House Sitting in Cheswold

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

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Top rated Cheswold 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: Busara C.
Verified Enhanced Background Check
Busara C.
Star Sitter
from
$50
per night
5.0 out of 5 stars
84 reviews
11 repeat clients
5 years of experience
Dover, DE, 19904

Busara was a delight! She gave a lot of feedback on her time with Jasper. Jasper seemed to enjoy having her here. I’d definitely ask her to come another time!

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Lois D.
Sitter Profile Image: Gabbi T.
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Gabbi T.
Star Sitter
from
$45
per night
5.0 out of 5 stars
26 reviews
8 repeat clients
20 years of experience
Smyrna, DE, 19977

Gabbi did a wonderful job taking care of my cats! She made sure medication was given on time and made sure they always had everything they needed. I would definitely book Gabbi again.

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Stephanie H.
Sitter Profile Image: Kathleen M.
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Kathleen M.
from
$60
per night
5.0 out of 5 stars
16 reviews
4 repeat clients
5 years of experience
Dover, DE, 19904

We felt secure leaving our Beloved Rebel and our home in the care of Kate. Although it made us sad to see how much he seemed not to miss us (L.O.L). Kate sent us updates daily along with pictures of how much fun Rebel was having with her. It was our first time leaving Rebel. The daily updates from Kate as well as the pictures she provided made our trip more bearable. We were able to not worry and just relax knowing Kate was with him providing excellent care and attention in every way. Kate was a Excellent Care Giver to Our Baby Boy Rebel. She also took great care of our home. We highly recommend Kate and will use her services again in the future. THANK YOU KATE!!!

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Diane M.
Sitter Profile Image: Faith R.
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Faith R.
from
$45
per night
5.0 out of 5 stars
31 reviews
6 repeat clients
15 years of experience
Dover, DE, 19901

Faith was great! She went above and beyond with Dexter. My home was clean and tidy when I returned and she spent a lot of time with, making sure he wasn’t left alone and felt safe with his family gone! He got lots of attention and walks and I felt great about leaving him.

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Jessica P.
Sitter Profile Image: Elizabeth B.
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Elizabeth B.
Star Sitter
from
$40
per night
5.0 out of 5 stars
87 reviews
19 repeat clients
20 years of experience
Dover, DE, 19904

Ms.Liz was so great with my Bogart. I couldn't even believe that my Bogart gave him kissess and plays with her which means, Ms.Liz is kind and can be trusted. She even sent me pictures and videos that kept myself from worrying about my baby. Now I know which one to call and can leave my baby safely. Highly recommended.. Thanks again Ms.Liz for taking care of my boy.. Me and Elmar appreciate it sooooo much.. Thank you a million times..😊😊😊🥰🥰🥰

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yhang e.
Sitter Profile Image: Taylor G.
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Taylor G.
from
$25
per night
5.0 out of 5 stars
49 reviews
2 repeat clients
10 years of experience
Smyrna, DE, 19977

Taylor was great with Maxwell! On time, open communication, and most importantly, took excellent care of Maxwell. Look forward to working with her for future visits!

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Ryan G.
Sitter Profile Image: Christina B.
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Christina B.
from
$70
per night
5.0 out of 5 stars
33 reviews
6 repeat clients
13 years of experience
Dover, DE, 19904

Christina was so helpful and accommodating. She even sent me pics of my dog while I was away, assuring me that my dog was doing well. I was very happy with her services. I would definitely hire her again!

