Pet Sitting Great Barrington

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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Over 16
pet parents in Great Barrington have booked pet sitting

Great Barrington, Find top rated pet sitting

Prices are estimates per visit for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.

1 / 1
Sitter Profile Image: Sydney R.
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Sydney R.
$45
total per visit
5.0 out of 5 stars
10 reviews
3 repeat clients
12 years of experience
Great Barrington, MA, 01230

Sydney did a great job taking care of Maya, our 50 lb lab mix. She was very responsive during the booking process, arrived right on time, and sent pictures of their walk together. She is very friendly and personable as well as being reliable, we would happily book her again the next time we are in town.

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Alex B.
Sitter Profile Image: Makayla F.
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Makayla F.
$50
total per visit
5.0 out of 5 stars
15 reviews
3 repeat clients
10 years of experience
Great Barrington, MA, 01230

Makayla is so sweet with our dog - making sure he's having fun and getting all his needs met. She is timely and an excellent communicator which gives us great peace of mind. We highly recommend her!

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Juliet N.
Sitter Profile Image: McKenna P.
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McKenna P.
Star Sitter
$28
total per visit
5.0 out of 5 stars
394 reviews
150 repeat clients
8 years of experience
Lenox, MA, 01240

McKenna was amazing with our 2 cats, Pepper and Maggie. She was very reliable and easy to contact. We would definitely use her services again. We can't thank you enough!

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Alice P.
Sitter Profile Image: Taylor W.
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Taylor W.
Star Sitter
$20
total per visit
5.0 out of 5 stars
20 reviews
9 repeat clients
20 years of experience
Lee, MA, 01238

Taylor was new to our two cats. Even though they were shy, she stayed to help them meet a new person. Taylor was very thoughtful to check the house for safety as well. I would definitely book Taylor again!

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Patricia S.
Sitter Profile Image: Ashley A.
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Ashley A.
$23
total per visit
4.9 out of 5 stars
41 reviews
9 repeat clients
10 years of experience
Canaan, CT, 06031

Ashley did such a fabulous job watching our kitties when we were out of town. She even extended an extra couple of days when we were delayed. 10/10 recommend!

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Anna C.
Sitter Profile Image: Lauren S.
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Lauren S.
$28
total per visit
15 years of experience
Lenox, MA, 01240

About: While working as a travel nurse, I had the privilege of staying in many homes with pets of all personalities and needs, giving me experience adapting to different routines and environments. I bring a calm, grounded, and intuitive presence that helps animals feel safe and at ease. I'm naturally nurturing (a mama to my own two kitties), attentive to the little details, and I truly enjoy building trust with every animal. My goal is for your pet to feel loved, comfortable, and well cared for while you're away, and for you to have complete peace of mind. I genuinely enjoy starting and ending my day with walks, playtime, feeding, and quality time with animals. My schedule is flexible, allowing me to provide dependable care while giving pets the attention, exercise, and companionship they deserve. I love being outdoors, so daily walks are something I truly look forward to, and I always make time for cuddles, enrichment, and keeping pets comfortable in their own routine. My parents have an elderly cockapoo who has taught me the importance of patience, gentle care, and paying attention to the little changes that come with aging. My husband and I also have two cats, so I'm familiar with their daily routines, from feeding and litter box care to playtime, affection, and respecting each cat's unique personality. I understand that every pet has different needs, and I strive to make them feel safe, comfortable, and loved every day.

Sitter Profile Image: Ellen J.
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Ellen J.
$28
total per visit
5.0 out of 5 stars
16 reviews
4 repeat clients
15 years of experience
Kinderhook, NY, 12106

Ellen took wonderful care of our cat Seven while my husband and I were out of town for several days. She sent detailed updates daily with photos, made sure to give Seven lots of playtime with his favorite toys, and kept our home in spotless condition as well. I highly recommend her if you're looking for a responsible, communicative sitter who loves cats!

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Kaylen S.
Sitter Profile Image: Reymon B.
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Reymon B.
$30
total per visit
5.0 out of 5 stars
3 reviews
1 repeat client
20 years of experience
Pittsfield, MA, 01201

Lovely, high energy, reliable Dog Sitter! Looking forward to having Reymon again.

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Elizabeth S.
Sitter Profile Image: Kelly H.
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Kelly H.
$73
total per visit
5.0 out of 5 stars
66 reviews
31 repeat clients
14 years of experience
Otis, MA, 01253

As always, our dogs were SUPER excited to see Kelly!

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Eric L.
Sitter Profile Image: Diana G.
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Diana G.
$16
total per visit
5 years of experience
Valatie, NY, 12184

About: I’ve been surrounded by animals of all kinds my entire life, so caring for them has always come naturally to me. I truly love animals and treat every pet I care for as if they were my own. I’ve been pet sitting for several years and understand how important it is to have someone you can trust with your furry family members. Whether it’s walks, playtime, cuddles, feeding, or just keeping them company, I make sure every pet feels safe, comfortable, loved, and well cared for while you’re away. 🐾❤️ I currently work part-time, which gives me plenty of flexibility in my schedule to care for your pets. I’m available throughout the day for walks, drop-ins, feeding, playtime, or just some extra love and attention. My flexible schedule allows me to work around your pet’s normal routine and make sure they get the care and companionship they’re used to while you’re away. 🐾❤️ My home is a safe and comfortable place for your pet to relax and feel at home. I have a partially fenced-in yard where dogs can safely enjoy some fresh air, play, and stretch their legs. I also have a screened-in porch that’s perfect for lounging and enjoying the outdoors while staying safe and secure. Your pet will be treated like part of the family while they’re here! 🐾❤️

Sitter Profile Image: Trista S.
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Trista S.
$28
total per visit
5.0 out of 5 stars
21 reviews
9 repeat clients
30 years of experience
Pittsfield, MA, 01201

Trista was wonderful! She sent great pictures of all the pets. They all look so happy and well cared for. Great communication and followed all instructions. You can tell she really cares for your pets. We would highly recommend! 😊

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Alana L.
Sitter Profile Image: Chelsea M.
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Chelsea M.
$17
total per visit
25 years of experience
Lenox, MA, 01240

About: I have had animals (cats, dogs, gerbils, you name it!) all my life. They are what brings me joy no matter what. I love creating fun and loving environments for pets especially when they or their owners are anxious about being apart. After having to find my own sitters while moving to the Berkshires, I realized how wonderful it is to have someone you can trust to take care of your loved ones. I'd like to help be that person for you. I work in hospitality in Lenox part time (usually 10-6 with an hour break) 4 days a week. Would be willing to come by in the morning for a few hours, at lunch, after work and stay overnight if needed. In my home, I love my two boy cats more than anything! One is indoors and one is a mix. They are groomed often and always have a flea and tic collar. The boys get a small breakfast and then wet food at night. Jaylen usually sleeps at my feet and Oswald roams about until breakfast! Their litter is kept downstairs in an entire room of their own and they have their own food bowls away from each other and water is kept fresh and separate. Although I only have 2 cats right now I grew up training family dogs and am just as comfortable with them!

Sitter Profile Image: Clara M.
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Clara M.
$50
total per visit
5.0 out of 5 stars
17 reviews
3 repeat clients
11 years of experience
Tyringham, MA, 01264

Clara was wonderful! If you’re looking for someone who is responsible and great with animals, then Clara is the right choice. We were away all day so Clara came by to walk and hang out with our very energetic yellow Labrador named Lulu. She did a great job and Lulu was nice and calm when we got back home! Thank you Clara!

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Lisa
Sitter Profile Image: Keri H.
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Keri H.
Star Sitter
$39
total per visit
5.0 out of 5 stars
58 reviews
20 repeat clients
20 years of experience
Lenox, MA, 01240

Keri provided drop in visits for my cat. Not only was my cat content in knowing that she would be fed, played with, and taken care of - but my house was taken care of as well. I could enjoy my time away with no worries.

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Karen B.
Sitter Profile Image: Lindsay L.
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Lindsay L.
$28
total per visit
5.0 out of 5 stars
5 reviews
20 years of experience
Canaan, NY, 12029

Lindsay was super responsive to our request and did an excellent job taking care of Fletch for us!

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Erin M.
Sitter Profile Image: Abigail H.
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Abigail H.
$56
total per visit
5.0 out of 5 stars
4 reviews
4 repeat clients
5 years of experience
Hillsdale, NY, 12529

Abigail was the perfect cat sitter. I was so nervous leaving my cats for so long but it turns out, I didn't have to worry at all. She came for a meet and greet, learned all their names, and followed every instruction during the entire two week period. I needed twice a day drop ins for one hour each. She stayed for the entire hour, played with the cats, fed them, pet them, cleaned food bowls, replaced water bowls and cleaned their litter. She took pictures of them every time and by the end, my cats were so comfortable with her. I would hundred percent recommend her if you want a sweet, caring sitter who you can rely on.

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John S.
Sitter Profile Image: Brenna B.
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Brenna B.
$50
total per visit
5.0 out of 5 stars
7 reviews
1 repeat client
12 years of experience
Pittsfield, MA, 01201

About: I’ve been caring for pets informally for my entire life and professionally starting 12 years ago. I care for each pet like they are my own. I am sensitive to their energy and needs. I am able to work with animals who have unique social/emotional and medical needs. I mainly work with dogs and cats but am also experienced in caring for small animals like rabbits, birds, reptiles and fish. I’m currently working part-time, and my schedule varies a bit week to week. I am free mornings and evenings, most Thursdays, as well as Mondays after 2 pm. I usually work shifts under 8 hours, so with good communication I would be thrilled to come up with a plan that will suit you and your pet(s). For now, I am able to care for and board cats and small animals in my home. In the summer, I can board dogs in my fenced in yard. For dogs and larger animals, I can take them for walks and pet sit by traveling to your home. I look forward to meeting you and your pet(s)! I have managed to ensure my pet rabbit feels safe while also living with a rambunctious one-year-old labrador retriever. I am always cautious about my pets and my clients’ pet’s whereabouts. I’ve helped return missing neighborhood cats and dogs to their owners as well as assist with unexpected visits to the vet.

