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Middlebrook Vacation Rentals

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5 mi
52 rentals in Middlebrook.
Mountain Pond House, vacation rental in Middlebrook
Mountain Pond House, vacation rental in Middlebrook
Mountain Pond House, vacation rental in Middlebrook

Mountain Pond House

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Spacious Retreat on 34 Acres in the Country - Short Scenic Drive to Lexington!, vacation rental in Middlebrook
Spacious Retreat on 34 Acres in the Country - Short Scenic Drive to Lexington!, vacation rental in Middlebrook
Spacious Retreat on 34 Acres in the Country - Short Scenic Drive to Lexington!, vacation rental in Middlebrook

Spacious Retreat on 34 Acres in the Country - Short Scenic Drive to Lexington!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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The following properties within 20 miles of Middlebrook match all your filters:
Country Retreat,  An Amateur Astronomer's Dream, vacation rental in Middlebrook
Country Retreat,  An Amateur Astronomer's Dream, vacation rental in Middlebrook
Country Retreat,  An Amateur Astronomer's Dream, vacation rental in Middlebrook

Country Retreat, An Amateur Astronomer's Dream

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cardinal Cottage Beautiful Shenandoah Valley getaway w/ stunning mountain views, vacation rental in Middlebrook
Cardinal Cottage Beautiful Shenandoah Valley getaway w/ stunning mountain views, vacation rental in Middlebrook
Cardinal Cottage Beautiful Shenandoah Valley getaway w/ stunning mountain views, vacation rental in Middlebrook

Cardinal Cottage Beautiful Shenandoah Valley getaway w/ stunning mountain views

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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The Firefly Cottage, vacation rental in Middlebrook
The Firefly Cottage, vacation rental in Middlebrook
The Firefly Cottage, vacation rental in Middlebrook

The Firefly Cottage

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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North Central Loft: Walk Downtown Staunton, vacation rental in Middlebrook
North Central Loft: Walk Downtown Staunton, vacation rental in Middlebrook
North Central Loft: Walk Downtown Staunton, vacation rental in Middlebrook

North Central Loft: Walk Downtown Staunton

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Find out why this property is Almost Heaven, vacation rental in Middlebrook
Find out why this property is Almost Heaven, vacation rental in Middlebrook
Find out why this property is Almost Heaven, vacation rental in Middlebrook

Find out why this property is Almost Heaven

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Inn at Meadowcroft, a restored 1795 Log Cabin, Margaret June Baylor-Swoope Suite, vacation rental in Middlebrook
Inn at Meadowcroft, a restored 1795 Log Cabin, Margaret June Baylor-Swoope Suite, vacation rental in Middlebrook
Inn at Meadowcroft, a restored 1795 Log Cabin, Margaret June Baylor-Swoope Suite, vacation rental in Middlebrook

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

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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The red house, vacation rental in Middlebrook
The red house, vacation rental in Middlebrook
The red house, vacation rental in Middlebrook

The red house

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Firefly Springhouse, vacation rental in Middlebrook
The Firefly Springhouse, vacation rental in Middlebrook
The Firefly Springhouse, vacation rental in Middlebrook

The Firefly Springhouse

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Creekside historic log cabin with all modern amenities at historic Wade's Mill, vacation rental in Middlebrook
Creekside historic log cabin with all modern amenities at historic Wade's Mill, vacation rental in Middlebrook
Creekside historic log cabin with all modern amenities at historic Wade's Mill, vacation rental in Middlebrook

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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BEARADISE “Glamping Paradise”, vacation rental in Middlebrook
BEARADISE “Glamping Paradise”, vacation rental in Middlebrook
BEARADISE “Glamping Paradise”, vacation rental in Middlebrook

BEARADISE “Glamping Paradise”

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Life is better at the Cabin, vacation rental in Middlebrook
Life is better at the Cabin, vacation rental in Middlebrook
Life is better at the Cabin, vacation rental in Middlebrook

Life is better at the Cabin

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Inn at Meadowcroft, a restored 1795 Log Cabin, Eliza Trent Swoope Suite, vacation rental in Middlebrook
Inn at Meadowcroft, a restored 1795 Log Cabin, Eliza Trent Swoope Suite, vacation rental in Middlebrook
Inn at Meadowcroft, a restored 1795 Log Cabin, Eliza Trent Swoope Suite, vacation rental in Middlebrook

