House Sitting in Cherry Plain

Find a loving house sitter to watch over your pets and your home.

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Top rated Cherry Plain house sitters

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Anna C.
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Anna C.
Star Sitter
from
$40
per night
5.0 out of 5 stars
38 reviews
12 repeat clients
12 years of experience
Troy, NY, 12180

Anna was absolutely amazing with our dog!! She sent us lots of pics while we were away and took such great care of our pup and home! We wholeheartedly feel so lucky to have found her—our dog took to her right away and was very comfortablewi to her ! We will absolutely be repeat customers!!

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Dre F.
Sitter Profile Image: Trista S.
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Trista S.
Star Sitter
from
$30
per night
5.0 out of 5 stars
17 reviews
6 repeat clients
30 years of experience
Pittsfield, MA, 01201

Trista was wonderful with my two dogs. I appreciated her last minute availability and professionalism. Both dogs warmed up to her very quickly even my shy one.

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Theresa S.
Sitter Profile Image: Stephanie B.
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Stephanie B.
Star Sitter
from
$60
per night
5.0 out of 5 stars
34 reviews
14 repeat clients
15 years of experience
Troy, NY, 12182

Repeat customer, Stephanie (Net) is the best and goes above and beyond. We have a bunch of pets including a senior dog and a high energy middle age pup (cats, a lizard, oh my!) and she’s great with everyone. Highly recommend!

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Elise P.
Sitter Profile Image: Skylar R.
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Skylar R.
Star Sitter
from
$75
per night
5.0 out of 5 stars
14 reviews
7 repeat clients
15 years of experience
North Adams, MA, 01247

We got home and our dog was happy to see us, but she was so calm. She was clearly so comfortable with Skylar. Skylar left our house clean. She is great! We will use her again.

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Kyle C.
Sitter Profile Image: Gillian G.
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Gillian G.
from
$32
per night
5.0 out of 5 stars
18 reviews
8 repeat clients
10 years of experience
Williamstown, MA, 01267

Gillian was great! Took great care of my dogs! I highly recommend her!

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Alice T.
Sitter Profile Image: Lauren B.
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Lauren B.
from
$60
per night
5.0 out of 5 stars
15 reviews
3 repeat clients
4 years of experience
West Sand Lake, NY, 12196

Lauren watched my bernedoodle pup so I could get a rare night out. Very pleased with her overall care and will definitely book her again!

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Jan B.
Sitter Profile Image: Bella G.
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Bella G.
from
$65
per night
5.0 out of 5 stars
13 reviews
2 repeat clients
10 years of experience
lanesborough, MA, 01237

Highly Recommend - Bella first met our dogs and asked great questions so she could understand their temperaments and provide the best care. She was on-time and made it a super easy stay with the dogs!

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Frank K.
Sitter Profile Image: Daniel V.
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Daniel V.
from
$70
per night
5.0 out of 5 stars
3 reviews
1 repeat client
16 years of experience
Melrose, NY, 12121

About: I've been pet sitting for many years and now will be expanding onto Rover. I know our pets do so much for us and should be treated as family I'm dedicated to taking care of each customer with respect and professionalism, with or without 4 legs. I know you will feel at ease when away from your pet I'm dedicated to taking care of each customer with respect and professionalism, with or without 4 legs. I know you will feel at ease when away from your pet

Sitter Profile Image: Mariana F.
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Mariana F.
from
$32
per night
5.0 out of 5 stars
1 review
10 years of experience
North adams, MA, 01247

