House Sitting in Pleasant Plains

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

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

Rose was an absolute dream of a sitter. They made sure we got pictures of the boys, left our house probably cleaner than my husband and I left it and was more than willing to meet with us on two separate occasions before our boarding sesh to help acclimate our more skittish doggo son. By mid-weekend, both dogs were fans of Rose and honestly, so am I. 10/10 would recommend.

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Carel B.
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
15 reviews
7 repeat clients
15 years of experience
Milton, NY, 12547

Thomas was terrible! JUST KIDDING! I just want to keep him only for when I need him!😁 I couldn’t ask for anything more. He initially responded quickly. Showed up when we planned. He kept in touch with me. Sent pictures of my dogs when he was with them and left my house tidy. TJ, thank you again!

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Lisa M.
Sitter Profile Image: Lee C.
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Lee C.
Star Sitter
from
$50
per night
5.0 out of 5 stars
11 reviews
4 repeat clients
12 years of experience
Kingston, NY, 12401

Lee is the best! He stayed with and cared for our two labradors for a week while we went to Florida. Our girls love him and thoroughly enjoyed their time with Lee. He also kept the house spotless and made sure it was clean for us upon our return. I think the dogs appreciated his musical talents too while we were away. I would highly recommend Lee to anyone in need of a sitter, dog walker, or house stay with their pets. They would be well-loved and cared for with Lee!

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Linda C.
Sitter Profile Image: Regan F.
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Regan F.
from
$37
per night
5.0 out of 5 stars
5 reviews
1 repeat client
8 years of experience
Kingston, NY, 12401

Regan did a wonderful job caring for my dog Daisy and my cat Eleanor. She did house sitting for the entire week if not longer while I was out of town. She maintained great communication and also was very perceptive about what the animals needed. Thank you, Regan. I look forward to working with you again

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Willow H.
Sitter Profile Image: Dan B.
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Dan B.
from
$45
per night
5.0 out of 5 stars
57 reviews
15 repeat clients
10 years of experience
Hyde Park, NY, 12538

Dan just got finished watching our two dogs and I can confidently say he is the best. I got daily updates (most days twice a day) with pictures. My boys always looked content. Dan even cleaned the house before we came home and everything was spotless. It was very obvious when we got back that the boys were well taken care of and enjoyed having him here. Will definitely use again in the future and would highly recommend to others!

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Jess R.
Sitter Profile Image: Carolyn S.
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Carolyn S.
from
$50
per night
5.0 out of 5 stars
3 reviews
2 repeat clients
16 years of experience
Kingston, NY, 12401

Carolyn was great. She arrived early, was greeted by Bodhi and after a little playing he jumped in her car and off they went for a walk on the rail trail. He really enjoyed the exercise and I’m sure he’ll be glad to see her again.

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Douglas H.
Sitter Profile Image: Amanda L.
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Amanda L.
from
$95
per night
5.0 out of 5 stars
12 reviews
1 repeat client
33 years of experience
Kingston, NY, 12401

About: I’ve cared for dogs of all breeds since childhood, ranging from energetic puppies to senior dogs needing extra care. I’m a trained dog handler with the Ulster County SPCA and regularly provide dog sitting, walking and drop-in services. Whether your dog wants quiet peaceful snugs, or enthusiastic playtime and hikes… I’m your lady! Clients often tell me their dogs have even better times on vacation than they do! 🩷🐾 I care for each pup like it’s my own. Happy to provide references ups on request! I have a flexible, hybrid work schedule that allows me to accommodate walls, drop-ins, and overnight care throughout the week and on weekends (and even a few work from home days for more time with your pup!). I’m able to provide consistent attention, timely visits, and plenty of engagement, whether your dog needs a quick walk, regular check-ins or more extended care. Your dog’s safety and comfort are my top priorities. I take time to understand each pet’s routine, personality and needs, and I follow all instructions closely. In your home, I aim to keep your dog’s environment familiar and stress-free. For boarding, I offer a calm, quiet, child/pet-ffee space where your dog will receive attentive, individualized care and supervision (and lots of walks or hikes, if you like!).

