House Sitting in Canaan

Find a loving dog sitter to watch your dog overnight in your home.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
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Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Siri C.
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Sitter Profile Image: Siri C.
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1. Siri C.

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

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!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Caitlin H.
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Sitter Profile Image: Caitlin H.
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2. Caitlin H.

Flexiblity to meet your pet needs
Pittsfield, MA, 01201
9.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
1 repeat client
from
$50
per night

Caitlin was a wonderful sitter! Our animals were very comfortable with her and well taken care of.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Bella B.
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Sitter Profile Image: Bella B.
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3. Bella B.

Lakeside Sitter, Works from Home.
Stockbridge, MA, 01262
9.1 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
$60
per night

I am so pleased to have found Bella on this site. I have an older dog who needs some extra attention and Bella was absolutely amazing. I left Chilli (13.5 yr old Golden) with Bella for a couple of nights and everything went perfectly. She is caring, attentive, responsive and communicative. She understands the specific needs of my dog and I've already booked another (this time longer) stay.

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Sitter Profile Image: Andrea L.
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Sitter Profile Image: Andrea L.
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4. Andrea L.

I got you covered!
Great Barrington, MA, 01230
12.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
14 reviews
4 repeat clients
from
$65
per night

Andrea is a sweetheart! So easy to talk with, caring, professional, and competent. We felt totally good about her house- and dog-sitting; we knew our girls were in good hands.

Sitter Profile Image: Logan A.
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Sitter Profile Image: Logan A.
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5. Logan A.

Sitter, Walker, Sled Dog Handler
Pittsfield, MA, 01201
10.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
4.5 out of 5 stars
15 reviews
9 repeat clients
from
$60
per night

Logan took good care of Lucy and Chippy! He communicated with us throughout the week long stay and also took good care of the house. When we had a heating issue during a big storm he coordinated with the heating company and was very helpful and professional. Highly recommend! Plus doggies got a good brushing ?

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Sitter Profile Image: Maeve D.
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Sitter Profile Image: Maeve D.
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6. Maeve D.

dog person; outdoor adventurer 🌱🐕
Housatonic, MA, 01236
10.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
5 repeat clients
from
$50
per night

About: Calm, experienced, loving, empathic and conscientious - I am your dog’s next best friend 🩷 I’ve trained Australian Shepherd’s since I was 13, reaching amateur level junior competitions throughout high school. Today I have two rescue dogs of my own - a border collie mix and a beagle /chihuahua/pit mix (lots of energy). Because of my two dogs, I hike everyday. I love spending time outside in nature with animals, and will be sure to keep your pup happy and healthy! I am an organic vegetable farmer during the growing season (April-November) and work seasonal odd jobs and non profit work when I am in the off season. I have a lot of flexibility in my schedule and love to walk/hike/swim/adventure at all times of day and during any weather. In my house, pets rule. We have done agility, obedience and scent training with both dogs so I have a lot of tools in my toolbox to keep a dog busy and occupied.

Sitter Profile Image: Madison S.
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Sitter Profile Image: Madison S.
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7. Madison S.

Pawsitively Passionate Pet Pal
Lanesborough, MA, 01237
14.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
6 reviews
2 repeat clients
from
$60
per night

Madison was great. She shared several pictures and texts throughout the weekend. Hazy went on a hike with Madison and looked like she had a great time. We highly recommend Madison and look forward to using her again in the future.

Sitter Profile Image: Laura R.
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Sitter Profile Image: Laura R.
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8. Laura R.

Passion for Pet Sitting
Pittsfield, MA, 01201
8.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
1 review
from
$119
per night

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

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Sitter Profile Image: Sally M.
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Sitter Profile Image: Sally M.
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9. Sally M.

Whisperer, Gentle Pet&Home Care 🥰
Sand Lake, NY, 12153
14.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
34 reviews
9 repeat clients
from
$100
per night

Sally did an amazing job house and pet sitting for my two dogs and two cats. She takes care of your house and your pets like they are her own. She was in frequent contact, sending pictures and messages which I very much appreciated. I already confirmed her to pet sit for me again in September. I highly recommend Sally for house and pet sitting. She did an outstanding job with my two dogs, two cats and house.

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Sitter Profile Image: Colleen W.
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Sitter Profile Image: Colleen W.
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10. Colleen W.

Pet loving retired Postmaster!
PITTSFIELD, MA, 01201
7.6 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
1 review
from
$85
per night

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!

