Dog Boarding in Berkshire

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Top rated Berkshire dog boarders

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Sitter Profile Image: Elli S.
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Elli S.
from
$40
per night
5 out of 5.0 stars
163 reviews
63 repeat clients
10 years of experience
Bennington, VT, 05201

I’m so beyond grateful to Elli for taking such good care of my beloved doggy. He was content when he got home and tired from lots of play time with the other dogs. About two weeks before I brought Theo for sitting, he had an unexpected health crisis and Elli went above and beyond to be caring and accommodating.

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Emily W.
Sitter Profile Image: Deanne R.
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Deanne R.
Star Sitter
from
$48
per night
5 out of 5.0 stars
35 reviews
11 repeat clients
6 years of experience
Kinderhook, NY, 12106

Deanne was a lifesaver - not only did she agree to take our cat Tulip on such short notice, but she helped me with my separation anxiety with such kindness and empathy. Deanne went out of her way to send pictures and videos of Tulip having a great time, which meant the world to me. Tulip was clearly happy, well taken care of, and now I have to buy her a cat tree since the one Deanne provided brought her so much joy. Thank you so much from the bottom of my heart - Brianna

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Evan B.
Sitter Profile Image: Cheryle W.
Verified Enhanced Background Check
Cheryle W.
Star Sitter
from
$40
per night
5 out of 5.0 stars
25 reviews
11 repeat clients
30 years of experience
WATERVLIET, NY, 12189

Cheryle is a great dog-sitter. Her house is well set-up for a little dog, with low couches, ramps and lots of cozy spots. Her dachsund was a great companion for my dog, Roscoe. Roscoe came home calm and happy after 5 days at Cherlye's. He was on a variety of meds for a sore back and she managed all those well and took great care of him.

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Ellen B.
Sitter Profile Image: Brooke B.
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Brooke B.
Star Sitter
from
$40
per night
5 out of 5.0 stars
116 reviews
32 repeat clients
25 years of experience
Pittsfield, MA, 01201

Brooke immediately set our minds at ease by texting us just several hours after dropping our dog off, telling us that Ella had eaten and was getting along with everybody. We were then able to relax and begin to enjoy our trip. She kept the messages and photos coming which was so nice! If we every go away again we will definitely leave Ella with Brooke.

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Tory S.
Sitter Profile Image: Ericca B.
Verified Enhanced Background Check
Ericca B.
Star Sitter
from
$63
per night
5 out of 5.0 stars
33 reviews
11 repeat clients
36 years of experience
Bennington, VT, 05201

Ericca was so lovely and accommodating to our timing. She is a pro and has her routine down for how best to make dogs feel comfortable, introduce them to her dogs. Our dog looked happy when we picked her up and even gave her a sweet goodbye out the window.

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Jessie C.
Sitter Profile Image: Kate B.
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Kate B.
from
$60
per night
5 out of 5.0 stars
11 reviews
30 years of experience
Bennington, VT, 05255

Kate clearly has a lot of experience with dogs, and was the perfect place for our pup to spend the night. We’d definitely use her again and highly recommend her.

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Kassia R.
Sitter Profile Image: Sylva & Mark M.
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Sylva & Mark M.
Star Sitter
from
$55
per night
5 out of 5.0 stars
45 reviews
12 repeat clients
8 years of experience
Troy, NY, 12180

Sylva & Mark were absolutely perfect. They took such good care of my boys and kept me updated daily on how they were doing. I couldn't have asked for a better couple to watch my boys. If you ever need a sitter I would 1000% recommend them. I don't trust many people to watch my pups but I would send my Buddy & Connor to them anytime. Thank you again from the bottom of my heart for taking care of them.

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Chanel S.
Sitter Profile Image: Tetiana M.
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Tetiana M.
Star Sitter
from
$60
per night
5 out of 5.0 stars
41 reviews
10 repeat clients
2 years of experience
Pittsfield, MA, 01201

Tetiana is an amazing petsitter! She is communicative, attentive to details and, most importantly, has a loving and giving heart. She and her lovely mom Maria treated my Edna like their own, with play and cuddles and outdoor adventures — many pictures clearly showing to me Edna’s enjoyment. I hope Edna can return to Tetiana’s and I highly recommend her.

