moment, so I will be available as needed for any bookings to check in, play, feed, walk, and care for your pets. I regularly pet and house sit for friends and family and can adjust to the routines your pets are used to. I am always careful to follow any directions provided and make sure any gates, harnesses, leashes, etc. are secured. I do require meet & greets before confirming any bookings, not just to make sure your pets are fine with me, but so that pet owners and I can get a feel for each other as well and make sure we're all a good fit!
“Kayla was checking in on the animals while we were on a trip, she was awesome and made a few extra trips over to the house when we got stuck to make sure everyone was okay until we were able to get back. Super grateful for her!”

Upper Hill pet parents share their Rover experiences
Anna is absolutely amazing! I was so nervous to hire a “stranger” last minute for my trip but Anna made everything soooo stress free!!! She took perfect care of my pup, sent daily updates & was easily accessible via message! Anna is the best of the best!! ♥️♥️ so happy she is no longer a stranger !

I am so glad that I booked with Seth. He truly loves animals and treated my pup as if she were his own family’s pet. He engaged her in playtime and much needed cuddles. Seth is dependable and trustworthy. I appreciated the updates and pictures he sent faithfully after each and every visit. I will definitely have Seth care for my furry family again! THANKS for a job well done!

He is the best! Extremely dependable, diligent about following all directions and meeting needs of your animals. We have used him twice now and know our cats are in great hands! One warmed right up and met him every day with purrs and demands for brushing. The other was her usual, stand-offish self but still came out for a few sniffs and investigation. He respected their boundaries and gave them time to get to know him on their terms. He stays in great contact as well and we were very comfortable with him as a caretaker. We highly recommend him and wouldn't hesitate to hire him again. Thank you so much!!

Hannah was awesome dropping in to feed and care for our two cats. She was able to handle our cat’s medication and subcutaneous fluids like a pro, and was very communicative with updates. We would book her again no doubt. She is a top notch pet sitter! Thank you so much Hannah!

Nikki and Britney thank you for your committed and consistent effort ensuring Cali received the best care. From the start , we felt confident in your abilities to understand our dog and offer her exactly what she needed. We appreciate your time spent with weekly visits and even a few overnight stays over the years.

Popular requests near you
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1. Search
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2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets while you’re away
3. Book & Pay
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Why Choose Rover?
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Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your pet 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.
Pet Sitting FAQs
Frequently asked questions about Rover
Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, pet sitters on Rover respond in under an hour.
Experience can vary widely from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when comparing pet sitters available in Upper Hill.
Rover makes it easy to find Upper Hill pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:
- Pets of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Pets who’d love to socialize with their pet sitter’s pets
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet 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 pet 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 pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
