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Karen B.
Sitter Profile Image: Heather M.
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Heather M.
from
$50
per night
5.0 out of 5 stars
5 reviews
1 repeat client
12 years of experience
Dover, DE, 19901

About: Going away for the night, weekend, week or however long just contact me! I absolutely love dogs no matter the size! I have been watching friends dogs for a few years now and have really enjoyed it. I do have a full time job from 8-5 Monday thru Friday but would be with the dogs before and after work and they would get the full attention that they require when I am with them. My full time job does not require any overtime so I am always done on time. In the past I have stayed with a cat that had diabetes and had to have shots which was not a problem for me to handle. I do have a teenage daughter who would occasionally come with me if that is not a problem with the owners. I work full time but I have plenty of time in the evening to play with your dog(s), spend time with them if they would rather just cuddle or take them for a walk. I am patient and calm with pets that are withdrawn or missing their owners. I try to help them feel comfortable by playing with them or petting them white cuddling. When the pet is feeling comfortable I will send pictures to the client, letting them know that the pet is relaxed and comfortable with me in the house

Sitter Profile Image: Erin R.
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Erin R.
from
$50
per night
5.0 out of 5 stars
8 reviews
1 repeat client
10 years of experience
Dover, DE, 19901

Erin was super flexible with meeting our pets ahead of time, was responsive, dependable and neat. Sent pics and txts. Very appreciative of the last minute fill in on a holiday weekend!

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Christine D.
Sitter Profile Image: Ethan D.
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Ethan D.
from
$55
per night
5.0 out of 5 stars
3 reviews
6 years of experience
Clayton, DE, 19938

Ethan was a great help and was accommodating for a last minute booking. He made sure that Maxwell would be comfortable with a meet and greet as well. He was punctual, communicative, and made sure Maxwell was well cared for. Maxwell warmed right up to him with no issue and we will definitely use Ethan again in the future.

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Ryan G.
Sitter Profile Image: Samantha N.
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Samantha N.
from
$42
per night
5.0 out of 5 stars
204 reviews
47 repeat clients
15 years of experience
Dover, DE, 19901

We always appreciate Samantha! Our pup clearly loves her and we know she's in good hands with Samantha. I also appreciate the pictures and updates she sends throughout her stay.

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Melanie B.
Sitter Profile Image: Jena-lynn C.
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Jena-lynn C.
from
$100
per night
5.0 out of 5 stars
26 reviews
7 repeat clients
10 years of experience
Smyrna, DE, 19977

All went as planned. In fact Jena went above the scope of the assignment and kept us updated . Very polite, Knowledgeable, and willing to assist in the care of our pet , plus giving us peace of mind

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Thomas H.
Sitter Profile Image: Kara K.
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Kara K.
from
$55
per night
5.0 out of 5 stars
32 reviews
8 repeat clients
8 years of experience
Dover, DE, 19904

Working with Kara was wonderful! She took very good care of our somewhat needy senior dog. And we returned to a happy and healthy pup! We will definitely request her assistance the next time we travel!

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Elaine S.
Sitter Profile Image: Hannah Y.
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Hannah Y.
Star Sitter
from
$80
per night
5.0 out of 5 stars
6 reviews
3 repeat clients
12 years of experience
Rising Sun-Lebanon, DE, 19934

Hannah did an outstanding job for us. Our dog loved her; she has a superb understanding of dogs combined with wonderful energy and personality. We look forward to seeing again when we next need help.

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Charlie S.
Sitter Profile Image: Luie R.
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Luie R.
Star Sitter
from
$55
per night
5.0 out of 5 stars
221 reviews
63 repeat clients
25 years of experience
Magnolia, DE, 19962

Luie really came to the rescue when we had to cancel our dog's weekend stay at our friends' kennel due to our dog being under the weather. Luie was able to house sit and dog sit, and he doted on the dog so much, I don't think she even knew we were gone! When Luie cares for our dog, we have 100% peace of mind.

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Kathleen D.
Sitter Profile Image: Jordan M.
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Jordan M.
from
$20
per night
4 years of experience
Smyrna, DE, 19977

About: Hello everyone! I am an animal lover, I grew up around animals all my life. Our furry friends are extended family members. I hope you entrust me with your furry loved ones. I am currently an active college student, but I have somewhat situated myself with a work-life balance. I am available and flexible for weekdays and weekends! I currently have a kitten almost a year old. Having him has taught me patience, and having complete responsibility. Milo is my profile picture! I feel as though I am completely up to any challenge, I hope I can help with your furry loved ones!

