House Sitting Whispering Woods

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

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Over 102
pet parents in Whispering Woods have booked house sitting

Whispering Woods, 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: Alexia M.
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Alexia M.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 48 reviews
18 repeat clients
10 years of experience
Annapolis, MD, 21409

“Alexis took care of my fur babies and helped me out with a last minute trip to take care of a sick family member.”

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Emily S.
Sitter Profile Image: Jean L.
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Jean L.
Star Sitter
from
$75
per night
5.0 out of 5 stars
• 95 reviews
30 repeat clients
10 years of experience
Cape St Claire, MD, 21409

“Jean did a great job looking after our pets. She gave us great updates and pictures and all of our pets loved her. Great communication and super reliable! Thanks so much Jean!”

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Alexandra N.
Sitter Profile Image: Jamie P.
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Jamie P.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 127 reviews
50 repeat clients
45 years of experience
Annapolis, MD, 21403

“Jamie was great. She sent pictures every day and answered my texts immediately. The three timid cats even came out enough to have their picture taken.”

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Lane G.
Sitter Profile Image: Karen R.
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Karen R.
Star Sitter
from
$60
per night
5.0 out of 5 stars
• 11 reviews
5 repeat clients
15 years of experience
Annapolis, MD, 21401

“Karen was great with our four animals (dogs and cats)! Karen was communicative, provided great updates, and let us know when one of our cats was having a minor potential health issue. Would recommend and I know our pets are already looking towards when Karen will be back to see them again!”

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Marie C.
Sitter Profile Image: Code & Dana S.
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Code & Dana S.
from
$50
per night
5.0 out of 5 stars
• 3 reviews
10 years of experience
Severna Park, MD, 21146

“Code and Dana were amazing! They sent pics daily of their walks and kept me updated on my picky eater. Code came early the day we left to feed and walk the dogs with me to understand what challenges they may see. We have 3 dogs so it’s not always easy to find sitters who can handle them but they made it seem easy. I really can’t recommend them enough. The house was cleaner than how I left it too!! Don’t question it-just book them!!”

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Nicole D.
Sitter Profile Image: Amber C.
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Amber C.
Star Sitter
from
$110
per night
5.0 out of 5 stars
• 62 reviews
18 repeat clients
12 years of experience
Annapolis, MD, 21409

“Best river experience we have had thus far! Highly recommend Amber!!!”

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Richard C.
Sitter Profile Image: Alexandra M.
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Alexandra M.
from
$90
per night
4.6 out of 5 stars
• 11 reviews
4 repeat clients
8 years of experience
Annapolis, MD, 21409

“Absolutely! Here’s a warm, genuine Rover review: Ally was absolutely wonderful with our dog Daisy! She took care of her for a long weekend and was so sweet, communicative, and attentive throughout her stay. We felt completely comfortable knowing Daisy was in such great hands. To top it off, all of our fire alarms unexpectedly went off while we were away, and Ally handled the situation so calmly and responsibly. We really appreciated how she kept us informed and took care of everything. We would absolutely recommend Ally and would love to have her watch Daisy again!”

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Jessica & Matthew O.
Sitter Profile Image: Lee M.
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Lee M.
from
$40
per night
5.0 out of 5 stars
• 11 reviews
3 repeat clients
8 years of experience
Annapolis, MD, 21409

“Lee did a great job staying with our kitty for a week. He was very communicative before and during his stay, sent pictures and updates every day, and left our house in great shape. I wouldn't hesitate to hire Lee again.”

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Elihu M.
Sitter Profile Image: James B.
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James B.
from
$50
per night
5.0 out of 5 stars
• 10 reviews
30 years of experience
Annapolis, MD, 21403

About: I've had dogs my whole life. Grew up in a house with 2+ dogs near constantly. All family dogs were 60+ lbs each with the largest being 110lbs. My 75lb dog crossed the rainbow bridge Sept 2025, I am not ready for a dog full time but I do miss the company. I will spoil your dog. I do not care about breed. I am looking for weekends. I work full time, so I am ready to go around noon on Friday and depending on the needs can be around all weekend. Generally I do leave the house during the weekend for a couple hours during the day to do chores and stuff but other than that can be a total home body. If the dog is good on leash I have a great neighborhood to take walks. If you are looking for me to stay at your house over the weekend, I can provide as much potty coverage as you request. If you want me to stay over the week, I do have a day job with my schedule being 7-3. I have a 8ft privacy fence the whole way around my backyard with a dog door. I do not have a crate, but I can use yours if you want your dog crated. I follow your food rules. I used to make hot breakfast/dinner for my dog. I do keep some dog treats in the house but I will check with you if your dog can have that specific treat first and if there are any dietary needs. If you want me to stay in your house, lets write the rules down and I'm happy to do whatever. If you have poor cellphone service, it'd be great to get a wifi password.

