House Sitting Stockbridge

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Stockbridge, 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%.

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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
18 reviews
9 repeat clients
25 years of experience
Austerlitz, NY, 12017

Ashley is my favorite of all of the wonderful Rover sitters! My pets were super happy upon my return and my home was exactly as I handed it to her! Super responsible, exacting time and a lovely, peaceful nature!

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Jennifer B.
Sitter Profile Image: Taylor W.
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Taylor W.
Star Sitter
$76
total per night
5.0 out of 5 stars
19 reviews
8 repeat clients
20 years of experience
Lee, MA, 01238

Taylor was great to work with. She communicated during her stay at our house about our dog who takes many medication and how he was doing. Even sent us a great picture of him lounging on the couch. I would recommend her highly.

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Dawn K.
Sitter Profile Image: Sidonie K.
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Sidonie K.
$36
total per night
5.0 out of 5 stars
6 reviews
2 repeat clients
5 years of experience
Stockbridge, MA, 01262

About: I love animals! I’ve grown up with dogs and cats so I have been exposed to the needs of animals since being a child. I have 2 of my own cats, Mushu and Micha, so I understand how hard it can be to leave them behind. Let me assure you that I will take great care of your cats and treat them like they are my own! I have 3 years of experience cat-sitting for families. I know how hard it is to find reliable care for your animals, that’s why I’m here to help! Hi! I am a college student who is home for the summer. I have a part time job, but I can easily accommodate visits. Please reach out, I would love to take care of your pet! In my home I feed, brush, and cut the nails of my cats. I also clean and change their litter boxes when necessary. I have some experience administering medicine, but only pills and tick medicine.

Sitter Profile Image: Hannah L.
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Hannah L.
$56
total per night
5.0 out of 5 stars
4 reviews
7 years of experience
Lenox, MA, 01240

excellent

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Keralyn R.
Sitter Profile Image: Sydney R.
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Sydney R.
$56
total per night
5.0 out of 5 stars
10 reviews
3 repeat clients
12 years of experience
Great Barrington, MA, 01230

Sydney was completely wonderful! Our dogs loved their time with her. She took Louie on a hike and on several walks in a nearby woods. She sent us photos of them , both on walks and when hanging out together. It was clear that she had done everything that we had asked- and much more.

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

Keri was a pleasure to communicate with before and during the pet sit. Our dog, Katy, who is a somewhat recent rescue who doesn't love everyone, took to Keri right way and rested at her feet when we reviewed my long and detailed instructions in our orientation. Katy has a weird behavior associated with her anxiety and that didn't phase Keri at all. Our house has some idiosyncrasies and Keri didn't seem to mind managing those things, like our Berkey water filter needs refilling in a specific way and the AC drips into a bucket so has to be on a timer, etc. Katy also takes medication and other supplements and Keri was great with all that too. We felt confident leaving Katy in her care and, according to our friend who took over for the second week we were gone, all was well with the house (tidy and clean) and all was well with Katy (relaxed and easy). Keri sent me daily communications and photos. Keri even took Katy to the river that we left instructionsn for. I was impressed that Keri took the trouble to do that special outing with Katy. Keri included her husband (with our permission) who also seemed great with Katy. I highly recommend Keri for pet-sitting. She's just super!

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

McKenna was incredible! My picky dog loved her right away, and she navigated his separation anxiety so lovingly and effectively. Her knack and intuition with animals shows. She was extremely communicative, clear and thoughtful at every step. Can't wait to book her again!

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Alexandra R.
Sitter Profile Image: Trista S.
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Trista S.
$45
total per night
5.0 out of 5 stars
21 reviews
9 repeat clients
30 years of experience
Pittsfield, MA, 01201

Trista took amazing care of our two girls during our long weekend in Pennsylvania - she sent photos regularly so we could see how they were getting along with her and that they were having fun while we were away. We will definitely be booking with her again!

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Jessica M.
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

This was our second time booking Sally to care for our one year old corgi and six hens. We were at ease our entire vacation because we knew how well they were all being cared for. Sally took our corgi on daily, multiple walks. Sally took excellent care of the hens and kept their coop nice and clean. All of our animals were well cared for, safe and attended to. We will be booking again and we so appreciate her!

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Angelica B.
Sitter Profile Image: Lauren S.
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Lauren S.
$36
total per night
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: Sophie H.
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Sophie H.
$139
total per night
5.0 out of 5 stars
29 reviews
10 repeat clients
15 years of experience
Hudson, NY, 12534

Sophie cared for our very active Australian Shepherd puppy, cat, and our home with love, skill, and the highest level of professionalism. She was very responsive and eased my anxiety over leaving my boys with pictures and prompt communication. I trust her completely.

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Aimee M.
Sitter Profile Image: Caitlin H.
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Caitlin H.
$56
total 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!!

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Kyle W.
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: 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: Leona O.
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Leona O.
$49
total per night
4.7 out of 5 stars
7 reviews
2 repeat clients
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!

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Liane T.
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: Brian L.
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Brian L.
$77
total per night
4.9 out of 5 stars
159 reviews
84 repeat clients
20 years of experience
Schenectady, NY, 12306

Brian was great with my dog and with my house. My dog was well taken care off and Brian did a great job communicating and being flexible on dates.

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Mitesh M.
Sitter Profile Image: Valentina M.
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Valentina M.
$36
total per night
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: Mariah C.
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Mariah C.
$84
total per night
5.0 out of 5 stars
13 reviews
5 repeat clients
19 years of experience
Egremont, MA, 01230

Mariah did an excellent job watching Joey overnight while we were out of town. She was on-time, very communicative and provided pictures while we were away. Would definitely recommend and plan to use her again for when we need to go out of town.

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Chris F.
Sitter Profile Image: Julie G.
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Julie G.
$56
total per night
5.0 out of 5 stars
9 reviews
1 repeat client
4 years of experience
Holyoke, MA, 01040

Julie was amazingly flexible, as our schedule was unknown, and was there when we needed her. More importantly, she was good with Ricky, took him out for walks as well as for his sanitary needs, and kept us regularly informed, with pictures. If we are in the area again we will seek her to assist us, and Ricky, again.

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John M.
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The median cost per night for house sitting in Stockbridge is $60

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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
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Popular requests for house sitting - Stockbridge

Select a filter and find qualifying sitters offering house sitting.

Sitters in Stockbridge average 3
repeat house sitting clients

FAQs for House Sitting - Stockbridge

Frequently asked questions about Rover

As of August 2026, there are 312 sitters on Rover offering House Sitting across Stockbridge. 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 Stockbridge 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 Stockbridge 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 Stockbridge 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 Stockbridge. On Rover:

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