House Sitting Woods Landing

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

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Over 6
pet parents in Woods Landing have booked house sitting

Woods Landing, 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: Jean L.
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Jean L.
Star Sitter
from
$75
per night
5.0 out of 5 stars
92 reviews
30 repeat clients
10 years of experience
Cape St Claire, MD, 21409

We left our 9year old Yorkie in the care of Jean. Our sweet little dog has separation anxiety that prevents us from boarding here. Thus the need for a dog sitter who will stay in our home. Jean took great care of both our home and our sweet Eloise.

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Ann H.
Sitter Profile Image: Cheri F.
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Cheri F.
Star Sitter
from
$65
per night
5.0 out of 5 stars
83 reviews
37 repeat clients
22 years of experience
Arnold, MD, 21012

Cheri was extremely helpful and accommodating to our last minute travel plans. She also won over our shy rescue and was cuddling her in 2 days! Thank you, Cheri!

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Sydney D.
Sitter Profile Image: Alexia M.
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Alexia M.
Star Sitter
from
$35
per night
5.0 out of 5 stars
37 reviews
13 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: Lee M.
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Lee M.
from
$40
per night
5.0 out of 5 stars
7 reviews
3 repeat clients
8 years of experience
Annapolis, MD, 21409

Lee was an excellent dog and house sitter: sent lots if updates and pictures, took great care of both my dog and house, asked questions when necessary, and left everything in good shape. Highly recommend!

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Rob H.
Sitter Profile Image: Leigh Ann E.
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Leigh Ann E.
Star Sitter
from
$31
per night
5.0 out of 5 stars
14 reviews
5 repeat clients
37 years of experience
Annapolis, MD, 21403

Highly recommend Leigh Ann! She took great care of my 2 pups, provided pictures every day kept me updated. If there were any issues not only that tidied up my house before we returned, which I don’t think should always be expected, but 100% appreciated. Highly recommend if you want peace of mind with your precious fur babies.

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Julie G.
Sitter Profile Image: Alexandra M.
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Alexandra M.
Star Sitter
from
$75
per night
5.0 out of 5 stars
5 reviews
3 repeat clients
8 years of experience
Annapolis, MD, 21409

About: I have worked alongside my mom who has been with Rover for 8 years! I took care of my own dog in my college dorm for a year as well! I’m currently a student at AACC and I’m working on weekend at a restaurant! Most days, I work on schoolwork and hangout with my own dogs at home! I try to take my dog out every hour to two hours because she loves being outside! I try to give her fresh water every few hours and she is feed twice a day! We also go on walks when it’s nice out!

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

Jamie is a sweetheart and takes such good care of our Bear. He got excited when she came to take care of him. Jamie keeps us posted on how he is doing. We are grateful to have found Jamie.

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Lorene B.
Sitter Profile Image: Lisa H.
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Lisa H.
from
$31
per night
5 years of experience
Arnold, MD, 21012

About: I've been taking care of family and friends dogs for over 5 years. And used to have dogs and cats of my own. I have many fur-nieces and fur-nephews and love them as my own. Because I work remotely, I can take my work anywhere. So, I will be able to stay with your pet for the duration you are gone. I work from home. And have the ability to work from anywhere. I will bring my laptop and be able to work and keep your baby company. Taking care of them in familiar surroundings.

Sitter Profile Image: Catherine J.
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Catherine J.
from
$40
per night
5.0 out of 5 stars
7 reviews
2 repeat clients
11 years of experience
Annapolis, MD, 21061

Cat was amazing with our fur babies and sent us multiple updates a day to reassure us that they were adjusting well while we were away! We also came home to our space cleaner than we left it which was so nice to come home to! We will absolutely be using Cat again!!