Sitter Profile Image: Tiffany D.
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Tiffany D.
from
$55
per night
5.0 out of 5 stars
• 2 reviews
8 years of experience
Annapolis, MD, 21403

“Tiffany was ABSOLUTELY WONDERFUL!!! She truly went above and beyond for our 2 kitties. She took perfect care of our home while we were gone and even washed her sheets and towels before she left, she even tidied up our litter room for us!! She was very responsive through the week sending lots of photos and was available for any check in or additional task we needed from her. She really prioritized our kitties play time and they clearly had an amazing time (given the graveyard of toys all over the house🤩). She even hand made these cute little toys, created little kitty forts with blankets and hand drew these adorable paper bugs she put on the windows to make sure they were stimulated in brand new ways!!! Tiffany will have our business as long as she is doing this and she will be recommended to all our friends. VERY THANKFUL FOR TIFFANY!!!”

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Nicole B.
Sitter Profile Image: Michael P.
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Michael P.
from
$90
per night
5.0 out of 5 stars
• 75 reviews
38 repeat clients
10 years of experience
Arnold, MD, 21012

“Michael is very delightful and gave devoted attention to our dog. Michael followed our dog’s daily details and we had a happy pup when we returned. Michael was very communicative and included photos to us throughout his stay. Five paws given!”

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Laura V.
Sitter Profile Image: Avery B.
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Avery B.
from
$65
per night
5.0 out of 5 stars
• 2 reviews
7 years of experience
Annapolis, MD, 21409

“Avery stepped up when we really needed her with only a couple of weeks notice for our honeymoon, and stayed for a full 2 weeks watching our two young goldens, including one that’s still a 8 month old puppy. She did an awesome job with them, was a great communicator, and sent tons of good pictures. Don’t know how we would have been able to enjoy our big trip without knowing they were in good hands with her. She also helped out around the house with cleaning, watering plants, pool maintenance, and even dealing with a repairman on a dryer issue that happened right as we were leaving town. She certainly went above and beyond and we couldn’t recommend her enough!!”

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Clay K.
Sitter Profile Image: Dylan V.
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Dylan V.
from
$50
per night
5.0 out of 5 stars
• 11 reviews
7 repeat clients
20 years of experience
Glen Burnie, MD, 21061

“Dylan was wonderful with our pets! This was our first time leaving our dog so we were a bit nervous but our dog loved him! He took such great care of them and sent picture which we appreciated immensely. Definitely recommend and will be booking again for our next trip.”

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Marijka V.
Sitter Profile Image: Lindsay M.
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Lindsay M.
Star Sitter
from
$70
per night
5.0 out of 5 stars
• 55 reviews
13 repeat clients
40 years of experience
Annapolis, MD, 21402

“Lindsay was a lifesaver. We had some issues while we were on our trip with a different sitter and Lindsay stepped in and looked after our two dogs. She immediately connected with our pups and they absolutely loved her. I would highly recommend to anyone looking for a sitter!”

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Ryan S.
Sitter Profile Image: Ella O.
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Ella O.
from
$55
per night
5.0 out of 5 stars
• 2 reviews
2 repeat clients
7 years of experience
Severna Park, MD, 21146

About: I’ve been caring for dogs of all sizes and personalities since I was young. I grew up with dogs in my home and currently have two dogs of my own, so I know how much our pets mean to us and how important it is to find someone you can trust with them. I love getting to know each pet’s unique personality and making sure they feel safe, comfortable, and loved while their owners are away. I truly love all fur babies and would be so excited to care for yours! 🐾❤️ I am currently a part time student at Anne Arundel community college. I also have a part time job. My weekends are available. Weekdays I have a lot of free time during the day between classes before I head to work at 2:30-5:30 (usual hours). Safety is my top priority when caring for your pets. I will always make sure they are supervised, secure, and comfortable, whether we are out on a walk, during a drop-in visit, or staying overnight. I follow each pet’s routine and any instructions you provide, including feeding schedules, medications, walks, and anything else that helps them feel at home.

Sitter Profile Image: Cassandra R.
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Cassandra R.
from
$40
per night
5.0 out of 5 stars
• 26 reviews
7 repeat clients
8 years of experience
Annapolis, MD, 21403

“Cassandra took impeccable care of our senior pup and we would highly recommend her to anyone! She was proactively communicative and provided lots of updates and photos. Her stay was seamless and it was as if we had never been away. Thank you Cassandra!”