Sitter Profile Image: Margaret C.
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Margaret C.
from
$65
per night
4.9 out of 5 stars
25 reviews
2 repeat clients
12 years of experience
Dover, DE, 19904

Lots of experience with different dogs. She kept my dog company and took good care of her while I was away. Will likely be using her services again in the future.

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Kaitlyn R.
Sitter Profile Image: Tiffany C.
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Tiffany C.
from
$75
per night
5.0 out of 5 stars
90 reviews
25 repeat clients
17 years of experience
Dover, DE, 19901

About: Chelon Oasis | A maison of calm for modern pets Paws and Peace --- 🐾 About Chelon Oasis Tiffanys assistant is a former Professional Medical Assistant, and Retired Female Air Force Veteran. She leads with calm authority, clean structure, and intentional presence. Pets feel safe with me because the environment is steady, the routines are clear, and the energy is peaceful. Chelon Oasis is a coastal‑inspired maison where modern pets decompress, reset, and enjoy a serene retreat designed with their comfort in mind. --- 🌴 About Chelon Oasis Your pet stays in a peaceful, coastal single family Home • 6 tons of beach sand for sensory play and grounding • A tiki‑hut hideaway for shade and calm lounging • A 6‑ft fully fenced backyard for safe roaming • Full access to Chelon Play & Paws Park — included with every stay • Indoor spaces that are clean, quiet, and structured The environment is intentionally curated to feel like a soft seaside exhale. --- 🌞 Our Pet Care Style We provide care that is: • Intentional — every routine has purpose • Calm — no chaos, no overstimulation • Structured — clear boundaries, gentle leadership • Reliable — veteran precision in communication and timing • Warm — coastal softness, steady presence Your pet receives individual attention, consistent routines, and a peaceful environment that supports their emotional and physical well‑being. --- 🐕 What Your Pet Can Expect • Sunbathing in the sand • Exploring the tiki hut • Free play in the private park • Quiet indoor rest time • Clear routines and gentle structure • A calm, grounded human leading their day Photo updates available upon request. --- 🏡 Safety, Cleanliness & Routine Safety is a non‑negotiable standard here. Due to insurance policies, we are not equipped to accommodate Pit Bulls, Rottweilers, or Dobermans. • 6‑ft secure fencing • Controlled introductions • Clean, sanitized spaces • Structured feeding and potty schedules • Constant supervision during outdoor time • No overcrowding — ever Your pet’s peace and safety come first. Smile Your Pets on Camera --- 📍 Location Chelon Oasis is located just off Route 9 behind Dover AFB. (No Base access needed but we are available to support our veterans on base with in home pet sitting as well) 10 minutes from Bally’s Casino & Racetrack. Exactly 2 miles from Pickering Beach and Little Creek Fire Department. --- 🤝 Courtesy Expectations Please text your ETA and communicate any pick‑up adjustments within a 30‑minute window. Clear communication keeps everything smooth and respectful. --- 🐾 Optional Day‑Use Chelon Play & Paws Park is also available for independent visits with your own pup through Sniffspot — $4 per day (insurance requirement). --- ✨ In Closing thanks for checking us out! Gratuity with paw prints, Aurelia, for Tiffany, Lulu & Nyla A Message from Tiffany, Owner of Turtle Lounge As a retired veteran, I am available to be home about 80% of the time to ensure your pets receive the top-notch care, cuddles, structure, and love they deserve here at Turtle Lounge. We’re dedicated to treating your furry treasures like family, and we take pride in offering them a safe, comfortable, and loving environment. That said, we do have a few guidelines to keep things running smoothly for everyone: 1. Booking Times: Your pet’s drop-off and pick-up times are set during booking, and we kindly ask that you stick to those times. If you need to adjust the schedule, please message us at least 48 hours in advance. 2. Late or Early Pick-Up/Drop-Off: • If your scheduled time is within 30 minutes of the original booking time, that’s perfectly fine—just let us know your ETA! • However, if you need to pick up or drop off your pet more than 30 minutes earlier or later, we kindly ask for a courtesy tip of $20-30 to accommodate the schedule change. 3. Text Your ETA: Always text your estimated arrival time so we can have your pet’s belongings ready and ensure a smooth transition. Thank you for understanding and respecting our structure and scheduling. Your cooperation helps us maintain the high level of care and organization that your pets deserve! Looking forward to caring for your furry treasures! With gratitude, Tiffany Owner of Turtle Lounge Your Pet’s Safety and Comfort Are Our Top Priority at Turtle Lounge At Turtle Lounge, we understand and celebrate diversity, and we’re committed to ensuring your pet’s safety and comfort while you’re away. As a Security Forces retiree, keeping your furry family members safe is my top priority. For added peace of mind, the Little Creek Fire Department is just 2 miles away, so help is never far away if needed. A Mini Paradise for Your Fur Babies Take a look at our photos to see how your pet will enjoy their time here. We have a sand yard, a fire pit, and a 60-foot dog trolley runner (perfect for pets up to 125lbs) where they can enjoy some fun outdoor exercise. Our 60x60ft backyard is fully enclosed with a 6-foot fence to keep your pet secure while they explore or relax. Inside, your pet will have their choice of: • A separate bedroom for a peaceful, private sleep space • A cozy den for those who enjoy being closer to the action • Plenty of room in our country kitchen and great room to relax and unwind. A 5-Star Experience We take pride in providing a 5-star stay for your precious pet. To ensure every pet receives the proper care and attention they deserve, we only board a maximum of 5 pets at a time. This allows us to give each dog the attention they need, and you the peace of mind that your pet is well taken care of. Special Care for Your Pet • Filtered water and treats are provided for your treasures. • Regular updates: We’ll send you pictures of your pet’s stay via text through the Rover app so you can see how much fun they’re having. • We take our time and yours seriously. Please be mindful of your scheduled time slot—this helps us maintain the highest level of care for all pets in our care. Important Notes • We are not equipped to handle Pit Bulls (even mixes) or Rottweilers. For the safety of all pets, we do not accept these breeds. • Our home is protected by security cameras for the safety and security of all pets in our care. We’re excited to welcome your pet into our mini-paradise and give them the best stay possible. Thank you for trusting us with your furry family member! With care and gratitude, Tiffany Owner of Turtle Lounge

