House Sitting in Sheffield

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Sitter Profile Image: Olivia V.
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Sitter Profile Image: Olivia V.
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1. Olivia V.

Reliable and Energetic Dog Lover!
Great Barrington, MA, 01230
5.0 mi. away
Boarding, House Sitting
from
$50
per night
5 out of 5.0 stars
8 reviews

You'll know the second you meet her (as will your furry friend) that Olivia is a kind, caring, and trustworthy person. She loves dogs and with her sweet and fun energy, your dogs are sure to love her right back!

Availability updated 55 days ago
Sitter Profile Image: Chrissie D.
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Sitter Profile Image: Chrissie D.
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2. Chrissie D.

Rover 101
Chrissie's Pet Care
Sharon, CT, 06069
17.2 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$65
per night
5 out of 5.0 stars
18 reviews
8 repeat clients
Profile image

Chrissie was fantastic with my two dogs! She stayed with them at our house and I could tell they were comfortable with her right away. She was easy to communicate with and sent plenty of pics! Highly recommend!

Availability updated yesterday
Sitter Profile Image: Alexis B.
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Sitter Profile Image: Alexis B.
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3. Alexis B.

Certified animal lover & caregiver!
Craryville, NY, 12521
12.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$75
per night
5 out of 5.0 stars
1 review
1 repeat client
Profile image

Alexis was great with Nancy Moo and obviously cares deeply about animals. Communication was awesome as were the photos, everything was left tidy, and most important of all I cam home to a happy pup. I would not hesitate to book Alexis again - highly recommend!

Availability updated 4 days ago
Sitter Profile Image: Scarlett R.
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Sitter Profile Image: Scarlett R.
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4. Scarlett R.

Happy Tails, Happy Trails!
Lee, MA, 01238
11.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$75
per night
5 out of 5.0 stars
1 review
1 repeat client

About: I’ve taken care of dogs since I was about 11. We have rescued dogs since I was little. I have two senior dogs and a puppy! I am currently a senior in high school, graduating in a few weeks and in the summer I will have lots of free time! I love walking and hiking so this is perfect! I know how much our babies mean to us and I have a knack for dogs! I have a fenced in yard and aswell am very good at acclimating to new places!

Availability updated yesterday
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Makayla F.
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Sitter Profile Image: Makayla F.
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5. Makayla F.

Trustworthy and nurturing
South Egremont, MA, 01258
6.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$100
per night
5 out of 5.0 stars
14 reviews
1 repeat client

I have known Makayla for many years now and she has always been an avid animal lover. She is a kind, compassionate, patient, reliable and nurturing human being. She has a bond with her own dog that I have been lucky enough to witness from the beginning. Makayla has worked professionally with dogs as well which only adds to her ability to care for your animal with the upmost sophistication and proficiency.

Availability updated yesterday
Sitter Profile Image: Sally A.
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Sitter Profile Image: Sally A.
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6. Sally A.

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

Sally is extraordinary. Her care for our two senior cats in our home was again top notch, of the highest quality. Sally is kind, communicative, knowledgeable, reliable and thoughtful, thorough and more. Her deep love for animals shines through in every text and photo she sends daily! She cares for our home as if it was her own. Emily and Charlotte cannot wait to have Sally back again soon, and we feel feel the same. We ❤️ Sally!

Availability updated 3 days ago
Sitter Profile Image: Evelyn C.
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Sitter Profile Image: Evelyn C.
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7. Evelyn C.

Reliable, Energetic, Caring Sitter
Ashley Falls, MA, 01222
3.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$100
per night
1 review

I highly recommend Evelyn to care for your pets. She has been caring for my three cats for a little over a year, and her reliability and attentiveness give me complete peace of mind whenever I’m away. As a cat owner herself, she goes above and beyond—checking in regularly, bringing in packages, sending adorable photo updates, and making sure my cats are happy, healthy, and well cared for. It’s clear she truly loves animals, and her considerate nature makes all the difference. If you’re looking for a trustworthy and caring pet sitter, Evelyn is the perfect choice!

Availability updated 27 days ago
Sitter Profile Image: Hannah S.
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Sitter Profile Image: Hannah S.
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8. Hannah S.

Loving caretaker for your pet
Salisbury, CT, 06068
7.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$100
per night
5 out of 5.0 stars
16 reviews
6 repeat clients
Profile image

Hannah is awesome. Our dogs are a bit high maintenance (dachshunds IYKYK) and she handled them beautifully. One of our dogs is scared of anyone who isn’t me or my wife and by the end of Hannah’s first visit they were buds.

Availability updated 15 days ago
Sitter Profile Image: Kelly H.
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Sitter Profile Image: Kelly H.
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9. Kelly H.

At home with a kind-caring sitter
Otis, MA, 01253
14.6 mi. away
House Sitting, Drop-In Visits
from
$125
per night
5 out of 5.0 stars
63 reviews
31 repeat clients
Profile image

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!

Availability updated 22 days ago
Sitter Profile Image: Kendra H.
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Sitter Profile Image: Kendra H.
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10. Kendra H.