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Breanne F.
Sitter Profile Image: Elizabeth W.
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Elizabeth W.
from
$80
per night
5.0 out of 5 stars
• 8 reviews
6 repeat clients
7 years of experience
Annapolis, MD, 21401

About: Hi! I’m Liz — an animal lover with a flexible remote work schedule and years of experience caring for friends’ and family members’ dogs. I’ve also fostered before, so I’m comfortable with dogs of all breeds, sizes, and personalities. As a dog owner myself, I know how important it is to find someone you can count on. I take that trust seriously and always aim to make things stress-free while you’re away — with regular updates, photos, and plenty of care and attention. Whether it’s daily walks, drop-in visits, or overnight stays, I’m dependable, patient, and genuinely enjoy spending time with dogs. Your pup will be in great hands with me. I currently work a hybrid schedule. I work in the office on Wednesdays and Thursdays, and I’m home the rest of the week, which gives me plenty of flexibility for walks, drop-ins, and overnight stays. When I’m caring for pets in a client’s home, I always treat it with the same care and respect as my own. I stick to your pet’s normal routine — walks, meals, and downtime — to keep them comfortable and relaxed. I make sure doors and gates are secure, follow all instructions closely, and leave your home just as I found it. You’ll get regular updates and photos so you always know how your pet’s doing while you’re away.

Sitter Profile Image: Kathleen M.
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Kathleen M.
from
$31
per night
26 years of experience
Severna Park, MD, 21146

About: I took care of my family dogs and cats, my own dogs and cats, rabbits, and I've helped friends with their dog, mostly to feed and walk them too. I used to train our own puppies back in the day, but it's been awhile. I just retired from being an elementary school counselor, so I'm more available to walk and care for animals. My schedule is fairly open if I'm not on a travel trip, so I can walk dogs during the day most anytime and care for some animals when needed. We don't have furry pets, because my husband has an allergy. However, I want to be with dogs without him as much as possible. I do walk my neighbor's dog when she's not available.

Sitter Profile Image: Susanne W.
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Susanne W.
from
$40
per night
5.0 out of 5 stars
• 2 reviews
6 years of experience
Annapolis, MD, 21409

About: My biggest priority is communication! I love to send check ins and pictures throughout the day, and often ask questions. I will always double check instructions to make sure your pet has the care you intended. I am also outdoorsy and love to walk! I will always extend a walk if I can, not cut it short or do the bare minimum. I am committed to giving your pet the exercise and attention the deserve! I am a nanny, student, and big fan of exercise! I have alot going on in my day, but often have gaps in between that allow me to visit your animals and get them outside. I can often be found doing homework in the evenings, and I always seem to get so much more done when dogsitting! I will always follow instructions and ask questions if I am not sure. I will never feed your pet anything that is not from you, and I will use proper precautions, leashes, harnesses, etc, when outside. I will always clean up after myself and be diligent about locking doors and leaving the house as I found it.

Sitter Profile Image: Yvonne S.
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Yvonne S.
from
$100
per night
5.0 out of 5 stars
• 4 reviews
1 repeat client
20 years of experience
Crownsville, MD, 21032

“I cannot say enough wonderful things about Yvonne. She took the best care of our pups while we were away. They loved spending the week with her. I highly recommend for all of your pet sitting needs.”

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Erin M.
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The median cost per night for house sitting in Whispering Woods is $50

Pet parents share their Rover experiences - Whispering Woods

1 / 1
5.0 out of 5 stars

Nico was amazing -- sent adorable pix daily, handled everything amazingly, perfect communication! HIGHLY RECOMMEND! PS my cats miss him already!

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Wendy S.
House Sitting
5.0 out of 5 stars

Alexxis was great. She stayed at my house and took great care of my two dogs and cat. Would definitely recommend.

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Elizabeth M.
House Sitting
5.0 out of 5 stars

Excellent sitters who paid special attention to the needs of my pups and kept me updated regalarly with photos and texts. I would definitely book again!

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Keith S.
House Sitting
5.0 out of 5 stars

Jean is fantastic! We have recently moved and my dog can be a bit anxious and is getting used to a new environment. Charlie (My Mini-Aussie) loved Jean immediately and Jean played with her, walked her and made sure that she felt comfortable. I would highly recommend Jean!

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Catina B.
House Sitting
5.0 out of 5 stars

Kayla did an amazing job dog sitting in my house for my 11 year old dog Zoey. Kayla was very friendly and Zoey loved her. Kayla cared so well for Zoey and when I got home I saw that Kayla had washed her own bed sheets!.I definitely recommend Kayla for any pet sitting job and would most definitely hire her again!

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Janine R.
House Sitting
5.0 out of 5 stars

Lisa is a fantastic pet sitter! Our mini-Australian Shephard loves her! She is a great communicator and provided updates and pictures of our dog! We highly recommend her!