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Makayla M.
Sitter Profile Image: Violet H.
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Violet H.
from
$45
per night
5.0 out of 5 stars
2 reviews
10 years of experience
Annapolis, MD, 21401

About: From an early age I would take care of my dog by giving him walks and baths etc. I have dog sit for people over night at their house as well as walked other peoples dogs. Im currently a college student home for the summer and am working part time so I have plenty of free time to take care of your pets. I’m available for dog walking and pet sitting throughout the week. I like to give dogs lots of long walks to get their energy out. Also, I like playing with them and snuggling with them. :)

Sitter Profile Image: Karen R.
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Karen R.
Star Sitter
from
$50
per night
5.0 out of 5 stars
10 reviews
5 repeat clients
15 years of experience
Annapolis, MD, 21401

Karen took wonderful care of our dogs, Sam and Tito, for a full week while we were on vacation. She was incredibly responsive, always sending updates and photos when we asked, which gave us so much peace of mind. It was clear our boys were happy, comfortable, and well cared for the entire time. She also left our home in perfect condition, which we really appreciated. We would absolutely book with Karen again and highly recommend her to anyone looking for a reliable, thoughtful sitter!

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Julie G.
Sitter Profile Image: Jerad B.
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Jerad B.
Star Sitter
from
$50
per night
5.0 out of 5 stars
11 reviews
4 repeat clients
15 years of experience
Annapolis, MD, 21401

Jerad did an awesome job with Samson. Followed the instructions perfectly and was a great friend to our little guy. Took him on walks and sent lots of updates. Would definitely recommend!

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Clay K.
Sitter Profile Image: Leticia S.
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Leticia S.
from
$50
per night
5.0 out of 5 stars
4 reviews
4 repeat clients
2 years of experience
Annapolis, MD, 21401

Leticia was wonderful with our two large dogs! She was punctual, communicative, followed all directions, and took good care of the house too. We’re looking forward to having her watch our dogs more in the future!

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Sarah L.
Sitter Profile Image: Emma W.
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Emma W.
from
$50
per night
5.0 out of 5 stars
97 reviews
43 repeat clients
13 years of experience
Pasadena, MD, 21122

Emma was so great! She always responded quickly to messages, and was very accommodating to our needs - she came over in advance so we could meet her and introduce her to our dog, and she dealt with some unconventional dog hand-offs while we were away. She also left the house just as it was. We will definitely be reaching out to her for dog-sitting needs in the future. Thank you, Emma!

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Molly S.
Sitter Profile Image: Justine P.
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Justine P.
from
$55
per night
5.0 out of 5 stars
63 reviews
27 repeat clients
31 years of experience
Pasadena, MD, 21122

Justine did a great job with my crazy crew and provided timely updates with super fast communication. I also appreciated her being available on relatively short notice. Would definitely reach out to her again for future needs!

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Lisa R.
Sitter Profile Image: Alina C.
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Alina C.
from
$35
per night
5.0 out of 5 stars
9 reviews
6 repeat clients
11 years of experience
Severna Park, MD, 21146

Alina is amazing! She is attentive and provides frequent updates that are detailed. I highly recommend using her. One of my dogs had a vomit issue and she handled it so well! Alina is also very sweet. I will definitely be contacting her again for when I’m traveling.

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Rocky
Sitter Profile Image: Ryan L.
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Ryan L.
from
$70
per night
5.0 out of 5 stars
7 reviews
1 repeat client
25 years of experience
Annapolis, MD, 21409

About: I’ve been a lifelong "dog guy" and have spent years caring for the pets of friends, family, and neighbors. As the saying goes, "There are no strangers here; only dog friends you haven't yet met." I’m an expert at making dogs feel loved and secure while their parents are away. I find that exercise and companionship make for happier fur friends. I am a freelancer, which allows me to be very punctual and reliable for morning, mid-day check-ins, or afternoon walks. I understand how hard it is to leave your pet, so I like to send updates and fun photos so you never feel out of the loop. I’m happy to help with: *Standard neighborhood walks/jogs *Drop-in visits for potty breaks and playtime. *Feeding and refreshing water bowls. Attuned to dogs with diet restrictions *Transporting your four-legged loved one to parks (example: Greenbury Point, Quiet Waters Park) *Transporting to the groomer, vet appointments I treat every dog I care for as if they were my own. I'd love to meet you and your pup soon! I have great flexibility in the mornings and afternoons. Mon- Friday Morning: 5:00 am - 2:00 pm Evening: 3:30 pm-9:00 pm Saturday-Sunday 5:30 am - 9:00 pm Care in my home: I have a large fenced yard, great for playing catch, if you require morning or afternoon care away from your home. Care at your home, where most pups prefer, I can follow your family's routine: potty breaks, exercise level.

