Cheswold Vacation Packages
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Your Cheswold Vacation
Our Cheswold vacation packages let you customize your own adventure. Tailor your getaway to your style and interests and make the most of your time in this lively city. Any trip to Cheswold needs a well-thought-out itinerary. Fill yours with leading attractions like Dover International Speedway, Dover Downs Casino and Delaware State University. Your ultimate Cheswold vacation is just a few clicks away. Search flights, hotels and more on Expedia for a trip that's tailored to suit your style.
Top Cheswold Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Residence Inn by Marriott Newark, DE
Price was CA $2,031, price is now CA $1,467 per person
CA $1,467
per person
Jun 18 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Wilmington (ILG)
8.8/10 Excellent! (33 reviews)
Overall, staff and hotel were good. Shower stall floor seemed a bit grimy and the toilet paper holder was broken off. One of the glasses in the kitchen had a lipstick print on it. Other then that we appreciated the location and the 2 bedroom suite. Check in/out was easy.
Reviewed on Apr 27, 2026
SpringHill Suites by Marriott Newark Downtown
Price was CA $1,770, price is now CA $1,612 per person
CA $1,612
per person
Jun 18 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Wilmington (ILG)
9.4/10 Exceptional! (833 reviews)
Nice hotel, clean, big size room. Helpful staff. Good option in Delaware.
Reviewed on May 7, 2026
Holiday Inn Express & Suites Middletown by IHG
Price was CA $1,768, price is now CA $1,651 per person
CA $1,651
per person
Jun 18 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Wilmington (ILG)
9.2/10 Wonderful! (678 reviews)
Great location and nice place to stay. Walk to nearby things to do and enjoy.
Reviewed on Mar 28, 2026
Cheswold Hotel Deals
Bally's Dover Casino Resort
1131 N Dupont Hwy Dover DE
Fully refundableReserve now, pay when you stay
The price is CA $91 per night from May 21 to May 22
CA $91
CA $127 total
May 21 - May 22
includes taxes & fees
8.8/10 Excellent! (3,555 reviews)
I just stayed for a one night stay but I really enjoyed the cleanliness and spacious room. Overall, I will stay again in the future.
Reviewed on May 13, 2026
Microtel Inn & Suites by Wyndham Dover
1703 E Lebanon Rd Dover DE
Fully refundableReserve now, pay when you stay
The price is CA $105 per night from May 28 to May 29
CA $105
CA $115 total
May 28 - May 29
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
I bring a cpap when I travel and plugging it in was a chore…I had to get on the floor to access the plug
Reviewed on May 13, 2026
MHO Hotel Dover
348 N Dupont Hwy Dover DE
Fully refundableReserve now, pay when you stay
The price is CA $96 per night from May 19 to May 20
CA $96
CA $106 total
May 19 - May 20
includes taxes & fees
4.6/10 (49 reviews)
Friendly staff
Reviewed on May 7, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
