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

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Check availability on Winchester Historic Hotels

Next weekend
7 Aug - 9 Aug
In two weeks
14 Aug - 16 Aug

Our top choices for Winchester historic hotels

Interior

1. ANS Inn has clean, spacious rooms located on 5 acres with little traffic.

ANS Inn has clean, spacious rooms located on 5 acres with little traffic.
Winchester
The price is AED 221
AED 588 total
includes taxes & fees
4 Aug - 5 Aug
ANS Inn has clean, spacious rooms located on 5 acres with little traffic.
Terrace/patio

2. The Cottage on Royal - Historic Leesburg Home

The Cottage on Royal - Historic Leesburg Home
Leesburg's Old and Historic District
10.0 out of 10, Exceptional, (21 reviews)
"Delightful cottage, super convenient, and our host was extremely nice and attentive. "
United States
Mark M.
The price is AED 1,160
AED 2,103 total
includes taxes & fees
5 Aug - 6 Aug
The Cottage on Royal - Historic Leesburg Home
Meeting facility

3. Airlie Hotel

Airlie Hotel
3.5 star property
Warrenton
8.6 out of 10, Excellent, (358 reviews)
"Nice updated room, wonderful and friendly staff, beautiful grounds with gardens and walk trails. Nice onsite restaurant. Overall a great experience and would definitely come back."
United States
Lynne
The price is AED 810
AED 961 total
includes taxes & fees
3 Aug - 4 Aug
Airlie Hotel
Outdoor dining

4. The Van Gogh Room in Villa

The Van Gogh Room in Villa
Purcellville
9.0 out of 10, Wonderful, (70 reviews)
"What a lovely place. Quiet and very prettyLots of good recommendations for the Lica areaWe’ll likely be back"
United States
Tom W.
The price is AED 1,194
AED 1,516 total
includes taxes & fees
3 Aug - 4 Aug
The Van Gogh Room in Villa
Outdoor dining

5. Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.

Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.
Purcellville
9.8 out of 10, Exceptional, (38 reviews)
"Beautiful location, quiet, and Maud is a wonderful person."
United States
Dennis G.
The price is AED 1,286
AED 1,784 total
includes taxes & fees
3 Aug - 4 Aug
Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.
Smart TV, books, stereo

6. Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
Harpers Ferry
10.0 out of 10, Exceptional, (169 reviews)
"Great place to stay. Perfect location. House was very clean and exactly as described"
United States
Maureen Q.
The price is AED 790
AED 1,591 total
includes taxes & fees
6 Aug - 7 Aug
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
Exterior

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

Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment
The Plains
10.0 out of 10, Exceptional, (6 reviews)
"This was a great place to escape to! Very quiet and peaceful but close to some great restaurants and vineyards."
United States
Jill M.
The price is AED 909
AED 1,480 total
includes taxes & fees
3 Aug - 4 Aug
Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment
Smart TV, fireplace, DVD player, books

8. Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Harpers Ferry
9.6 out of 10, Exceptional, (109 reviews)
"Wonderful place to stay. Comfotable beds and big enough for a large crowd. The property owners are incredibly kind and responsive. Our family loved our stay. "
United States
Jenn C.
The price is AED 526
AED 1,563 total
includes taxes & fees
26 Aug - 27 Aug
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Coffee/tea maker, fridge, microwave, oven

9. Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Harpers Ferry
9.8 out of 10, Exceptional, (113 reviews)
"The house was as advertised and served as a great location for our retreat! We had a freak plumbing emergency, and the host fixed it within literally an hour. "
United States
Connie V.
The price is AED 732
AED 2,215 total
includes taxes & fees
10 Aug - 11 Aug
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Outdoor spa tub

10. Private Home, Hot Tub, Wifi, Rural Setting, Gas Stove, 70" SmartTV

Private Home, Hot Tub, Wifi, Rural Setting, Gas Stove, 70" SmartTV
Harpers Ferry
9.6 out of 10, Exceptional, (19 reviews)
"Nice place. Had issues with ac they was quick to take care of it"
United States
Brett D.
The price is AED 423
AED 1,468 total
includes taxes & fees
10 Aug - 11 Aug
Private Home, Hot Tub, Wifi, Rural Setting, Gas Stove, 70" SmartTV
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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Top Winchester Hotel Reviews

Skyland

Skyland

10/10 Excellent
"It is magical. We stayed in a premium room. It was clean. Perfect. The views are spectacular!"
Linda 2-night trip
Posted 6 hours ago
Skyland

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 family-friendly 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. A couple of other options to soak up the local history include ANS Inn has clean, spacious rooms located on 5 acres with little traffic. and 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 77 hotel accommodations bookable on Expedia, including 4 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 Stonewall Jackson's Headquarters, Patsy Cline Historic House, and Abram's Delight. Cultural venues include Winchester Little Theater, Museum of the Shenandoah Valley, and Bright Box Theater. 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.

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