Old Town Winchester Travel Guide

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 Rp2.331.455 per night from 28 Oct to 29 Oct
Rp2.331.455
Rp2.641.539 total
28 Oct - 29 Oct
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
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 Rp1.645.144 per night from 1 Nov to 2 Nov
Rp1.645.144
Rp1.831.046 total
1 Nov - 2 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! (1,444 reviews)
"The room was clean but we picked this hotel so we could use the pool which was very dirty. Piles of dirt in every corner and water was quite cool. Room was clean and beds were comfortable. Bathroom very tight. Alarm on radio was set and woke us up at 3 AM! We passed on breakfast didn’t look too ..."

Reviewed on 3 Oct 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 Rp1.598.293 per night from 1 Nov to 2 Nov
Rp1.598.293
Rp1.778.900 total
1 Nov - 2 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. ...
9.2/10 Wonderful! (1,001 reviews)
"Stay was nice for 1 night. If it would have been longer it wouldn’t have been ideal. Can easily hear rooms next door."

Reviewed on 3 Oct 2026

TRU By Hilton Winchester
Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
The price is Rp1.382.279 per night from 2 Nov to 3 Nov
Rp1.382.279
Rp1.566.122 total
2 Nov - 3 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 ...
Spark by Hilton Winchester
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 Rp1.843.312 per night from 4 Oct to 5 Oct
Rp1.843.312
Rp2.051.717 total
4 Oct - 5 Oct
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 ...
La Quinta Inn & Suites by Wyndham Winchester
Quality Inn Winchester

Quality Inn Winchester

2.5 out of 5
1601 Martinsburg Pike Winchester VA
The price is Rp1.504.770 per night from 25 Oct to 26 Oct
Rp1.504.770
Rp1.674.810 total
25 Oct - 26 Oct
includes taxes & fees
Stay at this hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their reviews. ...
9.4/10 Exceptional! (1,003 reviews)
"Room was clean and quiet. Very good breakfast and easy access."

Reviewed on 2 Oct 2026

Quality Inn Winchester
See all 374 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 Bright Box Theater and Shenandoah Valley Discovery Museum.

Old Town Winchester Travel Guide