Drop-In Visits in Pittsfield

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

Tip: Contact sitters now to confirm availability.
Confirmed 4th of July Availability
1. Alyson

Flexible schedule, love walking

Dalton, MA, 01226

Drop-In Visits, Dog Walking

"Alyson LOVES dogs and loves to hike/walk, she is beyond reliable & trustworthy and I highly recommend her to take care of your beloved pet! (more)"

Confirmed 4th of July Availability
2. Rachel

Your dog’s future best friend

Valatie, NY, 12184

House Sitting, Drop-In Visits, Dog Walking

"Rachel was great! We will definitely use her again! (more)"

3. Heather

Home Full-Time Flexible Hours

Pittsfield, MA, 01201

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"We couldn’t be more pleased! Heather does drop-in visits for us to care for our German Shepherd when we’re away and there’s nothing like being able to leave ... (more)"

Confirmed 4th of July Availability
4. Danielle

10 years of excellent dog boarding

Pittsfield, MA, 01201

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

About: My name is Danielle and I have been watching dogs forever. I managed a local dog daycare and boarding facility and spent 7 years managing the city... (more)

Confirmed 4th of July Availability
5. Kaylee

Dependable, reliable, & dog loving

North Adams, MA, 01247

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"Kaylee and Lindsey took great care of Gypsy and Jake, and we really appreciated the updates and photos. Highly recommended. (more)"

6. Jeffrey

Love dogs, dog trainer, huge yard

Nassau, NY, 12123

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

About: We are very pet friendly couple. Wife is a dog trainer and very knowledgeable on all breeds. We have a big 2 acre yard (in the process of putting u... (more)

Confirmed 4th of July Availability
7. Samantha

Caring Dog Sitter Here to Help :)

Lanesboro, MA, 01237

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"I have found Samantha to be a very knowledgable and careing dog lover that is very conscious of my dogs needs and desires . Samantha has taken care of my... (more)"

8. Sara

Dependable and Active!

Pittsfield, MA, 01201

Dog Boarding, Drop-In Visits, Doggy Day Care

"Sara came to our resort unit on Sunday before the sitting day we needed which was Thursday. There was some confusion as to the times she would be available.... (more)"

9. Jeanne

Country setting, lots of hiking

pittsfield, MA, 01201

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"Jeanne has cared for my dog Millie many times. She loves going there and playing with Stella (Jeanne's dog). There's a lot of room to play inside and outsid... (more)"

10. Emma

Responsible, experienced dog lover!

Lee, MA, 01238

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Emma has recently taken care of my French bulldog, Beatriz, and was amazing! Beatriz always looks forward to her walks and play time with Emma. She provides ... (more)"

Confirmed 4th of July Availability
11. Holly

Know all the best dog walking spots

Williamstown, MA, 01267

House Sitting, Drop-In Visits, Dog Walking

"Holly takes pet sitting to the next level. She has cared for my dogs on numerous occasions. Holly has always stepped up even when it was on short notice. My... (more)"

12. Nathan

I'll take your dog to the park

Weststockbridge, MA, 01266

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: I love animals I'm kind and friendly I am respectful and responsible. I will keep your dog happy and we will become friends. I've had dogs througho... (more)

13. Emma

A dog depraved college student!

Williamstown, MA, 01267

House Sitting, Drop-In Visits, Dog Walking

"Emma is a very companionate and fun loving girl. She has a deep love for dogs and is a very great owner of her own dog. She constantly makes sure her dog has... (more)"

14. Taylor

Dog lover with big heart!

Hinsdale, MA, 01235

Drop-In Visits, Dog Walking

"Taylor is a fun and hardworking ray of sunshine. Who better to help you with your family pet than someone who would do anything to make her puppers smile ? R... (more)"

15. Ava-Lena

Loving, reliable and attentive!

Pittsfield, MA, 01201

House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Very professional and saved me in the last minute! (more)"

16. Kelly

Family of dogs love them like mine

Stephentown, NY, 12168

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

About: Worked fostering dogs for over 20 years and my mom was a vet tech we have always loved our animals like family they bring so much joy to our lives.... (more)

17. Emily

Willing to love on your dog 24/7

Cummington, MA, 01026

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

About: I love dogs and cats and the unconditional love they give back in return. I want to show your pet that love when you unfortunately can’t be home to... (more)

Confirmed 4th of July Availability
18. Tracy

Brisk walks with you dog

Nassau, NY, 12123

Drop-In Visits, Dog Walking

About: I’ve been caring for dogs for 13 years. Since I was a child I’ve loved dogs, and have had dogs most of my adult life. My own dog is a pit bull mi... (more)

19. Brandon

Loving care for your pet

Pittsfield, MA, 01201

House Sitting, Drop-In Visits, Dog Walking

About: I have had dogs in my house for the last 15 Year’s. I currently take care of two of my own. I enjoy taking my dogs on hikes on various trails aroun... (more)

Confirmed 4th of July Availability
20. Magdelin

Flexible availability!

Dalton, MA, 01226

Drop-In Visits, Dog Walking

"MAGDELINE IS THE MOST RESPONSIBLE PERSON I NO SHE TAKES SUPER CARE OF ALL HER ANIMALS CHICKEN HORSE DOG GOATS AND SHE HAS A HEART OF GOLD (more)"


Rover.com is the simple, savvy way to find and book drop in pet sitting. It's easy to find the perfect pet sitter — many sitters have worked through Rover for years pet sitting, and 95% of reviewed stays have received a perfect five-star rating. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Pet sitters on Rover have the option to complete a background check, which you can see from their background check badge. Pet sitters are booked on Rover every minute of every day, and 92% of the population lives within a short drive of one of the more 40,000 sitters who've listed their services on Rover, so you're sure to find the perfect pet sitter on Rover. When you book with one of our trusted pet sitters on Rover you get peace of mind that your home and pets are in loving hands.

All stays booked on Rover receive our Rover guarantee, 24/7 support, and our reservation protection.

How it works

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1) Browse Sitters

We make it easy to find affordable & reliable sitters near you.

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2) Contact Sitters

Chat about your dog and your specific needs. Even meet in person before booking if you really want to.

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3) Book & pay

Our platform makes it easy and secure. No cash necessary.

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4) Enjoy your trip

Drop off your dog without feeling guilty. Relax with regular photo updates from your sitter.