Holiday rentals near Winchester-Frederick County Convention & Visitors Bureau

We found 325 holiday rentals — enter your dates for availability

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October 2025

November 2025

Choose the right holiday home that's close to Winchester-Frederick County Convention & Visitors Bureau. Holiday homes offer the amenities that you expect for your stay with friends, family or just your pet, such as Wi-Fi and a fireplace. Whatever you're looking for, you're sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Winchester-Frederick County Convention & Visitors Bureau

Showing deals for:30 Jan - 6 Feb

Exceptional

(5 reviews)

Modern Chalet w Hot Tub, Large Deck, Grill & WiFi

Gerrardstown, WV

7% off

for 7 nights, 1 chalet

AU$289 per night

includes taxes & fees

Our living room seats 9; our dining room seats 8, plus 2 at the kitchen bar

Exceptional

(46 reviews)

Whitetail Summit - Shenandoah/hot tub/wineries

Front Royal, VA

8% off

for 7 nights, 1 chalet

AU$1,040 per night

includes taxes & fees

Exceptional

(11 reviews)

Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly

Gerrardstown, WV

7% off

for 7 nights, 1 chalet

AU$291 per night

includes taxes & fees

Take a look at the living room showing the balance of both basic and eye-popping colors.

Wonderful

(61 reviews)

Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin

Harpers Ferry, WV

7% off

for 7 nights, 1 cabin

AU$303 per night

includes taxes & fees

Wonderful

(9 reviews)

Cozy Shenandoah Cabin Mountian Escape w/ Private Hottub, Loft, & Fireplace

Linden, VA

8% off

for 7 nights, 1 cabin

AU$458 per night

includes taxes & fees

Wonderful

(38 reviews)

Amazing Views, Hot Tub, Fire Pit, Deck & Fireplace

Gerrardstown, WV

7% off

for 7 nights, 1 cabin

AU$320 per night

includes taxes & fees

Exceptional

(73 reviews)

Virginia Wine Country Retreat 60 mi. from DC<br><br><br>

Linden, VA

8% off

for 7 nights, 1 home

AU$786 per night

includes taxes & fees

Welcome to Sky Island Chalet. Only 1 hour from DC area. 5 Bedrooms 4 Bathroom.

Exceptional

(8 reviews)

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

Linden, VA

8% off

for 7 nights, 1 chalet

AU$742 per night

includes taxes & fees

Exceptional

(23 reviews)

Art Docko - Lakefront Artist Retreat w/ Hot Tub!

Harpers Ferry, WV

6% off

for 7 nights, 1 cottage

AU$436 per night

includes taxes & fees

Bedroom #1 with queen bed and full bathroom

Exceptional

(18 reviews)

Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More

Bluemont, VA

8% off

for 7 nights, 1 cabin

AU$724 per night

includes taxes & fees

Exceptional

(12 reviews)

Hot Tub Mountain View Dog Friendly Modern Chalet

Linden, VA

7% off

for 7 nights, 1 cabin

AU$509 per night

includes taxes & fees

Living room & dining room with comfortable seating & lots of natural light.

Exceptional

(9 reviews)

Cozy Chalet, 5-acres, Newly Renovated with WiFi, Deck, Fire Pit & Grill

Gerrardstown, WV

8% off

for 7 nights, 1 chalet

AU$327 per night

includes taxes & fees

Exceptional

(16 reviews)

Cozy Cabin in the Clouds . Hot Tub, Wineries, Skyline

Front Royal, VA

11% off

for 7 nights, 1 cabin

AU$375 per night

includes taxes & fees

Enjoy the sun in the wrap around deck with propane grill

Very good

(10 reviews)

Hot Tub, Wraparound Deck, & WiFi at Chalet Cabin

Gerrardstown, WV

6% off

for 7 nights, 1 cabin

AU$249 per night

includes taxes & fees

Very good

(9 reviews)

Modern Mountain Cottage w Hot Tub, Fire Pit, WiFi

Gerrardstown, WV

6% off

for 7 nights, 1 cabin

AU$259 per night

includes taxes & fees

Exceptional

(6 reviews)

New Hot Tub! Next to resort with spa and golf!

Capon Springs, WV

8% off

for 7 nights, 1 home

AU$465 per night

includes taxes & fees

This home is just a short walk to Lake Shannondale, and has wintertime views of the lake! Spend your mornings on the front porch, or take a leisurely stroll around the lake.

Exceptional

(21 reviews)

Lake View Retreat - Cottage Near a Peaceful Lake!

Harpers Ferry, WV

6% off

for 7 nights, 1 cottage

AU$277 per night

includes taxes & fees

Exceptional

(29 reviews)

Peaceful Lakefront Cottage with Mountain Views!

Harpers Ferry, WV

6% off

for 7 nights, 1 cottage

AU$323 per night

includes taxes & fees

Exceptional

(5 reviews)

Private apartment on a beautiful private farm!

Bluemont, VA

8% off

for 7 nights, 1 apartment

AU$321 per night

includes taxes & fees

Before you even enter, the hammock calls you to rest under the trees

Exceptional

(15 reviews)

Wineries & breweries, winter fun, year round hiking, biking

Harpers Ferry, WV

8% off

for 7 nights, 1 home

AU$414 per night

includes taxes & fees

Find spaces that suit your style

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Find the best place to stay - Winchester-Frederick County Convention & Visitors Bureau

Premier Host

A-Frame Mountain Retreat

Sleeps 4 · 2 bedrooms · 1 bathroom

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