Middletown Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Samantha Keyes
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    Better together

    Save up to NZ$616 when you book a flight and hotel together*
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    Find the right fit

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Middletown Holiday

Our pick of the best Middletown Hotel Deals

Wayside Inn
Wayside Inn
3.5 out of 5
7783 Main St, Middletown, VA
The price is NZ$194 per night from 20 July to 21 July
NZ$194
20 July - 21 July
includes taxes & fees
9.2/10 Wonderful! (390 reviews)
"We stayed last year on July 4th. ...really liked it...decided to make it an annual event. I like the small town atmosphere."

Reviewed on 7 Jul. 2025

Wayside Inn
Travelodge by Wyndham Winchester
Travelodge by Wyndham Winchester
2.5 out of 5
160 Front Royal Pike, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is NZ$125 per night from 20 July to 21 July
NZ$125
20 July - 21 July
includes taxes & fees
8.4/10 Very Good! (1,095 reviews)
Great stay!
"Very surprised! This is by far the best Travelodge I've ever stayed at. Clean, quick check in, friendly staff, quiet, safe. Cant say about breakfast."

Reviewed on 8 Jul. 2025

Travelodge by Wyndham Winchester
Holiday Inn Winchester Se-Historic Gateway by IHG
Holiday Inn Winchester Se-Historic Gateway by IHG
3 out of 5
333 Front Royal Pike, Winchester, VA
Fully refundable
The price is NZ$174 per night from 13 July to 14 July
NZ$174
13 July - 14 July
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
"The shower floor could be upgraded and I wish there was not carpet in room but other then that it was great! We will stay again! Breakfast was excellent and the bar/restaurant was open until 9pm and that was on July 4th holiday!"

Reviewed on 6 Jul. 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 597 properties in Middletown
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.

Discover the most popular places to visit in Middletown

Belle Grove Plantation

Belle Grove Plantation

Find out about the history of Middletown when you spend time at Belle Grove Plantation. Wander the riverfront or discover the mountain views in this vibrant area.

Belle Grove Plantation

Wayside Theater

Get tickets for a show at Wayside Theater, a popular theatre in Middletown. Amble around this vibrant area's riverfront or experience its entertainment venues.

Wayside Theater

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.