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 RM499 per night from 23 Aug to 24 Aug
RM499
RM566 total
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 RM315 per night from 2 Sept to 3 Sept
RM315
RM357 total
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 RM380 per night from 23 Aug to 24 Aug
RM380
RM435 total
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
The price is RM438 per night from 17 Aug to 18 Aug
RM438
RM487 total
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 RM330 per night from 23 Aug to 24 Aug
RM330
RM367 total
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 RM360 per night from 30 Aug to 31 Aug
RM360
RM400 total
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
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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 Shenandoah Valley Discovery Museum and Stonewall Jackson's Headquarters.

Old Town Winchester