Sitter Profile Image: Andrew C. S.
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Sitter Profile Image: Andrew C. S.
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11. Andrew C. S.

Rover 101
Dog lover who enjoys the outdoors
Lee, MA, 01238
12.5 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
30 reviews
9 repeat clients
from
$85
per night

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!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Steph F.
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Sitter Profile Image: Steph F.
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12. Steph F.

Animal lover who's happy to help!
Dalton, MA, 01226
15.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
1 repeat client
from
$75
per night

Steph was available to house and pet sit for us at the last minute. She was friendly and professional and sent photos of our pups during her stay. We would definitely book with her again. Thanks Steph!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jess L.
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Sitter Profile Image: Jess L.
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13. Jess L.

I care for the care of your pets
Pittsfield, MA, 01201
10.9 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
$65
per night

Jess is great with our dogs. She has watched the two of our dogs on multiple occasions and sometimes 3 or 4. She takes the time out of her day to make sure they get plenty of attention and time outside to play. She also stays at our house when she watches the dogs and the house is always in great shape afterwards too. I would highly recommend her to anyone who is looking for someone to stay with your dogs and make sure they get at the loving and attention they need while you are away.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Tetiana M.
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Sitter Profile Image: Tetiana M.
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14. Tetiana M.

I care for the dogs
Lenox, MA, 01240
10.0 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
$60
per night

About: I love dogs and cats since I remember myself, gentle and good behavior to any animal in the world. Safety, happiness and great care are my number one priority, always treat pets like my own pet. I am new in the rover and I have been care for the dogs during 1 year. I am available all the time, can drive to your home to take care about dog. walk with them, feed them. I am a student. I have a fenced yard, I can walk dogs, I can take care about dogs at your home, I know how to make dogs playful and enjoy.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Tiffany A.
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Sitter Profile Image: Tiffany A.
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15. Tiffany A.

A walk a day will keep the vet away
Pittsfield, MA, 01201
10.3 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
$35
per night

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.

Sitter Profile Image: Shelby L.
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Sitter Profile Image: Shelby L.
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16. Shelby L.

Pet sitter with lots of love!
Lee, MA, 01238
12.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
1 repeat client
from
$50
per night

Shelby is a very caring and responsible pet sitter.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Dana G.
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Sitter Profile Image: Dana G.
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17. Dana G.

Rover 101
Kind and loving leader
PITTSFIELD, MA, 01201
10.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
39 reviews
11 repeat clients
from
$125
per night

Dana was wonderful! She communicated daily with us and sent such cute photos. The house was in great shape when we got home and the animals were happy. We would be thrilled to have her come watch our animals again!

Sitter Profile Image: Amy B.
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Sitter Profile Image: Amy B.
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18. Amy B.

Love dogs more than humans!
Red Rock, NY, 12060
4.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
2 reviews
from
$95
per night

Amy is responsible, caring, and knowledgeable. I hope you will give her the opportunity to take care of your pets, too. We have used her for our pet care needs for several years. Amy is so dependable and flexible that we are spoiled and would never use anyone else.

Sitter Profile Image: Eleana H.
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Sitter Profile Image: Eleana H.
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19. Eleana H.

I love animals and caring for them
Old Chatham, NY, 12136
6.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
1 review
from
$85
per night

Eleana is a kind and compassionate person. Eleana is detailed oriented, a good listener and respectful of people and their belongings. Eleana loves all animals and follows through with your wishes. A very pleasant and responsible young lady.

Sitter Profile Image: Lauren B.
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Sitter Profile Image: Lauren B.
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20. Lauren B.

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

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!

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Canaan House Sitting ratings

Overall Rating:
5.0 out of 5 stars

House sitters in Canaan are rated on average 5 out of 5 stars based on 13 reviews.

Rover also offers House Sitting in:

Rover also offers other services in Canaan:


Never beg a friend to watch your dog again. With Rover, you can find your the perfect Canaan house sitter in seconds. When you book house sitting on Rover, your dog will enjoy a loving, relaxing stay in their own home. If you're looking for care for pets other than dogs, you can find a pet sitter who offers care for cats, caged pets, and even horses. No matter what, you'll know that your pet is getting loving care. By removing common pet care obstacles, Rover ensures dogs nationwide are happy and well-cared for even when their human is away, and empowers dog lovers to live happy and fulfilling lives. Founded on the belief that everyone should have the opportunity to experience the unconditional love of a dog, Rover makes it easy for you to reach trusted house sitters in Canaan who can provide the care your dog needs, when they need it.

House Sitting