Winchester Hotel Guide - Historic Hotels in Winchester, Virginia

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Check availability on Winchester Historic Hotels

Tonight
2 Aug - 3 Aug
Tomorrow
3 Aug - 4 Aug
Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug

Top Winchester Historic Hotels

Mimslyn Inn Historic Hotels Of America
Stunning two-story building with a grand central entrance and symmetrical facade.

Mimslyn Inn Historic Hotels Of America

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Loved the hotel & amenities. With 2 outdoor pools it never seemed crowded. "
The price is €120
includes taxes & fees
4 Aug - 5 Aug
Mimslyn Inn Historic Hotels Of America
Airlie Hotel
Relax in a serene outdoor setting with a cozy fire pit surrounded by Adirondack chairs.

Airlie Hotel

3.5 star property
8.8 out of 10, Excellent, (307)
"We love the old charm this hotel offers, while the rooms are cozy and new!"
The price is €119
includes taxes & fees
3 Aug - 4 Aug
Airlie Hotel
Historic Bluemont Village Home
Relax in a serene outdoor space surrounded by lush greenery and a stone wall.

Historic Bluemont Village Home

10.0 out of 10, Exceptional, (36)
"This was one of the best VRBO experiences I’ve had! Communication with the host was exceptional, and the home itself was gorgeous. It’s clear they have put a lot of thought into make this house a perfect getaway — it is beautifully decorated and has all the comforts of home. We will definitely stay here again!"
Historic Bluemont Village Home
❤️ Secluded 1940s Romantic Tiny House on the River
Relax by the fire pit surrounded by lush greenery and enjoy a peaceful atmosphere.

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (57)
"We truly loved this location and definitely will be back!"
The price is €128
includes taxes & fees
1 Sept - 2 Sept
❤️ Secluded 1940s Romantic Tiny House on the River
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Relax in a secluded hot tub surrounded by a forested landscape.

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

10.0 out of 10, Exceptional, (321)
"This is, I believe, my fourth time staying at Solitude. I keep coming back because it is perfect. "
The price is €230
includes taxes & fees
4 Aug - 5 Aug
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
The Cottage on Royal - Historic Leesburg Home
Relax by the fire pit in a serene outdoor space surrounded by Adirondack chairs and string lights.

The Cottage on Royal - Historic Leesburg Home

10.0 out of 10, Exceptional, (13)
"Thoroughly enjoyed our stay. The property was in a great location and was in excellent condition with all the amenities you needed to make your stay comfortable. I will definitely book this property again on my next visit!"
The Cottage on Royal - Historic Leesburg Home
Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view
Relax by the serene pool, surrounded by lush greenery and an atmosphere.

Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view

9.8 out of 10, Exceptional, (32)
"It is an amazing place with a gorgeous view of the mountains and welcoming host"
The price is €401
includes taxes & fees
3 Aug - 4 Aug
Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view
The Van Gogh Room in Villa
Relax by the serene pool surrounded by lush greenery and a lattice archway.

The Van Gogh Room in Villa

9.0 out of 10, Wonderful, (63)
"Good stay. Beautiful view. Having never been to Purceville, I was taken aback by the fact that the establishment on s dirt road. "
The price is €311
includes taxes & fees
14 Aug - 15 Aug
The Van Gogh Room in Villa
Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary
Traditional charm abounds in this historic building, featuring a covered porch with hanging flower baskets and a cozy outdoor seating area.

Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary

9.8 out of 10, Exceptional, (86)
"Great place that works well for Rixey Manor weddings "
The price is €366
includes taxes & fees
2 Sept - 3 Sept
Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
Sit and enjoy the view from this outdoor seating area with a round table and two chairs.

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

9.8 out of 10, Exceptional, (294)
"We stayed just 2 nights and absolutely loved it. Totally going back again! "
The price is €268
includes taxes & fees
10 Aug - 11 Aug
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
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.

Top Winchester Hotel Reviews

Spark by Hilton Winchester

Spark by Hilton Winchester

10/10 Excellent
"Friendly & easy check"
Andrea 1-night trip
Posted 15 hours ago
Spark by Hilton Winchester

Frequently asked questions

What should a history buff expect from a stay in Winchester?
Visitors love the significant historical sites they discover on a trip to Winchester. The major shopping area and top-notch restaurants are some of the places to visit while you're here. You can also discover the theatre scene during your holiday to this vibrant area.
What's the best accommodation in Winchester to absorb the local history?
Based on our travel expertise, Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed is a top guest house on Expedia for those interested in history, and it features on-site 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 stay is Secret Gardens Carriage House.
How many historically relevant hotels are located in Winchester?
Winchester has 73 hotels 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 Abram's Delight. Cultural venues include Bright Box Theater, Winchester Little Theater and Museum of the Shenandoah Valley. A couple of additional sights to add to your itinerary are Shenandoah Valley Discovery Museum and Apple Blossom Mall.
What is a historic hotel like in Winchester?
By choosing a historic hotel, you can sleep in a place that has an officially recognised national historic designation. A stately home, palace or even a lodge, old police station or skyscraper can be considered a historic hotel provided that it's of special interest. Traditional architecture and period features are typically found within the guestrooms or public spaces of historic hotels in Winchester, giving a historical feel.
What is the difference between a historic hotel and a heritage hotel?
These terms are 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 emphasise the architecture and building. Mainly a heritage hotel draws meaning from the place's cultural value and how it influenced the community.
Do historic hotels in Winchester have modern facilities?
Yes, every effort is made to preserve treasured traditions and historic facades, while interiors have safety features and modern conveniences. Visitors should expect the popular amenities from a contemporary hotel such as private rooms with updated bathroom facilities, heating and air conditioning, and free and fast Internet. When you book a historic hotel in Winchester, it doesn't mean you will stay in a place that's uncomfortable for guests or rundown.