Old Town Winchester

Winchester

A white neoclassical building with columns, an American flag, and a clock tower.
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 Old Town Winchester attractions

Shenandoah Valley Discovery Museum

8.6/10 (78 reviews)
You can take time to visit Shenandoah Valley Discovery Museum during your travels to Winchester. While in this walkable area, you can savour the top-notch restaurants.
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Top hotels in Old Town Winchester

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 9 Aug to 10 Aug
S$179
9 Aug - 10 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
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike Winchester VA
The price is S$107 per night from 27 Jul to 28 Jul
S$107
27 Jul - 28 Jul
includes taxes & fees
Stay at this motel in Winchester. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in their reviews. ...
Travelodge by Wyndham 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$123 per night from 9 Aug to 10 Aug
S$123
9 Aug - 10 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
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
The price is S$144 per night from 30 Jul to 31 Jul
S$144
30 Jul - 31 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. ...
TRU By Hilton 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 S$139 per night from 9 Aug to 10 Aug
S$139
9 Aug - 10 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 helpful staff and the clean rooms ...
9.2/10 Wonderful! (1,443 reviews)
"This is a gem. Great location off I81 with a gas station as you drive in or out. Parking waa ample. The property is pristine, we'll lit and quiet. The staff is wonderful and the breakfast had a nice variety of choices."

Reviewed on 25 Jul, 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 9 Aug to 10 Aug
S$116
9 Aug - 10 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
See all 365 properties in Old Town 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 Old Town Winchester

Find the best Old Town Winchester areas for the activities you enjoy most.
A red brick church with a blue door and a clock tower.
Photo by Fernando Begay
Open Photo by Fernando Begay

Winchester Historic District

While visiting Winchester Historic District, you might make a stop by sights like Winchester Little Theater and Shenandoah Valley Discovery Museum.

Old Town Winchester