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Winchester Cabins

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50 rentals in Winchester.
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City Charmer near Historic OldTown Winchester., vacation rental in Winchester
City Charmer near Historic OldTown Winchester., vacation rental in Winchester
City Charmer near Historic OldTown Winchester., vacation rental in Winchester

City Charmer near Historic OldTown Winchester.

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Colonial Getaway Near Old Town Historic Winchester, vacation rental in Winchester
Colonial Getaway Near Old Town Historic Winchester, vacation rental in Winchester
Colonial Getaway Near Old Town Historic Winchester, vacation rental in Winchester

Colonial Getaway Near Old Town Historic Winchester

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Modern Upscale Home, Historic Downtown Winchester, vacation rental in Winchester
Modern Upscale Home, Historic Downtown Winchester, vacation rental in Winchester
Modern Upscale Home, Historic Downtown Winchester, vacation rental in Winchester

Modern Upscale Home, Historic Downtown Winchester

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Clean, neat, peace and quiet, vacation rental in Winchester
Clean, neat, peace and quiet, vacation rental in Winchester
Clean, neat, peace and quiet, vacation rental in Winchester

Clean, neat, peace and quiet

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Yellow Submarine trendy basement apt w/courtyard, vacation rental in Winchester
Yellow Submarine trendy basement apt w/courtyard, vacation rental in Winchester
Yellow Submarine trendy basement apt w/courtyard, vacation rental in Winchester

Yellow Submarine trendy basement apt w/courtyard

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Spacious, cozy Studio space with balcony and washer and dryer., vacation rental in Winchester
Spacious, cozy Studio space with balcony and washer and dryer., vacation rental in Winchester
Spacious, cozy Studio space with balcony and washer and dryer., vacation rental in Winchester

Spacious, cozy Studio space with balcony and washer and dryer.

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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ANS Inn has clean, spacious rooms located on 5 acres with little traffic., vacation rental in Winchester
ANS Inn has clean, spacious rooms located on 5 acres with little traffic., vacation rental in Winchester
ANS Inn has clean, spacious rooms located on 5 acres with little traffic., vacation rental in Winchester

ANS Inn has clean, spacious rooms located on 5 acres with little traffic.

Rental Home
3 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Lofts for weekly rentals! 2 miles from historic downtown., vacation rental in Winchester
Lofts for weekly rentals! 2 miles from historic downtown., vacation rental in Winchester
Lofts for weekly rentals! 2 miles from historic downtown., vacation rental in Winchester

Lofts for weekly rentals! 2 miles from historic downtown.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
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Stunning Views & Sunsets, Plus Scrapbooking Center - New Owners and New Decor!, vacation rental in Winchester
Stunning Views & Sunsets, Plus Scrapbooking Center - New Owners and New Decor!, vacation rental in Winchester
Stunning Views & Sunsets, Plus Scrapbooking Center - New Owners and New Decor!, vacation rental in Winchester

Stunning Views & Sunsets, Plus Scrapbooking Center - New Owners and New Decor!

Rental Home
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Riverfront Getaway w/ Breathtaking Views!, vacation rental in Winchester
Riverfront Getaway w/ Breathtaking Views!, vacation rental in Winchester
Riverfront Getaway w/ Breathtaking Views!, vacation rental in Winchester

Riverfront Getaway w/ Breathtaking Views!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful Historic Home Overlooking Shenandoah River and Blue Ridge Mountains, vacation rental in Winchester
Beautiful Historic Home Overlooking Shenandoah River and Blue Ridge Mountains, vacation rental in Winchester
Beautiful Historic Home Overlooking Shenandoah River and Blue Ridge Mountains, vacation rental in Winchester

Beautiful Historic Home Overlooking Shenandoah River and Blue Ridge Mountains

Rental Home
4 bedrooms
5 bathrooms
Sleeps 9
Match: Sleeps
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Perfect Hunt Box in Clarke Co.  Minutes to Upperville and Middleburg., vacation rental in Winchester
Perfect Hunt Box in Clarke Co.  Minutes to Upperville and Middleburg., vacation rental in Winchester
Perfect Hunt Box in Clarke Co.  Minutes to Upperville and Middleburg., vacation rental in Winchester

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

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Cozy Chalet with beautiful Country Vista, vacation rental in Winchester
Cozy Chalet with beautiful Country Vista, vacation rental in Winchester
Cozy Chalet with beautiful Country Vista, vacation rental in Winchester

