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Middlebrook Holiday Rentals

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50 rentals in Middlebrook.
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Mountain Pond House, holiday rental in Middlebrook
Mountain Pond House, holiday rental in Middlebrook
Mountain Pond House, holiday rental in Middlebrook

Mountain Pond House

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
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Country Retreat,  Horse Hotel, An Amateur Astronomer's Dream, holiday rental in Middlebrook
Country Retreat,  Horse Hotel, An Amateur Astronomer's Dream, holiday rental in Middlebrook
Country Retreat,  Horse Hotel, An Amateur Astronomer's Dream, holiday rental in Middlebrook

Country Retreat, Horse Hotel, An Amateur Astronomer's Dream

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Second Creek Farm near Spy Rock, Crabtree Falls and the Appalachian Trail, holiday rental in Middlebrook
Second Creek Farm near Spy Rock, Crabtree Falls and the Appalachian Trail, holiday rental in Middlebrook
Second Creek Farm near Spy Rock, Crabtree Falls and the Appalachian Trail, holiday rental in Middlebrook

Second Creek Farm near Spy Rock, Crabtree Falls and the Appalachian Trail

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Couples Mountain Retreat in Blue Ridge Mountains, holiday rental in Middlebrook
Couples Mountain Retreat in Blue Ridge Mountains, holiday rental in Middlebrook
Couples Mountain Retreat in Blue Ridge Mountains, holiday rental in Middlebrook

Couples Mountain Retreat in Blue Ridge Mountains

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Shenandoah Valley Farm House, holiday rental in Middlebrook
Shenandoah Valley Farm House, holiday rental in Middlebrook
Shenandoah Valley Farm House, holiday rental in Middlebrook

Shenandoah Valley Farm House

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Tranquil And Secluded Cabin On 126 Acres With Mountain Views ~ AMAZING!, holiday rental in Middlebrook
Tranquil And Secluded Cabin On 126 Acres With Mountain Views ~ AMAZING!, holiday rental in Middlebrook
Tranquil And Secluded Cabin On 126 Acres With Mountain Views ~ AMAZING!, holiday rental in Middlebrook

Tranquil And Secluded Cabin On 126 Acres With Mountain Views ~ AMAZING!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Creekside historic log cabin with all modern amenities at historic Wade's Mill, holiday rental in Middlebrook
Creekside historic log cabin with all modern amenities at historic Wade's Mill, holiday rental in Middlebrook
Creekside historic log cabin with all modern amenities at historic Wade's Mill, holiday rental in Middlebrook

Creekside historic log cabin with all modern amenities at historic Wade's Mill

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Hilltop Home. Amazing Views. Curated for Couples., holiday rental in Middlebrook
Hilltop Home. Amazing Views. Curated for Couples., holiday rental in Middlebrook
Hilltop Home. Amazing Views. Curated for Couples., holiday rental in Middlebrook

Hilltop Home. Amazing Views. Curated for Couples.

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Windymile Cabin for Rent Near Lexington Va. Lexington Va Cabin Rental., holiday rental in Middlebrook
Windymile Cabin for Rent Near Lexington Va. Lexington Va Cabin Rental., holiday rental in Middlebrook
Windymile Cabin for Rent Near Lexington Va. Lexington Va Cabin Rental., holiday rental in Middlebrook

Windymile Cabin for Rent Near Lexington Va. Lexington Va Cabin Rental.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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Luxury cabin in the woods, 2 bedrooms plus loft, holiday rental in Middlebrook
Luxury cabin in the woods, 2 bedrooms plus loft, holiday rental in Middlebrook
Luxury cabin in the woods, 2 bedrooms plus loft, holiday rental in Middlebrook

Luxury cabin in the woods, 2 bedrooms plus loft

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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White Rock Cabin, On The Tye River ( see covid note in description), holiday rental in Middlebrook
White Rock Cabin, On The Tye River ( see covid note in description), holiday rental in Middlebrook
White Rock Cabin, On The Tye River ( see covid note in description), holiday rental in Middlebrook

White Rock Cabin, On The Tye River ( see covid note in description)

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Mountain Getaway-Deer Run-Sleeps 4, holiday rental in Middlebrook
Mountain Getaway-Deer Run-Sleeps 4, holiday rental in Middlebrook
Mountain Getaway-Deer Run-Sleeps 4, holiday rental in Middlebrook

Mountain Getaway-Deer Run-Sleeps 4

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Spacious Cottage. Lovely Shenandoah Valley Views.  Near Lexington And Staunton., holiday rental in Middlebrook
Spacious Cottage. Lovely Shenandoah Valley Views.  Near Lexington And Staunton., holiday rental in Middlebrook
Spacious Cottage. Lovely Shenandoah Valley Views.  Near Lexington And Staunton., holiday rental in Middlebrook

