Find the Perfect Match

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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: Jess L.
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Sitter Profile Image: Jess L.
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1. Jess L.

I care for the care of your pets
Pittsfield, MA, 01201
3.0 mi. away
5.0 out of 5 stars
32 reviews
6 repeat clients
from
$42
per night

Must hv her booked! Quick communicator. Overnight stay s extra special. U ll be assured that ur dog ll be at good place w kindered dogsitter.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Brooke B.
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Sitter Profile Image: Brooke B.
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2. Brooke B.

Rover 101
CRAZY DOG FAMILY
Pittsfield, MA, 01201
3.5 mi. away
5.0 out of 5 stars
89 reviews
25 repeat clients
from
$40
per night

So glad we found Brooke!!! We had deferred family vacations out of driving distance for the past two years because we no longer had family nearby who could watch our pups. That has all changed now. Rover.com was recommended by a friend and truthfully I was a bit hesitant until I met Brooke. She responded so quickly to my messages when I was exploring sitters and as soon as the pups met her I knew this would be a great match. She treated our girls like family, letting them nap on the furniture (just like at home), taking them for walks and playing fetch. She sent us pictures each day of the dogs and it made us feel so much more at ease seeing they were being loved on. I can not say enough kind things about Brooke and her family and I highly recommend her. She went exceedingly above what was necessary and we will certainly be calling on her again!

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

I care for the dogs
Lenox, MA, 01240
2.6 mi. away
5.0 out of 5 stars
7 reviews
4 repeat clients
from
$60
per night

Tetiana and her lovely mother were LIFE SAVERS! Our holiday plans changed at the last minute and Tetiana responded so quickly to our request. Our two cats had a wonderful stay and we loved receiving the adorable photos. I wholeheartedly recommend Tetiana for anyone who wants a caring, loving experience for their pets. THANK YOU :)

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

Love dogs!
Pittsfield, MA, 01021
3.0 mi. away
5.0 out of 5 stars
45 reviews
17 repeat clients
from
$30
per night

Absolutely fabulous! Sent pictures almost daily and took our Suki on lots of walks/hikes. I’m surprised she even wanted to come back home lol. Definitely will book in the future again.

Sitter Profile Image: Chelsea S.
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Sitter Profile Image: Chelsea S.
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5. Chelsea S.

Experience sitter and dog lover!
Pittsfield, MA, 01201
2.8 mi. away
from
$31
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.

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Sitter Profile Image: Mahayla G.
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Sitter Profile Image: Mahayla G.
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6. Mahayla G.

Exercise, training, and wellness!
Adams, MA, 01220
16.3 mi. away
5.0 out of 5 stars
29 reviews
14 repeat clients
from
$65
per night

Our dog had a fabulous stay with Mahayla! Since it was our first time, Mahayla offered to come to our home to get to know our pup before caring for her the next day. They hit it off immediately and Mahayla explained her background in animal/dog behavior studies and reassured us that all would go well... and it did! Our pup had a blast trail hiking and also just relaxing at Mahayla's home. Mahayla clearly understands and loves dogs, and it was clear that she was focused on our dog's enjoyment, comfort level and care. She was also focused on our needs as the owners. Leading up to care day she was extremely responsive. On care day she sent photos and updates. A perfect stay...thanks, Mahayla!

Sitter Profile Image: Mónica G.
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Sitter Profile Image: Mónica G.
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7. Mónica G.

Crazy lover for the animals
Pittsfield, MA, 01201
3.1 mi. away
3 years of experience
from
$39
per night

About: I am very sensitive to animals, it hurts me more than anything in the world when they are hurt! I love animals with great passion, more than a person! They are defenseless and pure beings, since I was a child and I have been pets, I had 8 dogs throughout my life, boxers, Great Danes, Labradors, I also had 7 cats that I loved very much until they died due to their advanced age, I feel that I have all the qualities and aptitudes to take care of a little 4-legged ange I can take care of them at any time, any day in the owners' house my schedule is completely free to take care of the 4-legged angels In my house and in the house of the people who hired me, I take care of them with love, pampering them, darling, having their fresh water all the time, watching what they do, taking into account their mealtimes, their hours of play, walks, pooping, I am like a mother to the animals

Sitter Profile Image: Mary & Todd H.
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Sitter Profile Image: Mary & Todd H.
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8. Mary & Todd H.

Weekend getaway with active people
Chatham, NY, 12037
18.0 mi. away
5.0 out of 5 stars
34 reviews
9 repeat clients
from
$45
per night

Mary and Todd were amazing! Sent us pics of Oakley having fun on her walks and other pups Communication was terrific and Oakley seemed so happy being there! We can’t wait until her next visit with them! Plus, she made friends with the chickens!!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Teresa D.
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Sitter Profile Image: Teresa D.
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9. Teresa D.

Dog Mom w/Rich Fostering Background
New Marlborough, MA, 01230
17.4 mi. away
5.0 out of 5 stars
9 reviews
1 repeat client
from
$45
per night

We were so happy with Teresa. She boarded our 1.5 year-old puppy for a few days—our dog looked so happy and comfortable within minutes of arrival and was exhausted when we picked her up (always a sign of a good time). Teresa was great at communication, sent daily photos of our puppy, and was very communicative via the app. we also really loved that Teresa had other dogs (both hers personally and others that she was boarding) so our dog really got to engage and play actively. We would definitely choose Teresa again!

Sitter Profile Image: Bella B.
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Sitter Profile Image: Bella B.
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10. Bella B.