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Ann D.
Sitter Profile Image: Karl K.
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Karl K.
from
$39
per night
5 out of 5.0 stars
7 reviews
1 repeat client
55 years of experience
West Hatfield, MA, 01088

Karl was an amazing dog sitter! He was punctual with returning my messages, kind, caring, and provided great service for my two big Doodles! Doodles! Karl sent images which were so great to get since we love our babies like their are our dogs ❤️ I highly recommend Karl for all your dog care needs.

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Eliza L.
Sitter Profile Image: Jennifer C.
Verified Enhanced Background Check
Jennifer C.
Star Sitter
from
$50
per night
5 out of 5.0 stars
86 reviews
25 repeat clients
30 years of experience
Averill Park, NY, 12018

I am blessed to have found Jennifer. She was quick to respond and provided picture and message updates while I was gone. Gus loves her already and I know that he would be comfortable with Jennifer again if the need arises. I would highly recommend her to others.

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Vickie F.
Sitter Profile Image: Peter K.
Verified Background Check
Peter K.
from
$50
per night
5 out of 5.0 stars
24 reviews
7 repeat clients
8 years of experience
South Egremont, MA, 01258

Peter was such a wonderful sitter. His updates were timely and detailed and I felt confident that Nutmeg was cared for, happy, and healthy during her stay. I will definitely ask Peter to sit again if I’m ever in the area again.

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Jana P.
Sitter Profile Image: Mary & Todd H.
Verified Background Check
Mary & Todd H.
from
$45
per night
5 out of 5.0 stars
37 reviews
11 repeat clients
40 years of experience
Chatham, NY, 12037

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!!

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Judi P.
Sitter Profile Image: Irene T.
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Irene T.
from
$65
per night
5 out of 5.0 stars
3 reviews
1 repeat client
20 years of experience
Pittsfield, MA, 01201

About: I’ve owned and taken care of dogs more than half my life. They are family and should be treated as such. I use a gentle approach and we will make sure we are the right fit before committing to a stay. I currently work from home with our fur baby Goldie. We go for walks or hang out in the AC, or by the warm fire. Offering play and enrichment throughout the day. I have a fenced in yard, plenty of doggie beds, treats and tons of affection. A super friendly medium sized dog named Goldie and a fast moving 8 year old daughter. Must be dog and kid friendly. No cats in home.

Sitter Profile Image: Mikayla H.
Verified Enhanced Background Check
Mikayla H.
Star Sitter
from
$40
per night
5 out of 5.0 stars
14 reviews
5 repeat clients
10 years of experience
Nassau, NY, 12123

It was a big deal for us to leave our 8 month old puppy with a sitter, but we knew after her daytime ventures that Marcie would be just fine. Mikayla communicated with us, and provided pictures. We highly recommend her!

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Katie V.
Sitter Profile Image: Yenifer V.
Verified Enhanced Background Check
Yenifer V.
from
$65
per night
5 out of 5.0 stars
11 reviews
1 repeat client
3 years of experience
Pittsfield, MA, 01201

Yenifer took excellent care of my dog. He was so happy with her! She made sure she communicated everyday with us during the stay, sent us pictures and updates. We are very happy with her services and would strongly recommend her. Thank you, Yenifer.

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Divya C.
Sitter Profile Image: Jess L.
Verified Enhanced Background Check
Jess L.
from
$45
per night
5 out of 5.0 stars
70 reviews
19 repeat clients
5 years of experience
Pittsfield, MA, 01201

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.

Profile image
Heidi A.
Sitter Profile Image: Mahayla G.
Verified Enhanced Background Check
Mahayla G.
from
$75
per night
5 out of 5.0 stars
44 reviews
22 repeat clients
15 years of experience
Adams, MA, 01220

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!

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Deb G.
Sitter Profile Image: Aura G.
Verified Enhanced Background Check
Aura G.
from
$50
per night
5 out of 5.0 stars
1 review
10 years of experience
Pittsfield, MA, 01201

Our puppy had a fabulous experience I. Aura’a household care. We will use her service again!

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Jane J.
Sitter Profile Image: Ivan O.
Verified Enhanced Background Check
Ivan O.
from
$60
per night
5 out of 5.0 stars
5 reviews
20 years of experience
New Lebanon, NY, 12125

Ivan was a great host for Sadie. He sent photos and updates during her stay. He was also understanding and accommodating to my travel arrangements.