Spacious Cottage. Lovely Shenandoah Valley Views. Near Lexington And Staunton.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Spacious Home, Private Pool, Tennis Court, Lake, Minutes from Town and Shopping, holiday rental in Middlebrook
Spacious Home, Private Pool, Tennis Court, Lake, Minutes from Town and Shopping, holiday rental in Middlebrook
Spacious Home, Private Pool, Tennis Court, Lake, Minutes from Town and Shopping, holiday rental in Middlebrook

Spacious Home, Private Pool, Tennis Court, Lake, Minutes from Town and Shopping

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 15
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Log Cabin Retreat On Picturesque Private Farm, holiday rental in Middlebrook
Log Cabin Retreat On Picturesque Private Farm, holiday rental in Middlebrook
Log Cabin Retreat On Picturesque Private Farm, holiday rental in Middlebrook

Log Cabin Retreat On Picturesque Private Farm

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Lyndhurst Log Cabin on Farm w/Pond+Stocked Stream!, holiday rental in Middlebrook
Lyndhurst Log Cabin on Farm w/Pond+Stocked Stream!, holiday rental in Middlebrook
Lyndhurst Log Cabin on Farm w/Pond+Stocked Stream!, holiday rental in Middlebrook

Lyndhurst Log Cabin on Farm w/Pond+Stocked Stream!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Rustic Mountain Retreat-bear Paw-Sleeps 4, holiday rental in Middlebrook
Rustic Mountain Retreat-bear Paw-Sleeps 4, holiday rental in Middlebrook
Rustic Mountain Retreat-bear Paw-Sleeps 4, holiday rental in Middlebrook

Rustic Mountain Retreat-bear Paw-Sleeps 4

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Quickly's Retreat - A Home Away from Home, holiday rental in Middlebrook
Quickly's Retreat - A Home Away from Home, holiday rental in Middlebrook
Quickly's Retreat - A Home Away from Home, holiday rental in Middlebrook

Quickly's Retreat - A Home Away from Home

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
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Lakeside Log Home on Picturesque Private Farm

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Find out why this property is Almost Heaven, holiday rental in Middlebrook
Find out why this property is Almost Heaven, holiday rental in Middlebrook
Find out why this property is Almost Heaven, holiday rental in Middlebrook

Find out why this property is Almost Heaven

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Timber Ridge Carriage House Loft, holiday rental in Middlebrook
Timber Ridge Carriage House Loft, holiday rental in Middlebrook
Timber Ridge Carriage House Loft, holiday rental in Middlebrook

Timber Ridge Carriage House Loft

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Oak Tree Cottage: a beautiful farm & mountain views., holiday rental in Middlebrook
Oak Tree Cottage: a beautiful farm & mountain views., holiday rental in Middlebrook
Oak Tree Cottage: a beautiful farm & mountain views., holiday rental in Middlebrook

Oak Tree Cottage: a beautiful farm & mountain views.

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Cozy Mountain House Near VMI, W&L, And Horse Center, holiday rental in Middlebrook
Cozy Mountain House Near VMI, W&L, And Horse Center, holiday rental in Middlebrook
Cozy Mountain House Near VMI, W&L, And Horse Center, holiday rental in Middlebrook

Cozy Mountain House Near VMI, W&L, And Horse Center

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Rambo Farm- Circa 1840 Farmhouse Located On A 100 Acre Working Farm, holiday rental in Middlebrook
Rambo Farm- Circa 1840 Farmhouse Located On A 100 Acre Working Farm, holiday rental in Middlebrook
Rambo Farm- Circa 1840 Farmhouse Located On A 100 Acre Working Farm, holiday rental in Middlebrook

Rambo Farm- Circa 1840 Farmhouse Located On A 100 Acre Working Farm

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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The Waterfall Cabin Estate on the Tye River, holiday rental in Middlebrook
The Waterfall Cabin Estate on the Tye River, holiday rental in Middlebrook
The Waterfall Cabin Estate on the Tye River, holiday rental in Middlebrook

The Waterfall Cabin Estate on the Tye River

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Inspired by Nature, relaxed cancellation policy, Safe & Immaculate, holiday rental in Middlebrook
Inspired by Nature, relaxed cancellation policy, Safe & Immaculate, holiday rental in Middlebrook
Inspired by Nature, relaxed cancellation policy, Safe & Immaculate, holiday rental in Middlebrook