Cozy Chalet with beautiful Country Vista

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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"Best Value": WATERFRONT! *5* Star-Rated & VIEWS- "So Clean. Cozy, bright home", vacation rental in Winchester
"Best Value": WATERFRONT! *5* Star-Rated & VIEWS- "So Clean. Cozy, bright home", vacation rental in Winchester
"Best Value": WATERFRONT! *5* Star-Rated & VIEWS- "So Clean. Cozy, bright home", vacation rental in Winchester

"Best Value": WATERFRONT! *5* Star-Rated & VIEWS- "So Clean. Cozy, bright home"

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Family Retreat w/ Deck Near Appalachian Trail!, vacation rental in Winchester
Family Retreat w/ Deck Near Appalachian Trail!, vacation rental in Winchester
Family Retreat w/ Deck Near Appalachian Trail!, vacation rental in Winchester

Family Retreat w/ Deck Near Appalachian Trail!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Ruby Summit Point - Your Home at the Track, vacation rental in Winchester
Ruby Summit Point - Your Home at the Track, vacation rental in Winchester
Ruby Summit Point - Your Home at the Track, vacation rental in Winchester

Ruby Summit Point - Your Home at the Track

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Spacious Cabin on Cedar Creek, Shenandoah's hidden getaway!, vacation rental in Winchester
Spacious Cabin on Cedar Creek, Shenandoah's hidden getaway!, vacation rental in Winchester
Spacious Cabin on Cedar Creek, Shenandoah's hidden getaway!, vacation rental in Winchester

Spacious Cabin on Cedar Creek, Shenandoah's hidden getaway!

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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The Outpost: A Rustic Respite in the Shenandoah Valley 4 Bikes For Use Tesla Ch, vacation rental in Winchester
The Outpost: A Rustic Respite in the Shenandoah Valley 4 Bikes For Use Tesla Ch, vacation rental in Winchester
The Outpost: A Rustic Respite in the Shenandoah Valley 4 Bikes For Use Tesla Ch, vacation rental in Winchester

The Outpost: A Rustic Respite in the Shenandoah Valley 4 Bikes For Use Tesla Ch

Rental Home
3 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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NEW! Peaceful Hideaway w/ Shenandoah River Access, vacation rental in Winchester
NEW! Peaceful Hideaway w/ Shenandoah River Access, vacation rental in Winchester
NEW! Peaceful Hideaway w/ Shenandoah River Access, vacation rental in Winchester

NEW! Peaceful Hideaway w/ Shenandoah River Access

Rental Home
1 bedroom
1 bathroom
Sleeps 7
Match: Sleeps
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Modern Chalet Cabin w Hot Tub, Deck/Grill, & WiFi!, vacation rental in Winchester
Modern Chalet Cabin w Hot Tub, Deck/Grill, & WiFi!, vacation rental in Winchester
Modern Chalet Cabin w Hot Tub, Deck/Grill, & WiFi!, vacation rental in Winchester

Modern Chalet Cabin w Hot Tub, Deck/Grill, & WiFi!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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New Construction- Private & Quiet -Cape Cod for 6, vacation rental in Winchester
New Construction- Private & Quiet -Cape Cod for 6, vacation rental in Winchester
New Construction- Private & Quiet -Cape Cod for 6, vacation rental in Winchester

New Construction- Private & Quiet -Cape Cod for 6

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More, vacation rental in Winchester
Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More, vacation rental in Winchester
Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More, vacation rental in Winchester

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

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
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NEW! Charles Town Home w/ Private Pool & Hot Tub, vacation rental in Winchester
NEW! Charles Town Home w/ Private Pool & Hot Tub, vacation rental in Winchester
NEW! Charles Town Home w/ Private Pool & Hot Tub, vacation rental in Winchester

NEW! Charles Town Home w/ Private Pool & Hot Tub

Rental Home
5 bedrooms
4 bathrooms
Sleeps 22
Match: Sleeps
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Cottage w/breathtaking Sunrise/Sunset views & Outdoor Hot Tub 9m from Winchester, vacation rental in Winchester
Cottage w/breathtaking Sunrise/Sunset views & Outdoor Hot Tub 9m from Winchester, vacation rental in Winchester
Cottage w/breathtaking Sunrise/Sunset views & Outdoor Hot Tub 9m from Winchester, vacation rental in Winchester

Cottage w/breathtaking Sunrise/Sunset views & Outdoor Hot Tub 9m from Winchester

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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NEW! Stunning Former Winery w/ Pool & Mtn Views!, vacation rental in Winchester
NEW! Stunning Former Winery w/ Pool & Mtn Views!, vacation rental in Winchester
NEW! Stunning Former Winery w/ Pool & Mtn Views!, vacation rental in Winchester

NEW! Stunning Former Winery w/ Pool & Mtn Views!

