--- title: "Cheswold Vacation Packages & Trips 2026 | Expedia" description: "FREE cancellation on select hotels Bundle Cheswold flight and hotel to build your own Cheswold vacation package & you can 𝘀𝗮𝘃𝗲 with Expedia! Choose from thousands of Cheswold holiday trips & travel deals." canonical: "https://www.expedia.ca/Cheswold.d553248634999403720.Destination-Travel-Guides" language: en-CA market: CA currency: CAD prices_as_of: 2026-11-15T07:43:10Z --- # Cheswold Vacation Packages ![A statue of soldiers with a flag, set against a brick building and trees.](https://images.trvl-media.com/place/553248634999403720/5480b2fc-2bb7-400f-b904-8ca897053fc9.jpg?impolicy=fcrop&w=1200&h=300&q=medium) ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $4,200 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 Plan, book, and manage your trip all in one place #### 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](https://www.expedia.ca/Dover-International-Speedway-Dover.d6099194.Vacation-Attraction), [Dover Downs Casino](https://www.expedia.ca/Dover-Downs-Casino-Dover.d6187498.Vacation-Attraction) and [Delaware State University](https://www.expedia.ca/Delaware-State-University-Dover.d6099192.Vacation-Attraction). 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 ### [Holiday Inn Express Hotel & Suites Dover by IHG](https://www.expedia.ca/Dover-Hotels-Holiday-Inn-Express-Hotel-Suites-Dover.h597727.Hotel-Information) ![A modern lobby with a grey sofa, blue armchairs, and a small table. There are artwork on the walls and a map.](https://images.trvl-media.com/lodging/1000000/600000/597800/597727/e1d792fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 1780 N Dupont Hwy, Dover, DE, 19901, US - Location: 3.5 km from Cheswold - Star rating: 2.5/5 - Guest rating: 8.8/10 (Excellent, 1003 reviews) - Price: CA $124, CA $138 total, includes taxes & fees, Dec 13 - Dec 14 ### [Hilton Garden Inn Dover](https://www.expedia.ca/Dover-Hotels-Hilton-Garden-Inn-Dover.h2232384.Hotel-Information) ![A modern grocery store with refrigerated sections for chilled and frozen items, shelves stocked with beverages, and a coffee machine.](https://images.trvl-media.com/lodging/3000000/2240000/2232400/2232384/852282e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 1706 N Dupont Hwy, Dover, DE, 19901, US - Location: 3.6 km from Cheswold - Star rating: 3/5 - Guest rating: 8.8/10 (Excellent, 1000 reviews) - Price: CA $151, CA $168 total, includes taxes & fees, Dec 11 - Dec 12 ### [Hampton Inn Dover](https://www.expedia.ca/Dover-Hotels-Hampton-Inn-Dover.h34429.Hotel-Information) ![A modern dining area with a long table, multiple chairs, and pendant lighting.](https://images.trvl-media.com/lodging/1000000/40000/34500/34429/0ae4c00d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 1568 N Dupont Hwy, Dover, DE, 19901, US - Location: 4.1 km from Cheswold - Star rating: 2.5/5 - Guest rating: 8.6/10 (Excellent, 1001 reviews) - Price: CA $138, CA $153 total, includes taxes & fees, Dec 2 - Dec 3 ### [Sleep Inn & Suites Dover University Area](https://www.expedia.ca/Dover-Hotels-Sleep-Inn-And-Suites.h2115064.Hotel-Information) ![A lobby with a sofa, two armchairs, a coffee table, and a floor lamp. There is a painting on the wall and a door leading outside.](https://images.trvl-media.com/lodging/3000000/2120000/2115100/2115064/e37ca31f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 1784 N Dupont Hwy, Dover, DE, 19901, US - Location: 3.5 km from Cheswold - Star rating: 2.5/5 - Guest rating: 8.4/10 (Very good, 1001 reviews) - Price: CA $120, CA $133 total, includes taxes & fees, Dec 6 - Dec 7 - Review: . ### [Fairfield Inn & Suites by Marriott Dover](https://www.expedia.ca/Dover-Hotels-Fairfield-Inn-Suites-By-Marriott-Dover.h861129.Hotel-Information) ![A modern lobby with a reception desk, seating area, and a colorful carpet.](https://images.trvl-media.com/lodging/1000000/870000/861200/861129/0f2f267f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 655 N Dupont Hwy, Dover, DE, 19901, US - Location: 6.8 km from Cheswold - Star rating: 3/5 - Guest rating: 8.6/10 (Excellent, 584 reviews) - Price: CA $102, CA $113 total, includes taxes & fees, Dec 3 - Dec 4 ### [Comfort Suites Dover University Area](https://www.expedia.ca/Dover-Hotels-Comfort-Suites-Dover.h42248.Hotel-Information) ![A lobby with a stone wall, a flat-screen TV, framed pictures, blue sofas, a fireplace, and a wooden bookshelf.](https://images.trvl-media.com/lodging/1000000/50000/42300/42248/63ed2504.