Profile image
Lyndsey W.
Sitter Profile Image: Sandra W.
Verified Enhanced Background Check
Sandra W.
from
$80
per night
5 out of 5.0 stars
12 reviews
2 repeat clients
12 years of experience
Pittsfield, MA, 01201

Sandra is super professional and took great care of our dog. She sent lots of great pictures and communicated really well. Sandra is clearly both a real dog lover and terrific caregiver.

Profile image
Michael E.
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Sitter Profile Image: Elli S.
Verified Enhanced Background Check
Sitter Profile Image: Elli S.
Verified Enhanced Background Check

Elli S.
Rover 101

I Want To Watch Your Darlings!
Bennington, VT, 05201
26.1 mi. away
Boarding, Drop-In Visits, Doggy Day Care
from
$40
per night
5 out of 5.0 stars
163 reviews
63 repeat clients
Profile image

I’m so beyond grateful to Elli for taking such good care of my beloved doggy. He was content when he got home and tired from lots of play time with the other dogs. About two weeks before I brought Theo for sitting, he had an unexpected health crisis and Elli went above and beyond to be caring and accommodating.

Availability updated yesterday
Sitter Profile Image: Deanne R.
Verified Enhanced Background Check
Sitter Profile Image: Deanne R.
Verified Enhanced Background Check

Deanne R.
Star Sitter

I would love to watch your pets!
Kinderhook, NY, 12106
28.4 mi. away
Boarding, Drop-In Visits, Doggy Day Care
from
$48
per night
5 out of 5.0 stars
35 reviews
11 repeat clients
Profile image

Deanne was a lifesaver - not only did she agree to take our cat Tulip on such short notice, but she helped me with my separation anxiety with such kindness and empathy. Deanne went out of her way to send pictures and videos of Tulip having a great time, which meant the world to me. Tulip was clearly happy, well taken care of, and now I have to buy her a cat tree since the one Deanne provided brought her so much joy. Thank you so much from the bottom of my heart - Brianna

Availability updated today
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Cheryle W.
Verified Enhanced Background Check
Sitter Profile Image: Cheryle W.
Verified Enhanced Background Check

Cheryle W.
Rover 101
Star Sitter

Small dogs spoiled here
WATERVLIET, NY, 12189
29.8 mi. away
Boarding, Doggy Day Care
from
$40
per night
5 out of 5.0 stars
25 reviews
11 repeat clients
Profile image

Cheryle is a great dog-sitter. Her house is well set-up for a little dog, with low couches, ramps and lots of cozy spots. Her dachsund was a great companion for my dog, Roscoe. Roscoe came home calm and happy after 5 days at Cherlye's. He was on a variety of meds for a sore back and she managed all those well and took great care of him.

Availability updated 4 days ago
Sitter Profile Image: Brooke B.
Verified Background Check
Sitter Profile Image: Brooke B.
Verified Background Check

Brooke B.
Rover 101
Star Sitter

Dog people
Pittsfield, MA, 01201
3.8 mi. away
Boarding
from
$40
per night
5 out of 5.0 stars
116 reviews
32 repeat clients
Profile image

Brooke immediately set our minds at ease by texting us just several hours after dropping our dog off, telling us that Ella had eaten and was getting along with everybody. We were then able to relax and begin to enjoy our trip. She kept the messages and photos coming which was so nice! If we every go away again we will definitely leave Ella with Brooke.

Availability updated 4 days ago
Sitter Profile Image: Ericca B.
Verified Enhanced Background Check
Sitter Profile Image: Ericca B.
Verified Enhanced Background Check

Ericca B.
Star Sitter

Ultimutt Dawg Sitter
Bennington, VT, 05201
25.0 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$63
per night
5 out of 5.0 stars
33 reviews
11 repeat clients
Profile image

Ericca was so lovely and accommodating to our timing. She is a pro and has her routine down for how best to make dogs feel comfortable, introduce them to her dogs. Our dog looked happy when we picked her up and even gave her a sweet goodbye out the window.

Availability updated 2 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Kate B.
Verified Enhanced Background Check
Sitter Profile Image: Kate B.
Verified Enhanced Background Check

Kate B.

