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Winchester Holiday Rentals

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42 rentals in Winchester.
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City Charmer near Historic OldTown Winchester., holiday rental in Winchester

City Charmer near Historic OldTown Winchester.

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Colonial Getaway Near Old Town Historic Winchester, holiday rental in Winchester

Colonial Getaway Near Old Town Historic Winchester

3 bedrooms
3 bathrooms
Sleeps 8
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Just Like Heaven Carriage House, holiday rental in Winchester

Just Like Heaven Carriage House

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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ANS Inn and Suites, holiday rental in Winchester

ANS Inn and Suites

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Historic Manor House on Shenandoah River in Virginia's Wine Country, holiday rental in Winchester

Historic Manor House on Shenandoah River in Virginia's Wine Country

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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The Mill House in Upperville - Cozy  fireplace, outside bonfire - fall is here!, holiday rental in Winchester

The Mill House in Upperville - Cozy fireplace, outside bonfire - fall is here!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Secluded, Cozy Cottage in the Shenandoah Valley, holiday rental in Winchester

Secluded, Cozy Cottage in the Shenandoah Valley

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Historic Home Overlooking Shenandoah River and Blue Ridge Mountains, holiday rental in Winchester

Beautiful Historic Home Overlooking Shenandoah River and Blue Ridge Mountains

3 bedrooms
4 bathrooms
Sleeps 9
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Breathtaking views  with an  indoor private pool, come escape with us, holiday rental in Winchester

Breathtaking views with an indoor private pool, come escape with us

6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Blue Mountain Log Cabin, holiday rental in Winchester

Blue Mountain Log Cabin

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Riverfront - Happy Peach on the Shenandoah, holiday rental in Winchester

Riverfront - Happy Peach on the Shenandoah

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Gorgeous English Hunt Country Cottage, holiday rental in Winchester

Gorgeous English Hunt Country Cottage

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Perfect Hunt Box in Clarke Co.  Minutes to Upperville and Middleburg., holiday rental in Winchester

Perfect Hunt Box in Clarke Co. Minutes to Upperville and Middleburg.

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Virginia Wine Country Retreat 60 mi. from DC, holiday rental in Winchester

Virginia Wine Country Retreat 60 mi. from DC

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Cozy Cabin Hidden Away on a Lake!, holiday rental in Winchester

Cozy Cabin Hidden Away on a Lake!

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Ruby Summit Point - Your Home at the Track, holiday rental in Winchester

Ruby Summit Point - Your Home at the Track

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Meadowbrook -Entire House - Close to Vineyards and Breweries, holiday rental in Winchester

Meadowbrook -Entire House - Close to Vineyards and Breweries

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Stunning Mountain, Vista, and Sunset Views; Theatre, Banquet Hall, holiday rental in Winchester

Stunning Mountain, Vista, and Sunset Views; Theatre, Banquet Hall

7 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps
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Quiet Renovated Historic Condo Above Abolitionist Ale Works w/ Washer Dryer #301, holiday rental in Winchester

Quiet Renovated Historic Condo Above Abolitionist Ale Works w/ Washer Dryer #301

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Dome Of Your Dreams!, holiday rental in Winchester

Dome Of Your Dreams!

2 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Historic Mountain Cottage at Blue Ridge Overlook, holiday rental in Winchester

Historic Mountain Cottage at Blue Ridge Overlook

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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The Outpost: a rustic respite in the Shenandoah Valley - 4 Tesla Bikes For Use, holiday rental in Winchester

The Outpost: a rustic respite in the Shenandoah Valley - 4 Tesla Bikes For Use

3 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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3 BR Chalet 60 Mi. West of Washington (Linden/Front Royal Va), holiday rental in Winchester

3 BR Chalet 60 Mi. West of Washington (Linden/Front Royal Va)

3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Great views, hike onsite, work remotely, huge smart TVs & hot-tub, holiday rental in Winchester

Great views, hike onsite, work remotely, huge smart TVs & hot-tub

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Cozy Apt in Harpers Ferry by the lake!, holiday rental in Winchester

Cozy Apt in Harpers Ferry by the lake!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Shannondale Lake House, holiday rental in Winchester

Shannondale Lake House

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Love Cottage in Harpers Ferry by the lake!, holiday rental in Winchester

The Love Cottage in Harpers Ferry by the lake!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Concord Retreat Center, holiday rental in Winchester

Concord Retreat Center

10 bedrooms
10 bathrooms
Sleeps 48
Match: Sleeps
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1200 SqFt Condo Above Abolitionist Ale Works Charles Town w/ Laundry & Deck #201, holiday rental in Winchester

1200 SqFt Condo Above Abolitionist Ale Works Charles Town w/ Laundry & Deck #201

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The Blueridge Cabin!, holiday rental in Winchester

The Blueridge Cabin!

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Private Downtown Charles Town Condo w/ Laundry Above Abolitionist Ale Works #202, holiday rental in Winchester

Private Downtown Charles Town Condo w/ Laundry Above Abolitionist Ale Works #202

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The Travelers Rest in Harpers Ferry by the lake, holiday rental in Winchester

The Travelers Rest in Harpers Ferry by the lake

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Franklin Manor - Close to Front Royal and Attractions, holiday rental in Winchester

Franklin Manor - Close to Front Royal and Attractions

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Idyllic Restored 18c cabin Not Available! Wine country! Views*All Amenities., holiday rental in Winchester

Idyllic Restored 18c cabin Not Available! Wine country! Views*All Amenities.

2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Private One Bedroom Condo in Downtown Charles Town Above Future Microbrewery, holiday rental in Winchester

Private One Bedroom Condo in Downtown Charles Town Above Future Microbrewery

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Private and Remodeled Historic 2 Bedroom Condo in Heart of Downtown Charles Town, holiday rental in Winchester

Private and Remodeled Historic 2 Bedroom Condo in Heart of Downtown Charles Town

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Pet-Friendly Home in Heart of Wine Country!, holiday rental in Winchester

Pet-Friendly Home in Heart of Wine Country!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Shenandoah Stone House With Kayaks & Self Check-in, holiday rental in Winchester

Shenandoah Stone House With Kayaks & Self Check-in

2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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The Outpost Suite 2- A Curated Farmhouse Suite, holiday rental in Winchester

The Outpost Suite 2- A Curated Farmhouse Suite

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The Outpost Whimsical Farmhouse Retreat +Tesla Charger, holiday rental in Winchester

The Outpost Whimsical Farmhouse Retreat +Tesla Charger

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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NEW! Hilltop Gerrardstown Home w/ Mtn View & Deck!, holiday rental in Winchester

NEW! Hilltop Gerrardstown Home w/ Mtn View & Deck!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Secluded Getaway w/Mtn Views, Deck & Fire Pit, holiday rental in Winchester

NEW! Secluded Getaway w/Mtn Views, Deck & Fire Pit

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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