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

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Inn at Meadowcroft, a restored 1795 Log Cabin, George Washington, Sr Suite, vacation rental in Middlebrook
Inn at Meadowcroft, a restored 1795 Log Cabin, George Washington, Sr Suite, vacation rental in Middlebrook
Inn at Meadowcroft, a restored 1795 Log Cabin, George Washington, Sr Suite, vacation rental in Middlebrook

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

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Inn at Meadowcroft, a restored 1795 Log Cabin,George Washington Swoope, Jr Suite, vacation rental in Middlebrook
Inn at Meadowcroft, a restored 1795 Log Cabin,George Washington Swoope, Jr Suite, vacation rental in Middlebrook
Inn at Meadowcroft, a restored 1795 Log Cabin,George Washington Swoope, Jr Suite, vacation rental in Middlebrook

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

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Inn at Meadowcroft, a restored 1795 Log Cabin, Honorable Jacob Swoope Suite, vacation rental in Middlebrook
Inn at Meadowcroft, a restored 1795 Log Cabin, Honorable Jacob Swoope Suite, vacation rental in Middlebrook
Inn at Meadowcroft, a restored 1795 Log Cabin, Honorable Jacob Swoope Suite, vacation rental in Middlebrook

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

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Blueberry Hill Farm in Historic Shenandoah Valley, vacation rental in Middlebrook
Blueberry Hill Farm in Historic Shenandoah Valley, vacation rental in Middlebrook
Blueberry Hill Farm in Historic Shenandoah Valley, vacation rental in Middlebrook

Blueberry Hill Farm in Historic Shenandoah Valley

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Spacious Good-Value Accommodation! Pets Allowed, Near Frontier Culture Museum, vacation rental in Middlebrook
Spacious Good-Value Accommodation! Pets Allowed, Near Frontier Culture Museum, vacation rental in Middlebrook
Spacious Good-Value Accommodation! Pets Allowed, Near Frontier Culture Museum, vacation rental in Middlebrook

Spacious Good-Value Accommodation! Pets Allowed, Near Frontier Culture Museum

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Enjoy a Hassle-Free and Suiting Stay! Near R.R. Smith Center for History and Art, vacation rental in Middlebrook
Enjoy a Hassle-Free and Suiting Stay! Near R.R. Smith Center for History and Art, vacation rental in Middlebrook
Enjoy a Hassle-Free and Suiting Stay! Near R.R. Smith Center for History and Art, vacation rental in Middlebrook

Enjoy a Hassle-Free and Suiting Stay! Near R.R. Smith Center for History and Art

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Great Unit in Historic Building, Walk to R.R. Smith Center for History and Art!, vacation rental in Middlebrook
Great Unit in Historic Building, Walk to R.R. Smith Center for History and Art!, vacation rental in Middlebrook
Great Unit in Historic Building, Walk to R.R. Smith Center for History and Art!, vacation rental in Middlebrook

Great Unit in Historic Building, Walk to R.R. Smith Center for History and Art!

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Experience Soothing Moments & Luxury! Pets Allowed, vacation rental in Middlebrook
Experience Soothing Moments & Luxury! Pets Allowed, vacation rental in Middlebrook
Experience Soothing Moments & Luxury! Pets Allowed, vacation rental in Middlebrook

Experience Soothing Moments & Luxury! Pets Allowed

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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The Revival Room: Historic Church in Downtown Staunton, Virginia, vacation rental in Middlebrook
The Revival Room: Historic Church in Downtown Staunton, Virginia, vacation rental in Middlebrook
The Revival Room: Historic Church in Downtown Staunton, Virginia, vacation rental in Middlebrook

The Revival Room: Historic Church in Downtown Staunton, Virginia

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Always a Great Idea To Unwind! Pets Allowed, Near Camera Heritage Museum, vacation rental in Middlebrook
Always a Great Idea To Unwind! Pets Allowed, Near Camera Heritage Museum, vacation rental in Middlebrook
Always a Great Idea To Unwind! Pets Allowed, Near Camera Heritage Museum, vacation rental in Middlebrook

Always a Great Idea To Unwind! Pets Allowed, Near Camera Heritage Museum

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Tranquility, Wonderful View From The Sun Room,In The Historic Shenandoah Valley, vacation rental in Middlebrook
Tranquility, Wonderful View From The Sun Room,In The Historic Shenandoah Valley, vacation rental in Middlebrook
Tranquility, Wonderful View From The Sun Room,In The Historic Shenandoah Valley, vacation 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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Mid-Century Downtown Staunton Loft, vacation rental in Middlebrook
Mid-Century Downtown Staunton Loft, vacation rental in Middlebrook
Mid-Century Downtown Staunton Loft, vacation rental in Middlebrook