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 1654 N Dupont Hwy, Dover, DE, 19901, US - Location: 3.8 km from Cheswold - Star rating: 2.5/5 - Guest rating: 7.2/10 (Good, 1003 reviews) - Price: CA $118, CA $131 total, includes taxes & fees, Nov 22 - Nov 23 - Review: Comfy bed. ### [Bally's Dover Casino Resort](https://www.expedia.ca/Dover-Hotels-Dover-Downs-Hotel-Casino.h1572988.Hotel-Information) ![A spacious lobby with a central fountain, a grand chandelier, and a curved staircase.](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572988/f76eefb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 1131 N Dupont Hwy, Dover, DE, 19901, US - Location: 5.5 km from Cheswold - Star rating: 4/5 - Guest rating: 8.8/10 (Excellent, 3827 reviews) - Price: CA $87, CA $125 total, includes taxes & fees, Dec 16 - Dec 17 ### [Residence Inn Marriott Dover](https://www.expedia.ca/Dover-Hotels-Residence-Inn-Marriott-Dover.h1710788.Hotel-Information) ![A patio area with outdoor seating, a fire feature, and a stone wall.](https://images.trvl-media.com/lodging/2000000/1720000/1710800/1710788/67eeb718.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 600 Jefferic Blvd, Dover, DE, 19901, US - Location: 6.9 km from Cheswold - Star rating: 3/5 - Guest rating: 9/10 (Wonderful, 511 reviews) - Price: CA $150, CA $166 total, includes taxes & fees, Dec 14 - Dec 15 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. [See all properties in Cheswold](https://www.expedia.ca/Hotel-Search?startDate=2026-11-29&endDate=2026-11-30®ionId=553248634999403720&adults=2&sort=RECOMMENDED&openPlayBack=true) ## Frequently Asked Questions ### How much does a Cheswold vacation package cost? Offering great value package deals on Expedia, you'll be surprised at how little a vacation to Cheswold costs! Our packages make travel planning easier and save you more. ### What are the cheapest months to go to Cheswold? To pick up cheap Cheswold vacation packages, organize your trip outside of busy periods like public holidays and major festivals. You'll typically find better availability and lower prices when it's less busy. ### How many days is enough for Cheswold? With a well-planned schedule, you can easily hit the top Cheswold sights in a few days. But if you'd like to explore off the beaten track or go on day tours, think about 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 destination and preferred travel dates under our "Packages" tab. Then apply some filters, like "Popular locations" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Cheswold package deal straight away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Cheswold getaway off to a flying start. ### Is it cheaper to book a Cheswold vacation as a package? An Expedia vacation package could land you great savings when compared to arranging flights and stays individually. Better still, you can tailor your Cheswold getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out 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 a week before you take off. Don't want to leave things to the last minute? You can find sensational deals on your hotels and flights by booking ahead. ### How to plan a trip to Cheswold? 1. Pick your travel dates: What you want to do in Cheswold and your preferred season can help you decide when to get away. 2. Calculate your budget: Make sure you have enough money to cover everything from transportation and food to flights and activities. Your accommodations will probably be the biggest expense during your trip to Cheswold. 3. Work out your trip length: Think about how long you'd like to spend exploring Cheswold. Plan your itinerary so you can get to all the attractions and activities you're interested in without rushing. 4. Combine your airfare and accommodations: After you've nailed down your dates and duration, book the ideal Cheswold vacation package for you. \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.