House Sitting Stephentown

Find a loving house sitter to watch over your pets and your home.

End
Search

Stephentown, 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.

1 / 1
Sitter Profile Image: Caitlin H.
Verified Background Check
Caitlin H.
from
$50
per night
5.0 out of 5 stars
17 reviews
3 repeat clients
4 years of experience
Pittsfield, MA, 01201

Caitlin was amazing! It was obvious that Ollie and Daisy loved her. She was very accommodating and took care of our pups with love and kindness. I would ask Caitlin to watch Ollie and Daisy again in a heartbeat! Thank you Caitlin!!

Profile image
Kyle W.
Sitter Profile Image: McKenna P.
Verified Background Check
McKenna P.
Star Sitter
from
$75
per night
5.0 out of 5 stars
382 reviews
149 repeat clients
8 years of experience
Lenox, MA, 01240

We couldn't be happier with the incredible care McKenna provided for our beloved dogs, Raynor and Mojo. From the moment she arrived, it was clear she had a genuine love for animals, and our pups took to her instantly. McKenna went above and beyond, ensuring Raynor and Mojo were not just fed and walked, but truly loved and engaged. We received regular updates and photos that put our minds completely at ease, showing our dogs happy, playful, and comfortable in her care. Beyond her exceptional attention to our furry family members, McKenna also left our home in pristine condition. It was such a relief to return to a clean and tidy house, exactly as we had left it. McKenna is reliable, responsible, and truly a gem. We highly recommend her to anyone looking for top-notch dog sitting services. She treated our dogs and our home with the utmost respect and care. We will absolutely be asking her to sit for us again!

Profile image
Krista N.
Sitter Profile Image: Brenna B.
Verified Enhanced Background Check
Brenna B.
from
$100
per night
5.0 out of 5 stars
7 reviews
1 repeat client
12 years of experience
Pittsfield, MA, 01201

Brenna was an amazing pet sitter for us. We have two dogs, both seniors, and one with significant health issues. It is always hard to leave him but had our son's wedding in Canada to attend. Brenna sent constant updates and photos to ease our mind while away. They were very well cared for and loved. I would use Brenna again in a heart beat!

Profile image
Nadine S.
Sitter Profile Image: Trista S.
Verified Enhanced Background Check
Trista S.
from
$30
per night
5.0 out of 5 stars
19 reviews
6 repeat clients
30 years of experience
Pittsfield, MA, 01201

Trista was wonderful with my two dogs. I appreciated her last minute availability and professionalism. Both dogs warmed up to her very quickly even my shy one.

Profile image
Theresa S.
Sitter Profile Image: Anna C.
Verified Background Check
Anna C.
Star Sitter
from
$40
per night
5.0 out of 5 stars
41 reviews
12 repeat clients
12 years of experience
Troy, NY, 12180

Anna was so good with my puppy! She was patient (he’s a baby land shark!) and attentive and took great care of him while I was gone. I will absolutely rebook with her! :)

Profile image
Jasenia C.
Sitter Profile Image: Alyssa M.
Verified Enhanced Background Check
Alyssa M.
from
$80
per night
5.0 out of 5 stars
3 reviews
10 years of experience
Valatie, NY, 12184

Alyssa is great! My pets and home were well cared for. My dog gets pretty anxious when I go out of town but he seemed very calm and relaxed when I came back. He seemed like he had a great time with Alyssa!

Profile image
James W.
Sitter Profile Image: Shantalee M.
Verified Enhanced Background Check
Shantalee M.
from
$45
per night
5.0 out of 5 stars
19 reviews
4 repeat clients
8 years of experience
Albany, NY, 12207

Shantalee did such an amazing job for us, I would define recommend her to family and friends. She was very respectful, responsible and caring to our pup. Thanks Shantalee!

Profile image
Tony C.
Sitter Profile Image: Reymon B.
Verified Enhanced Background Check
Reymon B.
from
$80
per night
20 years of experience
Pittsfield, MA, 01201

About: Working in various Grooming/Training facilities. I'm currently working with Bumblebee Pet Care with 5 of my own clients. My conversations with the pets are amazing. I'm currently walking dogs 2 days out of the week looking for more to work with within the week. I have an open schedule and interested. I have separate spaces available for each animal. In my care at anytime, I will use provided equipment for transportation. Your pet safety is number one.