Sitter Profile Image: Krista K.
Verified Enhanced Background Check
Krista K.
from
$111
per night
5.0 out of 5 stars
5 reviews
1 repeat client
10 years of experience
Camden, DE, 19934

Krista did an amazing job! She was very friendly and our dog Molly did great with her. Krista was very attentive to Molly and was very respectful of our home. She kept us updated and sent pictures! We will definitely be having Krista watch our fur baby again! Thank you Krista ❤️

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Jean D.
Sitter Profile Image: Elexis M.
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Elexis M.
from
$55
per night
5.0 out of 5 stars
4 reviews
5 years of experience
DE, 19934

Elexis was communicative and attentive and even cleaned the house before she left!

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Melanie B.
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Over 3
pet parents in Cheswold have booked house sitting

Cheswold pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Kathleen, Is a wonderful sitter very attentive and knows our Rebels needs as a matter of fact today she brought up a issue we already knew about which is he gets hot quickly n the warm months playing outside. Kathleen was concerned enough to let us know and due to this I will put this informationt in Rebels Profile as it should be there, Thank You Kathleen.

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Diane M.
House Sitting
5.0 out of 5 stars

Savannah did an amazing job taking care of Max and Hope, our 2 labradors. She kept me informed and i felt confident that they were happy and safe. When we returned home the house was clean and everything was as we left it. She was quick in responding. i highly recommend Savannah to care for your animals.

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Jocelyn S.
House Sitting
1 / 1
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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 Cheswold 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 Cheswold 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 Cheswold 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 Cheswold 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 474 house sitters in Cheswold. 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, 84% of Cheswold house sitters respond in under an hour.

House sitters in Cheswold have an average of 16 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 Cheswold.

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. Cheswold 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.