Rental Home
8 bedrooms
6 bathrooms
Sleeps 20
Match: Sleeps
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Summit Hill House - Private Pond with Blue Ridge Mountain Views, vacation rental in Winchester
Summit Hill House - Private Pond with Blue Ridge Mountain Views, vacation rental in Winchester
Summit Hill House - Private Pond with Blue Ridge Mountain Views, vacation rental in Winchester

Summit Hill House - Private Pond with Blue Ridge Mountain Views

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Hot Tub, Wraparound Deck, & WiFi at Chalet Cabin, vacation rental in Winchester
Hot Tub, Wraparound Deck, & WiFi at Chalet Cabin, vacation rental in Winchester
Hot Tub, Wraparound Deck, & WiFi at Chalet Cabin, vacation rental in Winchester

Hot Tub, Wraparound Deck, & WiFi at Chalet Cabin

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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Private Waterfront Retreat on the Shenandoah River, vacation rental in Winchester
Private Waterfront Retreat on the Shenandoah River, vacation rental in Winchester
Private Waterfront Retreat on the Shenandoah River, vacation rental in Winchester

Private Waterfront Retreat on the Shenandoah River

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Modern Chalet Cabin w Hot Tub, Deck/Grill, & WiFi!, vacation rental in Winchester
Modern Chalet Cabin w Hot Tub, Deck/Grill, & WiFi!, vacation rental in Winchester
Modern Chalet Cabin w Hot Tub, Deck/Grill, & WiFi!, vacation rental in Winchester

Modern Chalet Cabin w Hot Tub, Deck/Grill, & WiFi!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Modern Chalet Cabin w Hot Tub, Fire Pit, Huge Deck, vacation rental in Winchester
Modern Chalet Cabin w Hot Tub, Fire Pit, Huge Deck, vacation rental in Winchester
Modern Chalet Cabin w Hot Tub, Fire Pit, Huge Deck, vacation rental in Winchester

Modern Chalet Cabin w Hot Tub, Fire Pit, Huge Deck

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Hot Tub, Wraparound Deck, & WiFi at Chalet Cabin, vacation rental in Winchester
Hot Tub, Wraparound Deck, & WiFi at Chalet Cabin, vacation rental in Winchester
Hot Tub, Wraparound Deck, & WiFi at Chalet Cabin, vacation rental in Winchester

Hot Tub, Wraparound Deck, & WiFi at Chalet Cabin

Cabin
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Pet friendly cottage on 10 peaceful wooded acres. Close to Winchester and more!, vacation rental in Winchester
Pet friendly cottage on 10 peaceful wooded acres. Close to Winchester and more!, vacation rental in Winchester
Pet friendly cottage on 10 peaceful wooded acres. Close to Winchester and more!, vacation rental in Winchester

Pet friendly cottage on 10 peaceful wooded acres. Close to Winchester and more!

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Cottage, vacation rental in Winchester
The Cottage, vacation rental in Winchester
The Cottage, vacation rental in Winchester

The Cottage

Rental Home
1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
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Modern Chalet Cabin w Hot Tub, Fire Pit, Huge Deck, vacation rental in Winchester
Modern Chalet Cabin w Hot Tub, Fire Pit, Huge Deck, vacation rental in Winchester
Modern Chalet Cabin w Hot Tub, Fire Pit, Huge Deck, vacation rental in Winchester

Modern Chalet Cabin w Hot Tub, Fire Pit, Huge Deck

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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Shenandoah Valley luxury w/stunning orchard & Blue Ridge Mountain views, vacation rental in Winchester
Shenandoah Valley luxury w/stunning orchard & Blue Ridge Mountain views, vacation rental in Winchester
Shenandoah Valley luxury w/stunning orchard & Blue Ridge Mountain views, vacation rental in Winchester

