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

White Moose Inn
291 Main St Washington VA
$292 nightly
The price is $315 total per night
$315 total
Nov 22 - Nov 23
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 Legacy Inn
120 N Hawksbill St Luray VA
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

Briar Patch Bed & Breakfast Inn
23130 Briar Patch Ln Middleburg VA
Free Cancellation
Reserve now, pay when you stay
$245 nightly
The price is $279 total per night
$279 total
Dec 15 - Dec 16
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
Harpers Ferry WV
$199 nightly
The price is $222 total per night
$222 total
Nov 17 - Nov 18
Total with taxes and fees
This guesthouse is a smoke-free guesthouse.
Air conditioning
Parking available

The Bluebird Suite at Harpers Ferry Guest House
Harpers Ferry WV
$199 nightly
The price is $222 total per night
$222 total
Nov 17 - Nov 18
Total with taxes and fees
This guesthouse is a smoke-free guesthouse.
Free WiFi
Air conditioning

Riverview Suite at La Soledad
Harpers Ferry WV
$382 nightly
The price is $426 total per night
$426 total
Nov 15 - Nov 16
Total with taxes and fees
Guests staying at this guesthouse have access to laundry facilities, barbecue grills, and a garden.
Air conditioning
Parking available

Delightful and Serene Hundred Year Old Sweet Space Among the Gardens
Winchester VA
At this guesthouse, guests have access to features like laundry facilities. This adults-only guesthouse also has a garden.
Air conditioning
Parking available

2-Room Chickadee Suite @ Harpers Ferry Guest House
Harpers Ferry WV
$215 nightly
The price is $240 total per night
$240 total
Nov 15 - Nov 16
Total with taxes and fees
This guesthouse is a smoke-free guesthouse.
Air conditioning
Parking available

Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment
The Plains VA
$345 nightly
The price is $370 total per night
$370 total
Nov 16 - Nov 17
Total with taxes and fees
Guests staying at this guesthouse have access to laundry facilities, a garden, and barbecue grills.
Free WiFi
Air conditioning
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

Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$70 nightly
The price is $77 total per night from Dec 1 to Dec 2
$77 total
Dec 1 - Dec 2
Total with taxes and fees
8.8/10 Excellent! (1,064 reviews)

Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
$79 nightly
The price is $88 total per night from Nov 22 to Nov 23
$88 total
Nov 22 - Nov 23
Total with taxes and fees

La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
$93 nightly
The price is $103 total per night from Nov 29 to Nov 30
$103 total
Nov 29 - Nov 30
Total with taxes and fees
Winchester Guest Houses essential information
Accommodation | 16 Guest Houses |
|---|---|
Lowest Price | $77 |
Highest Price | $426 |
Popular accommodation | White Moose Inn, The Legacy Inn, Briar Patch Bed & Breakfast Inn, The Goldfinch Suite at Harpers Ferry Guest House, The Bluebird Suite at Harpers Ferry Guest House, Riverview Suite at La Soledad, Delightful and Serene Hundred Year Old Sweet Space Among the Gardens, 2-Room Chickadee Suite @ Harpers Ferry Guest House, Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment |
More to Explore
- Farmstay in White Post
- B&B in White Post
- Cabin Rentals in White Post
- Inns in White Post
- Hotels near Old Court House Civil War Museum
- Boutique Hotels in Winchester Historic District
- Cheap Hotels in Winchester Historic District
- Kid Friendly Hotels in Winchester Historic District
- Hotels with Pool in Winchester Historic District
- Luxury Hotels in Winchester Historic District
- Spa Resorts & in Winchester Historic District
- Winchester Historic District Hotels
- Hotels near The Kernstown Battlefield
- Hotels near Rocking S Ranch
- 3 Star Hotels in Boyce
- Farmstay in Boyce
- B&B in Boyce
- Cabin Rentals in Boyce
- Cottages in Boyce
- Boyce Hotels
- Motels in Boyce
- Villas in Boyce
- Hotels near Bright Box Theater
- Hotels near Handley Regional Library
- Gore Hotels
- Farmstay in Berryville
- B&B in Berryville
- Cabin Rentals in Berryville
- Chalets in Berryville
- Cottages in Berryville
- Extended Stay Hotels in Berryville
- Guest Houses in Berryville
- Gay Friendly Hotels in Berryville
- Hotels with Pool in Berryville
- Pet Friendly Hotels in Berryville
- Romantic Getaways & Hotels in Berryville
- Berryville Hotels
- Inns in Berryville
- Motels in Berryville
- Vacation Homes in Berryville
- Resorts in Berryville
- Hotels near Patsy Cline Historic House
- Apartments in Jordan Springs
- 3 Star Hotels in Old Town Winchester
- 4 Star Hotels in Old Town Winchester
- Boutique Hotels in Old Town Winchester
- Hotels with Balconies in Old Town Winchester
- Hotels with Bar in Old Town Winchester
- Hotels with Hot Tubs in Old Town Winchester
- Hotels with an Indoor Pool in Old Town Winchester
- Romantic Getaways & Hotels in Old Town Winchester
- Spa Resorts & in Old Town Winchester
- Old Town Winchester Hotels
- Hotels near Appleland Sports Center
- Hotels near Nalls Farm Market
- Hotels near Dinosaur Land
- Millwood Hotels
- Hotels near Winchester Medical Center
- Hotels near Museum of the Shenandoah Valley
- Apartments in Canterburg
- Hotels near Valerie Hill Winery
- Cross Junction Hotels
- Hotels near Shenandoah University
- Hotels near The Fire House Gallery
- Hotels near George Washington's Office
- Hotels near Mt Hebron Cemetery
- Hotels near Apple Blossom Mall
- Hotels near Rock Harbor Golf Course
- 4 Star Hotels in Stephenson
- 5 Star Hotels in Clear Brook
- Farmstay in Stephens City
- B&B in Stephens City
- Cabin Rentals in Stephens City
- Chalets in Stephens City
- Cottages in Stephens City
- Cheap Hotels in Stephens City
- Hotels with Hot Tubs in Stephens City
- Hotels with Restaurants in Stephens City
- Hotels with a Wedding Venue in Stephens City
- Winery Hotels in Stephens City
- Stephens City Hotels
- Motels in Stephens City
- Vacation Homes in Stephens City
- Hotels near Shenandoah Valley Discovery Museum
- Hotels near State Arboretum of Virginia
