Middletown Packages (Flight + Hotel)

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Top hotels in Middletown

Econo Lodge Inn & Suites Middletown - Winchester South

Econo Lodge Inn & Suites Middletown - Winchester South

2 out of 5
91 Reliance Road Middletown VA
Fully refundableReserve now, pay when you stay
The price is ฿2,359 per night from 19 Jul to 20 Jul
฿2,359
฿2,602 total
19 Jul - 20 Jul
includes taxes & fees
5.8/10 (320 reviews)
"Horrible experience, property is disgusting. The whole hotel smells like cigarettes and drugs. They don’t clean the rooms. There was diarrhea on the floor sheets had stains on them. I got a headache and sick to my stomachjust from being there.. not only did they refuse to give me a refund they tried ..."

Reviewed on 30 Jun 2026

Econo Lodge Inn & Suites Middletown - Winchester South
Wayside Inn

Wayside Inn

3.5 out of 5
7783 Main St Middletown VA
The price is ฿4,031 per night from 6 Jul to 7 Jul
฿4,031
฿4,778 total
6 Jul - 7 Jul
includes taxes & fees
9.2/10 Wonderful! (441 reviews)
"Quaint and quiet. Love historic places like this."

Reviewed on 30 Jun 2026

Wayside Inn
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
Fully refundableReserve now, pay when you stay
The price is ฿3,022 per night from 19 Jul to 20 Jul
฿3,022
฿3,363 total
19 Jul - 20 Jul
includes taxes & fees
9.2/10 Wonderful! (1,009 reviews)
"Good location but floor was sticky in room and no closets, just open hooks."

Reviewed on 4 Jul 2026

TRU By Hilton Winchester
See all 635 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.

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.
See properties

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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.