Former Trainer, Forever Pet Lover
Bennington, VT, 05255
28.0 mi. away
Boarding, House Sitting, Drop-In Visits
from
$60
per night
5 out of 5.0 stars
11 reviews
Profile image

Kate clearly has a lot of experience with dogs, and was the perfect place for our pup to spend the night. We’d definitely use her again and highly recommend her.

Availability updated 6 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Sylva & Mark M.
Verified Enhanced Background Check
Sitter Profile Image: Sylva & Mark M.
Verified Enhanced Background Check

Sylva & Mark M.
Star Sitter

Our whole family loves dogs
Troy, NY, 12180
29.4 mi. away
Boarding, Doggy Day Care
from
$55
per night
5 out of 5.0 stars
45 reviews
12 repeat clients
Profile image

Sylva & Mark were absolutely perfect. They took such good care of my boys and kept me updated daily on how they were doing. I couldn't have asked for a better couple to watch my boys. If you ever need a sitter I would 1000% recommend them. I don't trust many people to watch my pups but I would send my Buddy & Connor to them anytime. Thank you again from the bottom of my heart for taking care of them.

Availability updated today
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Tetiana M.
Verified Enhanced Background Check
Sitter Profile Image: Tetiana M.
Verified Enhanced Background Check

Tetiana M.
Star Sitter

I care for the dogs
Pittsfield, MA, 01201
7.3 mi. away
Boarding, Doggy Day Care
from
$60
per night
5 out of 5.0 stars
41 reviews
10 repeat clients
Profile image

Tetiana is an amazing petsitter! She is communicative, attentive to details and, most importantly, has a loving and giving heart. She and her lovely mom Maria treated my Edna like their own, with play and cuddles and outdoor adventures — many pictures clearly showing to me Edna’s enjoyment. I hope Edna can return to Tetiana’s and I highly recommend her.

Availability updated 62 days ago
Sitter Profile Image: Karl K.
Verified Enhanced Background Check
Sitter Profile Image: Karl K.
Verified Enhanced Background Check

Karl K.

I've always lived with dogs or cats
West Hatfield, MA, 01088
29.1 mi. away
Boarding, Drop-In Visits, Dog Walking
from
$39
per night
5 out of 5.0 stars
7 reviews
1 repeat client
Profile image

Karl was an amazing dog sitter! He was punctual with returning my messages, kind, caring, and provided great service for my two big Doodles! Doodles! Karl sent images which were so great to get since we love our babies like their are our dogs ❤️ I highly recommend Karl for all your dog care needs.

Availability updated 3 days ago
Sitter Profile Image: Jennifer C.
Verified Enhanced Background Check
Sitter Profile Image: Jennifer C.
Verified Enhanced Background Check

Jennifer C.
Star Sitter

Smile, your pet is safe and happy!
Averill Park, NY, 12018
20.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care
from
$50
per night
5 out of 5.0 stars
86 reviews
25 repeat clients
Profile image

I am blessed to have found Jennifer. She was quick to respond and provided picture and message updates while I was gone. Gus loves her already and I know that he would be comfortable with Jennifer again if the need arises. I would highly recommend her to others.

Availability updated 48 days ago
Sitter Profile Image: Peter K.
Verified Background Check
Sitter Profile Image: Peter K.
Verified Background Check

Peter K.

Dogs speak to those who listen.
South Egremont, MA, 01258
27.5 mi. away
Boarding, Doggy Day Care
from
$50
per night
5 out of 5.0 stars
24 reviews
7 repeat clients
Profile image

Peter was such a wonderful sitter. His updates were timely and detailed and I felt confident that Nutmeg was cared for, happy, and healthy during her stay. I will definitely ask Peter to sit again if I’m ever in the area again.

Availability updated 12 days ago
Sitter Profile Image: Mary & Todd H.
Verified Background Check
Sitter Profile Image: Mary & Todd H.
Verified Background Check

Mary & Todd H.

Weekend getaway with active people
Chatham, NY, 12037
22.9 mi. away
Boarding, Doggy Day Care
from
$45
per night
5 out of 5.0 stars
37 reviews
11 repeat clients
Profile image

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!!

