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Vacation Home Rentals in Winchester, Virginia

Vacation Home Rentals in Winchester, Virginia

Winchester Vacation Rentals - Brownstone Cottage Bed & Breakfast
Winchester Vacation Rentals - Brownstone Cottage Bed & Breakfast
Bed and breakfast
1.3 miles to Winchester
Winchester, Virginia, 22602
Enjoy the quiet and peaceful country setting of Brownstone Cottage, a private home nestled in the Shenandoah Valley outside historic Winchester,...
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Winchester Vacation Rentals - Old Waterstreet Inn
Winchester Vacation Rentals - Old Waterstreet Inn
Bed and breakfast
0.2 miles to Winchester
Winchester, Virginia, 22601
A grand old home in the historic district of Winchester is now a new bed and breakfast inn Winchester is a lovely small city with an historic...
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Beautifully Restored Historic Town Home - Recently Updated Bathrooms & Wifi
Beautifully restored historic town home - recently updated bathrooms & wifi
House with 4 bedroom(s), 2.5 bathrooms(s), sleeps 8
0.3 miles to Winchester
Winchester, 22601
Step back in time with a stay in the historic, completely renovated Peter Miller house, established 1802. It is like having the run of your very...

from 840 USD

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Come Back Soon To See Our Specials
Cottage with 3 bedroom(s), 1.5 bathrooms(s), sleeps 6
10.9 miles to Winchester
Winchester, 22602
Escape the city for the weekend! This cozy cottage is located in the majestic mountains of the Shenandoah Valley. It accommodates six people...

from 500 USD

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Vacation Home Rentals in the Winchester, Virginia Area

Stephens City Vacation Rentals - The Inn At Vaucluse Spring
Bed and breakfast
6.7 miles to Winchester
Stephens City, Virginia, 22655
We knew it the moment we saw it. An old mansion - nearly in ruins - rich in one family's history and vacant for decades. The dream of a young...
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White Post Vacation Rentals - L'auberge Provençale French Country Inn
Bed and breakfast
9.3 miles to Winchester
White Post, Virginia, 22663
Experience scenic Virginia Wine Country and enjoy our five- course menu, which blooms into seven, with freshly selected vegetables and herbs...
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Berryville Vacation Rentals - Lost Dog Bed & Breakfast
Bed and breakfast
10.3 miles to Winchester
Berryville, Virginia, 22611
Imagine a short drive through rolling hills, leaving all of the hustle and hassle of work and the city behind you… Imagine driving into an older,...
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Berryville Vacation Rentals - Smithfield Farm Bed & Breakfast
Bed and breakfast
10.3 miles to Winchester
Berryville, Virginia, 22611
Smithfield Farm Bed and Breakfast welcomes you to the foothills of the Blue Ridge Mountains and the Shenandoah Valley near Berryville, Virginia,...
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Paris Vacation Rentals - Ashby Inn
Bed and breakfast
15.5 miles to Winchester
Paris, Virginia, 20130
'The Ashby Inn' was built about 1829 by Manley Pierce. The original house had four rooms with additions over the years. It was on the original...
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Strasburg Vacation Rentals - The Carver House Bed & Breakfast
Bed and breakfast
16.8 miles to Winchester
Strasburg, Virginia, 22657
The Carver House b&b is nestled between the Blue Ridge and Allegheny Mountains in historic Strasburg, Virginia, within easy walking distance of...
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Star Tannery Vacation Rentals - Pembroke Springs
Bed and breakfast
17.2 miles to Winchester
Star Tannery, Virginia, 22654
We are closing the inn and baths starting July 15, 2006 for additions and renovations. Reopening date will be sometime in Spring of 2007. We will...
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Front Royal Vacation Rentals - Killahevlin B&B Inn
Bed and breakfast
17.3 miles to Winchester
Front Royal, Virginia, 22630
Your hosts, Tom and Kathy Conkey, invite you to experience Irish-style warmth and charm in their historic hilltopKillahevlin - Bed and Breakfast...
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Front Royal Vacation Rentals - Lackawanna B&B
Bed and breakfast
17.3 miles to Winchester
Front Royal, Virginia, 22630
Lackawanna is nestled on two acres of land between the North and South Fork of the Shenandoah River. Four miles from the entrance to Skyline Drive...
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Front Royal Vacation Rentals - Woodward House On Manor Grade Bed & Breakfast
Bed and breakfast
17.3 miles to Winchester
Front Royal, Virginia, 22630
Welcome to Front Royal's best kept secret Perched on a hill overlooking our village with incredible views, yet close to all of it's charms. The...
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Charles Town Vacation Rentals - Cottonwood Inn Bed & Breakfast
Bed and breakfast
17.5 miles to Winchester
Charles Town, West Virginia, 25414
Before the French and Indian War, young surveyor George Washington purchased his first land along the Bullskin Run, a few miles from the present...
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Charles Town Vacation Rentals - Historic Shenandoah Oaks Bed & Breakfast
Bed and breakfast with 3 bedroom(s)
17.5 miles to Winchester
Charles Town, West Virginia, 25414
Historic Shenandoah Oaks is a 27-room antebellum Greek Revival mansion nestled in the foothills surrounding the Shenandoah River in beautiful...
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Charles Town Vacation Rentals - The Carriage Inn Bed & Breakfast
Bed and breakfast
17.5 miles to Winchester
Charles Town, West Virginia, 25414
Welcome to The Carriage Inn Bed and Breakfast located in historic Charles Town, West Virginia. This 1836 Federal Style grand home is listed on the...
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Charles Town Vacation Rentals - Washington House Inn Bed & Breakfast
Bed and breakfast
17.5 miles to Winchester
Charles Town, West Virginia, 25414
In charming Colonial Charles Town, nestled in the Blue Ridge Mountains where the Shenandoah and Potomac Rivers meet, the Washington House Inn is a...
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Shenandoah Vacation Rentals - New Riverfront Home On The Shenandoah
Vacation rental with 3 bedroom(s), 3 bathrooms(s)
21.2 miles to Winchester
Shenandoah, Virginia, 22660
This home is located directly on the Shenandoah River and backs up to the George Washington National Forest. It is located on ten acres and...

