Dog Boarding Whaleys Crossroads

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Whaleys Crossroads, Find top rated dog boarding

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Sylvia L.
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Sylvia L.
Star Sitter
from
$60
per night
5.0 out of 5 stars
• 27 reviews
12 repeat clients
20 years of experience
Millsboro, DE, 19966

“Sylvia kept our nervous dog for three days and she was so patient and caring with her. We got updates during the visit with photos. She made sure she felt at home and knew all of her needs. Then we returned for another three days the following week and our dog was so excited to see her and relaxed right in with no anxiety. Sylvia is really wonderful and a fabulous dog sitter. I would highly recommend her.”

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Anne S.
Sitter Profile Image: Jessica R.
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Jessica R.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 30 reviews
11 repeat clients
40 years of experience
Milton, DE, 19968

“Really great sitter! I was in a last minute jam and she responded so quickly and sent update photos through out the time my kitten was there. Highly recommend:)”

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Alondra S.
Sitter Profile Image: Amy A.
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Amy A.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 13 reviews
5 repeat clients
50 years of experience
Laurel, DE, 19956

“Amy is an angle. She was so down to earth and I felt at ease leaning my boy with her. She kept me updated throughout the entire day with pictures and videos. She took my baby on an adventure with lots of trips and care rides which he loves. I told her what he likes and didn’t and she made sure to do all the things he loves. In every picture and video she sent I saw how happy my baby boy was. Definitely booking with her again! Thank you so much he had so much fun and you showed him so much love. 😊😊”

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Sterline P.
Sitter Profile Image: Carlie A.
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Carlie A.
from
$60
per night
5.0 out of 5 stars
• 74 reviews
22 repeat clients
15 years of experience
Ocean Pines, MD, 21811

“Highly recommend Carlie to care for your fur baby. She cared for our Corgi mix for 6 days while we were on vacation. Carlie sent us pictures of our baby taking walks and having treats. He was happy and well cared for and the peace of mind knowing he was so well cared for was priceless. So grateful for the love and care she gave to our sweet boy.”

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Heather W.
Sitter Profile Image: Daniel W.
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Daniel W.
Star Sitter
from
$35
per night
5.0 out of 5 stars
• 46 reviews
18 repeat clients
4 years of experience
Fruitland, MD, 21826

“Daniel was excellent! He kept us updated throughout our dog’s stay, and all the pictures showed a happy, well cared for pup. Seeing how happy our dog was gave us great peace of mind. We couldn’t have asked for a better experience! We would absolutely book with Daniel again whenever we’re in the Salisbury area. Highly recommend!”

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Vernon C.
Sitter Profile Image: Christina M.
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Christina M.
Star Sitter
from
$30
per night
5.0 out of 5 stars
• 13 reviews
5 repeat clients
9 years of experience
Delmar, MD, 21875

“Christina was awesome!! Super great with my maple & made it a friendly experience! I’d definitely recommend booking with her!!”

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Autumn B.
Sitter Profile Image: Jenna C.
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Jenna C.
Star Sitter
from
$55
per night
5.0 out of 5 stars
• 226 reviews
61 repeat clients
10 years of experience
Ocean View, DE, 19970

“Jenna kept me updated with photos throughout Sunny’s stay. She was super responsive from our first contact. I could tell Sunny was relaxed in her home and happy to hang out with her new kitty friend, Boo.”

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Cheri S.
Sitter Profile Image: Karen L.
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Karen L.
from
$48
per night
5.0 out of 5 stars
• 25 reviews
9 repeat clients
10 years of experience
Lewes, DE, 19958

“We moved to the area recently and searched for a new pet sitter. My husband and I could not be anymore happier with the care Karen and Sean provided to our Molly! Our Molly felt right at home on her first stay. Karen and Sean took Molly on walks and gave her plenty of playtime. Definitely will be using Karen again in the future ❤️”

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Robin P.
Sitter Profile Image: Morgan A.
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Morgan A.
from
$50
per night
5.0 out of 5 stars
• 3 reviews
1 repeat client
20 years of experience
Bridgeville, DE, 19933

“Morgan truly enjoyed my babies and took amazing care of them! I’d book her again any time!”

