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

Things to do


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 ฿4,381 per night from 19 Nov to 20 Nov
฿4,381
฿4,964 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 ...
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
The price is ฿2,363 per night from 1 Dec to 2 Dec
฿2,363
฿2,606 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 ฿2,782 per night from 8 Nov to 9 Nov
฿2,782
฿3,096 total
8 Nov - 9 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! (1,440 reviews)
"J’ai apprécié la proximité de la grande route. Ce que j’ai aimé moins c’est le bruit. C’est pas très bien isolé, nous étions au 3eme étage et on s’est fait réveillé par les gens au-dessus de nous à 4:00 le matin. Et on les entendais parler fort. Heureusement ils sont partis quelque temps après ..."

Reviewed on 5 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 ฿2,740 per night from 15 Nov to 16 Nov
฿2,740
฿3,050 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. ...
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 ฿2,542 per night from 12 Nov to 13 Nov
฿2,542
฿2,829 total
12 Nov - 13 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 ...
8.2/10 Very good! (1,016 reviews)
"We always like to stay at the hotel if we are needing a stay in that area. It is always very good and the onsite restaurant is excellent"

Reviewed on 3 Nov 2026

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 ฿3,496 per night from 8 Nov to 9 Nov
฿3,496
฿3,891 total
8 Nov - 9 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 ...
9.2/10 Wonderful! (2,262 reviews)
"We only spent one night but we loved the location close to some shops, the beds were comfortable and the staff were helpful! I would recommend."

Reviewed on 5 Nov 2026

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