House Sitting Pleasant Plains

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

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Over 40
pet parents in Pleasant Plains have booked house sitting

Pleasant Plains, 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: Rose V.
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Rose V.
Star Sitter
from
$40
per night
4.9 out of 5 stars
• 264 reviews
90 repeat clients
25 years of experience
Kingston, NY, 12401

“Rose was so fantastic with my two rescue pups. I have one particularly shy pup, and Rose was patient and gentle while she warmed up. By the end of the stay, both pups were very comfortable with Rose and looking forward to her next sit!”

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Elizabeth M.
Sitter Profile Image: Thomas-James C.
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Thomas-James C.
Star Sitter
from
$65
per night
5.0 out of 5 stars
• 33 reviews
9 repeat clients
15 years of experience
Milton, NY, 12547

“TJ was great! He took care of my two babies with such love and attention. He was at my house when he said he would be and cuddled with my boys to make them feel safe. I would highly recommend TJ to watch your pets!”

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Michelle M.
Sitter Profile Image: Colleen M.
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Colleen M.
from
$90
per night
5.0 out of 5 stars
• 10 reviews
3 repeat clients
23 years of experience
Staatsburg, NY, 12580

“Colleen is a gem. A total pro- lovely, easy going, compassionate, professional, and she clearly bonded with my kitty after just one visit. She’s a pleasure and we will most definitely entrust our cat, and our home, with her in the future!”

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Lauren T.
Sitter Profile Image: Sofia S.
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Sofia S.
from
$45
per night
5.0 out of 5 stars
• 22 reviews
5 repeat clients
3 years of experience
Tivoli, NY, 12583

“Sofia was wonderful! She was always responsive, and took such wonderful care of the dogs. They loved her and were in great hands. She left the house in great shape and was a super respectful guest. Would highly recommend using Sofia!”

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Brittany S.
Sitter Profile Image: Karla R.
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Karla R.
from
$110
per night
5.0 out of 5 stars
• 7 reviews
1 repeat client
11 years of experience
Kingston, NY, 12401

“Took really great care of our dog & our family’s dogs. 3 dogs for 1 person can be a lot, so thank you for helping us out and following our requests!!”

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Shailaja I.
Sitter Profile Image: Arsen S.
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Arsen S.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 10 reviews
2 repeat clients
5 years of experience
Bard College, NY, 12504

“Arsen and Sophia did a great job. They communicated well, sent funny pics and we returned to a calm dog who clearly liked them and was sad to see them leave. House was clean. Would hire them again anytime.”

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Marnie T.
Sitter Profile Image: Margaret S.
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Margaret S.
from
$57
per night
4.9 out of 5 stars
• 20 reviews
6 repeat clients
17 years of experience
Wappingers Falls, NY, 12590

“We had a wonderful experience with our pet sitter Margaret! She took excellent care of my dog, Otto, and made sure he was happy, comfortable, and well-loved while I was traveling. I really appreciated the regular updates with pictures and great communication—it gave me so much peace of mind. Highly recommend to anyone looking for a reliable, responsible, kind and caring pet sitter!”

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Vanessa R.
Sitter Profile Image: Emily F.
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Emily F.
from
$105
per night
5.0 out of 5 stars
• 69 reviews
14 repeat clients
20 years of experience
Tivoli, NY, 12583

“From the moment that I met Emily, I understood that her relationships with animals are deeply reciprocal. She is a patient and caring friend and enjoys the love that they offer in return. Emily stayed with my senior Boxer for 10 days at my home. She was a conscientious sitter -- taking perfect care of my home and of my pet. Knuckie typically experiences a few days of depression and hives when I leave but with Emily he was in good spirits, eating and in his normal routine. Honestly, he looked fantastic when I returned -- like he'd had a week at a spa. Emily's communication was perfect and she even went above and beyond to have a food order for us when our late flight arrived! I give Emily my highest recommendation!”

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Jesse P.
Sitter Profile Image: Manuel J.
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Manuel J.
from
$40
per night
4.8 out of 5 stars
• 13 reviews
5 repeat clients
5 years of experience
Poughkeepsie, NY, 12601

About: If you have an athletic or active dog, we are the hosts for you!!! Trips to parks (on and off leash), running the trails, and swimming in a Lake will happen every day. If your dog is less active, we can bring our activity level to where your dog is most happy and comfortable. I have a very open schedule. Usually I go to the park go with my family who enjoy the day doing things outside the house. If you have a last minute appointment or you need anything on the same day I do take them I have a very open schedule one works in the morning and the other one works in the afternoon so your pet will never be alone. I had pets before they pass away. We used to love our pets so much. We took CPR classes and emergency classes for pets just in case.

Sitter Profile Image: Edward M.
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Edward M.
from
$100
per night
10 years of experience
Kingston, NY, 12401

About: I excel at making dogs feel calm and like their owners never even left the house. Learning their schedules, quirks, and favorite walking spots helps me make them feel comfortable for extended stays. Energetic puppy? I’ll run around w them and tire them out. Senior dog? We can relax and go at their pace. What sets me apart is my intuition and caring heart. I have a flexible, remote job so I am able to stay with your pet as long as needed through the day and take them on frequent walks in the neighborhood good or to the dog park! I do live-in dogsitting/housesitting at the client’s house. I like to learn about your dog (how they like to play, chill, etc..) so I can make them feel as comfortable as possible.

