Compare Winchester Chalets

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Featured Winchester Chalets

Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>

Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>

Front Royal VA
Guests of this chalet enjoy a hot tub, an arcade/game room, and laundry facilities. Other amenities at this family-friendly chalet include barbecue grills and a garden.
Hot Tub
Kitchen
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI

Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI

Harpers Ferry WV
$277 nightly
The price is $298 total per night
$298 total
Jan 14 - Jan 15
Total with taxes and fees
This chalet features a hot tub and barbecue grills. This smoke-free chalet also has a garden.
Hot Tub
Kitchen
Cozy w/Fire Pit, Grill, Screened Porch & WiFi

Cozy w/Fire Pit, Grill, Screened Porch & WiFi

Harpers Ferry WV
$283 nightly
The price is $304 total per night
$304 total
Jan 12 - Jan 13
Total with taxes and fees
This chalet is a smoke-free chalet.
Kitchen
Pet friendly
3 Fireplaces, Hot Tub, Fire Pit, Deck, Pool Access

3 Fireplaces, Hot Tub, Fire Pit, Deck, Pool Access

Hedgesville WV
$432 nightly
The price is $470 total per night
$470 total
Jan 19 - Jan 20
Total with taxes and fees
Guests of this chalet enjoy features like a gym, a hot tub, and laundry facilities. Additional amenities include a garden and barbecue grills.
Pool
Hot Tub
Modern Harpers Ferry Cabin w Hot Tub, Deck, WiFi!

Modern Harpers Ferry Cabin w Hot Tub, Deck, WiFi!

Harpers Ferry WV
$315 nightly
The price is $340 total per night
$340 total
Jan 26 - Jan 27
Total with taxes and fees
This chalet features a hot tub and a garden. This smoke-free chalet also has barbecue grills.
Hot Tub
Kitchen
Cabin w Hot Tub, WiFi, Deck, Grill & Dog-Friendly!

Cabin w Hot Tub, WiFi, Deck, Grill & Dog-Friendly!

3 out of 5
Berkeley Springs WV
$349 nightly
The price is $377 total per night
$377 total
Jan 19 - Jan 20
Total with taxes and fees
Guests staying at this chalet enjoy a hot tub, laundry facilities, and barbecue grills. This smoke-free chalet also has a garden.
Hot Tub
Kitchen
Chalet w Hot Tub, Fire Pit, Grill & Deck

Chalet w Hot Tub, Fire Pit, Grill & Deck

2 out of 5
Luray VA
Guests staying at this chalet enjoy a hot tub, laundry facilities, and a garden. This smoke-free chalet also has barbecue grills.
Hot Tub
Kitchen
5 Bedroom Suites, Hot Tub, Jacuzzi Tub & Game Room

5 Bedroom Suites, Hot Tub, Jacuzzi Tub & Game Room

Berkeley Springs WV
$739 nightly
The price is $809 total per night
$809 total
Jan 19 - Jan 20
Total with taxes and fees
Guests staying at this chalet enjoy a hot tub, laundry facilities, and barbecue grills.
Hot Tub
Kitchen
Timber frame chalet with incredible views minutes from Shenandoah National Park.

Timber frame chalet with incredible views minutes from Shenandoah National Park.

Linden VA
Guests staying at this chalet enjoy a hot tub, laundry facilities, and barbecue grills. Transportation is made easy with limo/town car service. Friendly staff can provide concierge services, and also offer advice about sightseeing.
Hot Tub
Kitchen
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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.