Lakeside Sitter, Works from Home.
Stockbridge, MA, 01262
7.8 mi. away
5.0 out of 5 stars
4 reviews
1 repeat client
from
$60
per night

Left my dog for two nights with Bella and he looks like he had a lot of fun! She was very responsive at all times and seems very knowledgeable about dogs!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Brit L.
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Sitter Profile Image: Brit L.
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11. Brit L.

The queer dog walker
NORTH ADAMS, MA, 01247
20.6 mi. away
5.0 out of 5 stars
17 reviews
8 repeat clients
from
$45
per night

Brit is an absolutely wonderful pet sitter! My cat, who is generally pretty picky about who he lets care for him, loves her. She is attentive, reliable, generous with pets and scritches, and is even good at giving pills. I’ve been thrilled with Brit as a cat sitter, and you and your pets are going to adore her, too. I highly recommend Brit!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Kim C.
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Sitter Profile Image: Kim C.
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12. Kim C.

Your dog’s staycation starts here!
Adams, MA, 01220
15.3 mi. away
5.0 out of 5 stars
4 reviews
1 repeat client
from
$65
per night

Our two dachshunds stayed with Kim over one night. They had a good experience also enjoying in particular Kim's dachshund. Kim updated us every few hours with text and photos. Since she is also a dog trainer she had a professional approach, and gave our dogs time and space to get used to their new environment. Picking our dogs up the next day up they were easygoing and relaxed. When we return to the Berkshires we would board our dogs with Kim again and recommend her highly. Thank you, Kim!

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Sitter Profile Image: Peter K.
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Sitter Profile Image: Peter K.
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13. Peter K.

Dogs speak to those who listen.
South Egremont, MA, 01258
20.3 mi. away
5.0 out of 5 stars
17 reviews
7 repeat clients
from
$50
per night

Peter and Monique were so attentive to our dog for a whole week. Peter was very thorough in asking all about Sooty’s needs and preferences. We really appreciated the updates and photos, our dog had a lovely time and was very well cared for. I booked Peter based on reading the reviews and would say exactly the same as others have. Definitely recommend and will be booking again in future.

Sitter Profile Image: Jonathon M.
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Sitter Profile Image: Jonathon M.
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14. Jonathon M.

10 Miles from Jiminy Peak!
Stephentown, NY, 12168
14.7 mi. away
5.0 out of 5 stars
15 reviews
4 repeat clients
from
$63
per night

Jonathon did an amazing job with Juice. He was welcoming from the very beginning, I knew that Juice would be in good hands! He sent us daily updates, with photos and videos of Juice playing in his yard. Juice made some new friends this past weekend with Jonathon’s dog. If you have a big dog, and you are nervous that no one will want to take care of him, he is your guy! He made us so happy that our Juice man would be in such a nice home.

Sitter Profile Image: Steve F.
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Sitter Profile Image: Steve F.
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15. Steve F.

Down to earth and fun loving
Lee, MA, 01108
7.8 mi. away
2 repeat clients
from
$75
per night

About: I'm very happy to be around pets. Have experience taking care of pets as I have had pets growing up I have been called to dog wisper because I have that connection with dogs. Your pet will be well cared for and loved in my care I'm open mornings and at night.i do food delivery and housekeeping part time.i can usually be available for whatever times you need just reach out and let me know I have a eye for detail and.very alert so your pet will be safe. What ever kind of pet sitting you need I can do

Sitter Profile Image: Amber S.
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Sitter Profile Image: Amber S.
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16. Amber S.

Trusted care for your pet
Dalton, MA, 01226
4.7 mi. away
15 years of experience
from
$90
per night

About: I have had animals my whole life and I understand how hard it is to leave them I proved a caring environment to nurture your pet I have plenty of time to play with and take care of your pets. Walks, trips to the dog park. Your pets will get 1 on one attention. I have a fenced in yard and a large property for your pets to play and enjoy their day inside and out. Lots of room to run.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Candice S.
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Sitter Profile Image: Candice S.
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17. Candice S.

Dog lover with great pet space!
Stuyvesant, NY, 12173
26.2 mi. away
5.0 out of 5 stars
13 reviews
5 repeat clients
from
$55
per night

Candice was amazing and Barry absolutely adored her and her kids! he had a great time there and came home so happy! 10/10 would recommend and will def be going back!

Sitter Profile Image: Jennifer C.
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Sitter Profile Image: Jennifer C.
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18. Jennifer C.

Smile, your pet is safe and happy!
Averill Park, NY, 12018
22.6 mi. away
5.0 out of 5 stars
59 reviews
21 repeat clients
from
$50
per night

Jenn was a magnificent sitter for our pup, Mac. She made our trip much more enjoyable by constantly communicating with us and sending us pictures and videos. I could not recommend her enough for your pet needs!

Sitter Profile Image: Nikki R.
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Sitter Profile Image: Nikki R.
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19. Nikki R.

Apartment but I’m able to go out
Adams, MA, 01220
16.0 mi. away
from
$25
per night

What I know about Nikki is that she's a kind and caring person and has been around dogs most of her life. When she has been around any of my dogs she has always been attentive.

Sitter Profile Image: Melanie & Sean H.
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Sitter Profile Image: Melanie & Sean H.
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20. Melanie & Sean H.

Dog-loving home with large dog run!
Richmond, MA, 01254
6.9 mi. away
from
$100
per night

We are new to the area and we were SO fortunate to find Melanie and Sean! They have a huge fenced yard for the dogs to play together with fun spots to explore and lots of shade. Melanie is very hands on and playful with all the dogs! She treats each and every dog as if they were her own. We highly recommend puppy hollow to anyone in the Berkshires.

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