Mid-Century Downtown Staunton Loft

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Georgie House - your second "home", vacation rental in Middlebrook
Georgie House - your second "home", vacation rental in Middlebrook
Georgie House - your second "home", vacation rental in Middlebrook

Georgie House - your second "home"

Rental Home
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Cute 2 Bedroom House, vacation rental in Middlebrook
Cute 2 Bedroom House, vacation rental in Middlebrook
Cute 2 Bedroom House, vacation rental in Middlebrook

Cute 2 Bedroom House

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Queen City Hideaway - walk downtown, newly reno, classic, and cozy with views!, vacation rental in Middlebrook
Queen City Hideaway - walk downtown, newly reno, classic, and cozy with views!, vacation rental in Middlebrook
Queen City Hideaway - walk downtown, newly reno, classic, and cozy with views!, vacation rental in Middlebrook

Queen City Hideaway - walk downtown, newly reno, classic, and cozy with views!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Lovely Apartment on theHill, vacation rental in Middlebrook
Lovely Apartment on theHill, vacation rental in Middlebrook
Lovely Apartment on theHill, vacation rental in Middlebrook

Lovely Apartment on theHill

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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The Revival Room in Historic Downtown Staunton!, vacation rental in Middlebrook
The Revival Room in Historic Downtown Staunton!, vacation rental in Middlebrook
The Revival Room in Historic Downtown Staunton!, vacation rental in Middlebrook

The Revival Room in Historic Downtown Staunton!

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Make Your Trip More Enjoyable! 2 Pleasant Units, Minutes to Gypsy Hill, vacation rental in Middlebrook
Make Your Trip More Enjoyable! 2 Pleasant Units, Minutes to Gypsy Hill, vacation rental in Middlebrook
Make Your Trip More Enjoyable! 2 Pleasant Units, Minutes to Gypsy Hill, vacation rental in Middlebrook

Make Your Trip More Enjoyable! 2 Pleasant Units, Minutes to Gypsy Hill

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Always a Great Idea To Unwind! 2 Family-friendly Units, Pets Allowed, vacation rental in Middlebrook
Always a Great Idea To Unwind! 2 Family-friendly Units, Pets Allowed, vacation rental in Middlebrook
Always a Great Idea To Unwind! 2 Family-friendly Units, Pets Allowed, vacation rental in Middlebrook

Always a Great Idea To Unwind! 2 Family-friendly Units, Pets Allowed

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Historic Staunton Home ~ 1 Mi to Downtown!, vacation rental in Middlebrook
Historic Staunton Home ~ 1 Mi to Downtown!, vacation rental in Middlebrook
Historic Staunton Home ~ 1 Mi to Downtown!, vacation rental in Middlebrook

Historic Staunton Home ~ 1 Mi to Downtown!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Newly renovated 2BR in downtown Staunton.  Apt A, vacation rental in Middlebrook
Newly renovated 2BR in downtown Staunton.  Apt A, vacation rental in Middlebrook
Newly renovated 2BR in downtown Staunton.  Apt A, vacation rental in Middlebrook

Newly renovated 2BR in downtown Staunton. Apt A

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
More info
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Victorian 5th Ave row house meets modern SoHo loft, vacation rental in Middlebrook
Victorian 5th Ave row house meets modern SoHo loft, vacation rental in Middlebrook
Victorian 5th Ave row house meets modern SoHo loft, vacation rental in Middlebrook

Victorian 5th Ave row house meets modern SoHo loft

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Bear Den Cottage, vacation rental in Middlebrook
Bear Den Cottage, vacation rental in Middlebrook
Bear Den Cottage, vacation rental in Middlebrook

Bear Den Cottage

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Cabin on Penmerryl Farm - (2-Night Minimum Stay), vacation rental in Middlebrook
Cabin on Penmerryl Farm - (2-Night Minimum Stay), vacation rental in Middlebrook
Cabin on Penmerryl Farm - (2-Night Minimum Stay), vacation rental in Middlebrook

Cabin on Penmerryl Farm - (2-Night Minimum Stay)

