The Best Historic Hotels in Winchester, VA from AED 392 in 2026

A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check availability on Winchester Historic Hotels

Tonight

Tomorrow

Next weekend

In two weeks

Our top choices for Winchester historic hotels

1. ❤️ Secluded 1940s Romantic Tiny House on the River

Shepherdstown

Joseph

AED 152

AED 392 total

includes taxes & fees

1 Oct - 2 Oct

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

Rileyville

Dave A.

AED 544

AED 978 total

includes taxes & fees

24 Sep - 25 Sep

Coffee/tea maker, fridge, microwave, oven

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

Rileyville

Elise D.

AED 544

AED 970 total

includes taxes & fees

22 Sep - 23 Sep

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

Rileyville

Bernard L.

AED 544

AED 978 total

includes taxes & fees

24 Sep - 25 Sep

2 restaurants; breakfast, lunch, dinner, and brunch served

5. Mimslyn Inn Historic Hotels Of America

Luray

Alison Smillie

AED 463

AED 572 total

includes taxes & fees

28 Sep - 29 Sep

6. Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment

The Plains

Jill M.

AED 909

AED 1,480 total

includes taxes & fees

24 Sep - 25 Sep

Smart TV, DVD player, books, video library

3 bedrooms, desk, iron/ironing board, travel crib

7. BEST LOCATION: Historic Shepherdstown Getaway

Shepherdstown

Dave D.

AED 808

AED 1,584 total

includes taxes & fees

28 Sep - 29 Sep

8. Airlie Hotel

Warrenton

Holly

AED 934

AED 1,093 total

includes taxes & fees

22 Sep - 23 Sep

View all properties

Top Winchester Hotel Reviews

Travelodge by Wyndham Winchester

10/10 Excellent

"Very nice stay great staff and very clean"

La Quinta Inn & Suites by Wyndham Winchester

8/10 Good

"Good economical stay. Very close to restaurants and stores."

Spark by Hilton Winchester

8/10 Good

"Staff were attentive and welcoming! Check in and out was easy. The location was great. Near several food and gas options. Only negative was the shower seal leaked."

Candlewood Suites Winchester by IHG

8/10 Good

"Friendly young man at front desk. Clean hotel, very comfy beds and pillows and a lot of water pressure. Large room with kitchen and large fridge with a freezer."

Fairfield Inn & Suites by Marriott Winchester

8/10 Good

"We stayed for 1 on night on our way back home. Comfortable beds, clean room & friendly staff. Breakfast had a lot of options, just the eggs looked water and rubbery. Wasn't hard to find something else to eat instead. We didn't use the pool and the rooster behind the building confused me when loading our items back into our truck in the morning, thought I was loosing my mind till I walked over a bit and seen him staring at me. Gave me a good chuckle. We would 100% stay here again."

Days Inn by Wyndham Winchester

8/10 Good

"Not too shabby. I would stay again"

Frequently asked questions

What should I expect on my historical trip to Winchester?

Visitors love the fascinating history they can explore on a trip to Winchester. The array of shops and top-notch restaurants are some of the places to visit while you're here. You can also discover the theater scene during your vacation in this vibrant area.

What's the best hotel in Winchester to be near historical sites?

Based on our travel expertise, Delightful and Serene Hundred Year Old Sweet Space Among the Gardens is a top guesthouse on Expedia for those interested in history, and it features onsite laundry facilities and in-room kitchens. Patsy Cline Historic House is a short 4-minute drive away. If you're interested in local history, another option for your trip is Peaceful Secret Gardens Tiny Home - A space to relax and get away from it all..

How many historically relevant hotels will I find in Winchester?

In Winchester, you'll find 76 hotel accommodations bookable on Expedia, including 3 designated as historic hotels or close to historic sites.

What are the top historical sites and other places in Winchester?

Winchester is notable for landmarks like Patsy Cline Historic House, Stonewall Jackson's Headquarters, and George Washington's Office. Cultural venues include Bright Box Theater, Museum of the Shenandoah Valley, and Old Court House Civil War Museum. A couple of additional sights to add to your agenda are Shenandoah Valley Discovery Museum and Apple Blossom Mall.

What is a historic hotel like in Winchester?

Guests who choose a historic hotel can stay someplace that has a national historic designation. A palace, castle, grand home or even an old police station, pub, lodge, or skyscraper can be identified as a historic hotel provided that it's of special interest. Traditional architecture and period features are often found in the public spaces and guestrooms of historic hotels in Winchester, giving a historical feel.

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

They are quite similar. "Historic hotel" is a term often used in the U.S., whereas "heritage hotel" is common in Asia and Europe. Historic hotels tend to place more significance on the building and architecture itself. Heritage hotels draw their meaning mainly from the cultural value and how it shaped the community.

Do historic hotels in Winchester have modern facilities?

Yes, every effort is made to preserve treasured traditions and historic facades, but hotel interiors are fitted with modern conveniences and safety features. Visitors should expect the popular amenities you'd get from a hotel such as private rooms with updated bathroom facilities, WiFi, and more. When you book a historic hotel in Winchester, it doesn't mean you will stay in a place that's rundown or uncomfortable for guests.

Explore a world of travel with Expedia

Millwood Vacations

Luxury Car Rentals in Cross Junction

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Winchester Historic Hotels

Our top choices for Winchester historic hotels

1. ❤️ Secluded 1940s Romantic Tiny House on the River

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

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

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

5. Mimslyn Inn Historic Hotels Of America

6. Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment