House Sitting Great Barrington

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Over 6
pet parents in Great Barrington have booked house sitting

Great Barrington, Find top rated house sitting

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

1 / 1
Sitter Profile Image: Ashley & Robert D.
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Ashley & Robert D.
Star Sitter
$111
total per night
5.0 out of 5 stars
20 reviews
11 repeat clients
25 years of experience
Austerlitz, NY, 12017

Ashley is so helpful and so kind. My senior dog is downright high maintenance, and she took special care of him and the others, too. Highest recommendation!

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Susie N.
Sitter Profile Image: Clara M.
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Clara M.
$62
total per night
5.0 out of 5 stars
17 reviews
3 repeat clients
11 years of experience
Tyringham, MA, 01238

Clara is wonderful! Followed all of my dog care instructions, kept the house tidy and, above all, provided excellent company and love to my doggies in my absence! She would regularly share photos and video footage of how they were getting on as well which is always a plus. Would recommend her to anyone who wants top quality dog-sitting.

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John S.
Sitter Profile Image: McKenna P.
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McKenna P.
Star Sitter
$84
total per night
5.0 out of 5 stars
402 reviews
151 repeat clients
8 years of experience
Lenox, MA, 01240

McKenna did such a wonderful job looking after our Addie. It was clear how much the two of them bonded and how much love and attention McKenna put into looking after her. Would recommend her to anyone!

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Vickie & John W.
Sitter Profile Image: Danielle C.
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Danielle C.
$73
total per night
4.8 out of 5 stars
9 reviews
30 years of experience
Hillsdale, NY, 12529

Danielle was very flexible with timing and availability. Our dog enjoyed his stay with her overnight. He came home very relaxed and happy. I will definitely use Danielle again.

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Jane G.
Sitter Profile Image: Taylor W.
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Taylor W.
Star Sitter
$76
total per night
5.0 out of 5 stars
21 reviews
9 repeat clients
20 years of experience
Lee, MA, 01238

Taylor took wonderful care of our sweet senior girl (15yo!) who has particular needs and takes meds. Sasha was happy and content when we got home, and our house looked great, too. We’re very grateful for the thoughtful care and would absolutely recommend Taylor.

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MA
Sitter Profile Image: Valentina M.
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Valentina M.
$36
total per night
5.0 out of 5 stars
2 reviews
6 years of experience
Stockbridge, MA, 01262

About: I grew up with 2 dogs and 2 cats. My family was part of helping a farm when i was little, I got to take care of ducks. They were so cute. I love animals and let me know if you had questions. I work at Marshall’s. I will be taking care of the animals during my days off. I will make sure they have everything they need I grew up with cats and dogs. I love all kinds of animals. I will take good care of them. I can bring them to my house as well.

Sitter Profile Image: Keri H.
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Keri H.
Star Sitter
$106
total per night
5.0 out of 5 stars
59 reviews
20 repeat clients
20 years of experience
Lenox, MA, 01240

Keri is THE BEST!! Our dog is a bit shy around humans and it was honestly stunning how quickly they became friends. Not only was Keri extremely responsive when we were setting up this last minute booking, but she kept us updated regularly throughout our entire trip. It was clear that she showed him so much love, taking him on adventures and cuddling with him. We could tell Keri really understood his unique personality and she made our trip completely worry-free. When we got back, our house was even better off than it was before. If I could give 100 stars, I would!!

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Brenna L.
Sitter Profile Image: Sally A.
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Sally A.
$167
total per night
5.0 out of 5 stars
46 reviews
13 repeat clients
50 years of experience
Richmond, MA, 01254

Sally is the best! This is the second time that she has stayed with our dog, Sybil. Sybil was so excited when Sally arrived at our house, she adores Sally and Sally takes excellent care of her. They have so much fun together, going on walks and playing with Sybil's favorite toys. I highly recommend Sally! I know that Sybil will be thrilled to hang out with her again in the future!

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William B.
Sitter Profile Image: Trista S.
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Trista S.
$45
total per night
5.0 out of 5 stars
23 reviews
10 repeat clients
30 years of experience
Pittsfield, MA, 01201

Completely trust Trista. Second time I used her. Copper loves her. He is happy and calm when I get home. Means everything we do not have to worry when on vacation

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Allen K.
Sitter Profile Image: Makayla F.
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Makayla F.
$134
total per night
5.0 out of 5 stars
15 reviews
3 repeat clients
10 years of experience
Great Barrington, MA, 01230

About: I've always carried a deep passion to care for animals since I can remember. I love dogs that are not mine as if they were my own! I have many years experience caring for dogs and other animals. Ive always had jobs in kennels and daycares. I am confident your pet will be very happy in my care. I have taken care of dogs who need extra medical attention, older dogs, puppies, etc. I am more than happy to meet your expectations and accommodate your needs for your furry friend. I am offering day long care for your pet. We can do walks, hikes, swimming, even a play day at the park. Single walks, hikes, swimming, trips to the park. Drop ins to your home for up to 2 hours at a time. Available late night and early morning. I take pride in loving your pet like my own and I hope we can work together :) I have a lot of available time to help your pets in need! My schedule is very flexible. I am currently transitioning from being a stay at home mom. I’m very trustworthy and make sure your pet is safe at all times! Whether off leash walks are allowed or on leash at all times. I will make sure your pet is always treated as if it were my own.

Sitter Profile Image: Kelly H.
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Kelly H.
$139
total per night
5.0 out of 5 stars
66 reviews
31 repeat clients
14 years of experience
Otis, MA, 01253

Kelly was organized and attentive to every detail about our three dogs with wide ranging needs. She visited in advance, took copious notes and followed up on everything to double check. We will use her again and are very appreciative of her services.

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Marianne D.
Sitter Profile Image: Lauren S.
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Lauren S.
$100
total per night
5.0 out of 5 stars
3 reviews
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: Brenna B.
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Brenna B.
$111
total 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!

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Nadine S.
Sitter Profile Image: Elishamaria R.
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Elishamaria R.
Star Sitter
$84
total per night
5.0 out of 5 stars
26 reviews
9 repeat clients
20 years of experience
Catskill, NY, 12414

Elisha was great. She wasn't intimidated by Arlo's epilepsy which was a huge relief to me. She seemed immediately at ease with the boys and they with her. When I got home my dogs were calm, happy and not anxious so I could tell that they were indeed comfortable with her. I will definitely book with Elisha again.

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Sharon P.
Sitter Profile Image: Reymon B.
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Reymon B.
$111
total per night
5.0 out of 5 stars
4 reviews
1 repeat client
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: Christine A.
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Christine A.
Star Sitter
$178
total per night
4.9 out of 5 stars
99 reviews
33 repeat clients
33 years of experience
Stanfordville, Stanfordville, NY, 12581

Christine is a down-to-earth person who is easy to talk with and pays attention to important details. At our meet & greet, she asked good questions that reflected her experience and commitment to making both pets and their owners feel comfortable with her. My young adult cat Suki had never been left alone with someone she didn’t already know. In my absence, however, Christine eased her way into Suki’s territory by setting the right balance between showing her some quiet attention and giving her the time and space she needed to adjust and come out of her shell. The photos Christine sent me proved that once she had won Suki over, the little kitty was her sweet, affectionate self and the two of them had a delightful time together! I will be asking Christine to Suki-sit in my house again!

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Carena P.
Sitter Profile Image: Sophie H.
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Sophie H.
$139
total per night
5.0 out of 5 stars
31 reviews
10 repeat clients
15 years of experience
Hudson, NY, 12534

Sophie is a pleasure to work with. Second time now! She is great with my dogs, very communicative and I feel very comfortable while I’m away!

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Tamar B.
Sitter Profile Image: Julie G.
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Julie G.
$59
total per night
5.0 out of 5 stars
14 reviews
1 repeat client
4 years of experience
Holyoke, MA, 01040

Having Julie G house sit and care for my 85 lb. hound Dave was dreamlike. She seemed to accept and appreciate Dave and his coonhound ways seamlessly from the jump. She took copious notes about Da daily needs and expectations at the meet & greet, asked intelligent questions about his routine and I was able to leave town completely confident Dave was in good loving hands. She sent me daily pics and reports while I was away, and left Dave mellower and the house cleaner than it was when I left. A terrific experience from my perspective Can't recommend Julie G strongly enough as a house and hound sitter.

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Bob S.
Sitter Profile Image: Katie O.
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Katie O.
$84
total per night
5.0 out of 5 stars
23 reviews
3 repeat clients
20 years of experience
Torrington, CT, 06790

Katie was fantastic! She kept me updated on the excitement and was extremely respectful and trustworthy in my home. The animals are loved her. She was on time and followed all my directions and I would absolutely trust her with my animals in the future.

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Jamesia B.
Sitter Profile Image: Ashley G.
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Ashley G.
$63
total per night
4.8 out of 5 stars
6 reviews
4 repeat clients
4 years of experience
Rensselaer, NY, 12144

Ashley was a fantastic sitter. She stepped in when my sitter fell through at the last minute and took great care of my very energetic 11 month old and 60 pound pup. Grace is an energetic pup and Ashley had no problem keeping her entertained; she even took her for car rides. Ashley was able to give Grace her medication and took her on multiple walks a day. She also took great care of my house, took out the garbage, and left everything in perfect condition. Grace was obviously very well looked after and Ashley's attentiveness made me feel comfortable being so far away from home for the first time. i would recommend Ashley for any and all types pet care and sitting. She was a lifesaver on short notice and I will use her any time I travel in the future.

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Maureen S.
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The median cost per night for house sitting in Great Barrington is $68

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  • 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

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  • 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. 1. Search

    Browse profiles of sitters near you who offer house sitting
  2. 2. Meet In Person

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

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Popular requests for house sitting - Great Barrington

Select a filter and find qualifying sitters offering house sitting.

Sitters in Great Barrington average 4
repeat house sitting clients

FAQs for House Sitting - Great Barrington

Frequently asked questions about Rover

The average cost for House Sitting in Great Barrington on Rover is $35 per night (as of September 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 September 2026, there are 288 sitters on Rover offering House Sitting across Great Barrington. 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 Great Barrington 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 Great Barrington 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 Great Barrington 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 Great Barrington. On Rover:

  • 100% of sitters can help with special care needs
  • 100% 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.

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