House Sitting in Stockbridge

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

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Top rated Stockbridge house sitters

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: Keri H.
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Keri H.
Star Sitter
$106
total per night
5.0 out of 5 stars
55 reviews
19 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: Ashley & Robert D.
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Ashley & Robert D.
Star Sitter
$89
total per night
5.0 out of 5 stars
12 reviews
5 repeat clients
25 years of experience
Austerlitz, NY, 12017

Ashley and Bob were great with my 10 year old, nervous & quirky pup! They stayed at the house with her for 3 days and 3 nights and during that time, sent frequent updates and pictures. I was so grateful for their communication and care of my dog.

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Tara J.
Sitter Profile Image: Elizabeth B.
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Elizabeth B.
$40
total per night
5.0 out of 5 stars
6 reviews
1 repeat client
1 year of experience
Lee, MA, 01238

Liz met us at our campsite right on time and she immediately got along with our Catahoula, Annie. They were quick friends. Liz did a great job keeping her safe and entertained while me and my family attended a concert, and Annie was safe and relaxed when we got back to our site. Liz did great and I'll recommend her to anyone who needs help watching their fur baby for a few hours.

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Greg M.
Sitter Profile Image: Taylor W.
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Taylor W.
$76
total per night
5.0 out of 5 stars
14 reviews
1 repeat client
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: Tara D.
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Tara D.
$56
total per night
5.0 out of 5 stars
2 reviews
30 years of experience
Pittsfield, MA, 01201

Tara was so amazing with our dog and our cat. She sent us lots of updates while house sitting, took our dog for lots of walks, and gave them both lots of attention 😊 Great job with our pets and great communication. Would book her again in a heartbeat!

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Jen B.
Sitter Profile Image: Trista S.
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Trista S.
Star Sitter
$34
total per night
5.0 out of 5 stars
13 reviews
4 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.

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Theresa S.
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: 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: Sally A.
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Sally A.
Star Sitter
$167
total per night
5.0 out of 5 stars
45 reviews
12 repeat clients
50 years of experience
Richmond, MA, 01254

I was very nervous about leaving my older dog for a quick trip but Sally was an absolute dream. Right off the bat she eased my concerns and my dog was very comfortable with her. It was clear she was highly knowledgeable about animals and definitely an animal lover! I'm very happy with Sally's communication and I can honestly say she went above and beyond for my fella. I was able to relax and enjoy my trip knowing my precious pup was being spoiled at home. Rest easy with booking Sally, she's a dream to have as a sitter!

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Jen L.
Sitter Profile Image: Brenna B.
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Brenna B.
$111
total per night
5.0 out of 5 stars
6 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: Gabrielle H.
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Gabrielle H.
$36
total 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: Kelly H.
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Kelly H.
$139
total per night
5.0 out of 5 stars
65 reviews
31 repeat clients
14 years of experience
Otis, MA, 01253

We are so grateful to have found Kelly and Nabil! They are incredibly attentive, caring, and down to earth. We are already planning another trip knowing our dog will have such amazing care.

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Joey W.
Sitter Profile Image: Shannon M.
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Shannon M.
$89
total per night
5.0 out of 5 stars
2 reviews
10 years of experience
Pittsfield, MA, 01201

About: I have always lived in household with a minimum of 3 dogs, dogs have been my companions before I could walk. Now I’m always with my service dog, Winnie. I worked with a program to train my own service dog. He’s a friendly little golden retriever, and a fast friend. During his training I learned the importance of trust routine, and patience with dogs. I’m currently working part time from 7:30 to 2 pm Monday, Wednesday, Thursday and 10-3 on Saturdays. I am always up for hiking or a short walk with dogs. I have a service dog who comes with me everywhere, he’s a gentle and easy friend, and generally good with other dogs. He’s just as happy to play as he is to nap.