Inspired by Nature, relaxed cancellation policy, Safe & Immaculate

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Historic Home - Relax, Hike, Fish, & Write!, holiday rental in Middlebrook
NEW! Historic Home - Relax, Hike, Fish, & Write!, holiday rental in Middlebrook
NEW! Historic Home - Relax, Hike, Fish, & Write!, holiday rental in Middlebrook

NEW! Historic Home - Relax, Hike, Fish, & Write!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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New Listing! Mountain Views & Close To Downtown, Sanitized & Self Check-in, holiday rental in Middlebrook
New Listing! Mountain Views & Close To Downtown, Sanitized & Self Check-in, holiday rental in Middlebrook
New Listing! Mountain Views & Close To Downtown, Sanitized & Self Check-in, holiday rental in Middlebrook

New Listing! Mountain Views & Close To Downtown, Sanitized & Self Check-in

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Tranquility, Wonderful View From The Sun Room,In The Historic Shenandoah Valley, holiday rental in Middlebrook
Tranquility, Wonderful View From The Sun Room,In The Historic Shenandoah Valley, holiday rental in Middlebrook
Tranquility, Wonderful View From The Sun Room,In The Historic Shenandoah Valley, holiday rental in Middlebrook

Tranquility, Wonderful View From The Sun Room,In The Historic Shenandoah Valley

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Blueberry Hill Farm in Historic Shenandoah Valley, holiday rental in Middlebrook
Blueberry Hill Farm in Historic Shenandoah Valley, holiday rental in Middlebrook
Blueberry Hill Farm in Historic Shenandoah Valley, holiday rental in Middlebrook

Blueberry Hill Farm in Historic Shenandoah Valley

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Inn at Meadowcroft, a restored 1795 Log Cabin, Margaret June Baylor-Swoope Suite, holiday rental in Middlebrook
Inn at Meadowcroft, a restored 1795 Log Cabin, Margaret June Baylor-Swoope Suite, holiday rental in Middlebrook
Inn at Meadowcroft, a restored 1795 Log Cabin, Margaret June Baylor-Swoope Suite, holiday rental in Middlebrook

Inn at Meadowcroft, a restored 1795 Log Cabin, Margaret June Baylor-Swoope Suite

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Inn at Meadowcroft, a restored 1795 Log Cabin, Honorable Jacob Swoope Suite, holiday rental in Middlebrook
Inn at Meadowcroft, a restored 1795 Log Cabin, Honorable Jacob Swoope Suite, holiday rental in Middlebrook
Inn at Meadowcroft, a restored 1795 Log Cabin, Honorable Jacob Swoope Suite, holiday rental in Middlebrook

Inn at Meadowcroft, a restored 1795 Log Cabin, Honorable Jacob Swoope Suite

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Preferring rentals of 3 wks or more.  $390. per wk.  3 week minimum.  Dogs free., holiday rental in Middlebrook
Preferring rentals of 3 wks or more.  $390. per wk.  3 week minimum.  Dogs free., holiday rental in Middlebrook
Preferring rentals of 3 wks or more.  $390. per wk.  3 week minimum.  Dogs free., holiday rental in Middlebrook

Preferring rentals of 3 wks or more. $390. per wk. 3 week minimum. Dogs free.

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Tentrr Signature Site - Honeysuckle Hideaway, holiday rental in Middlebrook
Tentrr Signature Site - Honeysuckle Hideaway, holiday rental in Middlebrook
Tentrr Signature Site - Honeysuckle Hideaway, holiday rental in Middlebrook

Tentrr Signature Site - Honeysuckle Hideaway

Holiday Rental House
0 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Rose Cottage at Steeles Tavern, holiday rental in Middlebrook
Rose Cottage at Steeles Tavern, holiday rental in Middlebrook
Rose Cottage at Steeles Tavern, holiday rental in Middlebrook

Rose Cottage at Steeles Tavern

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Historic Staunton, Downtown Dwelling, holiday rental in Middlebrook
Historic Staunton, Downtown Dwelling, holiday rental in Middlebrook
Historic Staunton, Downtown Dwelling, holiday rental in Middlebrook

Historic Staunton, Downtown Dwelling

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Inn at Meadowcroft, a restored 1795 Log Cabin,George Washington Swoope, Jr Suite, holiday rental in Middlebrook
Inn at Meadowcroft, a restored 1795 Log Cabin,George Washington Swoope, Jr Suite, holiday rental in Middlebrook
Inn at Meadowcroft, a restored 1795 Log Cabin,George Washington Swoope, Jr Suite, holiday rental in Middlebrook

