House Sitting Cherry Plain

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Cherry Plain, Find top rated house sitting

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
45 reviews
14 repeat clients
12 years of experience
Troy, NY, 12180

We were so grateful to have found Anna for this stay!! She was very helpful and stayed in touch with updates and photos. We were extra worried about leaving Lexi for this trip, as it was our first time away after our other dog passed. Anna was so understanding and took great care of our baby (and house!) while we were gone!! Thank you so much Anna!!!

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Katie W.
Sitter Profile Image: Ashley & Robert D.
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Ashley & Robert D.
Star Sitter
from
$100
per night
5.0 out of 5 stars
18 reviews
9 repeat clients
25 years of experience
Austerlitz, NY, 12017

Ashley and Bob were great with my 10 year old, nervous & quirky pup! They stayed at the house with her for 3 days and 3 nights and during that time, sent frequent updates and pictures. I was so grateful for their communication and care of my dog.

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Tara J.
Sitter Profile Image: Leona O.
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Leona O.
from
$44
per night
4.7 out of 5 stars
7 reviews
2 repeat clients
10 years of experience
North Adams, MA, 01247

Leona was wonderful with Romeo - he was really calm and happy when I returned. She communicated well, sent updates with photos and left my home better than she found it. I’m booking her for another cat/housesit right now!

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

About: ive had a couple of dogs 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. 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 keeping me company! 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, but I have an electric scooter thanks to a helpful couple I babysat for! drop off would be ideal, if youre close enough to walk to i can do that too! 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: Gillian G.
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Gillian G.
from
$32
per night
5.0 out of 5 stars
19 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: Monika B.
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Monika B.
from
$40
per night
25 years of experience
Wynantskill, NY, 12198

About: Experience with house sitting, dog walking, frequent drop-ins, light tidying, giving excessive amounts of cuddles and kisses! Operate with respect for pets and homes :) I have a full-time job, but open and flexible availability outside of work hours and weekends. I work from home 50% of the time as well, so can work from your home on those days if needed! I care for pets in client’s homes in accordance with the care instructions provided! Lead with respect and love for the animals I am caring for.

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: Trista S.
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Trista S.
from
$30
per night
5.0 out of 5 stars
20 reviews
6 repeat clients
30 years of experience
Pittsfield, MA, 01201

Trista stayed overnight with our fur babies. She was so good with our 3 dogs. She put our mind at ease. She sent updates and pictures throughout the day. The pups were happy too :) Will definitely book again.

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Sylvia P.
Sitter Profile Image: Stephanie B.
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Stephanie B.
Star Sitter
from
$60
per night
5.0 out of 5 stars
40 reviews
18 repeat clients
15 years of experience
Troy, NY, 12182

Stephanie was great very attentive and caring. Handling my old dogs low vision well and I was sent updates and pictures of my boys daily. I would definitely recommend her to anyone!

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Stephen M.
Sitter Profile Image: Ashley G.
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Ashley G.
from
$56
per night
4.5 out of 5 stars
2 reviews
3 years of experience
Rensselaer, NY, 12144

Ashely was quick at responding, especially in such short notice! Our dog took to her instantly, so it was very comforting knowing they were going to be great together!

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Theresa L.
Sitter Profile Image: Reymon B.
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Reymon B.
from
$80
per night
5.0 out of 5 stars
2 reviews
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: brisa u.
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brisa u.
from
$50
per night
5.0 out of 5 stars
5 reviews
2 repeat clients
6 years of experience
Lenox, MA, 01240

About: As a dog and cat owner myself, I’m happy to treat any pets as my own. I have two pets, an elder dog and a cat who both have unfortunately needed medication throughout the years, so I’m experienced in administering medicine to pets. I’ve also fostered dogs and cats with all types of different personalities, and love running along with dogs and cats alike. 😸🐶 I’m a college student and have finished all my classes for the semester, meaning I have plenty of time to help out with fur babies. I’m used to incorporating my own pets into my routine, so any pet schedule works with my own! I’ve fostered both dogs and cats before, so I’m experienced with crating and transporting dogs or cats. Whatever you need for your pets in your home I’m happy to offer!

