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Hotels in Middletown

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Check prices for these dates

Tonight
Dec 22 - Dec 23
Tomorrow
Dec 23 - Dec 24
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Where to stay in Middletown?

Dining
Wayside Inn
Wayside Inn
3.5 star property
9.2 out of 10, Wonderful, (417)
The price is $72
$89 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Wayside Inn
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.
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Budget hotels in Middletown and vicinity

Premium bedding, desk, soundproofing, iron/ironing board
Econo Lodge Woodstock - Shenandoah Valley I-81

Econo Lodge Woodstock - Shenandoah Valley I-81

Econo Lodge Woodstock - Shenandoah Valley I-81
2.0 star property
Woodstock
7.2 out of 10, Good, (636)
The price is $51
$57 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Econo Lodge Woodstock - Shenandoah Valley I-81
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.
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When is the best time to visit Middletown?

Our prices for hotels in Middletown are cheapest in February
Price trends for hotels in Middletown
Pricing is based on two traveler single night rates
View properties in December
Currently viewing crowd sizes and weather for December.
Typical weather for Middletown
December
Low crowds
High 7°C / low -1°C. Partly sunny.
View properties in December
7°
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December, Low crowds, average high temperature 7 degrees Celsius, average low temperature -1 degrees Celsius. Partly sunny.
-1°
4°
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January, High crowds, average high temperature 4 degrees Celsius, average low temperature -4 degrees Celsius. Snow likely.
-4°
7°
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February, Moderate crowds, average high temperature 7 degrees Celsius, average low temperature -3 degrees Celsius. Snow likely.
-3°
12°
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March, Low crowds, average high temperature 12 degrees Celsius, average low temperature 1 degrees Celsius. Partly sunny.
1°
18°
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April, Moderate crowds, average high temperature 18 degrees Celsius, average low temperature 6 degrees Celsius. Sunny most days.
6°
23°
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May, High crowds, average high temperature 23 degrees Celsius, average low temperature 11 degrees Celsius. Sunny most days.
11°
28°
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June, Low crowds, average high temperature 28 degrees Celsius, average low temperature 16 degrees Celsius. Sunny most days.
16°
31°
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July, High crowds, average high temperature 31 degrees Celsius, average low temperature 18 degrees Celsius. Sunny most days.
18°
30°
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August, Moderate crowds, average high temperature 30 degrees Celsius, average low temperature 18 degrees Celsius. Sunny most days.
18°
26°
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September, Moderate crowds, average high temperature 26 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
14°
19°
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October, High crowds, average high temperature 19 degrees Celsius, average low temperature 8 degrees Celsius. Sunny most days.
8°
12°
weather_partly_sunny
November, Low crowds, average high temperature 12 degrees Celsius, average low temperature 2 degrees Celsius. Partly sunny.
2°
Monthly weather averages (˚C)

Top landmarks in Middletown

Belle Grove Plantation

If you're planning a bit of sightseeing during your trip, head to Belle Grove Plantation— just one of the landmarks located 1.4 mi (2.2 km) from central Middletown.
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Cedar Creek Battlefield Foundation

If seeing the sights is on your list of things to do, head to Cedar Creek Battlefield Foundation— just one of the landmarks located 1.2 mi (1.9 km) from central Middletown.
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Learn more about Middletown

Middletown is well-known for its attractions such as Belle Grove Plantation and Shenandoah River. Visitors to this historical city speak highly of the bars whereas sights include Wayside Theater and Cedar Creek and Belle Grove National Historical Park.

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Nana’s Irish Pub was a great and delicious stop off the main road on the way to Asheville, NC. Super cute redesigned bank. The bank door is still in the corner and is not a closet. Highly suggested for a pit stop!
Photo by Samantha Keyes
Open Photo by Samantha Keyes

Check out reviews of Middletown hotels guests love

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"The breakfast staff is helpful "
Martin 1-night trip
Posted 4 hours ago
La Quinta Inn & Suites by Wyndham Winchester

Frequently asked questions

What accommodations do travelers recommend in Middletown?
Guests like Econo Lodge Inn & Suites Middletown - Winchester South, Comfort Inn & Suites Winchester and Hampton Inn Front Royal.
Can I book refundable accommodations in Middletown?
If you need the flexibility to change your plans to Middletown, most hotels provide refundable* bookable rates. You can see these properties by searching our site and using the "fully refundable" filter to narrow down the results.
What will the weather in Middletown be like during my visit?
July and August are typically the warmest months in Middletown when the average temp is 72°F. January and February are the coldest months when the average temperature is 36°F. September and May are the months with the most rain.
Why should I book my Middletown hotel with Hotels.com?
There are lots of reasons to book your Middletown trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.