Middletown Holidays
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- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Top hotels in Middletown
Wayside Inn
7783 Main St Middletown VA
S$184
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (444 reviews)
"There was not an elevator. We were not able to stay at the Wayside Inn. We were taken aback when we were informed that the front door would be locked at 9pm. While there is a pad with a code for access, there is no staff on site. It was not what we expected, that is not the fault of staff or management. ..."
Reviewed on 1 Aug, 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
Fully refundable
S$136
12 Aug - 13 Aug
includes taxes & fees
9/10 Wonderful! (1,014 reviews)
"Had to go back to desk 2 times after checking in while my wife stood outside our room with luggage in the hall because the keys didn't work. Very frustrating! Also, only 7 channels worked on the TV, was told this was Comcast fault."
Reviewed on 6 Aug, 2026
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
Fully refundableReserve now, pay when you stay
S$177
13 Aug - 14 Aug
includes taxes & fees
9.4/10 Exceptional! (1,014 reviews)
"It's hard to pick out one thing that makes the George Washington excellent. Is it the staff? Yes. But is it the ambiance of an historic hotel? Certainly. How about the location? For sure! Can it be the memories of past stays? Oh, yes as we always celebrate our anniversary in Winchester. What about ..."
Reviewed on 7 Aug, 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.
Stay near popular Middletown attractions
Belle Grove Plantation
8.4/10 (8 reviews)
This Jeffersonian-inspired Manor House showcases antebellum plantation life and Civil War history. Explore the heritage apple orchard and original outbuildings while enjoying panoramic mountain views.
Cedar Creek Battlefield Foundation
8.6/10 (7 reviews)
The Cedar Creek Battlefield Foundation preserves this pivotal 1864 Civil War site through exhibits and trails. Experience history during October's annual reenactment featuring authentic battle scenarios.
Cedar Creek and Belle Grove National Historical Park
9.0/10 (6 reviews)
Explore the pivotal Civil War battlefield where Union forces secured the Shenandoah Valley in 1864. Tour the elegant Belle Grove Manor House and follow interpretive trails detailing strategic troop movements.
Jackson's Chase Golf Course
6.0/10 (1 review)
This scenic 18-hole course weaves through the rolling Shenandoah Valley, challenging golfers of all abilities. Enjoy the serene natural setting while navigating its strategically designed par-72 layout.
Frequently asked questions
How much does a Middletown holiday package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a holiday to Middletown costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Middletown?
January, February and June are the best times to search for cheap Middletown holiday packages. Opting to travel in quieter months means you can typically find reduced prices on accommodation and flights.
How many days is enough for Middletown?
With a well-planned schedule, you can easily visit the most popular Middletown attractions in a few days. But if you'd like to explore off the beaten track or go on day trips, think about booking your Middletown holiday for longer.
How to find the best Middletown package deals?
Use Expedia's handy filters to find some of the best Middletown package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Middletown package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your holiday package well in advance.
Is it cheaper to book a Middletown holiday as a package?
You can enjoy significant savings on your next Middletown escape by booking a personalised holiday package. Click on the "Package" heading, then select your travel dates and destination to see some great flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Middletown?
Land amazing discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Middletown adventure.
How to plan a trip to Middletown?
- Pick the best time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to travel to Middletown.
- Budget wisely: As well as the cost of your stay, you should consider other expenses. These include flights, food and transportation. Also, set aside some extra funds for unexpected expenses that could crop up during your trip to Middletown.
- Set the duration of your trip: Start by compiling a list of the sights and activities you'd like to get to in Middletown. Then, estimate how long you'll need at each, as well as any travel time.
- Combine your accommodation and airfare: After you've settled on your travel dates and duration, lock in the perfect Middletown holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