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Johanna D.
Sitter Profile Image: Robert R.
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Robert R.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 240 reviews
79 repeat clients
61 years of experience
Lewes, DE, 19958

“Susan and Bob are great doggy caretakers and people. They certainly understand dogs and how to integrate multiple dog personalities into “doggy camp” in their home. We appreciate that they will make every effort to meet each dog’s individual needs. And together, Susan and Bob provide all the love that your dog needs while in their care. Lulu had a blast socializing with other pups and we had great peace of mind while on our vacation. 100% thumbs up!!!”

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Nancy B.
Sitter Profile Image: Jen G.
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Jen G.
from
$50
per night
4.9 out of 5 stars
• 17 reviews
5 repeat clients
30 years of experience
Milton, DE, 19968

“My pup looked happy in all of the pics and videos. Jen kept me updated and was so nice to not worry about my pup. Was first time leaving her but Jen made it bearable.”

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Michelle P.
Sitter Profile Image: Lori S.
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Lori S.
Star Sitter
from
$65
per night
5.0 out of 5 stars
• 127 reviews
31 repeat clients
30 years of experience
Harbeson, DE, 19951

“Lori was able to accommodate a last-minute sitter request for our senior dog and we are so appreciative. Our little guy, Finn, didn’t make it easy for her either particularly during feeding times. Lori hung in there and worked with him patiently. There was a high level of communication throughout his stay and lots of updates and photos too. Thank you Lori!!”

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Kristin L.
Sitter Profile Image: Lauren C.
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Lauren C.
from
$28
per night
15 years of experience
Ocean View, DE, 19970

About: I’m a lifelong animal lover who believes pets deserve their own little staycation while you’re away! Whether it’s a neighborhood walk, some backyard playtime, belly rubs on the couch, or simply keeping them company, I’ll make sure your pet feels happy, comfortable, and loved. I’m dependable, attentive, and happy to stick to your pet’s normal routine — meals, walks, medications, playtime, and all the extra snuggles they’ll allow. I’ll also send plenty of photo updates, so you can relax knowing your furry family member is being well cared for and getting lots of love while you’re gone. 🐾 My schedule is flexible as my husband is a business owner and I work part-time for him, which gives me plenty of time to work pet care into my day. I’m happy to plan visits, walks, feeding times, and check-ins around your pet’s normal routine whenever possible. Whether you need occasional help, vacation coverage, or regular visits, I’ll do my best to make things easy and stress-free for both you and your pet. 🐾 Your pet’s safety, comfort, and routine will always come first. I’ll carefully follow any instructions you provide for feeding, walks, medications, doors or gates, and anything else that helps your pet feel secure. I’m also very respectful of your home and belongings and will keep you updated with photos and messages, so you always know how your pet is doing. My goal is for you to come home to a happy pet and a home just as you left it. 🐾

Sitter Profile Image: Nichole P.
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Nichole P.
from
$65
per night
5.0 out of 5 stars
• 4 reviews
20 years of experience
Salisbury, MD, 21804

“I would definitely recommend and book again. Keeps you updated with pictures and videos. Took care of our dog like if it was her own. I had no worries during my trip about my dog being cared for b/c I know my dog was in good hands. I dropped a list minutes book and she responded quickly, which we are very appreciative for.”

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Shery V.
Sitter Profile Image: Debra H.
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Debra H.
from
$76
per night
5.0 out of 5 stars
• 7 reviews
1 repeat client
50 years of experience
Lewes, DE, 19958

“Debra was incredibly sweet. This was a last minute booking with the holidays 1-2 days away. Debra was incredibly responsive throughout he process. She took our dog on frequent walks, provided photos/videos and updates how he was doing. Simply put, we couldn’t have asked for more. We’d definitely recommend.”

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Biren J.
Sitter Profile Image: Sandra N.
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Sandra N.
from
$55
per night
5.0 out of 5 stars
• 1 review
4 years of experience
Georgetown, DE, 19947

“Sandra took the time to meet with our dogs prior to boarding, sent several updates throughout their stay, and made me feel comfortable leaving them in her care. Most importantly, my dogs seemed to love her. I plan to come to Sandra for any future boarding needs!”