from 275 USD


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Gore Getaway Secluded Mountain Home
House with 3 bedroom(s), 2 bathrooms(s), sleeps 8
8.3 miles to Winchester
Gore, 24293
Situated in the middle of 45, mostly wooded acres, this house was built in 2000. It features covered front and back porches that offer total...

from 650 USD

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Charming Historic Home On 36 Acres Near The Shenandoah River And Skyline Drive
Farmhouse with 5 bedroom(s), 3.5 bathrooms(s), sleeps 14
9.9 miles to Winchester
Millwood, 22646
We offer a charming historic country house on 36 acres of wooded land located in historic Clarke County, Virginia. Come enjoy Historic Clarke...

from 1,200 USD

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Beautiful Home Overlooking Shenandoah River
House with 6 bedroom(s), 4 bathrooms(s), sleeps 14
10.8 miles to Winchester
Boyce, 22620
The Play Garden is a charming country home located in the foothills of the Blue Ridge Mountains in historic Clarke County, Virginia, about an hour...

from 2,900 USD

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Lovely Country Retreat Close To Winchester, Va & Washington Dc
House with 4 bedroom(s), 3.5 bathrooms(s), sleeps 7
11.5 miles to Winchester
Boyce, 22620
Private Country Home situated on 14 acres with large outdoor porches and patios with extensive gardens conveniently located to major highways and...
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Shenandoah Valley Lakefront Home With Spectacular View.
House with 4 bedroom(s), 4.5 bathrooms(s), sleeps 10
12.6 miles to Winchester
Cross Junction, 22625
Located in the heart of the Shenandoah Valley in a private gated community, lakefront home with spectacular view of the lake. All main rooms and...

from 1,400 USD

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Quaint Converted Granary With Breathtaking Views Near Winchester
House with 1 bedroom(s), 1 bathrooms(s), sleeps 2
13.8 miles to Winchester
High View, 26808
The Granary is located on 200 rolling acres located on the Virginia, West Virginia border, sitting on the highest point of Timber Ridge. Just 90...

from 750 USD

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Shenandoah River Cottage - Comfortable And Charming - Recreation And Relaxation
Cottage with 2 bedroom(s), 1 bathrooms(s), sleeps 5
14.4 miles to Winchester
Front Royal, 22630
At 'Little Red,' you can relax in the comfort of the nicely furnished, newly updated cottage while enjoying the abundant recreation and beauty of...

