House Sitting in Pittsfield

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

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Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
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Confirmed availability: Memorial Day Weekend
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
1.1 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.

Sitter Profile Image: Logan A.
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Sitter Profile Image: Logan A.
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2. Logan A.

Sitter, Walker, Sled Dog Handler
Pittsfield, MA, 01201
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
4.5 out of 5 stars
15 reviews
9 repeat clients
from
$100
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 ?

Sitter Profile Image: Maeve D.
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Sitter Profile Image: Maeve D.
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3. Maeve D.

dog person; outdoor adventurer 🌱🐕
Housatonic, MA, 01236
14.2 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: Bella B.
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Sitter Profile Image: Bella B.
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4. Bella B.

Lakeside Sitter, Works from Home.
Stockbridge, MA, 01262
9.9 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.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Adrienne H.
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Sitter Profile Image: Adrienne H.
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5. Adrienne H.

Love dogs!
Pittsfield, MA, 01021
1.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
46 reviews
17 repeat clients
from
$60
per night

Adrienne is an avid dog lover! She's great at making sure they get lots of love, attention, and long walks. She is also an experienced dog trainer. Adrienne is very reliable and never misses an appointment. She's great with large and small breeds and dogs of all ages. She is the perfect choice if you are looking for someone to love on your pet and give them a great time!

Sitter Profile Image: Madison S.
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Sitter Profile Image: Madison S.
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6. Madison S.

Pawsitively Passionate Pet Pal
Lanesborough, MA, 01237
6.4 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 is fabulous. She was responsive, prompt and very respectful of our expectations. And most important she took wonderful care of our dogs. They were cared for just as we hoped and our home was exactly as we had left it. Madison sent photos and kept in touch which I really appreciated.

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Sitter Profile Image: Colleen W.
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Sitter Profile Image: Colleen W.
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7. Colleen W.

Pet loving retired Postmaster!
PITTSFIELD, MA, 01201
3.1 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!

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

Animal lover who's happy to help!
Dalton, MA, 01226
4.8 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!

Sitter Profile Image: Shelby L.
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Sitter Profile Image: Shelby L.
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9. Shelby L.

Pet sitter with lots of love!
Lee, MA, 01238
10.2 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.

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
9.8 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 amazing!!! We have a 2 and a 1/2 year old golden and a 5 month old golden. He came over prior to our trip to meet the new puppy (as he had worked with the older one already). He asked many questions to be clear on our expectations. While away, we received daily pictures and updates on the puppies. He reached out with questions to make sure he was doing what we would if we were home with them. Andrew stayed in home and this was the first time we had done this. He was respectful of our space and treated it like his own. We would absolutely be using Andrew again and would strongly recommend that you consider him for your next trip!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Rick & Autumn C.
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Sitter Profile Image: Rick & Autumn C.
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11. Rick & Autumn C.

Rover 101
Loving Doggy Care
Pittsfield, MA, 01201
0.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
27 reviews
6 repeat clients
from
$49
per night

Rick & Autumn were fantastic. They stayed with our 2 crazy pups in our hotel room during our wedding. They spent over 10 hours with them and went above and beyond transporting them to our reception site for pictures and then bringing them back to the hotel. We would absolutely use Rick & Autumn again when we visit the area.

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

A walk a day will keep the vet away
Pittsfield, MA, 01201
0.4 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: Tetiana M.
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Sitter Profile Image: Tetiana M.
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13. Tetiana M.

I care for the dogs
Lenox, MA, 01240
4.9 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.

Sitter Profile Image: Chelsea S.
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Sitter Profile Image: Chelsea S.
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14. Chelsea S.

Experience sitter and dog lover!
Pittsfield, MA, 01201
1.2 mi. away
Boarding, House Sitting, Dog Walking
2 reviews
from
$32
per night

Chelsea is possibly the most kind, gentle, and responsible person I know. She watched my extremely high energy and high-maintenence dog Harley when she was in her puppy stage, and I could tell from the photos Chelsea sent that Harley absolutely adored her. For years after their visit together, Harley responded to seeing Chelsea by "crazy pupping" and doing her zoomies. You can trust Chelsea with your fur baby, guaranteed. Walks, overnights, feedings, anything.

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

I care for the care of your pets
Pittsfield, MA, 01201
0.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
32 reviews
7 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: Dana G.
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Sitter Profile Image: Dana G.
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16. Dana G.

Rover 101
Kind and loving leader
PITTSFIELD, MA, 01201
0.8 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 took care of our young puppy while we were away on vacation. She is very responsible, compassionate & dedicated to her caring for dogs. You can tell she really loves what she does! She kept us updated with information and pictures daily, including videos. It was a pleasure to see our puppy healthy, happy & having fun with Dana. We definitely look forward to booking with Dana again!!

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
2.7 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.

Sitter Profile Image: Jaden K.
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Sitter Profile Image: Jaden K.
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18. Jaden K.

I love all dogs! Happy to help!
Pittsfield, MA, 01201
2.2 mi. away
House Sitting
5.0 out of 5 stars
2 reviews
from
$39
per night

Jaden was fantastic with my two dogs. Can not recommend him more.

Sitter Profile Image: Kate B.
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Sitter Profile Image: Kate B.
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19. Kate B.

Animal lover ready to meet your pet
Pittsfield, MA, 01201
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
3 reviews
from
$85
per night

Kate is a delightful, down-to-earth and trustworthy companion and caretaker for my cats. She has that "I love cats" energy that cats tend to gravitate toward. They are always excited to see her! When I travel, I can really relax and enjoy myself knowing Kate is taking good care of my fur babies. I highly recommend her!

Sitter Profile Image: Talya F.
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Sitter Profile Image: Talya F.
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20. Talya F.

I love animals
Pittsfield, MA, 01201
0.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
4 years of experience
from
$32
per night

About: I have volunteered at numerous shelters caring for many different dog breeds and ages. I have had pet rabbits for 4 years and currently house 3 bunnies. Very available during the day and need a distraction from real life and animals help me deal with stress. Would love to help care for dogs since I can’t house one myself. My bunnies in my home live better than me. They are in my bedroom so for temporary arrangements your dog would have the rest of my apartment to play.

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Pittsfield House Sitting ratings

Overall Rating:
4.9 out of 5 stars

House sitters in Pittsfield are rated on average 4.9 out of 5 stars based on 77 reviews.

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As dog lovers, we understand how difficult it can be to leave your pet when you have to head out of town. Luckily, you can find the perfect house sitter in seconds on Rover.com. If you're looking for trusted house sitters while you're away, whether it's for one night or a whole month, you can find a sitter who meets your - and your pet's - needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your pet - including background checks, sitter testimonials, community reviews. We also offer training and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your pet. Rover is proud to be the nation's largest network of pet lovers for hire.

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