House Sitting in West Stockbridge

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

Search

More resources

A focus on safety

Enjoy photo updates, easy messaging, and the knowledge that every sitter joining Rover needs to pass an enhanced background check. Learn more about RoverProtect

Top rated West Stockbridge house sitters

1 / 1
Sitter Profile Image: Caitlin H.
Verified Background Check
Caitlin H.
from
$50
per night
5 out of 5.0 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
Sitter Profile Image: Maggie T.
Verified Background Check
Maggie T.
from
$50
per night
5 out of 5.0 stars
10 reviews
4 repeat clients
10 years of experience
Lenox, MA, 01240

My puppy Zero is like my child. I trust Maggie with my baby all the time and have always been happy and impressed with the amount of love and care she shows him. Her judgement and decision making when watching Zero is impeccable. I know when he’s with her that he’ll always be closely watched, cared for, and loved. Zero loves his days with Maggie!

Sitter Profile Image: Catherine M.
Verified Enhanced Background Check
Catherine M.
from
$55
per night
5 out of 5.0 stars
9 reviews
1 repeat client
20 years of experience
East Schodack, NY, 12063

CATHERINE IS THE BEST!!! If you're looking for someone kind, compassionate, and EXCELLENT with your pup/pet, you won't find anyone better than Catherine. I could not recommend her more highly!!

Profile image
Sitter Profile Image: Collin S.
Verified Background Check
Collin S.
from
$70
per night
5 out of 5.0 stars
7 reviews
1 repeat client
20 years of experience
Great Barrington, MA, 01230

Collin was amazing with my dogs. He gave my big dog a shower and she was smelling delicious. My dogs went on hiking and I am sure they had a blast on their time with Collin. I will definitely recommend him to take care of your beloved pets.

Profile image
Sitter Profile Image: Bella G.
Verified Enhanced Background Check
Bella G.
from
$65
per night
5 out of 5.0 stars
9 reviews
10 years of experience
lanesborough, MA, 01237

Bella is highly recommended. With a last minute change in my plans, Bella was right there to help out. There was never a doubt that Mac & Cheez weren’t being loved as she sent frequent updates and photos of my babies. I’m so grateful and will definitely reach out to her again.

Profile image
Sitter Profile Image: Alannah K.
Verified Enhanced Background Check
Alannah K.
from
$50
per night
5 out of 5.0 stars
6 reviews
1 repeat client
8 years of experience
West Coxsackie, NY, 12192

Alannah was great with Cornelius! She was prompt in her response on availability and coming to meet us. She projects a calm and natural energy with dogs! Cornelius loved her and so did we and we will not hesitate to book her again!!💕

Profile image
Sitter Profile Image: Samantha B.
Verified Enhanced Background Check
Samantha B.
from
$55
per night
10 years of experience
Schodack Landing, NY, 12156

Samantha💕 B is an animal lover having four pets of her own, two cats and two dogs. She’s cared for my dogs on many occasions being responsible, reliable, and compassionate. They love her as she gives them her full attention.

Sitter Profile Image: Daniella S.
Verified Enhanced Background Check
Daniella S.
from
$50
per night
5 out of 5.0 stars
6 reviews
3 repeat clients
7 years of experience
Pittsfield, MA, 01201

Daniella did a terrific job with our two dogs this weekend. We are new to the area and Daniella made us feel confident to leave for 2 days. She handled her responsibilities perfectly and left the house in excellent shape.

Profile image
Sitter Profile Image: Amanda S.
Verified Enhanced Background Check
Amanda S.
from
$75
per night
5 out of 5.0 stars
24 reviews
8 repeat clients
25 years of experience
Pittsfield, MA, 01201

Amanda has stayed at the house for a long weekend watching my cat and dog. She sent photos, and the pets were happy and perky upon my return. She is an understanding pet owner herself, with her own dog and cats.

Sitter Profile Image: jess p.
Verified Enhanced Background Check
jess p.
from
$30
per night
5 out of 5.0 stars
11 reviews
1 repeat client
5 years of experience
Petersburg, NY, 12138

Jess was great with our animals. She stayed at our home with our two dogs and two cats while we were out of town. Jess was a great guest. She left the house clean and was very respectful of our space. She was very communicative during her stay, sending us several updates with pictures included. She bonded very well with all four of the animals and sent several photos of the cats snuggled up with her. She also brushed our saint bernard often and even offered to care for my plants!