Sitter Profile Image: Olivia A.
Verified Enhanced Background Check
Olivia A.
from
$35
per night
15 years of experience
Dalton, MA, 01226

About: I have cared for many pets my whole life. I love meeting new animals and learning about each and every personality. Had or cared for cats, dogs, and small animals, and willing to meet more! I am available most days and some nights. I can provide early morning care and mid day care, and night care but often after 10pm. I am always attentive to animal body language and keep an eye on how they are feeling in the environment or around me. I follow the guidlines closely that are given by owners on how to care for their pet.

Sitter Profile Image: Lindsey S.
Verified Background Check
Lindsey S.
from
$50
per night
5.0 out of 5 stars
1 review
25 years of experience
Cheshire, MA, 01225

About: I've grown up with dogs & cats. I am very involved in rescuing & fostering & have plenty of experience with all sizes, ages, temperaments & am experienced with most medical issues/medicating regimens. My schedule for work is Monday- Friday 7:30-4 pm. I'm available from 5-10 pm weekdays for drop ins and walks. I have open availability for weekends to house sit, go on walks and do drop in visits. I am currently in the process of relocating to New Hampshire permanently. I work full time Monday through Friday and offer pet care on evenings during the weekday, and full time on weekends :) I'm experienced with providing care for difficult dogs and cats and have no issues being able to give medications.

Sitter Profile Image: Gabrielle H.
Verified Enhanced Background Check
Gabrielle H.
from
$32
per night
15 years of experience
Pittsfield, MA, 01201

About: I have been a volunteer at the Berkshire Humane Society for about 6 months now working within the kennel and have been trusted with friends and family's dogs throughout my life! I have personally trained both of my large breed pups and have experience with both puppies and senior dogs! <3 I currently work part-time from Fri-Sun so I have full availability throughout the week to play with your pup(s)! I will always find the best time and place to give your pets what they need. I am not able to bring pets to my apartment, but will gladly give them all the care and attention they need in their home, or out and about!

Sitter Profile Image: Lauren B.
Verified Enhanced Background Check
Lauren B.
from
$60
per night
5.0 out of 5 stars
15 reviews
3 repeat clients
4 years of experience
West Sand Lake, NY, 12196

Lauren is great with our pups! Very reliable and communicative.

Profile image
Marcy C.
Sitter Profile Image: Gillian G.
Verified Enhanced Background Check
Gillian G.
from
$32
per night
5.0 out of 5 stars
19 reviews
8 repeat clients
10 years of experience
Williamstown, MA, 01267

Gillian was great! Took great care of my dogs! I highly recommend her!

Profile image
Alice T.
Sitter Profile Image: James S.
Verified Enhanced Background Check
James S.
from
$87
per night
5.0 out of 5 stars
8 reviews
10 years of experience
Williamstown, MA, 01267

About: I bring a unique level of structure, energy, and reliability to pet care through my experience as a college coach. My daily work revolves around building routines, paying attention to small details, and making sure individuals are supported and performing at their best — and I carry that same approach into caring for dogs. I am highly dependable and organized, so you can trust that your dog’s schedule, feeding routine, and exercise needs will be handled consistently. I also bring an active lifestyle, which is great for dogs that need engaging walks, playtime, and attention. What sets me apart is the level of care and awareness I provide. I pay close attention to behavior, energy levels, and any changes, and I prioritize clear communication so you always feel confident while you are away. My goal is to make sure your dog feels comfortable, safe, and well cared for at all times My schedule is currently wide open following the end of the swim season, which gives me plenty of flexibility for walks, drop-ins, and overnight care throughout the week and weekends. I understand how important it is to trust someone with your dog. I create a safe, comfortable environment where your pet feels secure and cared for at all times. I pay close attention to their needs, keep a watchful eye during walks, and always make sure you are updated so you can relax knowing they are in good hands.

