House Sitting in Stockbridge

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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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
11.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
1 repeat client
from
$50
per night
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Caitlin was a wonderful sitter! Our animals were very comfortable with her and well taken care of.

Sitter Profile Image: Maeve D.
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Sitter Profile Image: Maeve D.
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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
$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.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Tiffany A.
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Sitter Profile Image: Tiffany A.
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3. 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
$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.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jay W.
Sitter Profile Image: Jay W.

4. Jay W.

Hi fur parents!
Russell, MA, 01071
25.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
2 reviews
1 repeat client
from
$30
per night

I've known Jay for a very long time and they have always been the biggest animal person. When we finally got a dog, he has been apprehensive of most people because of his background before we got him but Jay is one of the few people he can recognize quickly and approves of. Every dog I've ever known them to have owned or be around has been in the most caring and loving hands. Hands down would recommend them for any level of pet care!!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jess L.
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Sitter Profile Image: Jess L.
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5. 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
33 reviews
9 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.

Sitter Profile Image: Kai C.
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Sitter Profile Image: Kai C.
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6. 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
$70
per night
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Kai was outstanding to work with and took great care of our bullmastiff. Kai was a great communicator, sent lots of photos and videos and the house was in perfect shape. Great job!

Sitter Profile Image: Logan A.
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Sitter Profile Image: Logan A.
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7. 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
$100
per night
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When we came back our dogs were relaxed and happy. Logan did a great job taking care of Hugo and Lila and even sent us photos. We highly recommend Logan!

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Sitter Profile Image: Sally M.
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Sitter Profile Image: Sally M.
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8. Sally M.

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

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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
13.1 mi. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
61 reviews
30 repeat clients
from
$125
per night
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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!

Sitter Profile Image: Andrew C. S.
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Sitter Profile Image: Andrew C. S.
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10. 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
$85
per night
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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!

Sitter Profile Image: Brandi D.
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Sitter Profile Image: Brandi D.
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11. Brandi D.

Run and Play While You’re Away!
Hillsdale, NY, 12529
16.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
1 repeat client
from
$100
per night
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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.

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Sitter Profile Image: Danielle C.
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Sitter Profile Image: Danielle C.
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12. Danielle C.

Large Property- Loving Family
Hillsdale, NY, 12529
14.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
9 reviews
from
$65
per night
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Danielle was very flexible with timing and availability. Our dog enjoyed his stay with her overnight. He came home very relaxed and happy. I will definitely use Danielle again.

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Sitter Profile Image: Colleen W.
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Sitter Profile Image: Colleen W.
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13. 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
$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!

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Sitter Profile Image: Shelby L.
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Sitter Profile Image: Shelby L.
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14. 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
$50
per night
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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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15. Dana G.

Rover 101
Kind and loving leader
PITTSFIELD, MA, 01201
12.5 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
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So glad to have found Dana. It’s clear she took good care of my gang while I was away, and even managed to keep her sense of humor after the power went out. I already have her booked for two more trips.

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

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

Sitter Profile Image: Laura R.
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Sitter Profile Image: Laura R.
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17. Laura R.

Passion for Pet Sitting
Pittsfield, MA, 01201
11.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
2 reviews
from
$119
per night
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Just wonderful. Laura kept by pup happy and entertained while we enjoyed an evening out with family.

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
11.2 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: Bre R.
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Sitter Profile Image: Bre R.
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19. Bre R.

All dogs welcome and loved !
dalton, MA, 01226
12.0 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
1 repeat client
from
$26
per night

Breanna is a loving person who takes pride in caring for any animal. She has been dog sitting ever since she was young and absolutely loves it. She always takes care of my dog and I trust her with him.

Sitter Profile Image: Joshua L.
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Sitter Profile Image: Joshua L.
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20. Joshua L.

Love dogs and pets!
Lenox, MA, 17842
5.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
2 reviews
from
$100
per night

I have known Josh L. for a very long time. His love and dedication to pets is easily seen and felt. I have trusted him to care for many pets in the past, and never disappointed.

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Stockbridge House Sitting ratings

Overall Rating:
5.0 out of 5 stars

House sitters in Stockbridge are rated on average 5 out of 5 stars based on 31 reviews.

Rover also offers House Sitting in:

Rover also offers other services in Stockbridge:


Never beg a friend to watch your dog again. With Rover, you can find your the perfect Stockbridge 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 Stockbridge who can provide the care your dog needs, when they need it.

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