Profile image
Sitter Profile Image: Keri H.
Verified Background Check
Keri H.
from
$95
per night
5 out of 5.0 stars
36 reviews
13 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
Sitter Profile Image: Bailey Y.
Verified Enhanced Background Check
Bailey Y.
from
$55
per night
25 years of experience
Pittsfield, MA, 01201

I couldn’t ask for a better dog walker and caregiver! Bailey is incredibly kind, knowledgeable, and responsible, always showing up on time and treating my dog with the utmost care. Their love for animals is evident in the way they handle every walk, ensuring my pup gets the exercise, attention, and affection they need. I trust them completely and highly recommend their services to anyone looking for a reliable and caring pet caregiver!

Sitter Profile Image: Michael T.
Verified Enhanced Background Check
Michael T.
from
$50
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: Sally M.
Verified Enhanced Background Check
Sally M.
from
$138
per night
5 out of 5.0 stars
38 reviews
10 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!

Profile image
Sitter Profile Image: McKenna P.
Verified Background Check
McKenna P.
from
$75
per night
5 out of 5.0 stars
319 reviews
124 repeat clients
8 years of experience
Lenox, MA, 01240

McKenna is absolutely wonderful with my dog. She took great care of her, and I came home to a very relaxed pup. She treats your house respectfully. I got numerous pictures and updates....all appreciated! I would not hesitate to recommend her and will certainly book her again soon.

Profile image
Sitter Profile Image: Lucy C.
Verified Enhanced Background Check
Lucy C.
from
$100
per night
8 years of experience
Great Barrington, MA, 01230

Lucy was perfect for our high energy but attention loving dog. She was respectful of our home and had great communication. We will continue to use her when she is available.

Profile image
Sitter Profile Image: Yenifer V.
Verified Enhanced Background Check
Yenifer V.
from
$55
per night
3 years of experience
Pittsfield, MA, 01201

We had several dogs at home and Yenifer has always been friendly and loving with them. She’s a caring person who’s always have a smile and a positive attitude towards the care of our loved ones.

Sitter Profile Image: Ashley J.
Verified Enhanced Background Check
Ashley J.
from
$30
per night
16 years of experience
Pittsfield, MA, 01201

We couldn't have asked for a better dog sitter than Ashley!Her genuine love for animals and exceptional care truly set them apart. From the moment we left our beloved pets in Ashley’s care, we knew they were in great hands. Ashley was incredibly attentive and responsive, always ensuring our pets' needs were met. The regular updates and photos they provided gave us so much peace of mind while we were away. When we returned, our animals were not only well-cared for, but they were also incredibly happy! It's clear that Ashley goes above and beyond to create a comfortable and joyful environment for every pet they look after. We can't thank Ashley enough and wholeheartedly recommend their services to anyone seeking a caring and dedicated pet sitter.

Sitter Profile Image: Caroline W.
Verified Enhanced Background Check
Caroline W.
from
$120
per night
5 out of 5.0 stars
3 reviews
5 years of experience
Lenox, MA, 01240

Caroline took great care of my large pit mix, June! June stayed with Caroline during a storm, and she is scared of thunder. Caroline was very communicative with me throughout the time I was gone and even sent great pictures showing that they were getting through the storm okay. I'm so grateful for Caroline taking such good care of my dog- helping both June's anxiety and my own! High recommendations all around.

Sitter Profile Image: William M.
Verified Enhanced Background Check
William M.
from
$60
per night
35 years of experience
Richmond, MA, 01240

Will is the most responsible and caring pet lover. He has had dogs his whole life and has never met one that didn't love him!

1 / 1
View more sitters

Loving house sitters in your neighborhood

Search Results

Sitter Profile Image: Caitlin H.
Verified Background Check
Sitter Profile Image: Caitlin H.
Verified Background Check

1. Caitlin H.

Flexiblity to meet your pet needs
Pittsfield, MA, 01201
8.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 5.0 stars
17 reviews
3 repeat clients
Profile image

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!!

Availability updated 7 days ago
Sitter Profile Image: Maggie T.
Verified Background Check
Sitter Profile Image: Maggie T.
Verified Background Check

2. Maggie T.

You love dogs? Me too!
Lenox, MA, 01240
6.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 5.0 stars
10 reviews
4 repeat clients

My puppy Zero is like my child. I trust Maggie with my baby all the time and have always been happy and impressed with the amount of love and care she shows him. Her judgement and decision making when watching Zero is impeccable. I know when he’s with her that he’ll always be closely watched, cared for, and loved. Zero loves his days with Maggie!

Availability updated 68 days ago
Sitter Profile Image: Catherine M.
Verified Enhanced Background Check
Sitter Profile Image: Catherine M.
Verified Enhanced Background Check

3. Catherine M.

Big or small, I love pets y'all!
East Schodack, NY, 12063
20.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$55
per night
5 out of 5.0 stars
9 reviews
1 repeat client
Profile image

CATHERINE IS THE BEST!!! If you're looking for someone kind, compassionate, and EXCELLENT with your pup/pet, you won't find anyone better than Catherine. I could not recommend her more highly!!

