House Sitting Middletown

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

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Over 4
pet parents in Middletown have booked house sitting

Middletown, 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.

1 / 1
Sitter Profile Image: Megan S.
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Megan S.
Star Sitter
from
$75
per night
5.0 out of 5 stars
91 reviews
29 repeat clients
10 years of experience
Stephens City, VA, 22655

Megan was great. She kept us updated daily with the dogs. Made things stress free while we was gone. Will definitely be booking with her again in the future.

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Tyler M.
Sitter Profile Image: Sherry R.
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Sherry R.
from
$45
per night
4.9 out of 5 stars
12 reviews
6 repeat clients
3 years of experience
Stephens City, VA, 22655

She is awesome. Did a great job, knowledgeable, very nice. Will definitely use again sometime.

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Elliot A.
Sitter Profile Image: Mackenzie D.
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Mackenzie D.
from
$40
per night
5.0 out of 5 stars
8 reviews
3 repeat clients
7 years of experience
Middletown, VA, 22645

Mackenzie stayed with my two dogs and two cats overnight. The whole crew is used to my being around a lot so I knew I needed someone to stay here. I came home to happy animals who didn’t seem to miss me at all! I will definitely use her again.

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Stephanie Q.
Sitter Profile Image: Haley Z.
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Haley Z.
from
$55
per night
5.0 out of 5 stars
140 reviews
45 repeat clients
17 years of experience
Stephens City, VA, 22655

Haley was great. She was knowledgeable, asked good questions, kept me updated with what was going on, cleaned up after the dogs, and left the house tidy and clean. I will definitely be using her again in the future.

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Miranda W.
Sitter Profile Image: Sierra C.
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Sierra C.
Star Sitter
from
$50
per night
5.0 out of 5 stars
10 reviews
3 repeat clients
7 years of experience
Boyce, VA, 22620

Sierra took great care of Izzy and left the house super clean.

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Becky J.
Sitter Profile Image: Kristine S.
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Kristine S.
from
$40
per night
5.0 out of 5 stars
8 reviews
1 repeat client
30 years of experience
Winchester, VA, 22601

Kristine is a warm and caring individual and my dogs picked up on that immediately. She was fantastic with our three German Shepherds. She took great care of our dogs and our home while we were away. She was respectful of our property, cleaned up after herself and the dogs, and went above and beyond by mopping up after a rainstorm and even throwing linens in the wash before we returned. It gave us so much peace of mind knowing everything was being handled so thoughtfully. Great communication, too. I would absolutely book Kristine again and highly recommend. Kristine, if you’re reading this, thank you so much for putting up with all the shedding, the Shepherds were dropping their coats like crazy.

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Alesha R.
Sitter Profile Image: Alyssa F.
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Alyssa F.
from
$50
per night
5.0 out of 5 stars
85 reviews
11 repeat clients
7 years of experience
Winchester, VA, 22601

Alyssa was an awesome sitter! My dog can be shy around new people and she did an amazing job getting my dog to warm up to her and she was excellent with sending updates and pictures! Will definitely use her again!!

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Jessica C.
Sitter Profile Image: charlotte g.
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charlotte g.
Star Sitter
from
$40
per night
5.0 out of 5 stars
6 reviews
4 repeat clients
8 years of experience
Winchester, VA, 22601

Our 130# Newfoundland and cat were well taken care of. Communication was great, even using a different app since we were in Europe. Would not hesitate to use Charlotte again, she cared for our animals like they were hers.

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Giovanna C.
Sitter Profile Image: Natalie B.
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Natalie B.
from
$60
per night
5.0 out of 5 stars
5 reviews
2 repeat clients
5 years of experience
Winchester, VA, 22601

Natalie is everything I was hoping to find in a dog sitter, and then some! She is trustworthy, compassionate, dependable, kindhearted, caring, and overall just a wonderful person to work with. From the moment we had our meet and greet, I just knew I found THE perfect person that I instantly trusted to take care of my dog in my home. She takes the time to get to know you and your pet, and even organizes all of the information into a detailed “cheat sheet” about your pet! She is now my go-to person for any future pet sitting needs!

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Lindsey R.
Sitter Profile Image: Matthew H.
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Matthew H.
from
$30
per night
5.0 out of 5 stars
6 reviews
1 repeat client
7 years of experience
Reseda, Stephens City, VA, 22655

Matt was amazing already booked again did a great job with all 4 including our new pup who is not completely house trained yet

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Ricky
Sitter Profile Image: Julia Z.
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Julia Z.
from
$60
per night
4.9 out of 5 stars
22 reviews
6 repeat clients
5 years of experience
Winchester, VA, 22601

She was so patient with our big dog and even played ball with him. It was so comforting to know our dog was being cared for as if we were there.

