Middletown Holidays

Photo by Stephanie Sutton
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Middletown

Wayside Inn
Wayside Inn
3.5 out of 5
7783 Main St, Middletown, VA
The price is S$154 per night from 10 Nov to 11 Nov
S$154
includes taxes & fees
10 Nov - 11 Nov
9.2/10 Wonderful! (356 reviews)
"This historical property was very well kept and welcoming! I rebooked on checkout."

Reviewed on 29 Sep,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 S$137 per night from 1 Dec to 2 Dec
S$137
includes taxes & fees
1 Dec - 2 Dec
9/10 Wonderful! (1,680 reviews)
"I always stay there and it clean"

Reviewed on 6 Nov,2024

La Quinta Inn & Suites by Wyndham Winchester
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 S$91 per night from 19 Nov to 20 Nov
S$91
includes taxes & fees
19 Nov - 20 Nov
8/10 Very Good! (1,118 reviews)
"Room was clean and the location was quiet."

Reviewed on 7 Nov,2024

Travelodge by Wyndham Winchester
See all 570 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 rentals 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.

Popular places to visit

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

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.