Availability updated yesterday
Confirmed availability for Easter Weekend
Sitter Profile Image: Collin S.
Verified Background Check
Sitter Profile Image: Collin S.
Verified Background Check

4. Collin S.

Experienced Pet Owner, I Love Dogs!
Great Barrington, MA, 01230
10.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$70
per night
5 out of 5.0 stars
7 reviews
1 repeat client
Profile image

Collin was amazing with my dogs. He gave my big dog a shower and she was smelling delicious. My dogs went on hiking and I am sure they had a blast on their time with Collin. I will definitely recommend him to take care of your beloved pets.

Availability updated 39 days ago
Sitter Profile Image: Bella G.
Verified Enhanced Background Check
Sitter Profile Image: Bella G.
Verified Enhanced Background Check

5. Bella G.

Rover 101
Huge animal lover
lanesborough, MA, 01237
13.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$65
per night
5 out of 5.0 stars
9 reviews
Profile image

Bella is highly recommended. With a last minute change in my plans, Bella was right there to help out. There was never a doubt that Mac & Cheez weren’t being loved as she sent frequent updates and photos of my babies. I’m so grateful and will definitely reach out to her again.

Availability updated today
Sitter Profile Image: Alannah K.
Verified Enhanced Background Check
Sitter Profile Image: Alannah K.
Verified Enhanced Background Check

6. Alannah K.

Hard core dog lover
West Coxsackie, NY, 12192
22.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 5.0 stars
6 reviews
1 repeat client
Profile image

Alannah was great with Cornelius! She was prompt in her response on availability and coming to meet us. She projects a calm and natural energy with dogs! Cornelius loved her and so did we and we will not hesitate to book her again!!💕

Availability updated 2 days ago
Sitter Profile Image: Samantha B.
Verified Enhanced Background Check
Sitter Profile Image: Samantha B.
Verified Enhanced Background Check

7. Samantha B.

Dogs are a girls best friend
Schodack Landing, NY, 12156
20.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$55
per night
3 reviews

Samantha💕 B is an animal lover having four pets of her own, two cats and two dogs. She’s cared for my dogs on many occasions being responsible, reliable, and compassionate. They love her as she gives them her full attention.

Availability updated 6 days ago
Sitter Profile Image: Daniella S.
Verified Enhanced Background Check
Sitter Profile Image: Daniella S.
Verified Enhanced Background Check

8. Daniella S.

Passionate animal lover!
Pittsfield, MA, 01201
9.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 5.0 stars
6 reviews
3 repeat clients
Profile image

Daniella did a terrific job with our two dogs this weekend. We are new to the area and Daniella made us feel confident to leave for 2 days. She handled her responsibilities perfectly and left the house in excellent shape.

Availability updated 12 days ago
Sitter Profile Image: Amanda S.
Verified Enhanced Background Check
Sitter Profile Image: Amanda S.
Verified Enhanced Background Check

9. Amanda S.

Star Sitter
Dogs, Cats and Chicks!
Pittsfield, MA, 01201
8.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$75
per night
5 out of 5.0 stars
24 reviews
8 repeat clients

Amanda has stayed at the house for a long weekend watching my cat and dog. She sent photos, and the pets were happy and perky upon my return. She is an understanding pet owner herself, with her own dog and cats.

Availability updated today
Sitter Profile Image: jess p.
Verified Enhanced Background Check
Sitter Profile Image: jess p.
Verified Enhanced Background Check

10. jess p.

Let me love your puppies!!
Petersburg, NY, 12138
18.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per night
5 out of 5.0 stars
11 reviews
1 repeat client
Profile image

Jess was great with our animals. She stayed at our home with our two dogs and two cats while we were out of town. Jess was a great guest. She left the house clean and was very respectful of our space. She was very communicative during her stay, sending us several updates with pictures included. She bonded very well with all four of the animals and sent several photos of the cats snuggled up with her. She also brushed our saint bernard often and even offered to care for my plants!

Availability updated 2 days ago
Sitter Profile Image: Keri H.
Verified Background Check
Sitter Profile Image: Keri H.
Verified Background Check

11. Keri H.

Rover 101
Ready to jog w/dogs & cuddle cats!
Lenox, MA, 01240
5.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$95
per night
5 out of 5.0 stars
36 reviews
13 repeat clients
Profile image

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!