Shenandoah Valley luxury w/stunning orchard & Blue Ridge Mountain views

Rental Home
3 bedrooms
5 bathrooms
Sleeps 7
Match: Sleeps
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Large Efficiency, vacation rental in Winchester
Large Efficiency, vacation rental in Winchester
Large Efficiency, vacation rental in Winchester

Large Efficiency

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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SUNSET/RIVER VIEWS, Secluded mountain chalet with hot tub, newly decorated, king, vacation rental in Winchester
SUNSET/RIVER VIEWS, Secluded mountain chalet with hot tub, newly decorated, king, vacation rental in Winchester
SUNSET/RIVER VIEWS, Secluded mountain chalet with hot tub, newly decorated, king, vacation rental in Winchester

SUNSET/RIVER VIEWS, Secluded mountain chalet with hot tub, newly decorated, king

Rental Home
4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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3 bedroom, 2 bath home in the mountains, vacation rental in Winchester
3 bedroom, 2 bath home in the mountains, vacation rental in Winchester
3 bedroom, 2 bath home in the mountains, vacation rental in Winchester

3 bedroom, 2 bath home in the mountains

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Crystal Lake House, vacation rental in Winchester
Crystal Lake House, vacation rental in Winchester
Crystal Lake House, vacation rental in Winchester

Crystal Lake House

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Forest Glade, vacation rental in Winchester
The Forest Glade, vacation rental in Winchester
The Forest Glade, vacation rental in Winchester

The Forest Glade

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Suite 4: Outpost · Gorgeous Farm Carriage House Loft, vacation rental in Winchester
Suite 4: Outpost · Gorgeous Farm Carriage House Loft, vacation rental in Winchester
Suite 4: Outpost · Gorgeous Farm Carriage House Loft, vacation rental in Winchester

Suite 4: Outpost · Gorgeous Farm Carriage House Loft

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Beautiful, cozy retreat in wine country!, vacation rental in Winchester
Beautiful, cozy retreat in wine country!, vacation rental in Winchester
Beautiful, cozy retreat in wine country!, vacation rental in Winchester

Beautiful, cozy retreat in wine country!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Mulberry Run Farmhouse - Steps away from family-run Farm Market!, vacation rental in Winchester
Mulberry Run Farmhouse - Steps away from family-run Farm Market!, vacation rental in Winchester
Mulberry Run Farmhouse - Steps away from family-run Farm Market!, vacation rental in Winchester

Mulberry Run Farmhouse - Steps away from family-run Farm Market!

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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The Farm House, vacation rental in Winchester
The Farm House, vacation rental in Winchester
The Farm House, vacation rental in Winchester

The Farm House

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Long Meadow Cabin - 4 BR A-frame cabin with pool

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Wedding Party Dream 14 BR Boutique in Berryville, vacation rental in Winchester
Wedding Party Dream 14 BR Boutique in Berryville, vacation rental in Winchester
Wedding Party Dream 14 BR Boutique in Berryville, vacation rental in Winchester

Wedding Party Dream 14 BR Boutique in Berryville

Rental Home
13 bedrooms
7 bathrooms
Sleeps 30
Match: Sleeps
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NEW! Mountain View Cottage * 66-acre Horse Farm, vacation rental in Winchester
NEW! Mountain View Cottage * 66-acre Horse Farm, vacation rental in Winchester
NEW! Mountain View Cottage * 66-acre Horse Farm, vacation rental in Winchester

NEW! Mountain View Cottage * 66-acre Horse Farm

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Modern House Barn & Farm Retreat, vacation rental in Winchester
Modern House Barn & Farm Retreat, vacation rental in Winchester
Modern House Barn & Farm Retreat, vacation rental in Winchester

Modern House Barn & Farm Retreat

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Stunning furnished studio with full kitchen in Stephens City, vacation rental in Winchester
Stunning furnished studio with full kitchen in Stephens City, vacation rental in Winchester
Stunning furnished studio with full kitchen in Stephens City, vacation rental in Winchester

Stunning furnished studio with full kitchen in Stephens City

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Stunning Basment Studio  10 min away from Shanndoah University, vacation rental in Winchester
Stunning Basment Studio  10 min away from Shanndoah University, vacation rental in Winchester
Stunning Basment Studio  10 min away from Shanndoah University, vacation rental in Winchester

Stunning Basment Studio 10 min away from Shanndoah University

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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