Sitter Profile Image: Steve F.
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Steve F.
$45
total per visit
5.0 out of 5 stars
1 review
2 repeat clients
12 years of experience
Lee, MA, 01108

About: I'm very happy to be around pets. Have experience taking care of pets as I have had pets growing up I have been called to dog wisper because I have that connection with dogs. Your pet will be well cared for and loved in my care I'm open mornings and at night.i do food delivery and housekeeping part time.i can usually be available for whatever times you need just reach out and let me know I have a eye for detail and.very alert so your pet will be safe. What ever kind of pet sitting you need I can do

Sitter Profile Image: Daniella S.
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Daniella S.
$34
total per visit
5.0 out of 5 stars
8 reviews
4 repeat clients
7 years of experience
Lenox, MA, 01240

Daniella took such amazing care of our sweet Gandalf, while he was sick and needed to take medicine orally. He didn’t make it easy but she was patient, kind, and kept our home in great condition while we were away so it was lovely to return home to. THANK YOU DANIELLA!

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Noelle B.
Sitter Profile Image: Kimberly P.
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Kimberly P.
$26
total per visit
5.0 out of 5 stars
13 reviews
3 repeat clients
33 years of experience
Hudson, NY, 12534

About: Hello! I've been an animal lover my entire life. My dog, Zeke and I had a companion kind of relationship, built on mutual respect and happiness; it's something I wouldn't have traded for the world. He sadly passed away in October 2025 after 12 years together, so it would be an understatement to say I'm more than happy to pour extra love to your pup. Times are tough; starting a new 'negotiations and bartering' acceptance. Reach out, the worst I can say is no! Partial payment in veggies, meat, mechanic work...etc. Community care✨ ___________________________________________________________________________ This is a new offering as of August 2024. I have discovered that adventures are my ideal experiences and would like to advertise as such! Mountain hikes, kayak paddles (>15 pounds) are my favorites, but I am open to other ideas/training requests! Paddleboarding, swimming lessons...the possibilities are endless. One hour minimum is preferred; gas and travel time to the adventure site are included. I have many mountains, lakes and trails on my list, so I do not see it as fair to charge you for that time! You will only be charged for adventure time. Depending on your pup(s) comfortability in the car, we may travel up to 45 minutes. You and I will decide together on location details, and this app will track where your pup(s) and I are at all times. Wilderness First Aid trained, canine safety versed, ample water provided, and pups will always be kept safely on the leash. Your pup will return home satisfied and tired! ____________________________________________________________________________ For a NORMAL NEIGHBORHOOD WALK, please book a drop-in visit and message to remind me that you would like a walk. Availability for walks and drop-ins will change after Labor Day. Unavailable most weekdays 8-3:30, I am a caretaker by nature, and have been a teacher for the past 4years, a live in nanny before that and most recently a grade school teacher. I'm going back to school to get my licensure. Honestly, care taking and fresh air gives me clarity of mind, and the chance to peel away from the screen helps process all the new information! I am trying to practice running again too, if your canine would like to train with me. Familiar with many local trails and parks. All weather is good weather! Experience with dogs with seizures and giving various medications. Feline friend as well. Looking forward to meeting you and your furry friends ! I work at a school, but often have days and weeks off. Feel free to request and negotiate for what you need. Finding a good fit is paramount. I offer boarding very rarely. When I am in your home, I try to leave it better than I found it. I have spent a fair amount of time farming and gardening, so plants will be well cared for if asked.

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The median cost per visit for pet sitting in Great Barrington is $25

Cat parents share their Rover experiences - Great Barrington

1 / 1
5.0 out of 5 stars

Camille is a sweetheart- arrives in time, sends lots of pictures, and most importantly, my cat was very content!

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Jennifer B.
Drop-In Visits
1 / 1
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Popular requests for pet sitting - Great Barrington

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Sitters in Great Barrington average 5
repeat pet sitting clients

FAQs for Drop-In Visits - Great Barrington

Frequently asked questions about Rover

The average cost for Pet Sitting in Great Barrington on Rover is $17.76 per visit (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Pet 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 Pet Sitting. For more information on service fees, click here .

As of August 2026, there are 494 sitters on Rover offering Pet Sitting across Great Barrington. Enter your ZIP code to see which available sitters are closest to your home.

A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.

Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Great Barrington stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.

Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.

If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.

The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.

Many pet parents provide a spare key or arrange a lockbox. You can also exchange keys during the Meet & Greet and show your walker how to use digital fobs or personalized codes. It helps to arrange access to your home, from spare keys to concierge introductions, before pet care begins.

If you live in an apartment or condo, don’t forget to discuss details like buzzer access, codes, or elevator etiquette. These details can help a pet sitter feel more comfortable going in and out of your building.

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 .

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.

Yes, you can find sitters who have experience with handling special pet needs in Great Barrington. On Rover:

  • 97% of sitters can help with special care needs
  • 97% can help with giving oral medications or injections
  • 97% 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.

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.

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