Middletown Holiday Packages

Save when you book Middletown package deals

Choose two or more items and save on your trip:

Book your Middletown holiday

Wotif can help you save some bucks!

So what's the secret? Simple, we can roll your accommodation and flights into one affordable little package.

Travelling in Middletown will be stress free with all those extra savings.

You might even see savings of up to . And with more than 550 airlines and 665,000 properties, it's easy to craft your dream holiday.

Some of the most competitive prices available are on Wotif. So pack your luggage, dust off your passport and hit the clouds!

Middletown Accommodation

With only 2 accommodations in Middletown to select from, it'd be smart to secure one of Wotif's terrific deals as soon as you can.

Wotif's got some great suggestions if you're wondering where to stay. Have a squiz at the rates and amenities at the Wayside Inn (7783 Main St) and the Econo Lodge Inn & Suites (91 Reliance Road), two popular options nearby.

Car Hire in Middletown

If you were thinking about renting a vehicle directly at Eastern West Virginia Regional Airport, you'll have to think again. But don't stress! Flag down a taxi, make the short journey to Enterprise (901 N Queen St) and you'll be driving away in a rental car before you know it.

Holidays to Middletown

Just like sipping on cocktails and scoffing down ice cream, it's never too early to start studying up on your next travel destination. If you're on your way to Middletown, here are some basics which will help you along the way.

So, how do you reach this unique neighbourhood from central Winchester? Easy. Travel southwest for 20 kilometres.

If you've heard travellers not only rave about Middletown but about Winchester in general, then you won't be at all surprised to learn that some 26 000 people call it their home.

Top Middletown hotels

Wayside Inn

Wayside Inn

3.5 out of 5
7783 Main St, Middletown, VA
The price is AU$196 per night from 16 Nov to 17 Nov
AU$196
16 Nov - 17 Nov
includes taxes & fees
Wayside Inn: Hotel with free WiFi and free parking. Located near the airport.
Friendly staff, historic atmosphere, terrific restaurant. Entire hotel was furnished with antiques, including the guest rooms

Reviewed on 28 Oct 2025

Opens in a new windowWayside Inn
Red Roof Inn Winchester, VA

Red Roof Inn Winchester, VA

2 out of 5
991 Millwood Pike, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is AU$114 per night from 2 Nov to 3 Nov
AU$114
2 Nov - 3 Nov
includes taxes & fees
Red Roof Inn Winchester, VA: Pet-friendly hotel with free WiFi and free parking. Located in the historical district.
Good Stay
Good stay for an overnight trip. Kumar treated us like very special people! Clean and very comfortable. Only problem - ADA shower very difficult to use for someone less then 5’4. Reaching the shower head was impossible. Would not recommend this place for special needs.

Reviewed on 22 Oct 2025

Opens in a new windowRed Roof Inn Winchester, VA
Econo Lodge Inn & Suites

Econo Lodge Inn & Suites

2 out of 5
91 Reliance Road, Middletown, VA
Fully refundableReserve now, pay when you stay
The price is AU$104 per night from 6 Nov to 7 Nov
AU$104
6 Nov - 7 Nov
includes taxes & fees
Econo Lodge Inn & Suites: Pet-friendly hotel with free WiFi and free parking. Located in the city centre.
Room was fine.

Reviewed on 20 Oct 2025

Opens in a new windowEcono Lodge Inn & Suites
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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.