About: ive had a couple of dog growing up in my childhood a sweet old black lab and a super crazy dingo.. in my free time after school and during summer i used to walk them, no amount of walking could satisfy my dingo.. id have her pull my bike to get all her energy out since we didnt have any closed in areas she could run off in.. ( i dont do this anymore! i realize its not very safe! she absolutely loved it for sure though) i love pups big and small old and energetic theyre all very unique and id love some new friends to get me out of the house. id ask you beforehand of course if youd be okay with them swimming, theres a pond i can bring them to after walking to cool off at. our backyard is fenced! i have two cats, so id like to know how your dog reacts around small creatures, if they cant be in contact i can always but them into a room while the dog is over. most likely theyd be outside! lots of shade and id keep em well hydrated and happy :3 i currently have been on a job hunt since what feels like forever, my schedule is very. very open.. since i dont have a car, drop off would be ideal, if your close enough to walk to i can do that too! weekends are the only time id be able to pick up your pooch my cats get their waters filled and cleaned almost daily, lots of love of course and are very spoiled. i dont have any dogs at the moment, so of course id love to chat about what youd expect and need for your lovely pup! im good with communication and friendly, special needs id be extra attentive to. im very good at remembering small things, though id still write em down incase!

Sitter Profile Image: Natasha M.
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Natasha M.
from
$35
per night
6 years of experience
Clifton park, NY, 12065

About: I have had family pets since I was three that I have helped care for. As a child, I volunteered at the Saratoga animal shelter and spent time caring for the cats and dogs there. When I was fourteen, I worked at a pet resort, where I checked dogs and cats into the hotel and made sure they were safely cared for. When I was eighteen I got two cats, Noodles and Drake, who I absolutely adore. I am a 23 year old university student who is currently working on my phd. I’m excited to have the opportunity to care for animals during the summer and part time during my semester. I have experience caring for a wide range of breeds and ages. I also have a cousin and cousin in-law who are veterinarians and can be of assistance in case of any emergency. I look forward to care for your pet!! I’m currently on break from university, where I am working on my phd for history. Therefore, I have almost completely open availability for taking care of your pets! I may have one online class from 6-9 pm on Wednesday. I am dedicated to provide your pet comfort and love so that you have peace of mind while you are away from home. I will watch your pet at all times while they are outside on a walk or going to the bathroom. I will keep good watch of them in the time and will provide frequent potty breaks. I have a cousin and cousin in law who are veterinarians, so if I have any concerns, I have a trusted vet who I can immediately get in contact with. I am always reachable in case you have any questions or concerns.

Sitter Profile Image: Joyce L.
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Joyce L.
from
$60
per night
5.0 out of 5 stars
10 reviews
6 years of experience
Rensselaer, NY, 12144

It is challenging to leave our anxious dog when we go away. Joyce made it so much easier! She is very thoughtful and went above and beyond to understand our dog and give her lots of attention. She sent us the sweetest daily updates. Also, it was very clear when we got home that she had taken very good care of our house. Joyce is now on our short list of favorite dog sitters. We will have her dog/house sit again without question.

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Leah W.
Sitter Profile Image: Brenna B.
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Brenna B.
from
$100
per night
5.0 out of 5 stars
7 reviews
1 repeat client
12 years of experience
Pittsfield, MA, 01201

Brenna was an amazing pet sitter for us. We have two dogs, both seniors, and one with significant health issues. It is always hard to leave him but had our son's wedding in Canada to attend. Brenna sent constant updates and photos to ease our mind while away. They were very well cared for and loved. I would use Brenna again in a heart beat!

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Nadine S.
Sitter Profile Image: Olivia A.
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Olivia A.
from
$35
per night
15 years of experience
Dalton, MA, 01226

About: I have cared for many pets my whole life. I love meeting new animals and learning about each and every personality. Had or cared for cats, dogs, and small animals, and willing to meet more! I am available most days and some nights. I can provide early morning care and mid day care, and night care but often after 10pm. I am always attentive to animal body language and keep an eye on how they are feeling in the environment or around me. I follow the guidlines closely that are given by owners on how to care for their pet.