Availability updated yesterday
Sitter Profile Image: Bailey Y.
Verified Enhanced Background Check
Sitter Profile Image: Bailey Y.
Verified Enhanced Background Check

12. Bailey Y.

Lover of all animals, big and small
Pittsfield, MA, 01201
9.5 mi. away
House Sitting, Drop-In Visits
from
$55
per night
1 review

I couldn’t ask for a better dog walker and caregiver! Bailey is incredibly kind, knowledgeable, and responsible, always showing up on time and treating my dog with the utmost care. Their love for animals is evident in the way they handle every walk, ensuring my pup gets the exercise, attention, and affection they need. I trust them completely and highly recommend their services to anyone looking for a reliable and caring pet caregiver!

Availability updated 6 days ago
Sitter Profile Image: Michael T.
Verified Enhanced Background Check
Sitter Profile Image: Michael T.
Verified Enhanced Background Check

13. Michael T.

Dog owner & care - 20 yrs.
Lee, MA, 01238
7.3 mi. away
House Sitting
from
$50
per night
40 years of experience

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. : )

Availability updated 13 days ago
Sitter Profile Image: Sally M.
Verified Enhanced Background Check
Sitter Profile Image: Sally M.
Verified Enhanced Background Check

14. Sally M.

Whisperer, Gentle Pet&Home Care 🥰
Richmond, MA, 01254
2.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$138
per night
5 out of 5.0 stars
38 reviews
10 repeat clients
Profile image

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!

Availability updated 18 days ago
Sitter Profile Image: McKenna P.
Verified Background Check
Sitter Profile Image: McKenna P.
Verified Background Check

15. McKenna P.

Rover 101
Star Sitter
Avid Dog Lover and Sitter
Lenox, MA, 01240
6.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$75
per night
5 out of 5.0 stars
319 reviews
124 repeat clients
Profile image

McKenna is absolutely wonderful with my dog. She took great care of her, and I came home to a very relaxed pup. She treats your house respectfully. I got numerous pictures and updates....all appreciated! I would not hesitate to recommend her and will certainly book her again soon.

Availability updated 74 days ago
Sitter Profile Image: Lucy C.
Verified Enhanced Background Check
Sitter Profile Image: Lucy C.
Verified Enhanced Background Check

16. Lucy C.

Flexible Schedule, Cats and Dogs
Great Barrington, MA, 01230
10.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$100
per night
2 reviews
Profile image

Lucy was perfect for our high energy but attention loving dog. She was respectful of our home and had great communication. We will continue to use her when she is available.

Availability updated 5 days ago
Sitter Profile Image: Yenifer V.
Verified Enhanced Background Check
Sitter Profile Image: Yenifer V.
Verified Enhanced Background Check

17. Yenifer V.

PET lover
Pittsfield, MA, 01201
8.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$55
per night
1 review

We had several dogs at home and Yenifer has always been friendly and loving with them. She’s a caring person who’s always have a smile and a positive attitude towards the care of our loved ones.

Availability updated 22 days ago
Confirmed availability for Easter Weekend
Sitter Profile Image: Ashley J.
Verified Enhanced Background Check
Sitter Profile Image: Ashley J.
Verified Enhanced Background Check

18. Ashley J.

Animal lover
Pittsfield, MA, 01201
9.5 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$30
per night
2 reviews

We couldn't have asked for a better dog sitter than Ashley!Her genuine love for animals and exceptional care truly set them apart. From the moment we left our beloved pets in Ashley’s care, we knew they were in great hands. Ashley was incredibly attentive and responsive, always ensuring our pets' needs were met. The regular updates and photos they provided gave us so much peace of mind while we were away. When we returned, our animals were not only well-cared for, but they were also incredibly happy! It's clear that Ashley goes above and beyond to create a comfortable and joyful environment for every pet they look after. We can't thank Ashley enough and wholeheartedly recommend their services to anyone seeking a caring and dedicated pet sitter.

Availability updated 10 days ago
Sitter Profile Image: Caroline W.
Verified Enhanced Background Check
Sitter Profile Image: Caroline W.
Verified Enhanced Background Check

19. Caroline W.

Remote Grad Student Loves to Dogsit
Lenox, MA, 01240
4.2 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$120
per night
5 out of 5.0 stars
3 reviews

Caroline took great care of my large pit mix, June! June stayed with Caroline during a storm, and she is scared of thunder. Caroline was very communicative with me throughout the time I was gone and even sent great pictures showing that they were getting through the storm okay. I'm so grateful for Caroline taking such good care of my dog- helping both June's anxiety and my own! High recommendations all around.

Availability updated 18 days ago
Sitter Profile Image: William M.
Verified Enhanced Background Check
Sitter Profile Image: William M.
Verified Enhanced Background Check

20. William M.

Typical pet lover
Richmond, MA, 01240
3.1 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
1 review

Will is the most responsible and caring pet lover. He has had dogs his whole life and has never met one that didn't love him!

Availability updated 83 days ago

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!

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.

House Sitting FAQs

Frequently asked questions about Rover

Connect anywhere with the Rover app