Find Hotels with WiFi in Old Town Winchester, VA

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Check availability on Old Town Winchester Hotels with WiFi

Our top choices for Old Town Winchester hotels with wifi

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel
3.5 star property
Old Town Winchester
9.4 out of 10, Exceptional, (1010)
"Great hotel!"
United States
CHARLES
The price is AED 465
AED 527 total
includes taxes & fees
22 Dec - 23 Dec
The George Washington Hotel, A Wyndham Grand Hotel

Yellow Submarine trendy basement apt and courtyard

Yellow Submarine trendy basement apt and courtyard
Old Town Winchester
7.6 out of 10, Good, (4)
"We loved the character and personality kf both Winchester and"
United States
Jenna N.
Yellow Submarine trendy basement apt and courtyard

WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Old Town Winchester
9.0 out of 10, Wonderful, (6)
"Indigo Blue is in a beautiful neighborhood and we loved the house and location!"
United States
Tricia M.
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

Pretty Little Apt by the Train II

Pretty Little Apt by the Train II
2.0 star property
Old Town Winchester
9.8 out of 10, Exceptional, (7)
"Great time. Love this city"
United States
Barbara B.
Pretty Little Apt by the Train II

Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city
Old Town Winchester
9.0 out of 10, Wonderful, (14)
"Adorable place and perfect for Winchester and surrounding parks, wineries, and farms."
United States
Tracy F.
The price is AED 735
AED 1,302 total
includes taxes & fees
16 Jan - 17 January 2026
Nostalgia Lane in the heart of the city

Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown

Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown
Old Town Winchester
Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown

Scarborough Fair walk to downtown two story apt

Scarborough Fair walk to downtown two story apt
Old Town Winchester
9.6 out of 10, Exceptional, (5)
"Charming home! Lovely decor. Was perfect for our stay. Great location, walkable to the historical district. Host was very friendly and communicative. "
United States
Stephanie L.
Scarborough Fair walk to downtown two story apt

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1382)
"Clean nice room with a hot breakfast, a lot nicer then other places in Winchester especially for the price. Highly recommend "
United States
Curtis
The price is AED 273
AED 297 total
includes taxes & fees
31 Dec - 1 January 2026
Microtel Inn & Suites by Wyndham Winchester

TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
Winchester
9.0 out of 10, Wonderful, (770)
"The hotel was clean and the staff was pleasant."
United States
Sherri
The price is AED 262
AED 285 total
includes taxes & fees
5 Jan - 6 January 2026
TRU By Hilton Winchester

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1077)
"Very clean, helpful staff"
United States
Kathleen
The price is AED 363
AED 395 total
includes taxes & fees
12 Jan - 13 January 2026
Comfort Inn & Suites 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.

Top Old Town Winchester Hotel Reviews

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