Winchester Ski Accommodation

    Hotel Strasburg

    Hotel Strasburg

    213 S. Holliday Street Strasburg VA
    Motel 6 Front Royal, VA

    Motel 6 Front Royal, VA

    141 West 15th Street Front Royal VA
    $58 nightly
    The price is $65 total per night from Jan 12 to Jan 13
    $65 total
    Jan 12 - Jan 13
    Total with taxes and fees
    6.8/10 (503 reviews)
    Ramada by Wyndham Strasburg/Shenandoah Valley

    Ramada by Wyndham Strasburg/Shenandoah Valley

    21 Signal Knob Dr Strasburg VA
    $73 nightly
    The price is $81 total per night from Jan 20 to Jan 21
    $81 total
    Jan 20 - Jan 21
    Total with taxes and fees
    8.2/10 Very Good! (1,000 reviews)
    The George Washington Hotel, A Wyndham Grand Hotel

    The George Washington Hotel, A Wyndham Grand Hotel

    103 E Piccadilly St Winchester VA
    $127 nightly
    The price is $143 total per night from Jan 18 to Jan 19
    $143 total
    Jan 18 - Jan 19
    Total with taxes and fees
    9.2/10 Wonderful! (1,007 reviews)
    TownePlace Suites by Marriott Winchester

    TownePlace Suites by Marriott Winchester

    170 Getty Ln Winchester VA
    $113 nightly
    The price is $123 total per night from Jan 12 to Jan 13
    $123 total
    Jan 12 - Jan 13
    Total with taxes and fees
    8.8/10 Excellent! (483 reviews)

Hotel Options in Winchester

    Microtel Inn & Suites by Wyndham Winchester

    Microtel Inn & Suites by Wyndham Winchester

    150 Faraday Plaza Winchester VA
    $80 nightly
    The price is $87 total per night from Feb 9 to Feb 10
    $87 total
    Feb 9 - Feb 10
    Total with taxes and fees
    9/10 Wonderful! (1,426 reviews)
    La Quinta Inn & Suites by Wyndham Winchester

    La Quinta Inn & Suites by Wyndham Winchester

    1055 Millwood Pike, Route 50 East Winchester VA
    $92 nightly
    The price is $100 total per night from Jan 13 to Jan 14
    $100 total
    Jan 13 - Jan 14
    Total with taxes and fees
    9.2/10 Wonderful! (2,241 reviews)
    Travelodge by Wyndham Winchester

    Travelodge by Wyndham Winchester

    160 Front Royal Pike Winchester VA
    $68 nightly
    The price is $74 total per night from Jan 13 to Jan 14
    $74 total
    Jan 13 - Jan 14
    Total with taxes and fees
    8.4/10 Very Good! (1,083 reviews)

Chalets

Book the best chalets in Winchester
Take a break from reality and kick back in a Winchester chalet on your next vacation. Stay right in the middle of all the action, but feel like you’re miles away. Be as active or as relaxed as you want. Your chalet is truly yours. No one can tell you what to do on your chalet stay—and it’s the best way to enjoy a getaway.

Get the most from your chalet stay
You’ll make incredible new memories at chalets in Winchester. They look great in your photos, with sunning backdrops and cozy touches like fireplaces and exposed beam ceilings. Wake up to light streaming through your big picture window and admire your incredible view. Don’t just look at the great outdoors, though. Get out there and experience all that Winchester has to offer.

Bring the whole group, because you’ll find plenty of space to spread out at Winchester chalet houses. Whether you use all those bedrooms for the kids or for your crazy crew, you can settle in quickly thanks to chalets’ convenient amenities. Whip up a meal in no time in the kitchen or kitchenette, or whip out your phone to call for delivery. Cozy up to the fire, or fire up the blender for some drinks. When you’ve got a chalet, it’s going to be good day.

Winchester Chalets essential information

Accommodation
60 Chalets
Lowest Price
$65
Highest Price
$809
Popular accommodation
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)
, Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI, Cozy w/Fire Pit, Grill, Screened Porch & WiFi, 3 Fireplaces, Hot Tub, Fire Pit, Deck, Pool Access, Modern Harpers Ferry Cabin w Hot Tub, Deck, WiFi!, Cabin w Hot Tub, WiFi, Deck, Grill & Dog-Friendly!, Chalet w Hot Tub, Fire Pit, Grill & Deck, 5 Bedroom Suites, Hot Tub, Jacuzzi Tub & Game Room, Timber frame chalet with incredible views minutes from Shenandoah National Park.