Sitter Profile Image: Jennifer G.
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Jennifer G.
from
$80
per night
5.0 out of 5 stars
6 reviews
1 repeat client
16 years of experience
Kingston, NY, 12401

About: I didn’t get to experience the joy of growing up with dogs or cats but as soon as I was able I began taking in fosters from the NYC shelter system. It was quite a learning experience spending time with many dogs (and a few cats) of all different types and personalities. I no longer foster but I bring the experience and dedication from working with so many shelter pets to caring for your furry family members. And as a pet parent now myself I have been through many sitters so I understand what makes a good one! A note on boarding and meet and greets: I’m happy to have boarding candidates come by to meet me and check out the space but I do not do meet and greets with my own dogs. My dogs are dog friendly but they are too chaotic and excitable to meet new dogs and owners right away. New dogs are kept separate at first and introduced at their own pace when everyone is calm. This minimizes stress for everyone and allows for better interactions. I currently work out of the house Monday/Wednesday/Friday but my schedule is somewhat flexible. The rest of the week I work at home and I am often available all weekend. Dogs in my home have access to a securely fenced large yard for running and fetch, as well as a quiet neighborhood for walks. If the weather is warm dogs have access to a dog door so they may go outside as they please. If your dog likes to play with other dogs mine will certainly be happy to accommodate but they can also have separate spaces if quiet time is needed. In your home I will make every effort to keep your pets schedule as familiar as possible while offering lots of love and stimulation. As someone who has had many sitters come through and stay at my house I understand the importance of trust and cleanliness so you can be away without worry.

Sitter Profile Image: Nathan B.
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Nathan B.
Star Sitter
from
$100
per night
5.0 out of 5 stars
18 reviews
6 repeat clients
30 years of experience
Highland, NY, 12528

Nathan did a wonderful job looking after our three eccentric cats. We have one cat who needs meds twice a day and he had no problem dosing him. Even the shy cat came out for him! We came home to calm, happy cats! Thank you Nate!

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Judith M.
Sitter Profile Image: Cassandra M.
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Cassandra M.
Star Sitter
from
$100
per night
5.0 out of 5 stars
65 reviews
17 repeat clients
25 years of experience
Rhinebeck, NY, 12572

Cassie is a wonderful sitter! This was our puppies’s first experience with a sitter and she was very communicative and reliable. She constantly sent us picture, videos, and updates so we were able to be at ease the whole time. Will definitely book her again in the future!

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Kayleen T.
Sitter Profile Image: Angellina B.
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Angellina B.
from
$45
per night
5.0 out of 5 stars
7 reviews
1 repeat client
2 years of experience
Hyde Park, NY, 12538

Angie was all we could hope for in a sitter for our new rescue pup. Our dog immediately warmed up to her calm and gentle nature, and she had everything under control, in addition to endless snuggles for our pup while we were away. There was full peace of mind that our fur child was in great hands! Would call her again in a heartbeat, esp since our dog clearly didn’t want her to leave after we came home! Haha

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Patti O.
Sitter Profile Image: Alesandra P.
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Alesandra P.
from
$100
per night
5.0 out of 5 stars
12 reviews
3 repeat clients
5 years of experience
Poughkeepsie, NY, 12601

Allie was great! She kept me updated throughout the day with photos and videos of all my dogs. She truly went above and beyond in every sense to make sure my dogs were well cared for and was attentive to every little detail. I would absolutely recommend Allie to anyone. I really felt good that my dogs were in good hands all day.

