House Sitting in West Stockbridge

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

End
Search

Every sitter passes an enhanced background check. Learn about RoverProtect

Top rated West 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%.

1 / 1
Sitter Profile Image: Keri H.
Verified Background Check
Keri H.
Star Sitter
$106
total per night
5.0 out of 5 stars
57 reviews
19 repeat clients
20 years of experience
Lenox, MA, 01240

Keri was great! She was able to jump in at the last minute and stay at our house with our 2 dogs. She communicated regularly and sent lots of pictures of our pups. I think they liked her so much they didn't even realize we were gone!

Profile image
lisa M.
Sitter Profile Image: Trista S.
Verified Enhanced Background Check
Trista S.
Star Sitter
$34
total per night
5.0 out of 5 stars
17 reviews
5 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!

Profile image
Jessica M.
Sitter Profile Image: Sally A.
Verified Enhanced Background Check
Sally A.
$167
total per night
5.0 out of 5 stars
45 reviews
13 repeat clients
50 years of experience
Richmond, MA, 01254

Sally is amazing! She took great care of our dog and two cats - she clearly loves animals. Additionally, she did a wonderful job looking after our home. She left everything looking tidy, and went the extra mile by washing sheets and towels before she left. She also left good notes about how it all went. She made the weekend easy and stress free! And she sent wonderful photos, too. This was our first time having her in our home and I would have her back in a second. A+ petsitter!

Profile image
kim p.
Sitter Profile Image: Tara D.
Verified Enhanced Background Check
Tara D.
$56
total per night
5.0 out of 5 stars
5 reviews
1 repeat client
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!

Profile image
Jen B.
Sitter Profile Image: Sydney R.
Verified Enhanced Background Check
Sydney R.
$56
total per night
5.0 out of 5 stars
2 reviews
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.

Profile image
Marie R.
Sitter Profile Image: Caitlin H.
Verified Background Check
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!!

Profile image
Kyle W.
Sitter Profile Image: Kelly H.
Verified Background Check
Kelly H.
$139
total per night
5.0 out of 5 stars
65 reviews
31 repeat clients
14 years of experience
Otis, MA, 01253

Kelly & Nabil are exceptional sitters. They left our home spotless, sent photos of our pets and took great care of them. Our pup was sad to see them go, we feel so fortunate to have found such loving and caring pet sitters!

Profile image
Katherine O.
Sitter Profile Image: Taylor W.
Verified Enhanced Background Check
Taylor W.
Star Sitter
$76
total per night
5.0 out of 5 stars
16 reviews
5 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.

Profile image
MA
Sitter Profile Image: Valentina M.
Verified Enhanced Background Check
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: Evelyn F.
Verified Enhanced Background Check
Evelyn F.
Star Sitter
$56
total per night
5.0 out of 5 stars
35 reviews
17 repeat clients
5 years of experience
Troy, NY, 12180

Evelyn was fantastic with my senior dog, and pup that can be lazy and have spurts of energy. Additionally, she was great with our cats, giving very detailed updates throughout the trip. I really appreciated the level of care, the attention to details, and the extra mile she went to ensure a smooth trip for not only her but myself. Incredibly grateful to have found her!

Profile image
Whitney G.
Sitter Profile Image: McKenna P.
Verified Background Check
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 was able to help with our Aussie-doodle at short notice and we are so grateful! They had a fun day together and she helped him to be active and busy instead of in his kennel for a very long day. McKenna has a lot of experience and knowledge about what dogs need. She communicates regularly and sent some photos during the day as well. Thank you McKenna!!

Profile image
Teri T.
Sitter Profile Image: Amy H.
Verified Enhanced Background Check
Amy H.
$36
total per night
5.0 out of 5 stars
4 reviews
1 repeat client
5 years of experience
Blandford, MA, 01008

About: Hello! I am a lifelong pet owner and animal lover with experience with everything from chickens and horses to cats and dogs. I have two canine family members myself: a medium-sized mix named Bonnie and a 10-pound Italian Greyhound/chihuahua named Rio. I know how hard it can be to find loving, reliable, and safe pet setters, which prompted me to open up my own home. My dogs love meeting new friends to play with. They get along well with others (though we always require a meet-and-greet before a sit) and are friendly with cats as well. My work-from-home career and spacious property allows me the flexibility to fully care for your pet without any interruptions such as commutes or 9-5 work hours. I am fortunate to enjoy a fully remote, flexible career, which means I am always present for your canine or feline family members. I can accommodate short or long-term stays, and am home throughout the day to maintain your pet's schedule, so they feel completely at home. I think it's important to a pet's sense of wellbeing to be able to keep to their usual schedule as best as possible while in my care. I live on five acres in a log home in a beautiful hilltown in Western Massachusetts, and have a fully fenced yard. I love taking my own pup on daily walks on our property or on nearby dirt roads, so if you have an active dog who needs exercise, I'm your person! If a less active lifestyle is better for your dog, I can fully accommodate that as well. Pets are allowed on my furniture and can make themselves cozy by my wood stove in winter or on my sunny deck in summer. I am familiar with using crates (if desired, but not required) and have a large finished basement perfect for playtime in the winter months.

Sitter Profile Image: Brenna B.
Verified Enhanced Background Check
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!

Profile image
Nadine S.
Sitter Profile Image: Olivia A.
Verified Enhanced Background Check
Olivia A.
$39
total 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: Clara M.
Verified Enhanced Background Check
Clara M.
$62
total per night
5.0 out of 5 stars
17 reviews
3 repeat clients
11 years of experience
Tyringham, MA, 01238

I cannot say enough about Claire. She took care of everything. In my opinion, tater ( the dog ) would rather live with Claire than me at this point. That’s how good she is with animals. 100% recommend her!!!

Profile image
Robert K.
Sitter Profile Image: Alyssa M.
Verified Enhanced Background Check
Alyssa M.
$89
total 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: Dana G.
Verified Background Check
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!!

Profile image
Liliana A.
Sitter Profile Image: Reymon B.
Verified Enhanced Background Check
Reymon B.
$89
total 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: Lindsay L.
Verified Enhanced Background Check
Lindsay L.
$134
total per night
5.0 out of 5 stars
3 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: Jennifer E.
Verified Enhanced Background Check
Jennifer E.
$111
total per night
5.0 out of 5 stars
2 reviews
1 repeat client
15 years of experience
Chatham, NY, 12037

Jennifer arrived promptly and was attentive to our elderly dog's needs. She has a lovely manner with animals and I would use her again.

Profile image
Susan A.
1 / 1
View more sitters

West Stockbridge pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Sally is great! She's detail-oriented, responsible, friendly, helpful, and my dogs loved her! The house was left in better condition than when she arrived! She was very clean and tidy and did some cleaning before she left. She was good about sending updates/pics. We will be using Sally again!

Profile image
Christin F.
House Sitting
5.0 out of 5 stars

We have used Sally again and are very happy with her highly professional services. Rusty enjoyed her company and the house was left in immaculate condition. She even dealt with freezer problem in a wonderful, smart manner! Great sitter!

Profile image
Barry S.
House Sitting
1 / 1
Find pet care near you

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 West Stockbridge is $65

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 West Stockbridge average 2
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 West Stockbridge on Rover as of Jun 2026 was about $65 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 West 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 Jun 2026, there are 121 house sitters in West 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, 83% of West Stockbridge house sitters respond in under an hour.

House sitters in West Stockbridge have an average of 15 years of experience. House sitters with repeat customers have an average of 2 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 West 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. West 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.