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Enjoy a Hassle-Free and Suiting Stay! 3 Comfortable Units, Pets Allowed, vacation rental in Middlebrook
Enjoy a Hassle-Free and Suiting Stay! 3 Comfortable Units, Pets Allowed, vacation rental in Middlebrook
Enjoy a Hassle-Free and Suiting Stay! 3 Comfortable Units, Pets Allowed, vacation rental in Middlebrook

Enjoy a Hassle-Free and Suiting Stay! 3 Comfortable Units, Pets Allowed

Rental Home
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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Rose Cottage at Steeles Tavern, vacation rental in Middlebrook
Rose Cottage at Steeles Tavern, vacation rental in Middlebrook
Rose Cottage at Steeles Tavern, vacation rental in Middlebrook

Rose Cottage at Steeles Tavern

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Spacious Cottage. Lovely Shenandoah Valley Views.  Near Lexington And Staunton., vacation rental in Middlebrook
Spacious Cottage. Lovely Shenandoah Valley Views.  Near Lexington And Staunton., vacation rental in Middlebrook
Spacious Cottage. Lovely Shenandoah Valley Views.  Near Lexington And Staunton., vacation rental in Middlebrook

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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The Sanctuary in Historic Downtown Staunton, vacation rental in Middlebrook
The Sanctuary in Historic Downtown Staunton, vacation rental in Middlebrook
The Sanctuary in Historic Downtown Staunton, vacation rental in Middlebrook

The Sanctuary in Historic Downtown Staunton

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Historic house, designer charm, downtown location, vacation rental in Middlebrook
Historic house, designer charm, downtown location, vacation rental in Middlebrook
Historic house, designer charm, downtown location, vacation rental in Middlebrook

Historic house, designer charm, downtown location

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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House on cul-de-sac, vacation rental in Middlebrook
House on cul-de-sac, vacation rental in Middlebrook
House on cul-de-sac, vacation rental in Middlebrook

House on cul-de-sac

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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The Sanctuary in Historic Downtown Staunton, Virginia, vacation rental in Middlebrook
The Sanctuary in Historic Downtown Staunton, Virginia, vacation rental in Middlebrook
The Sanctuary in Historic Downtown Staunton, Virginia, vacation rental in Middlebrook

The Sanctuary in Historic Downtown Staunton, Virginia

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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☆The Chessie House☆ Spacious Home + Great Walks DT, vacation rental in Middlebrook
☆The Chessie House☆ Spacious Home + Great Walks DT, vacation rental in Middlebrook
☆The Chessie House☆ Spacious Home + Great Walks DT, vacation rental in Middlebrook

☆The Chessie House☆ Spacious Home + Great Walks DT

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Great Relaxing Overnight Stay! 4 Pleasant Units, Pets Allowed, Near Gypsy Hill, vacation rental in Middlebrook
Great Relaxing Overnight Stay! 4 Pleasant Units, Pets Allowed, Near Gypsy Hill, vacation rental in Middlebrook
Great Relaxing Overnight Stay! 4 Pleasant Units, Pets Allowed, Near Gypsy Hill, vacation rental in Middlebrook

Great Relaxing Overnight Stay! 4 Pleasant Units, Pets Allowed, Near Gypsy Hill

Rental Home
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
More info
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Always a Great Idea To Unwind! 4 Family-friendly Units, Pets Allowed, vacation rental in Middlebrook
Always a Great Idea To Unwind! 4 Family-friendly Units, Pets Allowed, vacation rental in Middlebrook
Always a Great Idea To Unwind! 4 Family-friendly Units, Pets Allowed, vacation rental in Middlebrook

Always a Great Idea To Unwind! 4 Family-friendly Units, Pets Allowed

Rental Home
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
More info
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Pleasant Stay, Convenient Location! 4 Relaxing Units, Pet-friendly Property, vacation rental in Middlebrook
Pleasant Stay, Convenient Location! 4 Relaxing Units, Pet-friendly Property, vacation rental in Middlebrook
Pleasant Stay, Convenient Location! 4 Relaxing Units, Pet-friendly Property, vacation rental in Middlebrook

Pleasant Stay, Convenient Location! 4 Relaxing Units, Pet-friendly Property

Rental Home
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
More info
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Peaceful Raphine Cottage w/ Deck & Fireplace!, vacation rental in Middlebrook
Peaceful Raphine Cottage w/ Deck & Fireplace!, vacation rental in Middlebrook
Peaceful Raphine Cottage w/ Deck & Fireplace!, vacation rental in Middlebrook

Peaceful Raphine Cottage w/ Deck & Fireplace!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
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Showing results 1-50 of 52
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