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Felipe R.
Sitter Profile Image: Christine A.
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Christine A.
Star Sitter
from
$150
per night
4.9 out of 5 stars
94 reviews
32 repeat clients
33 years of experience
Stanfordville, Stanfordville, NY, 12581

Christine is a down-to-earth person who is easy to talk with and pays attention to important details. At our meet & greet, she asked good questions that reflected her experience and commitment to making both pets and their owners feel comfortable with her. My young adult cat Suki had never been left alone with someone she didn’t already know. In my absence, however, Christine eased her way into Suki’s territory by setting the right balance between showing her some quiet attention and giving her the time and space she needed to adjust and come out of her shell. The photos Christine sent me proved that once she had won Suki over, the little kitty was her sweet, affectionate self and the two of them had a delightful time together! I will be asking Christine to Suki-sit in my house again!

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Carena P.
Sitter Profile Image: Ady B.
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Ady B.
from
$100
per night
5.0 out of 5 stars
5 reviews
6 years of experience
Kingston, NY, 12401

Ady was amazing! She took such good care of our puppy Darwin. She genuinely cared about him. She also kept the house very clean and was very communicative the entire week. I would highly recommend Ady.

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Caitlin T.
Sitter Profile Image: Colleen M.
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Colleen M.
from
$90
per night
5.0 out of 5 stars
9 reviews
2 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: Janice A.
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Janice A.
Star Sitter
from
$160
per night
5.0 out of 5 stars
274 reviews
80 repeat clients
35 years of experience
RHINEBECK, NY, 12572

Thank you Janice...! You are the best. We appreciate you being available with such short notice. We left you with 2 crazy dogs only to return with both sleeping on each side of you..So glad we found you..! Thank you! Jeanne and Craig

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Craig N.
Sitter Profile Image: Margaret S.
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Margaret S.
from
$45
per night
5.0 out of 5 stars
10 reviews
1 repeat client
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
$100
per night
5.0 out of 5 stars
9 reviews
1 repeat client
13 years of experience
Elizaville, NY, 12523

Emily is such a wonderful person! She instantly connected with our dogs and they felt at home with her right away. She is extremely conscientious and shares lots of helpful updates. We felt super happy and comfortable on our trip with our pups in her care. Book with her if you have a chance!

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Victor V.
Sitter Profile Image: Arsen S.
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Arsen S.
from
$50
per night
5.0 out of 5 stars
1 review
5 years of experience
Annandale, 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: Kacey M.
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Kacey M.
from
$75
per night
5.0 out of 5 stars
107 reviews
38 repeat clients
8 years of experience
port ewen, NY, 12466

We couldn't have found a better dog sitter! Our skittish rescue was very well cared for and Kacey bonded with her right away. Kacey gets 2 thumbs up and a 5+ rating from us! S&M visiting from Virginia.

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Elena M.
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Pleasant Plains pet parents share their Rover experiences

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5.0 out of 5 stars

Dan may be our dogs’ best friend, besides us. They are always loved and well cared for when Dan stays with them. We feel very secure with him staying in our home, knowing that he’s taking care of everything. We were gone longer and much further away this time and never worried. That is as good as it gets!

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Diana M.
House Sitting
5.0 out of 5 stars

Kayley was great! So communicative and helpful. We knew our dog was in GREAT hands and we loved seeing all the pictures of her having fun!

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Amanda H.
House Sitting
5.0 out of 5 stars

Karin house sat for us while we took a quick getaway after several years. She was wonderful and very attentive to our senior dog. She sent us daily pictures and updated us throughout the stay. Will absolutely be asking her to sit for us again and again.

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Randi W.
House Sitting
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Find pet care near you

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 Pleasant Plains is $75

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 Pleasant Plains average 3
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 Pleasant Plains on Rover as of Jun 2026 was about $75 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 Pleasant Plains 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 448 house sitters in Pleasant Plains. 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 Pleasant Plains house sitters respond in under an hour.

House sitters in Pleasant Plains have an average of 17 years of experience. House sitters with repeat customers have an average of 3 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 Pleasant Plains.

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. Pleasant Plains 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.