House Sitting in Canaan

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Sitter Profile Image: Caitlin H.
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Sitter Profile Image: Caitlin H.
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1. Caitlin H.

Flexiblity to meet your pet needs
Pittsfield, MA, 01201
9.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5.0 out of 5 stars
16 reviews
2 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 4 days ago
Sitter Profile Image: Christine J.
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Sitter Profile Image: Christine J.
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2. Christine J.

A happy place for your pet!
North Canaan, CT, 06018
27.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$75
per night
5.0 out of 5 stars
14 reviews
9 repeat clients
Profile image

Christine goes above and beyond to ensure our two elderly dogs are well cared for and well loved. They are very different personalities and ability levels, and she cares for both splendidly. Christine could not be more organized and responsible with the dogs and the house as well. It is a luxury to leave home knowing our dogs are in such excellent hands. Anyone who Christine works with will be very lucky to know her.

Availability updated 31 days ago
Sitter Profile Image: McKenna P.
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Sitter Profile Image: McKenna P.
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3. McKenna P.

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

This was our first time using Rover and for our wedding weekend at that! McKenna was all-around phenomenal: Coming by early for a meet-and-greet, sending us updates and photos, and most importantly - she was great with our girl Skye ♥ She made both dog and pet parents completely comfortable, and I would one hundred percent recommend her to anyone! S+C

Availability updated 32 days ago
Sitter Profile Image: Ellen J.
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Sitter Profile Image: Ellen J.
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4. Ellen J.

Experienced, Reliable, Caring
Nassau, NY, 12123
13.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$75
per night
5.0 out of 5 stars
11 reviews
3 repeat clients
Profile image

Ellen did a fantastic job taking care of my two elderly cats that are on a very strict, and kind of confusing, medicine schedule. They get very lonely so I opted to have her house-sit while I was away for a week. She was inquisitive, responsive and sent pictures whenever needed! She kept the place very clean, and helped out with other house-sitting responsibilities. I would definitely recommend her!

Availability updated 32 days ago
Sitter Profile Image: Brian L.
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Sitter Profile Image: Brian L.
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5. Brian L.

Experienced Dog/House Sitter!
Troy, NY, 12180
23.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$69
per night
5.0 out of 5 stars
131 reviews
75 repeat clients
Profile image

This was my first experience with Rover. Brian came over to meet our dog and make sure it was a good fit before we decided to use him. Brian sent pics and left our house in perfect condition. I highly recommend Brian!

Availability updated 11 days ago
Sitter Profile Image: Siri C.
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Sitter Profile Image: Siri C.
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6. Siri C.

Rover 101
Licensed Veterinary Technician
Kinderhook, NY, 12106
13.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$100
per night
5.0 out of 5 stars
55 reviews
20 repeat clients
Profile image

If you are lucky enough to book Siri for your fur babies, you will have no worries. She is extremely attentive to all their needs. With frequent updates and pictures, rest assured you will be able to enjoy your time away without any concerns about your family members that are at home. 10 out of 10 recommend!

Availability updated 8 days ago
Sitter Profile Image: Meg E.
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Sitter Profile Image: Meg E.
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7. Meg E.

Experienced sitter up for any pet
Pittsfield, MA, 01201
9.2 mi. away
House Sitting
from
$75
per night
5.0 out of 5 stars
4 reviews
Profile image

Meghan took great care of my dog while I was on vacation. Very responsive and flexible when it came to scheduling and making sure he was cared for. Meghan also dog sat in my home and cared for it like it was her own. Would let her take care of Moose any time and highly recommend her for others searching for a dog sitter.

Availability updated yesterday
Sitter Profile Image: Samantha S.
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Sitter Profile Image: Samantha S.
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8. Samantha S.

My life revolves around my dogs!
Pittsfield, MA, 01201
11.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$75
per night
5.0 out of 5 stars
7 reviews
1 repeat client
Profile image

Sam was great! She helped me out very last minute and was so sweet and professional. My dog, Remi, loved her and she was great at communicating while I was away. I Will definitely be hiring Sam again for future dog-sitting!

Availability updated 3 days ago
Sitter Profile Image: Keri H.
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Sitter Profile Image: Keri H.
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9. Keri H.

Rover 101
Ready to jog w/dogs & cuddle cats!
Lenox, MA, 01240
10.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$95
per night
5.0 out of 5 stars
32 reviews
11 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 today
Sitter Profile Image: Isabel B.
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Sitter Profile Image: Isabel B.
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10. Isabel B.

Trusted dog walking & watching 🐾💗
Lanesborough, MA, 01237
14.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$75
per night
6 years of experience

About: As a college student who grew up with five dogs, I’ve always had a deep love for animals. I understand the importance of making sure your furry (or hairless) family member feels safe and happy while you’re away. With my background in dog behavior and safety, including handling aggression and territorial issues, you can trust that your pup will be in caring and capable hands. I’ve also worked in a doggy daycare, managing groups of 50-60 dogs, so I know how to keep things calm and fun! Whether it’s a peaceful walk along the best local trails or lots of cozy care, I’ll treat your dog like my own, always. Your pup’s safety and comfort are my top priorities and I look forward to meeting them!! 💅🐾💗 My flexible schedule allows me to offer plenty of availability for walks and sitting. On Mondays and Wednesdays, and Fridays I’m available early mornings, afternoons, and evenings. On Tuesdays and Thursdays, I’m available before 10:30 a.m. and after 2:15 p.m. On the weekends, I’m fully available for walks, sitting, or even adventure hikes, whenever!! No matter the time, your pup will have my full attention and care. Safety, trust, and a comfortable environment are my top priorities when caring for your dog(s) while at your home. I create a calm, secure space tailored to your dog’s unique needs. I’m highly attuned to their behavior, recognizing signs of stress or discomfort, and always respond with care. At your home, I follow your routine to keep things familiar for your pup, providing consistent care and attention. With my background in dog safety and behavior, including experience from small elderly dogs to large groups, you can trust that they will be okay in a variety of situations :)

Availability updated 4 days ago
Sitter Profile Image: jess p.
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Sitter Profile Image: jess p.
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11. jess p.

