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Middlebrook Holiday Apartments

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50 rentals in Middlebrook.
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3 bed /2 ba - Anxiety slips away in our hillside home surrounded  by nature., holiday rental in Middlebrook

3 bed /2 ba - Anxiety slips away in our hillside home surrounded by nature.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Mountain Pond House, holiday rental in Middlebrook

Mountain Pond 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

3 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

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Shenandoah Valley Farm House, holiday rental in Middlebrook

Shenandoah Valley Farm House

3 bedrooms
3 bathrooms
Sleeps 9
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

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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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)

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Mountain Getaway-Deer Run-Sleeps 4, holiday rental in Middlebrook

Mountain Getaway-Deer Run-Sleeps 4

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Hilltop Home. Amazing Views. Curated for Couples., holiday rental in Middlebrook

Hilltop Home. Amazing Views. Curated for Couples.

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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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

6 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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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

2 bedrooms
2 bathrooms
Sleeps 6
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

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Condo at Wintergreen! Join us for your winter vacation!, holiday rental in Middlebrook

Condo at Wintergreen! Join us for your winter vacation!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Rustic Mountain Retreat-bear Paw-Sleeps 4, holiday rental in Middlebrook

Rustic Mountain Retreat-bear Paw-Sleeps 4

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Log Cabin Retreat On Picturesque Private Farm, holiday rental in Middlebrook

Log Cabin Retreat On Picturesque Private Farm

2 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Mountain Escape at 'Wine-tergreen' Condo, holiday rental in Middlebrook

Mountain Escape at 'Wine-tergreen' Condo

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Dog friendly! Spectacular Views!, holiday rental in Middlebrook

Dog friendly! Spectacular Views!

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Find out why this property is Almost Heaven, holiday rental in Middlebrook

Find out why this property is Almost Heaven

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Lakeside Log Home on Picturesque Private Farm, holiday rental in Middlebrook

Lakeside Log Home on Picturesque Private Farm

3 bedrooms
3 bathrooms
Sleeps 7
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.

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Grand Manor Church Hill Birthplace of Sam Houston, holiday rental in Middlebrook

Grand Manor Church Hill Birthplace of Sam Houston

5 bedrooms
3 bathrooms
Sleeps 13
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

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Pet friendly condo at Overlook -Wintergreen Resort! Fantastic views!, holiday rental in Middlebrook

Pet friendly condo at Overlook -Wintergreen Resort! Fantastic views!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Enjoy winter on the mountain in our 4 bdrm/2 bath cabin!  Ski season is here!!!!, holiday rental in Middlebrook

Enjoy winter on the mountain in our 4 bdrm/2 bath cabin! Ski season is here!!!!

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Amazing mountain and valley views. Perfect for relaxing getaways!, holiday rental in Middlebrook

Amazing mountain and valley views. Perfect for relaxing getaways!

1 bedroom
2 bathrooms
Sleeps 2
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

4 bedrooms
2 bathrooms
Sleeps 8
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

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Blueberry Hill Farm in Historic Shenandoah Valley, holiday rental in Middlebrook

Blueberry Hill Farm in Historic Shenandoah Valley

1 bedroom
1 bathroom
Sleeps 3
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

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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The Landmark, Gospel Hill - a Modernized Historic Luxury Home, holiday rental in Middlebrook

The Landmark, Gospel Hill - a Modernized Historic Luxury Home

4 bedrooms
3 bathrooms
Sleeps 8
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.

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Mountain Home, Wintergreen Resort, Near Everything, Pet Friendly, Seasonal Views, holiday rental in Middlebrook

Mountain Home, Wintergreen Resort, Near Everything, Pet Friendly, Seasonal Views

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Rose Cottage at Steeles Tavern, holiday rental in Middlebrook

Rose Cottage at Steeles Tavern

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Hunker Down, Gospel Hill - a modern apartment in a historic home, holiday rental in Middlebrook

The Hunker Down, Gospel Hill - a modern apartment in a historic home

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Grand Manor Church Hill at Timber Ridge, holiday rental in Middlebrook

Grand Manor Church Hill at Timber Ridge

5 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Lyndhurst Cabin on Farm w/ Pond & Stocked Stream!, holiday rental in Middlebrook

Lyndhurst Cabin on Farm w/ Pond & Stocked Stream!

1 bedroom
1 bathroom
Sleeps 6
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

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

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Wintergreen Resort Cabin w/Deck-Small Dogs Allowed, holiday rental in Middlebrook

Wintergreen Resort Cabin w/Deck-Small Dogs Allowed

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Gospel Hill Manor, holiday rental in Middlebrook

Gospel Hill Manor

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Prvt Cabin w/Hot Tub, Mins to Wintergreen Rst, holiday rental in Middlebrook

Prvt Cabin w/Hot Tub, Mins to Wintergreen Rst

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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The Manor at Hunter Ridge Estate, holiday rental in Middlebrook

The Manor at Hunter Ridge Estate

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

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

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Blue Ridge Home with Mtn Views & On-Site Skiing!, holiday rental in Middlebrook

Blue Ridge Home with Mtn Views & On-Site Skiing!

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Historic Countryside Escape - Relax, Hike, & Fish!, holiday rental in Middlebrook

Historic Countryside Escape - Relax, Hike, & Fish!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Wintergreen Family Ski Retreat w/ Fireplace & View, holiday rental in Middlebrook

Wintergreen Family Ski Retreat w/ Fireplace & View

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Spacious Wintergreen Resort Home w/ Hot Tub!, holiday rental in Middlebrook

Spacious Wintergreen Resort Home w/ Hot Tub!

5 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Cozy 'Nonny Cottage' Near Appalachian Trail!, holiday rental in Middlebrook

NEW! Cozy 'Nonny Cottage' Near Appalachian Trail!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW! Wintergreen Resort Escape Near Leaf Peeping!, holiday rental in Middlebrook

NEW! Wintergreen Resort Escape Near Leaf Peeping!

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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