Middletown Vacations from $460
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The Latest Middletown Vacation Packages
- Red Roof Inn PLUS+ Wilmington - Newark
Sep 18 - Sep 20Red Roof Inn PLUS+ Wilmington - Newark + Flight
Newark2 nights2.5 star property6.8/10 - (1,001 reviews)"Bugs in the room. Shower water barely warm or scolding. Older building and dirty parking lot. Shady customers. Low price shows why there is many issues. Stay away and spend a few more dollars for a better hotel."Reviewed July 17, 2026Roundtrip • Chicago (CHI) - Wilmington (ILG)ORD - ILG • 1 stop ILG - ORD • 1 stop$479$460found 1 day agoper traveler - Budget Motor Lodge
Sep 18 - Sep 20Budget Motor Lodge + Flight
New Castle2 nights2.0 star property4.0/10 - (5 reviews)"When I got there they said it was no rims available like I didn’t book in advance "Reviewed November 29, 2020Roundtrip • Chicago (CHI) - Wilmington (ILG)ORD - ILG • 1 stop ILG - ORD • 1 stop$1,047$898found 1 day agoper traveler - Hampton Inn & Suites Wilmington Christiana
Sep 18 - Sep 20Hampton Inn & Suites Wilmington Christiana + Flight
Newark2 nights2.5 star property8.4/10 - Very Good (1,002 reviews)"Everything was amazing. The only issue I had was the beds are a little to firm for my liking, however my kids loved the firmness."Reviewed July 18, 2026Roundtrip • Chicago (CHI) - Wilmington (ILG)ORD - ILG • 1 stop ILG - ORD • 1 stop$535$508found 1 day agoper traveler - Embassy Suites by Hilton Newark Wilmington South
Sep 18 - Sep 20Embassy Suites by Hilton Newark Wilmington South + Flight
Newark2 nights3.5 star property8.4/10 - Very Good (1,010 reviews)"The carpet in the room is old and stained, the bathroom is old for the price per night I would expected something a bit newer, with amenities that are not old worn out. There is no free drinking water available in the room. The light fixture is missing the light bulb. I like the fact that it’s located in the heart of Newark, DE and it’s close and convenient. The breakfast lacks variety and is not appealing, the food are very salty."Reviewed July 18, 2026Roundtrip • Chicago (CHI) - Wilmington (ILG)ORD - ILG • 1 stop ILG - ORD • 1 stop$640$609found 1 day agoper traveler - Hyatt Place Newark - Main Street
Sep 18 - Sep 20Hyatt Place Newark - Main Street + Flight
Newark2 nights3.0 star property9.4/10 - Exceptional (504 reviews)Roundtrip • Chicago (CHI) - Wilmington (ILG)ORD - ILG • 1 stop ILG - ORD • 1 stop$774$743found 1 day agoper traveler
Discover the most popular places to visit in Middletown
Middletown Hotel Deals
Fairfield Inn & Suites by Marriott Middletown
Fairfield Inn & Suites by Marriott Middletown
Holiday Inn Express & Suites Middletown by IHG
Holiday Inn Express & Suites Middletown by IHG
Residence Inn By Marriott Wilmington
Residence Inn By Marriott Wilmington
Super 8 by Wyndham Havre De Grace Aberdeen Area
Super 8 by Wyndham Havre De Grace Aberdeen AreaFrequently Asked Questions
How much does a Middletown vacation package cost?
Offering great value package deals from $460 on Expedia, you'll be thrilled with how little a vacation to Middletown costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Middletown?
You can usually find lower rates and greater availability in March, August and December. Explore our cheap Middletown vacation packages and you could score some great off-season discounts.
How many days is enough for Middletown?
The ideal duration of your Middletown vacation depends on what you'd like to see. Typically, a handful of days to a week will give you enough time to visit all the leading attractions and discover some hidden treasures along the way.
Is it worth booking a vacation package to Middletown?
