Book the Best HISTORIC Hotels in Middletown in 2026

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Check availability on Middletown Historic Hotels

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Our top choices for Middletown historic hotels

1. "Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

Rileyville

Dave A.

CA $220

CA $392 total

includes taxes & fees

Sep 28 - Sep 29

Coffee/tea maker, fridge, microwave, oven

2. "The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA

Rileyville

Elise D.

CA $207

CA $352 total

includes taxes & fees

Sep 23 - Sep 24

3. "Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

Rileyville

Bernard L.

CA $207

CA $352 total

includes taxes & fees

Sep 23 - Sep 24

4. 1min walk to The Inn • Entire Colonial 3BR House Fast WiFi, tub & full kitchen .

Washington

Daniel R.

CA $224

CA $389 total

includes taxes & fees

Oct 12 - Oct 13

View all properties

Top Middletown Hotel Reviews

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent

"Great stay."

Quality Inn Winchester

8/10 Good

"J"

DoubleTree by Hilton Front Royal Blue Ridge Shadows

10/10 Excellent

"Always a great stay when golfing at Blue Ridge Shadows!"

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent

"Loved the room set up"

Hampton Inn Front Royal

10/10 Excellent

"The property was excellent only thing was the pool wasn’t working. We were willing to pay the price per night because we thought we would be able to swim. Breakfast was awesome lots of good food and always plenty."

Wayside Inn

8/10 Good

"This is a quaint, historical place to stay with lots of antiques and interesting furnishings. We enjoyed the patio, pub and live music on the night we stayed. We would stay again if we find ourselves in the area."

Super 8 by Wyndham Front Royal Near Shenandoah National Park

10/10 Excellent

"This motel was very easy to find and convenient to many things, plus just down the road from the entrance of the Skyline Drive. I was greeted by Brian and he was very pleasant and extremely helpful in a genuine manner. (Hate hotels were the staff is so stuffy) Room was clean , and the bed comfy. It's a non smoking hotel, but it would be nice to add a sitting area outside to smoke. While they do have little "smoking stations" for cigarettes.... To enjoy a pipe or cigar is a nice hour ...and a glass of bourbon."

Holiday Inn Express Woodstock-Shenandoah Valley by IHG

10/10 Excellent

"Very clean, bed was comfortable, breakfast was good, overall a pleasant stay."

Days Inn by Wyndham Winchester

8/10 Good

"Not too shabby. I would stay again"

Frequently asked questions

What can a history buff expect from a stay in Middletown?

A visit to the historical places in Middletown is likely first on your travel itinerary. While you're out exploring, you might want to check out the bars and restaurants.

How many historically relevant hotels will I find in Middletown?

In Middletown, you'll find 3 hotel accommodations bookable on Expedia though you won't find many designated historic hotels.

What are the must-see historical sites and other places to visit in Middletown?

Middletown is notable for landmarks like Belle Grove Plantation. The picturesque setting of Shenandoah River and Cedar Creek and Belle Grove National Historical Park exemplify the area's natural beauty. Additionally, you might want to add Jackson's Chase Golf Course to your agenda.

What is a historic hotel like in Middletown?

Guests who choose historic hotels have the chance to stay in a place that's been recognized with a national historic designation. Historic hotels throughout the world can be castles, stately homes, palaces or even pubs, lodges, old police stations or skyscrapers. These types of hotels in Middletown typically retain original characteristics like traditional architecture and period features in their public spaces or guestrooms.

What is the difference between a historic hotel and a heritage hotel?

They are quite similar. "Historic hotel" is more commonly used in the U.S., while "heritage hotel" is often used in Asia and Europe. Historic hotels tend to put more importance on the architecture and building. Heritage hotels draw their meaning mainly from the place's cultural value and how it influenced the community.

Do historic hotels in Middletown have modern facilities?

Yes, efforts are made to preserve treasured traditions and historic facades, while interiors have safety features and modern conveniences. Tourists who book a stay should expect the popular amenities from a contemporary hotel such as WiFi, heating and air conditioning, and updated bathroom facilities. Booking a historic hotel in Middletown doesn't mean you will stay in a place that's rundown.

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Things to do in Winchester

Book Historic Hotels in Middletown on Expedia.com

Find Historic Hotels in Middletown, VA from CA $352

Change your mind

Treat yourself

Be picky

Check availability on Middletown Historic Hotels

Our top choices for Middletown historic hotels

1. "Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

2. "The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA

3. "Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

4. 1min walk to The Inn • Entire Colonial 3BR House Fast WiFi, tub & full kitchen .

Top Middletown Hotel Reviews

Country Inn & Suites by Radisson, Winchester, VA

Quality Inn Winchester

DoubleTree by Hilton Front Royal Blue Ridge Shadows

La Quinta Inn & Suites by Wyndham Winchester

Hampton Inn Front Royal

Wayside Inn

Super 8 by Wyndham Front Royal Near Shenandoah National Park

Holiday Inn Express Woodstock-Shenandoah Valley by IHG

Days Inn by Wyndham Winchester

Frequently asked questions

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