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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
7 repeat clients
from
$42
per night

Jess was good. We booked her while we were in Berkshires for our weekend ski/snowboard trip. It was a basically a 2 day noticed thankfully she was available. We enjoyed ourselves knowing that our Shiba girl Yumi was taken care of. Twice a day updates as requested. Whenever were in the area again, will rebook. Thanks Jess!

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

Brooke and her son did a great job of caring for Bella. She came home ready for a nap after all of the play time. I'll definitely contact them again in the future.

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

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

Adrienne is a wonderful dog sitter! She’s watched my dog twice for me now and it’s been great both times! My dog is very happy and well cared for. I also get updates and photos! Highly recommend sitter!!!

Sitter Profile Image: Chelsea S.
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Sitter Profile Image: Chelsea S.
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4. Chelsea S.

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

If you are looking for the absolute ideal pet sitter, look no further. Chelsea is not only a highly responsible, dependable, and effective caretaker, she is also extremely loving, caring, patient, and kind with pets of all shapes and sizes. Chelsea has acted as caretaker for my dog Lemon countless times while we lived together (I literally refer to her as Auntie Chelsea), and is still beloved by Lemon every time they are reunited. Lemon is an anxious, slightly high maintenance 9yo chihuahua/mini pinscher girlie who doesn't take quickly to other people, and Chelsea is one of the few individuals beyond myself that she loves and trusts enough to be walked by, pet by, cared for, etc., and likewise is one of the few people I can confidently entrust Lemon's care to. Fun bonus fact: Chelsea is responsible for having taught Lemon 90% of the tricks she knows! I can't think of any other person to whom animals of any and all dispositions and all shapes and sizes take so easily to, or who would make a better pet sitter. Your pets will absolutely be in the best of hands with Chelsea!

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

I care for the dogs
Lenox, MA, 01240
2.6 mi. away
5.0 out of 5 stars
9 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: Teresa D.
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Sitter Profile Image: Teresa D.
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6. Teresa D.

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

From the moment we did the meet and greet I knew that I would feel comfortable having Teresa watch my little love Alfie. Teresa has her own rescue dog pack and they included Alfie immediately and he was so happy. Teresa kept me updated throughout his stay and sent daily pictures. I felt totally at ease and was able to relax and enjoy my vacation. I’m already planning to book with her again for my upcoming trips.

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

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

As I write this review I look down at my pup who is exhausted from her stay with Mary and Todd. They took Harper in last minute for an overnight/all day play date with their other dog pepper. Harper was treated as one of their own. Over the course of her stay we had daily updates and shared pictures of the trip to art Omi and for evening/morning walks. I can’t thank them enough so I figured this review would be accepted as my appreciation. I would highly recommend them, you will not be disappointed!!! Thanks again Mary and Todd

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

Lakeside Sitter, Works from Home.
Stockbridge, MA, 01262
7.8 mi. away
5.0 out of 5 stars
6 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!

Sitter Profile Image: Mahayla G.
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Sitter Profile Image: Mahayla G.
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9. 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!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Mónica G.
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Sitter Profile Image: Mónica G.
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10. 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

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
24 reviews
8 repeat clients
from
$45
per night

Brit is so friendly. My dog Arlo immediately felt comfortable at drop off. I loved getting picture updates and how accommodating Brit was about pick up. Thank you Brit!!!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jonathon M.
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Sitter Profile Image: Jonathon M.
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12. Jonathon M.

10 Miles from Jiminy Peak!
Stephentown, NY, 12168
14.7 mi. away
5.0 out of 5 stars
15 reviews
5 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.

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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.

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

Your dog’s staycation starts here!
Adams, MA, 01220
15.3 mi. away
5.0 out of 5 stars
5 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: 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: Talya F.
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Sitter Profile Image: Talya F.
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16. Talya F.

I love animals
Pittsfield, MA, 01201
2.7 mi. away
4 years of experience
from
$20
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.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Kathleen M.
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Sitter Profile Image: Kathleen M.
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17. Kathleen M.

Rover 101
Berkshires #1 Trusted Pet Sitter ❤️
Becket, MA, 01223
13.4 mi. away
5.0 out of 5 stars
118 reviews
34 repeat clients
from
$65
per night

I was in a pinch and needed someone to watch my reactive fearful rescue pup Kora for over a week. Kathleen took amazing care of Kora and sent updates and pics everyday. Kora had so much fun playing with Kathleen’s dogs and will definitely look forward to her next visit.

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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
60 reviews
22 repeat clients
from
$50
per night

Our dog was very happy with Jennifer. We are so happy to have found her. She's kind and gentle and she worked with us when we had unknowns about our needs because of a funeral we had to travel for. We were trying to book without full details of when and where we had to be. We feel very fortunate she was willing to be flexible. Our pup was happy that he was the only one she had with her during his stay. He got all of her love and attention. Thank you, Jennifer.

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

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

Melanie is an incredible person and a very responsible dog owner/caregiver. She is attentive, patient, and just so kind! She has lovingly watched my dog, Finn at my home and hers many times, over the last 5 years. Having two adorable dogs herself, she knows the dynamics of multiple dog interactions and care. She has a wonderful large fenced yard, perfect for lots of safe dog play and relaxation! As well as beautiful surroundings for nature walks. I highly recommend Melanie for a safe, loving, fun caregiving experience for your "Best Friend"!

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

Dog lover with great pet space!
Stuyvesant, NY, 12173
26.2 mi. away
5.0 out of 5 stars
14 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!

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