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

Falling Leaf Cabin - Rustic Charm With Modern Decor!

Falling Leaf Cabin - Rustic Charm With Modern Decor!

Rileyville VA
Falling Leaf Cabin - Rustic Charm With Modern Decor!: Family-friendly cabin with free WiFi and 1 hot tub. Located near skiing.
Cabin was as described and easy access with great communication with the host.

Reviewed on 18 Jan 2026

Opens in a new windowFalling Leaf Cabin - Rustic Charm With Modern Decor!
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3 out of 5
1055 Millwood Pike, Route 50 East Winchester VA
Fully refundableReserve now, pay when you stay
The price is AU$154 per night from 18 Feb to 19 Feb
AU$154
18 Feb - 19 Feb
includes taxes & fees
La Quinta Inn & Suites by Wyndham Winchester: Pet-friendly hotel with free breakfast and free WiFi. Located in a shopping district.
Staff was very courteous and friendly throught our entire stay! Everything was updated and very clean. Kids LOVED the pool and breakfast.

Reviewed on 10 Feb 2026

Opens in a new windowLa 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 AU$196 per night from 22 Feb to 23 Feb
AU$196
22 Feb - 23 Feb
includes taxes & fees
The George Washington Hotel, A Wyndham Grand Hotel: Business-friendly hotel with free WiFi and an indoor pool. Located in the business district.
Spotless

Reviewed on 15 Feb 2026

Opens in a new windowThe George Washington Hotel, A Wyndham Grand Hotel
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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.