Sitter Profile Image: Caitlin J.
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Caitlin J.
from
$32
per night
5.0 out of 5 stars
4 reviews
20 years of experience
Windsor, MA, 01270

About: I've loved animals forever and have cared for everything from a cockatiel to a chameleon, Great Pyrenees to Pekapoo. I currently have 1 Goldendoodle and 1 chocolate tabby cat in my home with fenced area and walking trails. I'm currently homeschooling my children at our 10+ acre home with fenced area and walking trails. We have a light schedule and are home more often than away. We currently walk our Goldendoodle daily and pet care is our love, in addition to our responsibility. I have a fenced area and multiple indoor secure areas where animals can get healthy time in a safe home without overstimulation. I have 1 Goldendoodle and 1 chocolate tabby cat who are the best of friends and are supportive to newcomers.

Sitter Profile Image: Leona O.
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Leona O.
from
$44
per night
4.7 out of 5 stars
6 reviews
10 years of experience
North Adams, MA, 01247

Leona was great with our boxer, Brussel Sprout. She was very responsive and let us know of any issues so we could help her out while we were away!

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Liane T.
Sitter Profile Image: Alyssa M.
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Alyssa M.
from
$80
per night
5.0 out of 5 stars
3 reviews
10 years of experience
Valatie, NY, 12184

Alyssa is great! My pets and home were well cared for. My dog gets pretty anxious when I go out of town but he seemed very calm and relaxed when I came back. He seemed like he had a great time with Alyssa!

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James W.
Sitter Profile Image: Dana G.
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Dana G.
from
$125
per night
5.0 out of 5 stars
40 reviews
11 repeat clients
20 years of experience
PITTSFIELD, MA, 01201

Dana stayed at our house for a week while we were traveling and gave our cats exceptional care. We appreciated getting daily updates with photos and could tell that our two sociable cats loved their time with her. We're also grateful that she went the extra mile in trying to help our most shy cat feel comfortable. We highly recommend Dana for pet care!

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Ginny M.
Sitter Profile Image: Melanie D.
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Melanie D.
from
$65
per night
20 years of experience
Dalton, MA, 01226

About: I grew up with dogs my whole life. My parents also run a dog sitting business on cape cod and I help out there when I can! I am also fully insured! I’m a current second grade teacher, so I’m completely free on the weekends and the summer months, as well as school vacations to take care of your furry friends! I will love your dog like my own! I’m a diligent, reliable and clean person that will leave your home and dog happier than I found it. I am also fully insured!

Sitter Profile Image: Reymon B.
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Reymon B.
from
$80
per night
20 years of experience
Pittsfield, MA, 01201

About: Working in various Grooming/Training facilities. I'm currently working with Bumblebee Pet Care with 5 of my own clients. My conversations with the pets are amazing. I'm currently walking dogs 2 days out of the week looking for more to work with within the week. I have an open schedule and interested. I have separate spaces available for each animal. In my care at anytime, I will use provided equipment for transportation. Your pet safety is number one.

Sitter Profile Image: Ariela T.
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Ariela T.
from
$100
per night
4.6 out of 5 stars
13 reviews
1 repeat client
27 years of experience
Valley Village, North Adams, MA, 01247

Ari was amazing. Our dog is a precious shelter dog and has some of the shelter dog nuisances and Ari understood exactly how to deal with him. I could tell he had a good time when we got home.

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Kaylan D.
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How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

The median cost per night for house sitting in Cherry Plain is $60

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

    It doesn’t happen often, but if your house sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Sitters in Cherry Plain average 4
repeat house sitting clients

House Sitting FAQs

Frequently asked questions about Rover

House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Cherry Plain on Rover as of Jun 2026 was about $60 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.

If you’re searching for a Cherry Plain house sitter for the first time, visit the house sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 308 house sitters in Cherry Plain. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 86% of Cherry Plain house sitters respond in under an hour.

House sitters in Cherry Plain have an average of 14 years of experience. House sitters with repeat customers have an average of 4 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Cherry Plain.

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Cherry Plain house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.