Winchester Historic District

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 S$179 per night from 2 Aug to 3 Aug
S$179
2 Aug - 3 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 ...
9.4/10 Exceptional! (1,004 reviews)
"The George Washington Hotel was amazing! Our room was immaculate, the beds were fabulous, bathroom and all amenities exactly what we needed. Every person that we encountered was helpful, friendly and very kind. The hotel clearly pays attention to the smallest of details to make sure that your stay ..."

Reviewed on 2 Jul, 2026

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 S$113 per night from 30 Jul to 31 Jul
S$113
30 Jul - 31 Jul
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 ...
9/10 Wonderful! (1,002 reviews)
"This newly renovated, squeaky clean hotel is a favorite of ours as a stop off on our I-81 journeys. It is at an excellent location, quiet, clean, and the rooms are spacious. Hotel gym, breakfast, and pool are excellent additions to our stay here. They are also pet friendly and have a nice spot to ..."

Reviewed on 28 Jun, 2026

Spark by Hilton Winchester
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
The price is S$131 per night from 26 Jul to 27 Jul
S$131
26 Jul - 27 Jul
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! (1,002 reviews)
"Very inviting front desk lobby. Staff was friendly and courteous. Area by lobby had information on area restaurants, things to do, very helpful."

Reviewed on 2 Jul, 2026

TRU 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 S$138 per night from 26 Jul to 27 Jul
S$138
26 Jul - 27 Jul
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 ...
9/10 Wonderful! (1,005 reviews)
"The breakfast was not very good. Save your 10bucks for McDonald's"

Reviewed on 2 Jul, 2026

Holiday Inn Winchester Se-Historic Gateway by IHG
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 S$136 per night from 21 Jul to 22 Jul
S$136
21 Jul - 22 Jul
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 and the clean rooms ...
9.2/10 Wonderful! (1,425 reviews)
"Very clean and comfortable hotel. Bathroom was very small, room a good size. A/C was comfortable. Reception pleasant"

Reviewed on 29 Jun, 2026

Microtel 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 S$116 per night from 26 Jul to 27 Jul
S$116
26 Jul - 27 Jul
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! (1,002 reviews)
"Hotel is starting to run down, needs some remodeling."

Reviewed on 1 Jul, 2026

Ramada by Wyndham Strasburg/Shenandoah Valley
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