Pet Sitting in Stockbridge

Book a pet sitter to stop by your home a few times a day to feed and play with your cat or dog.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
One Time
Repeat Weekly
Which dates do you need?
What size are your dogs (lbs)?
To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

Search Results

Sitter Profile Image: Heather H.
Verified Enhanced Background Check
Sitter Profile Image: Heather H.
Verified Enhanced Background Check

1. Heather H.

Retired, dog & cat loving mom
West Stockbridge, MA, 01266
4.3 mi. away
Drop-In Visits
5.0 out of 5 stars
25 reviews
7 repeat clients
from
$20
per visit

She loves our cat very much and takes care of our cat very well, she is a very reliable person, we will ask her to continue taking care of our cat in the future。

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Maeve D.
Verified Enhanced Background Check
Sitter Profile Image: Maeve D.
Verified Enhanced Background Check

2. Maeve D.

dog person; outdoor adventurer 🌱🐕
Housatonic, MA, 01236
2.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
5 repeat clients
from
$22
per visit

Maeve is amazing with my pup - remembering all his little quirks and needs. She's easy to communicate with, so kind, and attentive. Buster is always happy to see her!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Teresa D.
Verified Enhanced Background Check
Sitter Profile Image: Teresa D.
Verified Enhanced Background Check

3. Teresa D.

Dog Mom w/Rich Fostering Background
New Marlborough, MA, 01230
9.3 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
10 reviews
1 repeat client
from
$20
per visit

Teresa is a wonderful, caring & trustworthy animal lover who will provide your furry family member the best care & attention while you're away. For years, she has fostered & adopted many dogs of different breeds, temperaments & medical conditions so you can rest assured she is equipped to handle any situation. Enjoy your time away knowing your furbaby is in the best hands, being loved & spoiled by Teresa.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jess L.
Verified Enhanced Background Check
Sitter Profile Image: Jess L.
Verified Enhanced Background Check

4. Jess L.

I care for the care of your pets
Pittsfield, MA, 01201
12.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
32 reviews
6 repeat clients
from
$29
per visit

Very timely and took good care of Luna

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Caitlin H.
Verified Background Check
Sitter Profile Image: Caitlin H.
Verified Background Check

5. Caitlin H.

Flexiblity to meet your pet needs
Pittsfield, MA, 01201
11.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
1 repeat client
from
$25
per visit

Took good care of our fog

Calendar Recently Updated
Sitter Profile Image: Andrea L.
Verified Enhanced Background Check
Sitter Profile Image: Andrea L.
Verified Enhanced Background Check

6. Andrea L.

I got you covered!
Great Barrington, MA, 01230
3.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
14 reviews
4 repeat clients
from
$28
per visit

Andrea was very warm and the cats liked her immediately. She also made us very comfortable with leaving out cats and home in her care. Will definitely book again.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Tetiana M.
Verified Enhanced Background Check
Sitter Profile Image: Tetiana M.
Verified Enhanced Background Check

7. Tetiana M.

I care for the dogs
Lenox, MA, 01240
7.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
9 reviews
4 repeat clients
from
$20
per visit

Tetiana was so sweet to our Bardo and very communicative. She took care of him while we were away and he was recovering from hip surgery. Reliable and very loved by our pup! Would highly recommend

Sitter Profile Image: Logan A.
Verified Enhanced Background Check
Sitter Profile Image: Logan A.
Verified Enhanced Background Check

8. Logan A.

Sitter, Walker, Sled Dog Handler
Pittsfield, MA, 01201
12.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
4.5 out of 5 stars
15 reviews
9 repeat clients
from
$20
per visit

Logan was great with our two pups. Very attentive and professional. They loved him.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Tiffany A.
Verified Enhanced Background Check
Sitter Profile Image: Tiffany A.
Verified Enhanced Background Check

9. Tiffany A.

A walk a day will keep the vet away
Pittsfield, MA, 01201
11.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
2 reviews
1 repeat client
from
$15
per visit

Tiffany is an excellent dog walker/boarder. She is professional, friendly, reliable, and organized. Your fur babies will be in great hands with her, I know mine love her! Working with Tiffany has always been a pleasant experience and I highly recommend booking her.

Calendar Recently Updated
Sitter Profile Image: Colleen W.
Verified Enhanced Background Check
Sitter Profile Image: Colleen W.
Verified Enhanced Background Check

10. Colleen W.

Pet loving retired Postmaster!
PITTSFIELD, MA, 01201
10.8 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
1 review
from
$25
per visit

Colleen was a wonderful sitter for my two elderly dachshunds. She was very attentive to their needs and made sure they got their medications daily. Overall, Colleen is very warm and compassionate and you can tell she really loves animals! She’s also very communicative and would send us updates and pictures several times a day which made us feel much more relaxed and at ease. Would have her watch our pups again anytime!

