Compare Winchester Guest House Rentals

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Guest Houses in Winchester

$131 nightly

$151 total

Sep 7 - Sep 8

Total with taxes and fees

The Legacy Inn features free WiFi in public areas, free use of bicycles, and a library. If you decide to drive, there's free parking. Additional amenities include a terrace, laundry facilities, and wedding services.

Parking included

Free WiFi

$349 nightly

$376 total

Aug 26 - Aug 27

Total with taxes and fees

White Moose Inn features free WiFi in public areas, free use of bicycles, and a computer station. You can put free parking to good use if you drive. The front desk has multilingual staff that can help with concierge services and luggage storage. Other amenities at this golf guesthouse include a terrace, a garden, and wedding services.

Breakfast included

Parking included

The Bluebird Suite at Harpers Ferry Guest House

$236 nightly

$263 total

Aug 25 - Aug 26

Total with taxes and fees

This guesthouse is a smoke-free guesthouse.

Free WiFi

Air conditioning

Free Cancellation

Reserve now, pay when you stay

$322 nightly

$367 total

Aug 25 - Aug 26

Total with taxes and fees

Guests of Briar Patch Bed & Breakfast Inn enjoy free WiFi in public areas, a hot tub, and a seasonal outdoor pool. A stay here includes free parking. This guesthouse also has barbecue grills.

Pool

Hot Tub

The Goldfinch Suite at Harpers Ferry Guest House

$236 nightly

$263 total

Aug 25 - Aug 26

Total with taxes and fees

This guesthouse is a smoke-free guesthouse.

Air conditioning

Parking available

The Cardinal Suite at Harpers Ferry Guest House

$265 nightly

$295 total

Aug 30 - Aug 31

Total with taxes and fees

This guesthouse is a smoke-free guesthouse.

Free WiFi

Air conditioning

Riverfront Oasis with Mountain Views, close to town

At this guesthouse, guests have access to features like laundry facilities. This smoke-free guesthouse also has barbecue grills.

Free WiFi

Air conditioning

2-Room Chickadee Suite @ Harpers Ferry Guest House

$271 nightly

$302 total

Aug 25 - Aug 26

Total with taxes and fees

This guesthouse is a smoke-free guesthouse.

Air conditioning

Parking available

Delightful and Serene Hundred Year Old Sweet Space Among the Gardens

At this guesthouse, guests have access to features like laundry facilities. This adults-only guesthouse also has a garden.

Air conditioning

Parking available

Don't see what you're looking for?

See all available properties in Winchester

View all properties

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.

Hotel Options in Winchester

Spark by Hilton Winchester

150 Wingate Dr Winchester VA

$80 nightly

$91 total

Sep 17 - Sep 18

Total with taxes and fees

Holiday Inn Winchester Se-Historic Gateway by IHG

333 Front Royal Pike Winchester VA

$96 nightly

$107 total

Aug 30 - Aug 31

Total with taxes and fees

9/10 Wonderful! (1,025 reviews)

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St Winchester VA

$122 nightly

$138 total

Aug 30 - Aug 31

Total with taxes and fees

Winchester Guest Houses essential information

Accommodation	18 Guest Houses
Lowest Price	$91
Highest Price	$376
Popular accommodation	The Legacy Inn, White Moose Inn, The Bluebird Suite at Harpers Ferry Guest House, Briar Patch Bed & Breakfast Inn, The Goldfinch Suite at Harpers Ferry Guest House, The Cardinal Suite at Harpers Ferry Guest House, Riverfront Oasis with Mountain Views, close to town , 2-Room Chickadee Suite @ Harpers Ferry Guest House, Delightful and Serene Hundred Year Old Sweet Space Among the Gardens