Sitter Profile Image: Ava M.
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Ava M.
Star Sitter
from
$90
per night
4.9 out of 5 stars
118 reviews
33 repeat clients
18 years of experience
Annapolis, MD, 21401

Ava is consistently wonderful with our cat snd our anxious, senior dog. She’s super communicative, and puts us at ease. We never worry about leaving town if Ava is with our pets!

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Kelsey C.
Sitter Profile Image: Michael P.
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Michael P.
Star Sitter
from
$90
per night
5.0 out of 5 stars
73 reviews
38 repeat clients
10 years of experience
Arnold, MD, 21012

Michael is hands down the best pet sitter we’ve had. He is super communicative, obviously loves animals, follows directions and left the house super clean! Really appreciate it! Will definitely be using him again!

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Jennifer C.
Sitter Profile Image: Amber C.
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Amber C.
Star Sitter
from
$110
per night
5.0 out of 5 stars
56 reviews
17 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.
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The median cost per night for house sitting in Woods Landing is $50

Pet parents share their Rover experiences - Woods Landing

1 / 1
5.0 out of 5 stars

We had Cat stay with our fur babies again for a whole week & she was absolutely amazing as always!! we came back to our pets happy & healthy & our house clean. We also never wondered how our pets were doing because she always gave updates with lots of cute pics!! We love Cat 💖💖

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Makayla M.
House Sitting
5.0 out of 5 stars

Lee has been consistently wonderful. They always keep us updated on our dogs, with pictures and check ins. They are observant and caring towards our dogs, making sure anything out of the ordinary is communicated.

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Casey H.
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

We had a great experience with Alexxis. Our dogs absolutely loved her — it was clear they were comfortable and well cared for the entire time. She was communicative, kind, and made sure to keep us updated with photos. On top of that, we came home to a spotless house, which we really appreciated. It made the whole experience stress-free. Highly recommend and would definitely book with her again!

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Macey W.
House Sitting
5.0 out of 5 stars

Tiff was very easy to communicate with and she did a great job taking care of our dog while we were out of town!

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Katharine S.
House Sitting
5.0 out of 5 stars

I really appreciate that Hannah is willing to dogsitting at last minute notice for thanksgiving. I was scrambling to get both of my dogs at their usual boarding and it’s ending up booked in both locations. Hannah has saved me and the dogs loves her and very playful with her.

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Keith A.
House Sitting
5.0 out of 5 stars

We absolutely loved having Amber care for our two dogs while we were on vacation! She was so kind, reliable, and truly treated our pups like her own. We had a few changes to our vacation dates last minute and she was flexible to accommodate put change. It made things so much less stressful! She spent lots of time at home with the dogs, kept them on their normal routine, and made sure they got plenty of love and attention. We got regular updates and came home to two happy, relaxed dogs. We’re so grateful to have found her and will definitely be booking again!

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Macey W.
House Sitting
5.0 out of 5 stars

Lilly was so great, I can’t recommend her enough. She watched my 2 pups over Labor Day weekend and gave me such peace of mind while I left them. She sent lots of photos and videos of them and followed the care instructions perfectly.

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Courtney J.
House Sitting
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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 Rover works

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting
  2. 2. Meet & Greet

    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

Sitters in Woods Landing average 4
repeat house sitting clients

FAQs for House Sitting - Woods Landing

Frequently asked questions about Rover

The average cost for House Sitting in Woods Landing on Rover is $42 per night (as of July 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 July 2026, there are 7,328 sitters on Rover offering House Sitting across Woods Landing. 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 Woods Landing 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 Woods Landing 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 Woods Landing 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 Woods Landing. On Rover:

  • 92% of sitters can help with special care needs
  • 97% 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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