From cool attractions such as Dutch Country Farmers Market and Frog Hollow Golf Club to its excellent festivals, a Middletown vacation is sure to exceed your expectations. With so much to see and do, it's time to find out for yourself why Middletown is such a good vacation destination.
How to find the best Middletown package deals?
Landing a cheap Middletown package deal is a breeze with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget, apply a few filters and browse what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most economical Middletown package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Middletown vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and hotels individually. Better still, you can tailor your Middletown escape to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Middletown?
If you've got your Middletown travel dates locked in, book as early as you can to grab some outstanding deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for quick escapes.
Does Expedia offer Book Now, Pay Later Middletown vacation packages?
Jet off on your ideal getaway to Middletown with Expedia's Book Now, Pay Later vacations. No need to save up or hold off until your next payday — we've joined forces with online lender Affirm to offer you flexibility and choice. Our vacation packages with payment plans let you spread the cost across 3, 6 or 12 months. With no hidden or late payment fees, you can easily stick to your budget and snag great deals before they disappear.
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Things to do in and around Middletown
Middletown, Delaware, is perfect for family and outdoor vacations, offering a range of activities such as educational experiences and shopping at local centers and malls. Visitors can enjoy day tours, golf getaways, and romantic retreats, making it an ideal destination for great vacations. Whether you're exploring the city or indulging in leisure activities, Middletown has something for everyone.
Shopping
Middletown offers a delightful shopping experience with local boutiques and shops. If you're up for a drive, visit Christiana Mall, 16 miles away, featuring entertainment and family-friendly options. Brookside Shopping Center and University Office Plaza Shopping Center, both 15 miles away, also provide a variety of stores and dining choices.
Recreation
Experience the serene outdoors at Frog Hollow Golf Club, where lush greens invite relaxation and friendly competition. For a tranquil retreat, visit Kirkwood Soccer Complex, offering wellness vibes in a peaceful park setting. Alternatively, enjoy a rejuvenating session at Elkton Indoor Tennis, designed for wellness and relaxation.
Adventure
Experience the thrill of motorsports at Dover International Speedway, located 21 miles from Middletown. Get your adrenaline pumping with paintball at Mansion House, only 10 miles away. For family fun, visit Vince's Sports Center, an exciting arcade adventure zone 15 miles from Middletown.
Nightlife
Middletown's nightlife offers a vibrant mix of activities. Enjoy craft cocktails at The Barley Taproom, or indulge in live music at Crabby Dick's. For a laid-back atmosphere, visit 2nd Street Bar & Grill, where you can unwind with friends and savor delicious pub fare.
Find the best attractions in and around Middletown
Middletown, Delaware, is an ideal destination for family vacations, offering a blend of outdoor and city experiences. Visitors can explore popular attractions like urban parks, marinas, and nearby state parks, ensuring fun for all ages. For those seeking relaxation, the local beach provides a perfect spot to unwind. Whether you're looking for adventure or leisure, Middletown has something to offer every traveler.
- Frightland: Experience the thrill of Frightland, Delaware's premier theme park, located in Middletown. With a variety of haunted attractions and family-friendly entertainment, it's perfect for those seeking both scares and fun. Enjoy rides, games, and seasonal events that create a memorable outing for visitors of all ages.
- Back Creek Golf Club: This welcoming golf course and country club in Middletown offers a relaxed atmosphere for golf enthusiasts. With friendly staff and affordable rates, it’s an ideal spot to enjoy a round of golf while soaking in scenic views and connecting with fellow players.
- Historic Houses of Odessa: Just 3 miles from Middletown, explore the Historic Houses of Odessa, where rich cultural heritage meets stunning architecture. Wander through these beautifully preserved homes and learn about Delaware's history in an enchanting setting.
Best time to go to Middletown
The best time to visit Middletown is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.
Tips to save on your trip to Middletown
- Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Middletown.
- Consider traveling during the off-peak season (typically January to March) for more affordable package holidays to Middletown.
- Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
- Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.