In need of puppy/kitty love
Monterey, MA, 01245
7.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$65
per night
5 out of 5.0 stars
3 reviews
Profile image

Kendra was wonderful! Responsive and reliable. And Pierogi loved her right away (and she is usually quite shy with strangers)! Kendra sent pics and updates which helped us enjoy our time away more! Will definitely book again!

Availability updated 46 days ago
Sitter Profile Image: Eleanor K.
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Sitter Profile Image: Eleanor K.
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11. Eleanor K.

I’ll care for your pets
Lenox, MA, 01240
17.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$45
per night
5 out of 5.0 stars
1 review
1 repeat client

About: I have had two dogs my entire life and am constantly walking, feeding and caring for them. When I was 12 I started pet siting for friends and neighbors, and I have experience with all sorts of animals. I am currently a senior in high school. I love to spend time with pets and to make a little money on the side to save up for college. I have a large fenced yard and a nice neighborhood for walks. I also have dogs that your dog could play with, and all the toys and leashes that come with them.

Availability updated 13 days ago
Sitter Profile Image: Christine A.
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Sitter Profile Image: Christine A.
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12. Christine A.

Rover 101
Star Sitter
Home Full time...
Stanfordville, NY, 12581
21.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$155
per night
5 out of 4.9 stars
85 reviews
27 repeat clients
Profile image

Christine bailed us out at the last minute and totally saved us. She was just great, and I think our cats even decided they like her better than they like us. Couldn't be happier that we have made this connection.

Availability updated 3 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Lucy C.
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Sitter Profile Image: Lucy C.
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13. Lucy C.

Flexible Schedule, Cats and Dogs
Great Barrington, MA, 01230
5.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$100
per night
5 out of 5.0 stars
3 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 57 days ago
Sitter Profile Image: Janice A.
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Sitter Profile Image: Janice A.
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14. Janice A.

Star Sitter
Safe, Loving and Happy farm
RHINEBECK, NY, 12572
26.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$155
per night
5 out of 5.0 stars
238 reviews
72 repeat clients
Profile image

Janice has great rapport with our dog, Tala, and it was clear she was in good hands during the stay (as was our cat!). As a house sitter as well, we were very confident that Janice had everything covered, and she was very quick to effectively troubleshoot a few technical issues that came up during her stay, giving us less to worry about and be able to enjoy our trip. We've already booked her to watch the pets and house for another upcoming trip!

Availability updated today
Sitter Profile Image: Teresa M.
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Sitter Profile Image: Teresa M.
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15. Teresa M.

Caring, loving, compassion .
Great Barrington, MA, 01230
7.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$80
per night
5 out of 5.0 stars
4 reviews

About: I’ve taken care of dogs of every kind since 2009 working with Neighbors, friends and family help them with bathing, feeding, hair cut, nail trim. I’m concurrently don’t have a full time job, I have a lot time available to help you with your doggie with walking, car ride, park. I have a big yard to play, run, jumping, very responsible, have a finish basement with open room to play . I can cook a low diet food .

Availability updated 40 days ago
Sitter Profile Image: Alyssa M.
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Sitter Profile Image: Alyssa M.
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16. Alyssa M.

Your pet’s comfort is my priority
Valatie, NY, 12184
28.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5 out of 5.0 stars
1 review
Profile image

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!

Availability updated 8 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Ryan T.
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Sitter Profile Image: Ryan T.
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17. Ryan T.

Nurturing, Safe, & Quality Care
Elizaville, NY, 12523
21.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$120
per night
5 out of 5.0 stars
10 reviews
3 repeat clients

Ryan and his family always take the best care of our pups Jack and young guy, Bode. They always seem a little sad to come home to us since they had so much fun and exercise! I only could assume because they are always pooped after their wonderful visit! We have never had anyone else watch our dogs since we are very particular about who watches them! They are a perfect fit for our boys and we always look forward to our next visit. Thank you Ryan and family!

Availability updated 4 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Bella G.
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Sitter Profile Image: Bella G.
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18. Bella G.

Rover 101
Star Sitter
Huge animal lover
lanesborough, MA, 01237
29.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$65
per night
5 out of 5.0 stars
12 reviews
2 repeat clients
Profile image

Bella was terrific! She stayed over in my home to care for my dog and cat. I appreciated her proactive communications including text with pictures of my dog out on walks with her. She was respectful of my home and I will definitely be in touch with her again to help in the future. I highly recommend her services.

Availability updated today
Sitter Profile Image: Shelby L.
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Sitter Profile Image: Shelby L.
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19. Shelby L.

Pet sitter with lots of love!
Lee, MA, 01238
14.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$80
per night
5 out of 5.0 stars
9 reviews
1 repeat client
Profile image

Shelby is a very caring and responsible pet sitter.

Availability updated 9 months ago
Sitter Profile Image: Stacey G.
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Sitter Profile Image: Stacey G.
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20. Stacey G.

Love and care for all puppers
Winsted, CT, 06098
19.6 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$90
per night
5 out of 5.0 stars
25 reviews
5 repeat clients
Profile image

Stacey was wonderful! She was so easy to communicate with ahead of watching our dog and was also super self sufficient around our house. There was a bad storm when she was scheduled to watch our dog and we live in a pretty remote area and she had zero complaints. She was fantastic all around!

Availability updated 38 days ago

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