Inn at Meadowcroft, a restored 1795 Log Cabin,George Washington Swoope, Jr Suite

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Second Creek Farm near  Blue Ridge Parkway in Virg, holiday rental in Middlebrook
Second Creek Farm near  Blue Ridge Parkway in Virg, holiday rental in Middlebrook
Second Creek Farm near  Blue Ridge Parkway in Virg, holiday rental in Middlebrook

Second Creek Farm near Blue Ridge Parkway in Virg

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Skipping Rock, holiday rental in Middlebrook
Tentrr Signature Site - Skipping Rock, holiday rental in Middlebrook
Tentrr Signature Site - Skipping Rock, holiday rental in Middlebrook

Tentrr Signature Site - Skipping Rock

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Inn at Meadowcroft, a restored 1795 Log Cabin, George Washington, Sr Suite, holiday rental in Middlebrook
Inn at Meadowcroft, a restored 1795 Log Cabin, George Washington, Sr Suite, holiday rental in Middlebrook
Inn at Meadowcroft, a restored 1795 Log Cabin, George Washington, Sr Suite, holiday rental in Middlebrook

Inn at Meadowcroft, a restored 1795 Log Cabin, George Washington, Sr Suite

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Inn at Meadowcroft, a restored 1795 Log Cabin, Eliza Trent Swoope Suite, holiday rental in Middlebrook
Inn at Meadowcroft, a restored 1795 Log Cabin, Eliza Trent Swoope Suite, holiday rental in Middlebrook
Inn at Meadowcroft, a restored 1795 Log Cabin, Eliza Trent Swoope Suite, holiday rental in Middlebrook

Inn at Meadowcroft, a restored 1795 Log Cabin, Eliza Trent Swoope Suite

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Rock-n-Creek Cabin mile post 27 off BR Pkwy, holiday rental in Middlebrook
Rock-n-Creek Cabin mile post 27 off BR Pkwy, holiday rental in Middlebrook
Rock-n-Creek Cabin mile post 27 off BR Pkwy, holiday rental in Middlebrook

Rock-n-Creek Cabin mile post 27 off BR Pkwy

Cabin Holiday Rental
3 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Gospel Hill Manor, holiday rental in Middlebrook
Gospel Hill Manor, holiday rental in Middlebrook
Gospel Hill Manor, holiday rental in Middlebrook

Gospel Hill Manor

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Historic Osceola Mill A Lower McCormic Grist Mill, holiday rental in Middlebrook
Historic Osceola Mill A Lower McCormic Grist Mill, holiday rental in Middlebrook
Historic Osceola Mill A Lower McCormic Grist Mill, holiday rental in Middlebrook

Historic Osceola Mill A Lower McCormic Grist Mill

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Manor at Hunter Ridge Estate, holiday rental in Middlebrook
The Manor at Hunter Ridge Estate, holiday rental in Middlebrook
The Manor at Hunter Ridge Estate, holiday rental in Middlebrook

The Manor at Hunter Ridge Estate

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Tentrr Signature Site - Honeysuckle Hideaway, holiday rental in Middlebrook
Tentrr Signature Site - Honeysuckle Hideaway, holiday rental in Middlebrook
Tentrr Signature Site - Honeysuckle Hideaway, holiday rental in Middlebrook

Tentrr Signature Site - Honeysuckle Hideaway

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Skipping Rock, holiday rental in Middlebrook
Tentrr Signature Site - Skipping Rock, holiday rental in Middlebrook
Tentrr Signature Site - Skipping Rock, holiday rental in Middlebrook

Tentrr Signature Site - Skipping Rock

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Queen room with private entrance (weather permitting) balcony on the main floor, holiday rental in Middlebrook
Queen room with private entrance (weather permitting) balcony on the main floor, holiday rental in Middlebrook
Queen room with private entrance (weather permitting) balcony on the main floor, holiday rental in Middlebrook

Queen room with private entrance (weather permitting) balcony on the main floor

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Sanctuary in Historic Downtown Staunton, Virginia, holiday rental in Middlebrook
The Sanctuary in Historic Downtown Staunton, Virginia, holiday rental in Middlebrook
The Sanctuary in Historic Downtown Staunton, Virginia, holiday rental in Middlebrook

The Sanctuary in Historic Downtown Staunton, Virginia

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Revival Room: Historic Church in Downtown Staunton, Virginia, holiday rental in Middlebrook
The Revival Room: Historic Church in Downtown Staunton, Virginia, holiday rental in Middlebrook
The Revival Room: Historic Church in Downtown Staunton, Virginia, holiday rental in Middlebrook

The Revival Room: Historic Church in Downtown Staunton, Virginia

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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