House Sitting in Woods Landing

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Top rated Woods Landing house sitters

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: Cheri F.
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Cheri F.
Star Sitter
from
$65
per night
5.0 out of 5 stars
83 reviews
35 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
29 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: Leigh Ann E.
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Leigh Ann E.
Star Sitter
from
$31
per night
5.0 out of 5 stars
7 reviews
3 repeat clients
37 years of experience
Annapolis, MD, 21403

Leigh Ann was amazing taking care of our dogs and cat while we were on vacation. She sent us regular updates of time spent with our pets. Her attention and care was as if they were her own dogs.

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

Jamie is great. She took such good care of our dog and the house for a week. We have already booked her for a weekend in May. The pictures she took of our pup and the welcome home banner were a sweet surprise!

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Lorene B.
Sitter Profile Image: Jean L.
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Jean L.
Star Sitter
from
$95
per night
5.0 out of 5 stars
91 reviews
30 repeat clients
10 years of experience
Arnold, MD, 21012

Jean did an excellent job watching our 15 year old shih tzu. He’s an old guy with many medical needs so leaving him is stressful, but she gave us constant updates so our minds were at ease during the entire week. She definitely gave our boy lots of love and it was so reassuring to know she was here. Lots of picture and video updates, and she left the place sparkling clean. We’ll definitely be using her services again in the future if need be! 😊

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April C.
Sitter Profile Image: Jerad B.
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Jerad B.
Star Sitter
from
$50
per night
5.0 out of 5 stars
9 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: Delaney B.
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Delaney B.
from
$50
per night
5.0 out of 5 stars
5 reviews
3 years of experience
Arnold, MD, 21012

Delaney was amazing with our energetic 8-month old puppy! She was very communicative, on time, and was willing to accommodate us coming home later than expected. We came home to a very happy and tired puppy!

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Grace K.
Sitter Profile Image: Alina C.
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Alina C.
from
$35
per night
5.0 out of 5 stars
8 reviews
4 repeat clients
11 years of experience
Severna Park, MD, 21146

Alina was a great dog sitter for us and did so well with our pup while we were out of town. She’s very kind, responsible and responsive. She also communicated well with us, sent us pictures of walks and cuddles with our pup, and kept us updated, which made us feel very reassured while we were away. I highly recommend her for your pet needs!

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Annabeth K.
Sitter Profile Image: Ryan L.
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Ryan L.
from
$70
per night
5.0 out of 5 stars
3 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: Jacqueline B.
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Jacqueline B.
from
$55
per night
5.0 out of 5 stars
8 reviews
1 repeat client
10 years of experience
Annapolis, MD, 21401

Jacqueline was a wonderful sitter! She was responsive, understanding, and communicative. She listened to our care instructions and left our house very neat and tidy. We will definitely work with her again in the future.

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Jack S.
Sitter Profile Image: Alexandra M.
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Alexandra M.
from
$60
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: Lee M.
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Lee M.
from
$40
per night
5.0 out of 5 stars
7 reviews
2 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: Justine P.
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Justine P.
from
$55
per night
5.0 out of 5 stars
62 reviews
25 repeat clients
31 years of experience
Pasadena, MD, 21122

We couldn’t be more grateful for the care Justine provided. From the beginning, communication was clear, prompt, and professional and we received regular updates and photos, which made being away so much easier. When we returned home, our dog was happy, relaxed, and clearly well cared for. That says everything. We would absolutely book again and highly recommend them to anyone looking for a trustworthy, responsible, and compassionate dog sitter.

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Aaron C.
Sitter Profile Image: Owen K.
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Owen K.
from
$31
per night
4.9 out of 5 stars
48 reviews
4 repeat clients
10 years of experience
Severna Park, MD, 21146

