Cheswold Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

Your Cheswold Holiday

Our Cheswold holiday packages let you customise 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 holiday is just a few clicks away. Search flights, hotels and more on Expedia for a trip that's tailored to suit your style.

Cheswold Essential Information

Language
English
Currency
U.S dollars
Population
1,400
Max Temp Winter
7ºC
Max Temp Summer
27ºC
Top Sights
Woodland Beach, Air Mobility Command Museum and Hoppin Good Time

Top hotels in Cheswold

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
The price is £66 per night from 14 Dec to 15 Dec
£66
14 Dec - 15 Dec
includes taxes & fees
8.8/10 Excellent! (3,825 reviews)
"Clean well maintained, great housekeeping staff, concierge staff is great and so is the gift shop Young lady. had a great time. Oops let's not forgot front desk. Only one issue commode is low for taller people."

Reviewed on 11 Nov 2026

Bally's Dover Casino Resort
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
The price is £56 per night from 6 Dec to 7 Dec
£56
6 Dec - 7 Dec
includes taxes & fees
8.4/10 Very good! (1,000 reviews)
"The air conditioning was a little touchy in the room but other than it was a very good for the price. Sparse but sufficient continental breakfast. Very clean. Good WiFi."

Reviewed on 8 Nov 2026

Microtel Inn & Suites by Wyndham Dover
Comfort Inn & Suites Dover near Speedway

Comfort Inn & Suites Dover near Speedway

2.5 out of 5
764 Dover Leipsic Road Dover DE
Fully refundable
The price is £70 per night from 13 Dec to 14 Dec
£70
13 Dec - 14 Dec
includes taxes & fees
Comfort Inn & Suites Dover near Speedway
See all 142 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Cheswold travel package cost?
Our Cheswold travel packages, which start at just , are the perfect way to save. Select your favourite flights, hotels and rental cars to create your ideal trip.
If I'm not able to travel, can I cancel my Cheswold travel package?
Because we understand life is full of surprises, the answer is yes. For further information, head to our Customer Service Portal. But generally speaking, if you've booked your Cheswold travel package in the last 24 hours, you may be able to change or cancel it for no charge. Your hotel, airline or car rental company may charge a fee if you made your booking a while ago.
How do I get a cheap travel package to Cheswold?
One of the easiest ways to save dollars (and time) is to combine your bookings with Expedia. Hotels, flights, activities and rental cars — we've got everything you need. Pick the combination that suits your style and see your savings stack up. We know a package deal is never a one-size-fits-all. That's why we offer more than 550 partner airlines and 1,000,000 properties across the world, which lets you customize your Cheswold adventure.
Does Expedia offer Book Now, Pay Later Cheswold holidays?
Expedia has partnered with online lender Klarna to make your next break easier on the purse strings. Paying in instalments means you can spread the costs of your next dream escape, leaving you with more cash to splash while you're travelling. Klarna has several payment plans to choose from, so you're sure to find something that works with your budget. Take a look at these flexible payment options:

  • Pay monthly holidays: Jet off on that dream holiday sooner with Klarna's convenient monthly instalment plans. If making bite-sized repayments each month sounds right for you, choose this option during the checkout process.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay for your holiday over multiple transactions.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the full total upfront) makes it easier to click that "book now" button, choose a low deposit holiday payment plan from Klarna.

Where should I stay in Cheswold?
A holiday in Cheswold isn't complete without checking out Dover Mall, Delaware State Police Museum and Education Centre and Fork Branch Nature Preserve. Spend your nights near these top sights and make sightseeing simple.
What are the top hotels in Cheswold?
Reserve a room at Sheraton Suites Wilmington Downtown. It's one of the neighbourhood's most popular properties. Another top option in Cheswold is Atlantic Sands Hotel & Conference Centre.
How far in advance should I book my Cheswold holiday?
It's hard to pick the ideal time for airfares, but we usually say the earlier, the better. Plenty of international journeys on Expedia become available to compare up to 12 months in advance. If you're booking at the last minute, don't worry. Budget prices appear from time to time within a few weeks of departure dates.
What does an Expedia Cheswold travel package include?
Flights, hotels and rental cars — you'll discover them all here. With Expedia, you can create your Cheswold package the way you like it. All you have to do is decide what you need. Once you've made your booking, you can add on fun things like experiences and activities. The more you bundle, the bigger your savings!
What should I know before booking a Cheswold travel package?
A travel package can be customized for your circumstances and is a great way to stretch your dollars further. How little or much you include is completely up to you. Hotels, rental cars and flights — come up with a combination that works with your plans.
Can I choose my airline with a Cheswold Expedia travel package?
Yes, you're in control. We offer more than 550 airlines around the world, so you can design your Cheswold holiday according to your needs and budget.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.