Calendar Recently Updated
Sitter Profile Image: Jennifer M.
Verified Enhanced Background Check
Sitter Profile Image: Jennifer M.
Verified Enhanced Background Check

11. Jennifer M.

I have a warm heart for cold noses.
Pittsfield, MA, 01201
11.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
32 reviews
7 repeat clients
from
$30
per visit

Jennifer was great! She was easily accessible and pleasant and willing to do what was needed for my kitties. She was willing to other duties such as take out trash,

Sitter Profile Image: Kai C.
Verified Enhanced Background Check
Sitter Profile Image: Kai C.
Verified Enhanced Background Check

12. Kai C.

Rover 101
I'll run with + love your dog
Lee, MA, 01238
4.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
23 reviews
7 repeat clients
from
$25
per visit

My dog loves Ashley! I'm so glad that shes available to let my dog have a bathroom break, some lunch and belly scritches or play time. I highly recommend Ashley to anyone.

Calendar Recently Updated
Sitter Profile Image: Grace E.
Verified Background Check
Sitter Profile Image: Grace E.
Verified Background Check

13. Grace E.

Responsible, communicative
Lenox, MA, 01240
5.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
6 reviews
4 repeat clients
from
$25
per visit

I could not ask for a better companion while I am away from my furry friends! Grace is the most reliable, caring, and thoughtful dog sitter one could ever imagine. She continuously goes above and beyond for our pets. Now that she has moved away from our area, I want to encourage others to utilize her skillsets! She is just that good. 100% incredible human AND dog sitter. Thanks, Grace!

Calendar Recently Updated
Sitter Profile Image: Robert W.
Verified Enhanced Background Check
Sitter Profile Image: Robert W.
Verified Enhanced Background Check

14. Robert W.

I am full of pawsitivity
Lee, MA, 01238
3.9 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
2 repeat clients
from
$32
per visit

Once again, Robert was Excellent ‼️

Sitter Profile Image: Chloe O.
Verified Background Check
Sitter Profile Image: Chloe O.
Verified Background Check

15. Chloe O.

For the DOGaholics!
Lee, MA, 01238
4.9 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
9 reviews
from
$25
per visit

Stayed in contact and sent updates and pictures. Lovely human who clearly loves and cares for animals!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Bella B.
Verified Enhanced Background Check
Sitter Profile Image: Bella B.
Verified Enhanced Background Check

16. Bella B.

Lakeside Sitter, Works from Home.
Stockbridge, MA, 01262
2.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
5 reviews
1 repeat client
from
$25
per visit

Bella is my daughter so, of course, I am biased. But she has taken care of my dogs since she was little. I absolutely trust her with my animals' well-being. Also--again, I'm biased--but most people find her really fun to deal with and be around. I totally recommend her to take care of your dog.

Sitter Profile Image: Janet C.
Verified Background Check
Sitter Profile Image: Janet C.
Verified Background Check

17. Janet C.

animals are loving by nature
Great Barrington, MA, 01230
6.5 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
11 repeat clients
from
$16
per visit

All good.

Sitter Profile Image: Shelby L.
Verified Enhanced Background Check
Sitter Profile Image: Shelby L.
Verified Enhanced Background Check

18. Shelby L.

Pet sitter with lots of love!
Lee, MA, 01238
3.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
1 repeat client
from
$30
per visit

Shelby was great with our pups. The check-ins and photos after each visit were wonderful as well. We hope to work with her again!

Sitter Profile Image: Andrew C. S.
Verified Enhanced Background Check
Sitter Profile Image: Andrew C. S.
Verified Enhanced Background Check

19. Andrew C. S.

Rover 101
Dog lover who enjoys the outdoors
Lee, MA, 01238
4.0 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
30 reviews
9 repeat clients
from
$30
per visit

We were very happy to meet Andrew ! Our dog adored him as Andrew went out of his way to make him feel comfortable during his first visit. Andrew was very interested in learning everything about our fur baby, he asked important questions and he actively listened our recommendations. We can tell that Andrew loves his job, he is passionate about connecting with both, dogs and humans, and he wants to make his clients feel that they are leaving their pet in safe, warm, and caring hands. We look forward to continue working together!

Sitter Profile Image: Shayla H.
Verified Enhanced Background Check
Sitter Profile Image: Shayla H.
Verified Enhanced Background Check

20. Shayla H.

PAWSOME opportunities for your dog!
Lenox, MA, 01240
5.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
13 reviews
from
$25
per visit

Shayla is amazing and our boys absolutely love their time with her. She is a natural! They have so much fun on their long hikes and come home so tired! We highly recommend her! You will not regret it!

Search Map

Rover also offers Pet Sitting & Drop Ins in:

Rover also offers other services in Stockbridge:


Rover.com is the simple, savvy way to find and book Stockbridge drop in pet sitting. It's easy to find the perfect pet sitter — many sitters have offered pet sitting on Rover for years, and 95% of reviewed stays have received a perfect five-star rating. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Pet sitters on Rover have the option to complete a background check, which you can see from their background check badge. Pet sitters are booked on Rover every minute of every day, and 92% of the population lives within a short drive of one of the more 60,000 sitters who've listed their services on Rover, so you're sure to find the perfect pet sitter in Stockbridge. When you book with one of our trusted pet sitters on Rover you get peace of mind that your home and pets are in loving hands.

Drop-In Visits