Winchester Historic District Travel Guide

Tourist Guide

A stone building with a sign reading "W. 8th Street."
A building with a green roof and ornate architectural details.
A red brick church with a blue door and a clock tower.
A brick building with a cafe on the ground floor and a church steeple in the background.
A brick-paved street lined with shops and cafes, under a cloudy sky.

Stay near popular Winchester Historic District attractions


Our pick of the best Winchester Historic District Hotel Deals

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5
103 E Piccadilly St Winchester VA
The price is AU$193 per night from 7 Sept to 8 Sept
AU$193
7 Sept - 8 Sept
includes taxes & fees
Stay at this spa hotel in Winchester. Enjoy a full-service spa, 2 restaurants and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms ...
The George Washington Hotel, A Wyndham Grand Hotel
Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city

Winchester VA
The price is AU$464 per night from 30 Aug to 31 Aug
AU$464
30 Aug - 31 Aug
includes taxes & fees
Stay at this apartment in Winchester. Enjoy laundry facilities, an in-room coffee maker and air conditioning. Popular attractions Bright Box Theater and Old ...
9.2/10 Wonderful! (18 reviews)
"Perfect location for exploring Winchester. Beautiful rooms. Clean and comfortable."

Reviewed on 27 July 2026

Nostalgia Lane in the heart of the city
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

3 out of 5
333 Front Royal Pike Winchester VA
The price is AU$158 per night from 27 Sept to 28 Sept
AU$158
27 Sept - 28 Sept
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
Holiday Inn Winchester Se-Historic Gateway by IHG
Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
The price is AU$122 per night from 27 Sept to 28 Sept
AU$122
27 Sept - 28 Sept
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking and a fitness centre. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,002 reviews)
"Great stay! Very clean and the staff was great."

Reviewed on 26 Aug 2026

Spark by Hilton Winchester
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3 out of 5
1055 Millwood Pike, Route 50 East Winchester VA
The price is AU$152 per night from 30 Aug to 31 Aug
AU$152
30 Aug - 31 Aug
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
9.2/10 Wonderful! (2,268 reviews)
"Always a great stay! Friendly staff, convenient to the university. Clean and quiet! Thank you again"

Reviewed on 26 Aug 2026

La Quinta Inn & Suites by Wyndham Winchester
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza Winchester VA
The price is AU$135 per night from 30 Aug to 31 Aug
AU$135
30 Aug - 31 Aug
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking and a fitness centre. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,458 reviews)
"The property was clean! The rooms were comfortable and clean. Didn't like the small hard bed pillows! And when there's two people in the room, I wish they would provide two packets of regular coffee. Not one regular coffee and one decaf."

Reviewed on 25 Aug 2026

Microtel Inn & Suites by Wyndham Winchester
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.

Our guide on where to stay in Winchester Historic District

Find the best Winchester Historic District areas for the activities you enjoy most.

Old Town Winchester

Old Town Winchester is popular for its abundant dining options, and if you're looking for more to see and do, you might think about a trip to Shenandoah Valley Discovery Museum or Bright Box Theater.



Winchester Historic District Travel Guide

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