Sitter Profile Image: Stephanie B.
Verified Enhanced Background Check
Stephanie B.
Star Sitter
from
$60
per night
5.0 out of 5 stars
37 reviews
15 repeat clients
15 years of experience
Troy, NY, 12182

I couldn’t recommend Net (Stephanie B) anymore! We went away for a few days for thanksgiving and left her with our 2 dogs, 3 cats, lizard, and chickens and she was absolutely fantastic. She followed our feeding walking directions perfectly and had excellent communication. Our house was left nicer than we left it and our pups were clearly happy and well taken care of. She even made sure to give them a walk before we got home so we could unpack and relax. Don’t hesitate, book Net!

Profile image
Elise P.
Sitter Profile Image: Leona O.
Verified Enhanced Background Check
Leona O.
from
$44
per night
4.7 out of 5 stars
6 reviews
10 years of experience
North Adams, MA, 01247

Leona was great with our boxer, Brussel Sprout. She was very responsive and let us know of any issues so we could help her out while we were away!

Profile image
Liane T.
Sitter Profile Image: Dana G.
Verified Background Check
Dana G.
from
$125
per night
5.0 out of 5 stars
40 reviews
11 repeat clients
20 years of experience
PITTSFIELD, MA, 01201

We feel so lucky to have found Dana! Her attention to detail, her ability to tune into our particular needs and willingness to take care of chickens as well as our dog, plus a LOL sense of humor made us feel at ease leaving our home and loved ones in her care. Dana kept in contact with us just the right amount the whole week we were gone. When we came home it was if we had never left, happy dog and chickens and tidy home. We especially appreciated the thoughtful touches that all add up, like a full woodbox! We will definitely have her help again and highly recommend her.

Profile image
Katherine M.
Sitter Profile Image: Katelynn R.
Verified Enhanced Background Check
Katelynn R.
from
$80
per night
5.0 out of 5 stars
3 reviews
1 repeat client
15 years of experience
Pittsfield, MA, 01201

About: What sets me apart from other pet sitters is the genuine care and attention I give to every animal I look after. I treat each pet as if they were my own, taking the time to understand their unique personalities, routines, and needs. My goal is to keep them comfortable, happy, and stress-free while you’re away. I believe in open communication and send regular updates so you can have complete peace of mind knowing your pets are safe, loved, and well cared for. With a dependable and compassionate approach, I go above and beyond to make sure both pets and owners feel confident and at ease. 🖤🐾🐈‍⬛ 🐕 Because I’m a stay-at-home mom, I’m available around the clock to make sure your pets get the attention and care they deserve when you need it most. Your pet’s safety and comfort are always my top priorities. I provide a calm, secure environment where every animal feels safe and cared for. Whether I’m visiting your home or hosting your pet, I make sure their surroundings are clean, pet-friendly, and stress-free. You can trust that your pets are in responsible hands — I’m attentive to their needs, mindful of routines, and always alert to signs of discomfort or stress. My goal is to give you peace of mind knowing your pets are happy, protected, and treated with the same love and respect they receive from you.

Sitter Profile Image: Lindsay L.
Verified Enhanced Background Check
Lindsay L.
from
$120
per night
5.0 out of 5 stars
5 reviews
20 years of experience
Canaan, NY, 12029

Lindsay was great with Waldo. Would definitely have her again.

Profile image
Dianne F.
Sitter Profile Image: Melanie D.
Verified Enhanced Background Check
Melanie D.
from
$65
per night
20 years of experience
Dalton, MA, 01226

About: I grew up with dogs my whole life. My parents also run a dog sitting business on cape cod and I help out there when I can! I am also fully insured! I’m a current second grade teacher, so I’m completely free on the weekends and the summer months, as well as school vacations to take care of your furry friends! I will love your dog like my own! I’m a diligent, reliable and clean person that will leave your home and dog happier than I found it. I am also fully insured!

1 / 1
View more sitters

The median cost per night for house sitting in Stephentown is $60

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.

How Rover works

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting
  2. 2. Meet & Greet

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

Sitters in Stephentown average 3
repeat house sitting clients

FAQs for House Sitting - Stephentown

Frequently asked questions about Rover

As of July 2026, there are 490 sitters on Rover offering House Sitting across Stephentown. 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 Stephentown 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 Stephentown 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 Stephentown 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 Stephentown. On Rover:

  • 91% of sitters can help with special care needs
  • 98% can help with giving oral medications or injections
  • 95% 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.

Connect anywhere with the Rover app

Download on the App Store BadgeGet it on Google Play Badge