House Sitting Cheswold

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

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Over 3
pet parents in Cheswold have booked house sitting

Cheswold, 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: Kathleen M.
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Kathleen M.
Star Sitter
from
$60
per night
5.0 out of 5 stars
19 reviews
4 repeat clients
5 years of experience
Dover, DE, 19904

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

This was our first time using Gabbi….we were a little nervous at first, but she made us feel comfortable by sending pictures after pictures. My girls love her I definitely recommend Gabbi if you’re looking for a sitter .

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

My dog, Joy, loved Liz! They played together and snuggled together. Joy didn't even miss us! Liz spent 2 nights. The house was in perfect shape when we arrived home. She even washed sheets and towels! I would definitely book with Liz again.

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Pam L.
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: Kaylynn B.
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Kaylynn B.
from
$40
per night
5.0 out of 5 stars
11 reviews
2 repeat clients
7 years of experience
Dover, DE, 19904

We had an excellent today.kaylynn was so kind and patient with our little pup who has a tendency to get separation anxiety. Would definitely use her in the future !

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Sharon M.
Sitter Profile Image: Busara C.
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Busara C.
Star Sitter
from
$65
per night
5.0 out of 5 stars
84 reviews
12 repeat clients
5 years of experience
Dover, DE, 19904

Busara is the best! Maxwell has a great time and is always well cared for! I have no worries when I’m not there because I know Busara is always there to save the day and make sure Maxwell has great company

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Ryan G.
Sitter Profile Image: Robyn L.
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Robyn L.
from
$40
per night
5.0 out of 5 stars
3 reviews
15 years of experience
Clayton, DE, 19938

This was my first time using a dog sitter and Robyn went above and beyond. Incredibly attentive and provided frequent updates. My dogs absolutely loved her. Can’t recommend her enough!

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ani p.
Sitter Profile Image: Samantha N.
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Samantha N.
from
$42
per night
5.0 out of 5 stars
206 reviews
50 repeat clients
15 years of experience
Dover, DE, 19901

Samantha was wonderful! She was so patient with our dog who can be very timid and stubborn. Will definitely be using Samantha again for further stays!

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Kelly P.
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: 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 is a huge help and Maxwell loves spending time with her! She is attentive and makes sure Maxwell is entertained and has someone to snuggle with during the day. 10/10 for sure!

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Ryan G.
Sitter Profile Image: Hannah Y.
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Hannah Y.
Star Sitter
from
$80
per night
5.0 out of 5 stars
10 reviews
5 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: 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: Jordan M.
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Jordan M.
from
$35
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: Taylor P.
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Taylor P.
from
$40
per night
5.0 out of 5 stars
1 review
1 repeat client
16 years of experience
Dover, DE, 19904

About: I’ve had dogs my entire life and am super comfortable around them. I currently work for an animal sanctuary with older dogs and soon to have a couple horses and one goat there. I worked as an animal welfare officer previously therefore, I have a lot of knowledge on animals and their breeds. I also had chickens and Guinea pigs. I used to have bearded dragons too! Many many years of experience handling animals :) I currently work full time for a First State Animal Center and SPCA at their brand new sanctuary for rehabilitating dogs, senior dogs to enjoy the end of their life, and will have horses and a goat there soon. I am available Mondays, Tuesdays, and Saturdays all day. The rest of the week, I work 8am-6pm therefore, I can do evenings if needed after 6pm. I am more than willing to go to anyone’s house to pet/house sit or even just go to let them out or play/ feed them. I am willing to stay overnight for owner weekend trips if needed. Just need to let me know so I can arrange childcare for my son and also I have my full time job on Fridays and Sunday 8-6 but can be there after work if staying overnight! Also willing to pet sit any kind of pet!

Sitter Profile Image: Tricia L.
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Tricia L.
from
$45
per night
5.0 out of 5 stars
3 reviews
40 years of experience
Felton, DE, 19943

Tricia is, hands down, the best pet sitter we have ever had! ​From start to finish, she went so far above and beyond her basic duties to make sure our home and our dog were completely cared for. Our boy can be extremely picky and hesitant with new people, but Tricia bonded with him almost instantly. He is also a big boy which can intimidate some people. She knew exactly how to make him feel comfortable, safe, and loved while we were away. She played and brushed him daily and have him lots of cuddles! ​Her communication was incredible. She updated us multiple times every single day and sent plenty of photos and videos, which gave us total peace of mind the entire time we were gone and allowed us to enjoy our vacation. It was so reassuring to see how happy and relaxed he was with her! ​On top of being an absolute natural with dogs, Tricia took exceptional care of our house and garden, tackling extra tasks and leaving everything in pristine condition for our return. ​If you are looking for someone trustworthy, attentive, and genuinely caring—especially if you have a selective or picky dog—look no further than Tricia. We will absolutely be booking her again!

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Stacy R.
Sitter Profile Image: Krista K.
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Krista K.
Star Sitter
from
$111
per night
5.0 out of 5 stars
9 reviews
2 repeat clients
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: Lisa P.
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Lisa P.
from
$28
per night
5.0 out of 5 stars
1 review
12 years of experience
Dover, DE, 19901

Our elderly pups were well cared for and home was kept as we would have kept it. Lisa and Gary are very easy to work with and made adjustments on the fly. We would rebook with them again.

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Marie S.
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: Luie R.
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Luie R.
Star Sitter
from
$55
per night
5.0 out of 5 stars
222 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: Rebecca R.
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Rebecca R.
from
$70
per night
5.0 out of 5 stars
26 reviews
12 repeat clients
8 years of experience
Townsend, DE, 19734

Rebecca did an excellent job staying at our home with Pippin! She was really prepared with questions to help the weekend good smoothly and to understand his needs. She was very responsive to messages and sent detailed updates and pics. Our pup had a great time!

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Leah O.
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The median cost per night for house sitting in Cheswold is $50

Pet parents share their Rover experiences - Cheswold

1 / 1
5.0 out of 5 stars

Kathleen always takes great care of my pup and communicates throughout the time that she is booked for. I would not hesitate to recommend her to anyone needing a dog sitter

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Richard 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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  • 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

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  • Reservation protection

    It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Meet local sitters who will treat your pets like family

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit
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Popular requests for house sitting - Cheswold

Select a filter and find qualifying sitters offering house sitting.

Sitters in Cheswold average 4
repeat house sitting clients

FAQs for House Sitting - Cheswold

Frequently asked questions about Rover

The average cost for House Sitting in Cheswold on Rover is $55.5 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 478 sitters on Rover offering House Sitting across Cheswold. 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 Cheswold 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 Cheswold 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 Cheswold 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 Cheswold. On Rover:

  • 94% of sitters can help with special care needs
  • 94% can help with giving oral medications or injections
  • 97% 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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