Winchester Historic District Travel Guide

Winchester

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


Top hotels in Winchester Historic District

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 ฿4,376 per night from 19 Nov to 20 Nov
฿4,376
฿4,958 total
19 Nov - 20 Nov
includes taxes & fees
Stay at this spa hotel in Winchester. Enjoy free Wi-Fi, a full-service spa and 2 restaurants. Our guests praise the helpful staff and the clean rooms in their ...
9.4/10 Exceptional! (1,006 reviews)
"The property was clean, quiet and comfortable. We had a room not facing the street, others in our party were facing the street and it was noisy. The bar was great, as well as the staff. Will definitely try to go back."

Reviewed on 7 Nov 2026

The George Washington Hotel, A Wyndham Grand Hotel
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike Winchester VA
Fully refundableReserve now, pay when you stay
The price is ฿2,350 per night from 1 Dec to 2 Dec
฿2,350
฿2,592 total
1 Dec - 2 Dec
includes taxes & fees
Stay at this motel in Winchester. Enjoy free parking, a 24-hour front desk and daily housekeeping. Our guests praise the helpful staff and the clean rooms in ...
Travelodge 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 ฿2,739 per night from 15 Nov to 16 Nov
฿2,739
฿3,048 total
15 Nov - 16 Nov
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! (1,448 reviews)
"Great stuff and place to stop for the night. I would stop again for the price and convenience but not more than a night or two"

Reviewed on 8 Nov 2026

Microtel Inn & Suites by Wyndham Winchester
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
The price is ฿2,725 per night from 15 Nov to 16 Nov
฿2,725
฿3,033 total
15 Nov - 16 Nov
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. ...
9.2/10 Wonderful! (1,003 reviews)
"Front desk was very helpful"

Reviewed on 9 Nov 2026

TRU By Hilton Winchester
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 out of 5
21 Signal Knob Dr Strasburg VA
The price is ฿2,539 per night from 15 Nov to 16 Nov
฿2,539
฿2,826 total
15 Nov - 16 Nov
includes taxes & fees
Stay at this business-friendly hotel in Strasburg. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in ...
Ramada by Wyndham Strasburg/Shenandoah Valley
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 ฿3,476 per night from 15 Nov to 16 Nov
฿3,476
฿3,868 total
15 Nov - 16 Nov
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 ...
La Quinta 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.

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 Bright Box Theater or Shenandoah Valley Discovery Museum.



Winchester Historic District Travel Guide