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Catina B.
House Sitting
5.0 out of 5 stars

Cheri was absolutely amazing! She watched my puppy while I was getting ready for my wedding and during the evening. I was able to feel at ease knowing she was being taken care of. Cashew loved her right away! Thank you Cheri.

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Amanda M.
House Sitting
5.0 out of 5 stars

Avery stepped up when we really needed her with only a couple of weeks notice for our honeymoon, and stayed for a full 2 weeks watching our two young goldens, including one that’s still a 8 month old puppy. She did an awesome job with them, was a great communicator, and sent tons of good pictures. Don’t know how we would have been able to enjoy our big trip without knowing they were in good hands with her. She also helped out around the house with cleaning, watering plants, pool maintenance, and even dealing with a repairman on a dryer issue that happened right as we were leaving town. She certainly went above and beyond and we couldn’t recommend her enough!!

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Clay K.
House Sitting
5.0 out of 5 stars

Hiring Michael was our first ever experience with Rover. I was nervous about the whole thing. But I absolutely did not need to be. He was fantastic, and cared wonderfully for our two dogs and two cats while we were out of town. He really went above and beyond to send us updates and communicated well whenever our silly dogs did something naughty. Would definitely hire him again to stay with our pets.

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April N.
House Sitting
5.0 out of 5 stars

Leah was great! She sent photos and videos daily while we were gone, and she took great care of our place. We will definitely work with her again.

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Bobby M.
House Sitting
5.0 out of 5 stars

Absolutely! Here’s a warm, genuine Rover review: Ally was absolutely wonderful with our dog Daisy! She took care of her for a long weekend and was so sweet, communicative, and attentive throughout her stay. We felt completely comfortable knowing Daisy was in such great hands. To top it off, all of our fire alarms unexpectedly went off while we were away, and Ally handled the situation so calmly and responsibly. We really appreciated how she kept us informed and took care of everything. We would absolutely recommend Ally and would love to have her watch Daisy again!

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Jessica & Matthew O.
House Sitting
5.0 out of 5 stars

Ryleigh was great at house sitting our dog and apartment. Communicative and we came back to a happy dog!

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Jack S.
House Sitting
5.0 out of 5 stars

Caroline was awesome! Great with our dogs, sent a lot of great pictures, and a great communicator. Would definitely recommend

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Clay K.
House Sitting
5.0 out of 5 stars

Lee did another great job caring for our kitty Roxie and house sitting for a week. Lee communicates frequently with updates and pictures and is very responsive before and during the stay. Most importantly, Roxie and Lee bond with each other and it gives us peace of mind that both Roxie and our house are cared for when we are away.

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Elihu M.
House Sitting
5.0 out of 5 stars

Violet was the best pet sitter for our shy boy, Duke. She came over for meet and greets to ensure our pet was comfortable for her to stay with. Violet sent constant updates and pictures. We can’t recommend her enough!

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Adriana T.
House Sitting
5.0 out of 5 stars

Kevin was wonderful! He communicated with us regularly and included photos. He took excellent care of all our pets and our house. We are grateful to have Kevin as a sitter and will definitely use him again in the future.

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Eliza N.
House Sitting
5.0 out of 5 stars

Alexia took amazing care of my dog, Hazel. She sent me updates throughout her stay and kept in contact frequently. I would absolutely ask Alexia to watch my dog again!

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Kasey R.
House Sitting
5.0 out of 5 stars

Julia is a great dog sitter and has sat for our 2 dogs multiple times. The dogs love her and she has done a great job communicating and providing photos throughout the time she was watching the dogs.

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christina h.
House Sitting
5.0 out of 5 stars

Sara met the dogs and two separate occasions before the actual reserved time. The dogs instantly fell in love with her. Sara let the dogs sleep with her, as I do. It warmed my heart to know that someone else was willing to care for & love them as I do. She's a great sitter for your animals.

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Sylvia D.
House Sitting
5.0 out of 5 stars

We love having Cailin stay and care for our dog and cats when we are away. She is reliable and loves them like her own - we are so grateful to have found her! We always use her when she is available.

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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.

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

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Sitters in Whispering Woods average 4
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FAQs for House Sitting - Whispering Woods

Frequently asked questions about Rover

The average cost of House Sitting in Whispering Woods is $68 per night as of October 2026. Most bookings cost between $37 and $89 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 7,516 sitters on Rover offering House Sitting across Whispering Woods. 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 Whispering Woods 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 Whispering Woods 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 Whispering Woods 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 Whispering Woods. On Rover:

  • 87% of sitters can help with special care needs
  • 92% can help with giving oral medications or injections
  • 95% 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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