Middletown Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Stephanie Sutton
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Our pick of the best Middletown Hotel Deals

Microtel Inn & Suites by Wyndham Winchester
Microtel Inn & Suites by Wyndham Winchester
2.5 out of 5
150 Faraday Plaza, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is NZ$150 per night from 2 Jun to 3 Jun
NZ$150
per night
2 Jun - 3 Jun
8.8/10 Excellent! (768 reviews)
Great place
"Pool is cold, staff is super nice. Place is clean and very nice lots near it for food mall is only 8 min away. Breakfast was ok. Have stayed here several times and will continue to stay here as needed."

Reviewed on 19 May 2024

Microtel Inn & Suites by Wyndham Winchester
Wayside Inn
Wayside Inn
3.5 out of 5
7783 Main St, Middletown, VA
The price is NZ$190 per night from 26 May to 27 May
NZ$190
per night
26 May - 27 May
9.2/10 Wonderful! (331 reviews)
"A peek into the world of the past in a very comfortable environment!"

Reviewed on 21 May 2024

Wayside Inn
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 NZ$194 per night from 26 May to 27 May
NZ$194
per night
26 May - 27 May
8.8/10 Excellent! (1,338 reviews)
Great stay!
"Check in was fast and easy. Fresh coffee and lemon water greeted us in the entrence. Our room was super cozy and modern. Lots of plugs for devices. Desk area with chair for business use. Both beds were super comfy. Room was quiet and just what we needed after a long day of travel. Work out facilities ..."

Reviewed on 20 May 2024

La Quinta Inn & Suites by Wyndham Winchester
See all 544 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.

Frequently asked questions

How much does a Middletown holiday package cost?
Discover the best of Middletown from just . Choose from a wonderful selection of rental cars, hotels and flights to suit every budget. You can pick up even more discounts when you add a couple of sightseeing tours to your holiday package.
How do I get a cheap travel package to Middletown?
Browse and book everything in the one place with our Middletown holiday packages. You’ll discover deals on flights, hotels and more that’ll keep your hip pocket happy and your sense of adventure alive. And, with more than 550 air carriers and 1 000 000 properties around the world to pick from, there are endless opportunities to mix and match all you want.
Where should I stay in Middletown?
With loads to explore in Middletown, we suggest you book a hotel near its attractions. Belle Grove Plantation, Jacksons Chase Golf Course and Cedar Creek and Belle Grove National Historical Park are some popular ones to put on your must-see list.
What are the top hotels in Middletown?
If this will be your first visit to Middletown, secure a room at Wayside Inn or Econo Lodge Inn & Suites. Both hotels have good amenities and are popular options with many travellers.
How far in advance should I book my Middletown holiday?
Savvy travellers often reserve their seats as early as possible. You can normally look up international airfares on Expedia up to a year before your flight. If you’re purchasing your ticket at the last minute, don’t worry. Bargain prices sometimes become available just weeks prior to departure.
What does an Expedia Middletown travel package include?
From hotels and airfares to car rentals, Expedia can help you create a Middletown package that fits you. Heading away for a week or two? Check out a rental car, hotel and flight bundle. If you can only manage a quick getaway, a hotel and airfare deal may suit you better. Experiences can also be added after you’ve booked. Our travel packages make it easy to plan and save.
What should I know before booking a Middletown travel package?
Booking all the parts of your trip together is a simple way to save. Combine your car rentals, flights and hotels into a convenient package. But hotels aren’t your only option. Expedia has all sorts of properties, including holiday homes such as beachside villas and city apartments. You’ve got choices galore!
Can I choose my airline with a Middletown Expedia holiday package?
The choice is all yours! Expedia has access to more than 550 airlines worldwide, so you can customize your Middletown getaway according to your travel needs.
If I'm not able to travel, can I cancel my Middletown holiday package?
It’s good to know that you can cancel your Middletown booking if your travel plans have changed. Whether you’ll incur a fee or not depends on your airline, hotel or car rental company. It may be possible to cancel or change your booking free of charge if you booked in the last 24 hours. Visit our Customer Service Portal to find out more.

Discover the most popular places to visit in Middletown

Image for 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
Image for Cedar Creek Battlefield Foundation

Cedar Creek Battlefield Foundation

You can learn about the history of Middletown with a visit to Cedar Creek Battlefield Foundation. Stroll along the riverfront or experience the entertainment venues in this vibrant area.

Cedar Creek Battlefield Foundation
Image for Cedar Creek and Belle Grove National Historical Park

Cedar Creek and Belle Grove National Historical Park

Explore the great outdoors at Cedar Creek and Belle Grove National Historical Park, a lovely green space in Middletown. Stroll along the riverfront or experience the area's entertainment venues.

Cedar Creek and Belle Grove National Historical Park

More holiday ideas

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