from 850 USD

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Hillbrook Inn's Luxurious Fall Cottage
Cottage with 1 bedroom(s), 1 bathrooms(s), sleeps 3
14.6 miles to Winchester
Charles Town, 25414
Hillbrook Inn: A Country House Hotel in Charles Town, West Virginia One Hour from D.C. Picture a European style country house hotel cascading...
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Exquisite Riverfront Paradise...Over 100 Acres- Hike, Boat,Swim Without Leaving!
House with 3 bedroom(s), 2.5 bathrooms(s), sleeps 8
15.1 miles to Winchester
Front Royal, 22630
Rolling River Farm. (com) Private 100 Acre Riverfront Paradise surrounded by water- on a full bend in the legendary Shenandoah River. New from...

from 2,199 USD

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Fantasy Getaway Cottage On Private Pond With Waterfall, Rock Pool And Hot Tub
Bungalow with 0 bedroom(s), 1.5 bathrooms(s), sleeps 4
15.1 miles to Winchester
Front Royal, 22630
A Perfect Fantasy Escape. 650 sq ft Cottage is beautifully secluded on 10 acres with a private pond. Sit in the hot tub and watch the waterfall...

from 1,799 USD

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Shenandoah Chalet
Cabin with 3 bedroom(s), 1 bathrooms(s), sleeps 6
15.1 miles to Winchester
Front Royal, 22630
This three-bedroom/one-bath, cedar log cabin is situated directly on the Shenandoah River, in the Blue Ridge Mountains of Virginia. Special...

from 1,050 USD

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Spectacular Cottage Overlooking The Shenandoah River And Blue Ridge Mountains
Cottage with 3 bedroom(s), 2.5 bathrooms(s), sleeps 10
15.1 miles to Winchester
Front Royal, 22630
Stunning Designer Cottage on a private corner of a historic 100 acre farm. Situated on a scenic limestone bluff overlooking the legendary...

from 2,199 USD

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Shenandoah River Runs Through Your Living Room!
House with 3 bedroom(s), sleeps 8
15.2 miles to Winchester
Front Royal, 22630
Spend the weekend...or even a week. There's so much to do in and around Front Royal, Virginia. Or do nothing at all, except sink into the view of...
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Shenandoah River Runs Through Your Living Room!!
House with 3 bedroom(s), 2 bathrooms(s), sleeps 8
15.2 miles to Winchester
Front Royal, 22630
Spend the weekend...or even a week. There's so much to do in and around Front Royal, Virginia. Or do nothing at all, except sink into the view of...
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Point Of View
House with 3 bedroom(s), 4 bathrooms(s), sleeps 6
16.5 miles to Winchester
Berkeley Springs
Take a deep breath and kick back in this premier, architect-designed cedar sided home with spectacular views of the mountains of PA, MD, and WV as...

from 205 USD

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Shenandoah Mountain Cabin, River Front - Great For Kids, Dogs Welcome
Cabin with 2 bedroom(s), 1 bathrooms(s), sleeps 5
16.6 miles to Winchester
Strasburg, 22657
Key Features - Riverfront, river access, mountain views, gorgeous river view from the screened-in porch - Staircase access to the river from the...

from 900 USD

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Blue Mountain: 2 Acres, Hot Tub, Wifi, Specials, Best Location
House with 2 bedroom(s), 2 bathrooms(s), sleeps 6
16.7 miles to Winchester
Front Royal, 22630
Greeted by 2 acres of beautifully of landscaped property, step inside to find your modern mountain oasis. Top of the line HVAC unit for comfort...

from 875 USD

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Blue Ridge Mountain Top Retreat With Shenandoah Valley View
Cabin with 2 bedroom(s), 1 bathrooms(s), sleeps 4
17.4 miles to Winchester
Linden, 22642
Welcome to Rainbow View Cabin in the Blue Ridge Mountains with magnificent views overlooking the Shenandoah Valley! Get away to another world of...
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Charming Tranquil Mountain Retreat Nestled In Wine Country
Cottage with 3 bedroom(s), 2 bathrooms(s), sleeps 7
17.3 miles to Winchester
Linden, 22642
Sweetspire Cottage will charm you by it's original heart pine floors, stone fireplace and 18 foot tall window view into the wooded surroundings. ...

