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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.

Cheswold Hotel Deals

Bally's Dover Casino Resort

Bally's Dover Casino Resort

4 out of 5
1131 N Dupont Hwy, Dover, DE
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $107 total per night from Oct 13 to Oct 14
$107 total
Oct 13 - Oct 14
Total with taxes and fees
8.6/10 Excellent! (3,152 reviews)
"The staff was very accommodating with our unusually late arrival. The room was comfortable and clean. We would stay again if in the area."

Reviewed on Oct 3, 2025

Bally's Dover Casino Resort
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
764 Dover Leipsic Road, Dover, DE
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $102 total per night from Oct 20 to Oct 21
$102 total
Oct 20 - Oct 21
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
"Great breakfast choices"

Reviewed on Oct 5, 2025

Comfort Inn & Suites
Microtel Inn & Suites by Wyndham Dover

Microtel Inn & Suites by Wyndham Dover

2 out of 5
1703 E Lebanon Rd, Dover, DE
Fully refundableReserve now, pay when you stay
$86 nightly
The price is $93 total per night from Oct 12 to Oct 13
$93 total
Oct 12 - Oct 13
Total with taxes and fees
8/10 Very Good! (1,002 reviews)
"Helpful and kind staff. Excellent wi-fi."

Reviewed on Sep 29, 2025

Microtel Inn & Suites by Wyndham Dover
See all 120 properties in Cheswold
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.

Cheswold Essential Information

Language
English
Currency
U.S dollars
Population
1,400
Top Sights
Woodland Beach, Air Mobility Command Museum and Hoppin Good Time

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Frequently asked questions

How much does a Cheswold vacation package cost?
You'll find cheap prices on Expedia for your Cheswold break. However, a range of factors like the season, length of stay and your choice of hotel will influence how much your vacation to Cheswold costs.
What are the cheapest months to go to Cheswold?
You can generally find lower prices and better availability in November, December and January. Check out our cheap Cheswold vacation packages and you could score some great off-season deals.
How many days is enough for Cheswold?
With a well-organized travel plan, you can easily hit the most popular Cheswold sights in a handful of days. But if you'd like to venture off the beaten track or take day trips, consider booking your Cheswold vacation for longer.
How to find the best Cheswold package deals?
Start your search for a Cheswold package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Guest rating" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Cheswold package deal right away, just change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Cheswold adventure off to a flying start.
Is it cheaper to book a Cheswold vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging hotels and flights individually. Better still, you can personalize your Cheswold getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Cheswold?
If you're planning an impromptu Cheswold getaway, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can find amazing deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Cheswold vacation packages?
Your Cheswold trip is meant to be a relaxing escape from your daily routine, not a source of money-related stress. So to give you more flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.