House Sitting Pittsfield
Find a loving house sitter to watch over your pets and your home.
Over 11 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.
“This is the second time we have had Keirsten dog sit for us. We were able to book with her on short notice and she left our home in great condition. Better than she found it. Our dog was calm and happy to see us as if we had just returned from a short errand.”
“Excellent communication before and during her stay. We recently moved to the area and didn't realize how much information our past sitter "just knew" Amanda asked questions to get answers to instructions I didn't think to give. Her attention to detail is the foundation that the exceptional care she provided our crew on. Couldn't be happier with her service and care.”
“Courtney did a wonderful job caring for our two dogs while we were away! We came home to two happy dogs and a house that was clean and tidy. She responded quickly and kept us in the loop the entire time. I would highly recommend, Courtney.”
“Lani was great taking care of our two senior dogs that have special needs. One is blind, requires medications, and wound care; the other one can’t hear. Lani handled it all with ease and professionalism, communicated well, and the dogs seem very comfortable. Highly recommend!”
“Sarah was great! She took the time to meet with me ahead of time to review Lucy's special needs. She even did research ahead of time so she would be familiar with her disorder. She arrived on time and communicated quickly every time I reached out. Lucy seemed very happy upon my return. She helped keep the house in order and even watered my plants. She is extremely kind and caring. I have fully confidence in leaving Lucy in her care. I will definitely continue to request Sarah as I need assistance.”
“Jenny took wonderful care of our dog Millie while staying at our house. She left the house super clean and Millie seemed very happy when we returned. We are booking her again and would definitely recommend her to anyone!”
“Kristin is absolutely amazing! From start to finish, she provided outstanding care for our dog, Bruce, and truly went above and beyond to make sure he was happy, safe, and comfortable while we were away. She was extremely professional and reliable—always on time, communicative, and proactive. Kristin sent regular updates and photos, which gave me complete peace of mind. It was clear that Bruce wasn’t just being looked after; he was being loved. When we returned home, Bruce was relaxed, happy, and clearly well cared for. Kristin’s dedication, attention to detail, and genuine love for animals truly set her apart. We can’t recommend her highly enough—she’s our go-to from now on!”
About: I am a very detail oriented individual who has loved raised animals since I was a child. I have experience with different types of dogs and personalities including rescues and spicy personalities. I myself own 3 dogs. 2 rescues and a French Bulldog. I consider myself someone who can easily gain trust with nervous or territorial dogs. I also have a lot of experience cats as well. I really like to listen to what the animal requires to give the best care for your fur babies. Currently, I work a full-time job 7-3:30pm. I am looking to do nights and weekends with the goal of going full-time. Currently weekends and last minute walks during the weekdays after 4:00 will work best. First and foremost my animals are my babies and I feel the same way about yours! I like to make sure that anyone whose animal I care for feels comfortable and all questions have been asked prior to care. If possible, I like to meet the dogs and owners ahead of time which allows the owners to see our interactions together to make sure it is a great fit. I will send photos and updates while giving reassurance to those who worry when not at home. My animals are my babies and yours will be too during care.
“It's such a relief to find quality, reliable pet care for my sweet, aging golden-doodle. Ashley spent 5 days taking care of my dog and my home. She sent photos & videos, communicated with daily updates and was attuned to his physical limitations. It's clear that Ashley loves animals and she bonds easily with them. The added bonus was how well she took care of my home! It was spotless when I returned, sheets, neatly folded, and everything in its place. Highly recommend!”
“Abigail watched my two pups for the first time and was able to win over my skiddish dog who typically takes a while to warm up to people. She was prompt with replies and even walked the dogs!”
“I have used Rover twice now and both times with Erin. It was strange having someone you do not know stay in your house. Like I said, I never used the service before but I really wanted to be able to keep my dogs in their own home. Erin is unbelievable. She is great with the dogs and with my home. I’m not sure I would be able to adjust well in a strangers home, but she does a great job. When I get home, everything is in place as I left it and the dogs are happy and safe. Both of my experiences with Erin have been great. I would trust her again and again with Levy and Frank. ❤️❤️”
About: Everyone always asks me why dogs are so nice to me and quiet and I’m not really sure but I love all animals! So I hope you can trust me with yours! I work full time but after work I’m always available usually and on weekends. I’m very lenient towards everyone’s schedules so take your time! Don’t worry I will only be going to peoples homes to pet sit or walk because I live in an apartment that doesn’t allow dogs unfortunately maybe one day when I get my own house though!
“We were very happy with Lee! While we were away for the weekend, Lee stayed at our home watching our dog, Roxy. We received pictures and updates daily. When we returned, everything looked great! We appreciate Lee taking good care of Roxy and would have Lee dog sit again.”
“Carlie was wonderful!! A family wedding caused all normal dog sitters to be unavailable. Carlie came to meet my adult children’s’ dogs at my house where she ended up watching them over a long weekend. She was extremely responsive and the dogs loved her!! I would highly recommend her to anyone.”
“Autumn responded quickly after my initial request and all subsequent communications. The meet and greet went well. She kept me up to date with text and pictures during the housesit, and left the house and yard in great shape. I would not hesitate to have her help with my 3 pets again.”
The median cost per night for house sitting in Pittsfield is $63
Pet parents share their Rover experiences - Pittsfield
Kim was wonderful! I could tell from the first picture she sent that my dog was relaxed and happy with her staying with him. She was great at communicating and was flexible when we thought we might be late getting home because of a storm. I would 100% recommend Kim and I will be rebooking with her in the future.
This was my first time using Rover and I was pretty nervous to have someone watching my boy Oliver and staying in my house, but Meagan made it so easy and really put me at ease! She gave me updates on what they did each day and sent me lots of pictures and videos of him. Thank you Meagan!!
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
It's that easy! All payments are processed through Rover's secured platform
Popular requests for house sitting - Pittsfield
Select a filter and find qualifying sitters offering house sitting.Sitters in Pittsfield average 3 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 $99.52 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 643 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 with handling special pet needs in Pittsfield. On Rover:
- 98% of sitters can help with special care needs
- 98% can help with giving oral medications or injections
- 96% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, 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 use the Meet & Greet to walk your sitter through your expectations.
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