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 NZ$235 per night from 23 Aug to 24 Aug
NZ$235
23 Aug - 24 Aug
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
Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
The price is NZ$150 per night from 2 Sept to 3 Sept
NZ$150
2 Sept - 3 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! (1,004 reviews)
"Large size room, very clean! Personal hand written greeting from manager was a great touch in today's world!"

Reviewed on 13 Aug 2026

Spark by Hilton Winchester
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 NZ$181 per night from 23 Aug to 24 Aug
NZ$181
23 Aug - 24 Aug
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
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
Fully refundableReserve now, pay when you stay
The price is NZ$202 per night from 17 Aug to 18 Aug
NZ$202
17 Aug - 18 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! (2,263 reviews)
"This hotel was full of ants. I booked my hotel through Expedia Hotels.com, and now I have to do all the footwork to get reimbursed for my food that was in sealed bags wrapped up that was completely invaded by aunt. All of my clothing had ants in it. my bed had ants in it. There was four different ..."

Reviewed on 15 Aug 2026

La Quinta Inn & Suites by Wyndham 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 NZ$153 per night from 23 Aug to 24 Aug
NZ$153
23 Aug - 24 Aug
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
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 NZ$166 per night from 30 Aug to 31 Aug
NZ$166
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 ...
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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