Oh, I’m not quite sure where to begin. Owen is such an incredibly sweet, caring and kind young man! We’ve used Rover several times as well as neighbors and friends and family over the years to watch our dogs (we have a 1.5 year old golden doodle, a 7-year-old mini cockapoo, and a 12 yr old miniature boxer) we decided to take a last minute vacation to go see our daughter in North Carolina, which means we were gonna be a good 6 to 7 hours away as well from our dogs, which was nerve-racking and none of our usual people were available. In fact, I couldn’t find anyone available because of the short notice in the five star review arena. I was hesitant to book Owen because the Rover rating had him only like a 2 1/2 star review. But I read the comments and he had two other five star raving reviews and then just one pretty negative rating, but my gut just kept bringing me back to him telling me to give him a chance, so I did. Well you know the saying, “Always trust your gut?” Definitely didn’t fail us with Owen! Our dogs can be pretty intimidating when someone comes up to our dorm. They barrow and sound really ferocious and then they jump all over you be a handful. Owen took right to them and they took right to him! Oh, I forgot to mention the other thing I was nervous about with booking Owen is that he is male. My boxer is not usually a fan of guys whatsoever and he’s super protective if I’m the only one around and not only did he not growl or act standoffishat all towards Owen he seemed like he had known him forever! I honestly wish I could share the photos on here of that same dog Ling with Owen and one of the several photos he sent me. He did every single thing I asked 100% correctly! Which honestly that’s shocking because I leave a full one page document single spaced typed out for people staying at our house watching the dogs and I expect people to forget or missstuff it because it is a lot! Heck my husband and teenage son that live with the dogs full-time don’t remember everything that I want done. Lol Owen didn’t miss a single thing! On top of that, I also have Ringcameras all around the exterior of my home and he played with them and loved on them and they loved on him. In fact I think they even slept with him at night! Lol we got daily check ins from Owen and anything that he noticed was concerning or had questions on he messaged us. And was always super apologetic about disturbing us on vacation. He’s probably nice to a fault Ha! He also washed his bedding in the bedhe stayed in, put our dishes away and some other things which 110,000% is not expected at all! The other thing was shocking is whenever we leave even if family is watching the dogs the dogs will rarely eat and they were so comfortable with him they ate normally! Fortunately with us, we’ve never had any bad experiences with anyone we’ve used on Rover and I would have any of them back again! That being said, there’s just such a loving kind energy that comes off of him that the dogs pick up on so he will be my first call for our next vacation. My husband and I were so impressed with him. We’ve actually thought about reaching out to Rover and seeing if that one negative review could be removed because I get everyone has different experiences, but I just don’t know how there could’ve been such an enormouschange from that review to now is, it’s just not even his character or personality which you will understand if you book him which I highly recommend you do! He should be there with the other five star people, hands-down! So Owen, thank you so very much for loving our babies while we were gone and making us feel so so very comfortable that I don’t have to stress about leaving again! You are a kind soul and I know you had asked me for any tips or suggestions or feedback I can give you for the next time that you can improve on and young man I cannot think of a single thing and that is saying a lot coming from someone like me who is a perfectionist and OCD! We can’t wait to have you over again and I know Jax,Nahla and Montana can’t wait for you to come and stay again also!

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Vanessa B.
Sitter Profile Image: Karen R.
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Karen R.
from
$50
per night
5.0 out of 5 stars
10 reviews
3 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: Catherine J.
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Catherine J.
from
$40
per night
5.0 out of 5 stars
7 reviews
1 repeat client
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: Ryleigh P.
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Ryleigh P.
from
$65
per night
5.0 out of 5 stars
39 reviews
11 repeat clients
13 years of experience
Arnold, MD, 21012

Ryleigh is a true gem! She takes care of our “ little old men” as if they were her own. We get pictures of our pups throughout her stay. We love it! Thanks again!

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

Ava and our pup have formed a great bond and we appreciate that we have someone we can rely on to watch him when we go out of town. Ava always sends updates and photos and we know our pup has a great time!

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Ally K.
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: Emily B.
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Emily B.
from
$45
per night
4.9 out of 5 stars
23 reviews
8 repeat clients
4 years of experience
Arnold, MD, 21012

Emily was great with my dog, Elvis! She took excellent care of him and if my house while I was gone as well. She also communicated well and sent a lot of pictures. Highly recommend!

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Rob H.
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Woods Landing pet parents share their Rover experiences

1 / 1
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

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.
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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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 Woods Landing is $50

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 Woods Landing average 4
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 Woods Landing on Rover as of Jun 2026 was about $50 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 Woods Landing 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 2,427 house sitters in Woods Landing. 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, 87% of Woods Landing house sitters respond in under an hour.

House sitters in Woods Landing have an average of 14 years of experience. House sitters with repeat customers have an average of 4 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 Woods Landing.

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. Woods Landing 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.