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Mackenzie G.
Sitter Profile Image: John W.
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John W.
from
$60
per night
5.0 out of 5 stars
• 7 reviews
15 years of experience
Berlin, MD, 21811

About: I currently have a cat and a golden retriever and would love to help you take care of your dog while you are in need. I work from home Monday through Friday so my schedule allows me to be very flexible for potty breaks and general playtime while I'm taking care of your best friend. We have over 3/4 of an acre of property and are also located in the heart of Berlin...So a walk or outside playtime is no problem.

Sitter Profile Image: Marvina S.
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Marvina S.
from
$65
per night
5.0 out of 5 stars
• 98 reviews
32 repeat clients
15 years of experience
Lewes, DE, 19958

“Fred loves coming to Marvina's place. Such a great time playing with her dogs and I can tell he feels right at home. Love getting the pictures and updates.”

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Nancy M.
Sitter Profile Image: Cori B.
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Cori B.
from
$80
per night
4.9 out of 5 stars
• 73 reviews
17 repeat clients
25 years of experience
Lewes, DE, 19958

“We couldn't be happier with the care our pups received from Cori! From the moment we dropped them off, we knew they were in good hands. Cori went above and beyond to make them feel comfortable and at home. We loved getting regular updates and adorable pictures, which reassured us that our furry friends were happy and well taken care of. Thank you, Cori, for your exceptional service and for treating our pups like family!”

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Jackie M.
Sitter Profile Image: Gabrielle P.
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Gabrielle P.
from
$70
per night
5.0 out of 5 stars
• 5 reviews
1 repeat client
5 years of experience
Lewes, DE, 19958

“Gabrielle was great! I had to book last-minute and she was able to take my reservation on short notice, and she was great with my dog. She took her on multiple walks over the stay and when I came to pick Bug up she was happy and well taken care of”

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Peyton M.
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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?

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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.

How to book dog boarding

  1. 1. Search

    Browse profiles of sitters near you who offer dog boarding.
  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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FAQs for Dog Boarding - Whaleys Crossroads

Frequently asked questions about Rover

Rover is the largest marketplace for local pet care. Whether you're looking for pet sitters, dog walkers, or house sitters who specialize in pet sitting, you can narrow your search by entering your ZIP code to find sitters within walking distance in your neighborhood.

Every sitter on Rover has their own routine. Depending on the arrangements you agree on before the stay, a sitter can follow your dog’s regular feeding schedule, provide a comfortable place to sleep, offer companionship, and support their usual exercise and play needs.

Depending on the sitter, their home environment, and your dog’s needs, daily exercise may include walks, outdoor play, indoor enrichment activities, or supervised play with compatible dogs. These activities are not automatically included with every booking, so ask the sitter what a typical day looks like.

During the Meet & Greet, discuss your dog’s usual exercise and play routine, whether they can safely interact with other dogs, and any activities or restrictions the sitter should follow. You can also ask the sitter to send photo and message updates during the stay so you can see how your dog is spending their time.

Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Whaleys Crossroads home-away-from-home, packing:

  • Health and safety essentials such as their ID tags, vaccination records, medication, and emergency vet or secondary caregiver contacts.
  • Food and gear such as harnesses, collars, food (portioned by day), and an item that smells like you.
  • Special instructions such as a list of training cues, medical administration needs, or favorite hang-out spots in your Whaleys Crossroads.

<b>Tip:</b> You can upload your dog’s routine and medical info directly onto their profile so your sitter always has the details at their fingertips.

You and your Whaleys Crossroads sitter can schedule drop-off and pick-up in a way that works best for the both of you—and your dog. Most sitters offer flexible times for drop-off and pick-up but the easiest way to confirm those times will be through in-app messaging. Confirm your arrival time the day of pick-up and drop-off can also help keep the process smooth and organized.

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 .

While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.

Many sitters in DE ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies.

By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.

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 dog to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your dog 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.

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