Let me love your puppies!!
Petersburg, NY, 12138
12.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per night
5.0 out of 5 stars
8 reviews
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 today
Sitter Profile Image: Shelby L.
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Sitter Profile Image: Shelby L.
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12. Shelby L.

Pet sitter with lots of love!
Lee, MA, 01238
12.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5.0 out of 5 stars
9 reviews
1 repeat client
Profile image

Shelby is a very caring and responsible pet sitter.

Availability updated 76 days ago
Sitter Profile Image: Andrew C. S.
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Sitter Profile Image: Andrew C. S.
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13. Andrew C. S.

Rover 101
Dog lover who enjoys the outdoors
Great Barrington, MA, 01230
13.5 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$85
per night
5.0 out of 5 stars
32 reviews
10 repeat clients
Profile image

Andrew was very good with our nearly three-year-old Imhotep. "Imo" is a Basenji (a breed known for being challenging at times) who suffers from separation anxiety. Andrew stayed in contact with us from the beginning to the end of our time away and actively worked with us to resolve any minor issues that came up. He also sent much-appreciated photographs every day. We are grateful that he was able to make adjustments to accommodate Imo's special needs and we were pleased (and relieved) to return home to a happy and contented dog - a very, very different experience from our prior kennel boarding experiences. Thank you, Andrew!

Availability updated 18 days ago
Sitter Profile Image: Brandi D.
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Sitter Profile Image: Brandi D.
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14. Brandi D.

Run and Play While You’re Away!
Hillsdale, NY, 12529
14.7 mi. away
House Sitting
from
$100
per night
5.0 out of 5 stars
13 reviews
1 repeat client
Profile image

Brandi was amazing! Our dog Charlie can be shy and a little nervous around new people. Brandi was super thoughtful and took the time to make Charlie feel comfortable and happy. She also sent lots of photos and updates throughout her stay which was helpful and reassuring! We will definitely rebook.

Availability updated 32 days ago
Sitter Profile Image: Kaylee P.
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Sitter Profile Image: Kaylee P.
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15. Kaylee P.

Pets are family. Tech assistant 4yr
Nassau, NY, 12123
11.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$25
per night
5.0 out of 5 stars
8 reviews
2 repeat clients
Profile image

Kaylee was amazing! Poppy absolutely loved her and Kaylee was understanding of me being a little helicopter mom checking in and was sending updates and photos. I will 1000000% be rebooking with her in the future!

Availability updated yesterday
Sitter Profile Image: Sally M.
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Sitter Profile Image: Sally M.
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16. Sally M.

Whisperer, Gentle Pet&Home Care 🥰
Sand Lake, NY, 12153
14.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$130
per night
5.0 out of 5 stars
38 reviews
10 repeat clients
Profile image

Sally is amazing. She sent me pics and updates about my boys every day. She took care of my home leaving it cleaner than when we left. I enjoyed my vacation with complete peace of mind.

Availability updated 16 days ago
Sitter Profile Image: Craig M.
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Sitter Profile Image: Craig M.
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17. Craig M.

Dog Lover
Chatham, NY, 12037
8.2 mi. away
House Sitting, Dog Walking
from
$85
per night
5.0 out of 5 stars
2 reviews
Profile image

Craig was communicative both before and during his week with Nancy-Moo asking relevant questions and quickly arranging a meet and greet. She took to him straight away and seemed comfortable with his energy. The daily updates with photos were great and he was happy to cook up extra veggies for her and take Moo on plenty of adventures around town, to the local dog park, and hikes. Craig also left the house clean and tidy and watered the plants. I wouldn't hesitate to book him again and felt Nancy-Moo was in great hands.

Availability updated 69 days ago
Sitter Profile Image: Lauren B.
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Sitter Profile Image: Lauren B.
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18. Lauren B.

Certified Animal Lover🥰
Canaan, NY, 12029
1.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$50
per night
5.0 out of 5 stars
4 reviews
1 repeat client
Profile image

Lauren took such great care of our 2 puppies and our house. She was responsive, sent a bunch of pics, and the puppies just loved her! Highly recommend Lauren!

Availability updated today
Sitter Profile Image: Laura R.
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Sitter Profile Image: Laura R.
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19. Laura R.

Dog / Pet Sitting Services
Pittsfield, MA, 01201
8.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$200
per night
5.0 out of 5 stars
4 reviews
Profile image

Just wonderful. Laura kept by pup happy and entertained while we enjoyed an evening out with family.

Availability updated 40 days ago
Sitter Profile Image: Sadie K.
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Sitter Profile Image: Sadie K.
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20. Sadie K.

Fun energetic gal who loves dogs!
Valatie, NY, 12184
9.0 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
4.5 out of 5 stars
10 reviews
3 repeat clients
Profile image

Sadie was very understanding with my pup that has some pretty bad separation anxiety. She treated both my pups with care and I would recommend her!

Availability updated today

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