Sitter Profile Image: Konstantin T.
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Konstantin T.
from
$100
per night
5.0 out of 5 stars
• 2 reviews
14 years of experience
Red Hook, NY, 12571

“Konstantin was a wonderful communicator, easy to host while we were away, and had such nice photos and messages to share about our 4 month old puppy making us have peace of mind during our trip. We really appreciated Konstantin's professionalism and courtesy, and care of our space and pet. Thank you so much!”

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Beka G.
Sitter Profile Image: Celina I.
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Celina I.
from
$35
per night
5.0 out of 5 stars
• 28 reviews
8 repeat clients
6 years of experience
Poughkeepsie, NY, 12603

About: I’ve been taking care of dogs almost my entire life. I’ve taking care of family and neighbors dogs and it’s the best part of my day! Im currently working part time and I have plenty of extra time to take care of someone dog(s) for them. I want to help others out and this is something I would really enjoy doing! I have a dog and I walk him on nice days in my neighborhood after work and I play with him out in my back yard with a few of his favorite toys so he gets exercise.

Sitter Profile Image: Patricia H.
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Patricia H.
from
$125
per night
5.0 out of 5 stars
• 6 reviews
2 repeat clients
20 years of experience
Poughkeepsie, NY, 12601

“Patricia was amazing. Our newly adopted doghas separation anxiety and continued to give her a run for her money the whole first part of the second day. She was patient with Lucy and in the end we were so happy to be able to complete our vacation without worries. We will definitely have her back”

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nancy r.
Sitter Profile Image: Chana W.
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Chana W.
from
$60
per night
5.0 out of 5 stars
• 8 reviews
2 repeat clients
25 years of experience
Kingston, NY, 12401

“Chana took wonderful care of my pups! She communicated really well, sent me pictures and updates, and took nice care of my home. I returned to two happy dogs. Would recommend!”

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Devon T.
Sitter Profile Image: Michele F.
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Michele F.
from
$115
per night
5.0 out of 5 stars
• 11 reviews
2 repeat clients
11 years of experience
Poughkeepsie, NY, 12603

“Michele was fabulous!! Jasper was in great hands! She sent plenty of photos and I appreciated this! She also drove Jasper to his doggie daycare, Central Bark! This kept Jasper occupied and offered Michele a break! Although I know she would have kept him busy at home too.”

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Melissa G.
Sitter Profile Image: Miranda M.
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Miranda M.
from
$80
per night
5.0 out of 5 stars
• 11 reviews
2 years of experience
Hyde Park, NY, 12538

“Miranda was an awesome and calm dog sitter for our high strung Jack Russell for a weekend. She is a responsible person and excellent communicator. She came to meet us and followed all the instructions for feeding, walks and getting in and out of the house. Our dog was happy and I would highly recommend her!”

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Lynn K.
Sitter Profile Image: Elishamaria R.
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Elishamaria R.
Star Sitter
from
$85
per night
5.0 out of 5 stars
• 28 reviews
9 repeat clients
20 years of experience
Catskill, NY, 12414

“It was our first time working with Elisha and we will definitely work with her again. She was communicative, on time, and did a great job taking care of our 6 year old chihuahua.”

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Connor P.
Sitter Profile Image: Sammy C.
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Sammy C.
from
$75
per night
4.4 out of 5 stars
• 5 reviews
1 repeat client
15 years of experience
Poughkeepsie, NY, 12601

About: I know how stressful it can be leaving your pet behind, so my goal is to make the experience as smooth and comfortable as possible—for both you and your pet. I’m calm, attentive, and great at sticking to routines. Whether your pet is energetic, shy, or somewhere in between, I provide a safe, loving environment they can relax in. I currently am a student from home so I have more than enough time to take care of your furry companion while you are away. I used to walk my dog around my neighborhood sometimes to the river If it’s really nice out just get her some fresh air. Proper feeding times and bathroom breaks.

Sitter Profile Image: Rochelle M.
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Rochelle M.
from
$120
per night
5.0 out of 5 stars
• 10 reviews
1 repeat client
25 years of experience
Saugerties, NY, 12477

“Rochelle is a wonderful sitter and I'm so grateful to have found her to watch my dog Gogo. I've hired Rochelle for both short and long-term stays and she is my most entrusted sitter. Dedicated, responsible, caring, and experienced.”

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Nicole N.
Sitter Profile Image: Tiffany M.
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Tiffany M.
from
$80
per night
5.0 out of 5 stars
• 10 reviews
2 repeat clients
5 years of experience
Red Hook, NY, 12571

“Tiffany was so communicative and conscientious during her stay! She rolled with the punches when I had to shift my logistics around, which made things way easier. We so appreciate her attentive care for our shy, scaredy cat!”

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Hannah R.
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The median cost per night for house sitting in Pleasant Plains is $72

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.

How to book house sitting

  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 - Pleasant Plains

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Sitters in Pleasant Plains average 3
repeat house sitting clients

FAQs for House Sitting - Pleasant Plains

Frequently asked questions about Rover

The average cost of House Sitting in Pleasant Plains is $80 per night as of October 2026. Most bookings cost between $43 and $100 per night. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of October 2026, there are 618 sitters on Rover offering House Sitting across Pleasant Plains. 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 Pleasant Plains 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 Pleasant Plains 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 Pleasant Plains 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 , 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 .

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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first .

sitters on Rover set their own , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

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

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

  • 91% of sitters can help with special care needs
  • 94% can help with giving oral medications or injections
  • 96% 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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