from 1,350 USD

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Amazing Views, Private Mountain Retreat On 50 Acres
House with 4 bedroom(s), 3 bathrooms(s), sleeps 10
17.6 miles to Winchester
Linden, 22642
Trailview Cottage is a charming 4 bedroom 3 full bath home with 3 levels of living space located on 50 acres in beautiful northern Fauquier...

from 2,200 USD

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Hot Tub Heaven #3 Vacation Cabin. Dog Friendly!
Cabin with 2 bedroom(s), 1 bathrooms(s), sleeps 4
17.9 miles to Winchester
Front Royal, 22630
Our 9 cabins are located near Front Royal, Virginia, the Canoe Capital of Virginia and where Skyline Drive begins... Only 10 miles from...

from 1,100 USD

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Just Blocks From Hollywood Casino! Fully Furnished, Sleeps 5+
Apartment with 1 bedroom(s), sleeps 7
18.1 miles to Winchester
Ranson, 25438
Tired of the cramped feeling of a motel? This apartment allows you to spread out a bit for a more relaxing and enjoyable experience. Close to...
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Quiet Charm Of An Old Victorian, Elegantly Appointed, In Area Steeped In History
House with 3 bedroom(s), 2 bathrooms(s), sleeps 6
18.1 miles to Winchester
Corporation of Ranson, 25438
Step back in time to 1914, to a lovely solid brick Victorian. Enjoy the spacious rooms; the wrap-around porch; the summer porch overlooking the...
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Charming Mountain Cabin (1 Hour West Of Downtown Washington Dc)
Cabin with 2 bedroom(s), 1 bathrooms(s), sleeps 5
18.2 miles to Winchester
Linden, 22642
Enjoy the gorgeous views of the Blue Ridge Mountains! The cottage is surrounded by large trees and located on several acres of property in a...

from 630 USD

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Private Home In Gated Community!
Chalet with 3 bedroom(s), 2 bathrooms(s), sleeps 6
18.6 miles to Winchester
Front Royal, 22630
Beautiful chalet-style home in Front Royal. Situated in a gated community, High Knob, on a 1-acre lot, this home is private yet close to...
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3 Br Chalet 60 Mi. From Washington (Linden/Front Royal Va)
House with 3 bedroom(s), sleeps 7
19.4 miles to Winchester
Front Royal, 22630
Newer chalet-style mountain home on 3 levels with a 1/2 acre lot surrounded by forest on 3 sides. Three full bedrooms (Master Bedroom Loft with...
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Cute 2Br/2Ba Cottage In Virginia's Hunt Country.
Cottage with 2 bedroom(s), sleeps 4
19.7 miles to Winchester
Upperville, 20184
Cute cottage in the heart of Upperviile, VA where the country's oldest horse show takes place in June every year. The town is typical of historic...
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Hunt Country Cottage
Cottage with 3 bedroom(s), 2 bathrooms(s), sleeps 7
20.1 miles to Winchester
Upperville, 20184
The Hunt Country Cottage is located in the heart of Upperville Virginia, home to the nation’s oldest and most prestigious horse show. We bought...
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Linden Vacation Rentals - Mt Top Cabin In Virginia Wine Country
Vacation rental with 2 bedroom(s), 1 bathrooms(s)
20.5 miles to Winchester
Linden, Virginia, 22642
Blue Ridge Mountain Top Cabin with breathtaking views of the Shenandoah River, Shenandoah Valley, Mountain Ranges, amazing sunsets and bright...

from 139 USD


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Beautiful 200 Acre Farm With 1/2 Mile Of Riverfront
House with 6 bedroom(s), 4.5 bathrooms(s), sleeps 12
20.7 miles to Winchester
Toms Brook, 22660
This exceptional, elegant Southern Living home is situated on the Shenandoah River backing up to the George Washington National Forest. It is...

from 3,500 USD

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Rustic, Historic Creek Side Vacation Home In Va Mountains
Cottage with 5 bedroom(s), 2 bathrooms(s), sleeps 10
20.8 miles to Winchester
Front Royal, 22610
Gooney Lodge is located in the Browntown Valley below Shenandoah National Park. The earliest portion of the house was built in the 1700's. Gooney...

from 950 USD

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