Middletown Holidays

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Top hotels in Middletown

La Quinta Inn & Suites by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester
2.5 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is €82 per night from 7 Apr to 8 Apr
€82
includes taxes & fees
7 Apr - 8 Apr
9/10 Wonderful! (1,899 reviews)
"Overall everything was good !!!"

Reviewed on 3 Apr 2025

La Quinta Inn & Suites by Wyndham Winchester
The George Washington Hotel, A Wyndham Grand Hotel
The George Washington Hotel, A Wyndham Grand Hotel
3.5 out of 5
103 E Piccadilly St, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is €131 per night from 20 Apr to 21 Apr
€131
includes taxes & fees
20 Apr - 21 Apr
9.2/10 Wonderful! (1,000 reviews)
"Beautiful hotel, super easy check in, restaurant on the property is Unos Pizzeria, just one block away is Old Town and we had an enjoyable evening strolling that area after dinner. We’ve already booked another stay for ‘our stop on the way home.’"

Reviewed on 31 Mar 2025

The George Washington Hotel, A Wyndham Grand Hotel
Spark by Hilton Winchester
Spark by Hilton Winchester
3 out of 5
150 Wingate Dr, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is €92 per night from 20 Apr to 21 Apr
€92
includes taxes & fees
20 Apr - 21 Apr
8.8/10 Excellent! (1,002 reviews)
"Great location, right off the highway. Will definitely stay here again!"

Reviewed on 3 Apr 2025

Spark by Hilton Winchester
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.

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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.