Availability updated 45 days ago
Sitter Profile Image: Irene T.
Verified Enhanced Background Check
Sitter Profile Image: Irene T.
Verified Enhanced Background Check

Irene T.

Your fur babies home away from home
Pittsfield, MA, 01201
6.2 mi. away
Boarding, Doggy Day Care
from
$65
per night
5 out of 5.0 stars
3 reviews
1 repeat client

About: I’ve owned and taken care of dogs more than half my life. They are family and should be treated as such. I use a gentle approach and we will make sure we are the right fit before committing to a stay. I currently work from home with our fur baby Goldie. We go for walks or hang out in the AC, or by the warm fire. Offering play and enrichment throughout the day. I have a fenced in yard, plenty of doggie beds, treats and tons of affection. A super friendly medium sized dog named Goldie and a fast moving 8 year old daughter. Must be dog and kid friendly. No cats in home.

Availability updated 2 days ago
Sitter Profile Image: Mikayla H.
Verified Enhanced Background Check
Sitter Profile Image: Mikayla H.
Verified Enhanced Background Check

Mikayla H.
Star Sitter

Work from home, dog lover!
Nassau, NY, 12123
21.7 mi. away
Boarding, Doggy Day Care
from
$40
per night
5 out of 5.0 stars
14 reviews
5 repeat clients
Profile image

It was a big deal for us to leave our 8 month old puppy with a sitter, but we knew after her daytime ventures that Marcie would be just fine. Mikayla communicated with us, and provided pictures. We highly recommend her!

Availability updated 10 days ago
Sitter Profile Image: Yenifer V.
Verified Enhanced Background Check
Sitter Profile Image: Yenifer V.
Verified Enhanced Background Check

Yenifer V.

EXCLUSIVE PETSITTER 💕☘️✨
Pittsfield, MA, 01201
5.9 mi. away
Boarding, Doggy Day Care, Dog Walking
from
$65
per night
5 out of 5.0 stars
11 reviews
1 repeat client
Profile image

Yenifer took excellent care of my dog. He was so happy with her! She made sure she communicated everyday with us during the stay, sent us pictures and updates. We are very happy with her services and would strongly recommend her. Thank you, Yenifer.

Availability updated yesterday
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Jess L.
Verified Enhanced Background Check
Sitter Profile Image: Jess L.
Verified Enhanced Background Check

Jess L.

I care for the care of your pets
Pittsfield, MA, 01201
4.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$45
per night
5 out of 5.0 stars
70 reviews
19 repeat clients
Profile image

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.

Availability updated yesterday
Sitter Profile Image: Mahayla G.
Verified Enhanced Background Check
Sitter Profile Image: Mahayla G.
Verified Enhanced Background Check

Mahayla G.

Exercise, training, and wellness!
Adams, MA, 01220
9.1 mi. away
Boarding
from
$75
per night
5 out of 5.0 stars
44 reviews
22 repeat clients
Profile image

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!

Availability updated 17 days ago
Sitter Profile Image: Aura G.
Verified Enhanced Background Check
Sitter Profile Image: Aura G.
Verified Enhanced Background Check

Aura G.

Love, Care and Belly rubs!
Pittsfield, MA, 01201
4.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$50
per night
5 out of 5.0 stars
1 review
Profile image

Our puppy had a fabulous experience I. Aura’a household care. We will use her service again!

Availability updated 2 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Ivan O.
Verified Enhanced Background Check
Sitter Profile Image: Ivan O.
Verified Enhanced Background Check

Ivan O.

Peaceful farmhouse on quiet road!
New Lebanon, NY, 12125
9.2 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$60
per night
5 out of 5.0 stars
5 reviews
Profile image

Ivan was a great host for Sadie. He sent photos and updates during her stay. He was also understanding and accommodating to my travel arrangements.

Availability updated 2 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Sandra W.
Verified Enhanced Background Check
Sitter Profile Image: Sandra W.
Verified Enhanced Background Check

Sandra W.

Dog Enthusiast
Pittsfield, MA, 01201
10.3 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$80
per night
5 out of 5.0 stars
12 reviews
2 repeat clients
Profile image

Sandra is super professional and took great care of our dog. She sent lots of great pictures and communicated really well. Sandra is clearly both a real dog lover and terrific caregiver.

Availability updated 6 days ago

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