Sitter Profile Image: Au P.
Au P.
from
$30
per night
10 years of experience
Cohoes, NY, 12047

About: Collectively, I have accumulated many years (5+) of pet care experience throughout my life. Having been a pet owner and sitter for family members and friends, I have definitely gotten a head start in the pet care arena (haha)! I have walked dogs, given awesome night time baths, given excellent belly rubs, made home cooked meals for the pets, played fetch and tug-of-war, trained puppies to potty on puppy pads and I've even been know to teach an old dog a few new tricks! I have traveled domestically catering to the needs of our furry friends and I have enjoyed it tremendously! If you want a super sitter to care for your super cute fur babies, don't leave this profile without giving me a shout, a woof, or a meow! ;) I pet sit full time, and sometimes, around the clock. I work remotely as visual artists, so your fur babies would have plenty of company and love. Pet sitting is my main priority and a way of life for me! Just reach out to me for my availability! I will come to your house to sit with your furry friend or walk them for you when you need a helping hand. I make sure to establish a relationship with the fur babies where they feel safe, understood, and loved. I'd love to take care of your adorable fur babies. You'll be able to enjoy your travels knowing your beautiful fur babies, and your home are being well taken care of. I am a clean, caring mature person who loves traveling via pet-sitting. You can see 5 star reviews on my profile and references from trusted friends, family, and colleagues whom I've helped by looking after their furry family members. I also have experience with plant care. I'd love to talk more about pet sitting for you and taking care of your darlings. Please take a look at my profile, and feel free to set up a call or chat with me.

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: Jeanicia S.
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Jeanicia S.
from
$27
per night
10 years of experience
Pittsfield, MA, 01201

About: I have years of animal care experience. Starting with watching my GSD and American Husky as a teenager. I personally own a cat and an American Staffordshire Terrier mix. I have experience with large dog breeds, medium, and small. I currently am in school asynchronously, therefore allowing me full time scheduling for pet care needs. I also have a work from home position outside of Rover that allows me to adjust my own hours. 1. As a responsible dog sitter, I prioritize the well-being and happiness of your furry friend by ensuring regular walks, playtime, and affectionate attention throughout the day. 2. Your dog's comfort and safety are my top priorities, maintaining a clean and welcoming environment while following any specific care instructions or dietary needs provided. 3. With frequent updates and photos, I aim to provide peace of mind to pet owners, reassuring them that their beloved companion is in good hands and receiving the care and attention they deserve.

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: 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: 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

We feel so lucky to have found Dana! Her attention to detail, her ability to tune into our particular needs and willingness to take care of chickens as well as our dog, plus a LOL sense of humor made us feel at ease leaving our home and loved ones in her care. Dana kept in contact with us just the right amount the whole week we were gone. When we came home it was if we had never left, happy dog and chickens and tidy home. We especially appreciated the thoughtful touches that all add up, like a full woodbox! We will definitely have her help again and highly recommend her.

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Katherine M.
Sitter Profile Image: Rita M.
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Rita M.
from
$63
per night
2 repeat clients
18 years of experience
North Adams, MA, 01247

About: I’ve interned at my local vet clinic for two years now and have recently moved to a paid position as an assistant! through this internship i have not only learned substantial knowledge regarding pet care, such as how to most effectively administer medications, but also discovered my love for pet sitting, as i have become one of the veterinarian’s permanent pet sitter! i also plan to go to vet school after i earn my bachelors degree! i am currently enrolled in college, as well as working various part time jobs so my availability is limited at the moment, but i will try my best to arrange my schedule best for yours ( and your furry friend’s) needs! i’ll treat your furry family like my own! i come with treats ready (with permission of course) and never leave without a game of fetch or whatever else your babies might enjoy! they’ll definitely be the highlight of my day, so i’ll try to be there’s too!

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

Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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 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.

Meet local sitters who will treat your pets like family

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

Popular requests for house sitting - Cherry Plain

Select a filter and find qualifying sitters offering house sitting.

Sitters in Cherry Plain average 4
repeat house sitting clients

FAQs for House Sitting - Cherry Plain

Frequently asked questions about Rover

As of July 2026, there are 525 sitters on Rover offering House Sitting across Cherry Plain. Enter your ZIP code to see which available sitters are closest to your home.

Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:

  • Mail & deliveries: Collecting letters and packages so they don't pile up.
  • Plant care: Keeping your indoor or outdoor garden hydrated.
  • Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
  • Home security: Sitters can stay overnight to keep your home occupied.

The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Cherry Plain walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.

It’s helpful to think of house sitting as a "home base" service. Most sitters in Cherry Plain maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:

  • Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
  • Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
  • Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.

Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Cherry Plain choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

A Meet & Greet is a short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.

Yes, you can find sitters who have experience with handling special pet needs in Cherry Plain. On Rover:

  • 89% of sitters can help with special care needs
  • 96% can help with giving oral medications or injections
  • 98% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

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