Sitter Profile Image: McKenna P.
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McKenna P.
Star Sitter
$84
total per night
5.0 out of 5 stars
382 reviews
146 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 W.
Sitter Profile Image: Michael T.
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Michael T.
$56
total per night
40 years of experience
Lee, MA, 01238

About: I have care and experience with dog`s for more than 20 years. From puppies to adult and elderly. From Chihuahuas to Great Danes. Training Puppies from indoors to out doors potty training and pee pads is a + ... I recommend my own pee pads for training purposes! I own only 1 dog presently. A Chihuahua, Blue Tic Hound breed. Weighing in at 5.8lbs. She is now 19 years young. Gets along great with cats & other dogs. I am retired, so no worries about time, just scheduling. First come first served, so to speak. I will not turn down a client or pet/animal owner unless the animal is a potential threat to my well being and health. I have experience administering medications to needed pets/animals and care of feeding, washing (shower/bath care) and walks. Play time is essential, especially for young to middle aged pets because of the energy they posses. There is nothing more happier than a tired dog to sleep happy dreams from exertive play time or a cat playing laser tag and cat and mouse games. : )

Sitter Profile Image: Shelby L.
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Shelby L.
$89
total per night
5.0 out of 5 stars
9 reviews
1 repeat client
13 years of experience
Lee, MA, 01238

Shelby is a very caring and responsible pet sitter.

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Mark M.
Sitter Profile Image: Dana G.
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Dana G.
$139
total per night
5.0 out of 5 stars
40 reviews
11 repeat clients
20 years of experience
PITTSFIELD, MA, 01201

Dana took care of our young puppy while we were away on vacation. She is very responsible, compassionate & dedicated to her caring for dogs. You can tell she really loves what she does! She kept us updated with information and pictures daily, including videos. It was a pleasure to see our puppy healthy, happy & having fun with Dana. We definitely look forward to booking with Dana again!!

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Liliana A.
Sitter Profile Image: Katelynn R.
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Katelynn R.
$89
total 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: James S.
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James S.
$89
total per night
30 years of experience
West Stockbridge, MA, 01266

About: I've trained two dogs that I got when they were puppies. I currently have 1 dog and many chickens. I've watched dogs and cats in the past. I've also had cats, hamsters, fish, a rabbit, birds, guinea hens and chickens. I currently work from home most days. When I don't, I'm not gone for long. I prefer to be home if I'm pet sitting and that changes from time to time. My yard is fenced and blocked off on two sides. There is a field behind the house that's usually grass that's usually too tall for domestic animals to go into.

Sitter Profile Image: byron c.
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byron c.
$78
total per night
2 years of experience
CANAAN, CT, 06018

About: I've had my pets in my life but i've also looked after many pets. Sometimes I have had to look after more than one dog at a time and different ages and breeds. There has been times i have had to sleep over night with pets. I always feel a connection or a bond between animals as I believe they know our true intentions. m-f I Work at my main job which is at Webster Bank usually until 4 PM, But have off on holidays and weekends. Some nights I work late but I usually have a month ahead of what my schedule looks like. I treat anyone else's property as if it were my own or better than my own. I treat pets delicately and I like to find out what they are into, how they have fun, what treats they like etc. I am a very straight forward person and I am great communicating with. I work in my local surrounding towns and looking how I can serve.

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Over 7
pet parents in Stockbridge have booked house sitting

How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

The median cost per night for house sitting in Stockbridge is $63

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 house 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.

Sitters in Stockbridge average 3
repeat house sitting clients

House Sitting FAQs

Frequently asked questions about Rover

House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Stockbridge on Rover as of Apr 2026 was about $63 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.

If you’re searching for a Stockbridge house sitter for the first time, visit the house sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.

As of Apr 2026, there are 94 house sitters in Stockbridge. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 88% of Stockbridge house sitters respond in under an hour.

House sitters in Stockbridge have an average of 17 years of experience. House sitters with repeat customers have an average of 3 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Stockbridge.

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Stockbridge house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.