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Emalou D.
Sitter Profile Image: Jennifer L.
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Jennifer L.
Star Sitter
from
$50
per night
5.0 out of 5 stars
39 reviews
9 repeat clients
10 years of experience
Cross Junction, VA, 22625

Jennifer was a doll! She was so kind and caring. She even sent pics of our babies while we were on vacation and kept in touch with us. We can’t wait to call on her for next time!

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Kim C.
Sitter Profile Image: Linda S.
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Linda S.
from
$75
per night
4.9 out of 5 stars
103 reviews
53 repeat clients
40 years of experience
Clear Brook, VA, 22624

Linda was a life-saver and took such great care of our pets and house so we could attend to a last minute family emergency. She did a fantastic job and we will definitely use her again in the future.

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Mae-Beth M.
Sitter Profile Image: Darian C.
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Darian C.
from
$65
per night
5.0 out of 5 stars
16 reviews
3 repeat clients
20 years of experience
Strasburg, VA, 22657

Thank you so much! Darian was great with the pups and took care of both them and our house with the utmost care. She was also very responsive and really helped out us out of a jam, our sitter cancelled at the last minute and she stepped up and made it work!

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Patrick W.
Sitter Profile Image: Victoria L.
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Victoria L.
from
$35
per night
4.5 out of 5 stars
8 reviews
1 repeat client
23 years of experience
Winchester, VA, 22602

Victoria provided frequent comms and was very responsive. Great job, we will definitely use her again!

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Stu Y.
Sitter Profile Image: Katie R.
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Katie R.
from
$100
per night
5.0 out of 5 stars
33 reviews
8 repeat clients
24 years of experience
Wardensville, WV, 26851

Katie was absolutely amazing. Our retriever was quite anxious about us leaving, and she quickly calmed him. He was great with her. Both of the pups were happy and behaved as though we never left. We will definitely be reaching out again!

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Megan W.
Sitter Profile Image: Sarah M.
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Sarah M.
from
$25
per night
5.0 out of 5 stars
4 reviews
1 repeat client
20 years of experience
Winchester, VA, 22603

Sarah was very friendly and professional. Our dogs were taken care well. Would book her again.

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Nancy M.
Sitter Profile Image: Victoria S.
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Victoria S.
from
$27
per night
5.0 out of 5 stars
1 review
6 years of experience
Winchester, VA, 22602

Victoria stayed in our home to take care of our dog Mika. She was very conscientious and respectful of place and took great care of Mika. Victoria spent most of the day with Mika so she wasn’t alone. We returned to a very calm and relaxed pup. Victoria is a good communicator, anytime she had a question or concern she was quick to let me know. We won’t hesitate to use Victoria again.

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Belinda M.
Sitter Profile Image: Drew B.
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Drew B.
from
$40
per night
5.0 out of 5 stars
1 review
8 years of experience
Winchester, VA, 22603

Drew house sat for my reactive pity mix and I will 100% hire him again. He responded promptly after my initial request, communicated clearly his availability, showed up on time, treated my house as his own, kept me informed throughout his stay with pictures, left my house exactly as I left it. Drew understands dogs needs and the needs of pet parents.

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Suzanne C.
Sitter Profile Image: Kathy G.
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Kathy G.
from
$75
per night
5.0 out of 5 stars
58 reviews
18 repeat clients
30 years of experience
Winchester, VA, 22601

Kathy did a great job taking care of our two dogs and cat while we were away, even when a medical issue came up with one of our dogs the before we left. Kathy administered several meds to both dogs and communicated well with us. We plan on having her watch our fur family again in the future!

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Nathaniel H.
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The median cost per night for house sitting in Middletown is $50

Pet parents share their Rover experiences - Middletown

1 / 1
5.0 out of 5 stars

Mackenzie was wonderful. The boys were healthy and happy. She went above and beyond and I didn’t have to worry. Would book again and again. Great caretaker of my house and boys.

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Stacey P.
House Sitting
1 / 1
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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 - Middletown

Select a filter and find qualifying sitters offering house sitting.

Sitters in Middletown average 3
repeat house sitting clients

FAQs for House Sitting - Middletown

Frequently asked questions about Rover

The average cost for House Sitting in Middletown on Rover is $55.5 per night (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of House Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for House Sitting. For more information on service fees, click here .

As of August 2026, there are 338 sitters on Rover offering House Sitting across Middletown. 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 Middletown 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 Middletown 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 Middletown 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 Middletown. On Rover:

  • 92% of sitters can help with special care needs
  • 100% can help with giving oral medications or injections
  • 92% 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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