Vacation rentals in Simmons Gap, VA

155 available vacation rental offers

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Best vacation rentals and Airbnb offers in Simmons Gap, VA

New studio/country apartment - Simmons Gap, VA

New studio/country apartment

Apartment, Simmons Gap

New studio/country apartment is a apartment in Simmons Gap. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About New studio/country apartment

New studio/country apartment is a apartment in Simmons Gap. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, washer, dryer, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $836.

From$119/night
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Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP - Simmons Gap, VA

Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP

Apartment, Simmons Gap

Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP is a apartment in Simmons Gap, with pet-friendly space, parking, and kitchen access. This stay gives…

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About Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP

Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP is a apartment in Simmons Gap, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $873.

From$125/night
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Quiet-peaceful 2-bedroom house with AC in Stanardsville, VA. NO PETS! - Simmons Gap, VA

Quiet-peaceful 2-bedroom house with AC in Stanardsville, VA. NO PETS!

Holiday Home, Simmons Gap

Quiet-peaceful 2-bedroom house with AC in Stanardsville, VA. NO PETS! is a holiday home in Simmons Gap, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Quiet-peaceful 2-bedroom house with AC in Stanardsville, VA. NO PETS!

Quiet-peaceful 2-bedroom house with AC in Stanardsville, VA. NO PETS! is a holiday home in Simmons Gap, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $908.

From$130/night
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Shenandoah National Park: Cabin w/ Patio! - Simmons Gap, VA

Shenandoah National Park: Cabin w/ Patio!

Holiday Home, Simmons Gap

Shenandoah National Park: Cabin w/ Patio! is a holiday home in Simmons Gap, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for exploring…

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About Shenandoah National Park: Cabin w/ Patio!

Shenandoah National Park: Cabin w/ Patio! is a holiday home in Simmons Gap, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,306.

From$132/night
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Vacation rentals with a pool in Simmons Gap, VA

Add a pool to the search when you want an easy place to cool off between outings.

Massanutten Resort by Tripforth - Simmons Gap, VA

Massanutten Resort by Tripforth

Holiday Home, Simmons Gap

Massanutten Resort by Tripforth is a holiday home in Simmons Gap, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Massanutten Resort by Tripforth

Massanutten Resort by Tripforth is a holiday home in Simmons Gap, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,033.

From$99/night
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Massanutten Resort by TripForth - Simmons Gap, VA

Massanutten Resort by TripForth

Holiday Home, Simmons Gap

Massanutten Resort by TripForth is a holiday home in Simmons Gap, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Massanutten Resort by TripForth

Massanutten Resort by TripForth is a holiday home in Simmons Gap, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,179.

From$114/night
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Massanutten's Woodstone Meadows by Tripforth - Simmons Gap, VA

Massanutten's Woodstone Meadows by Tripforth

Holiday Home, Simmons Gap

Massanutten's Woodstone Meadows by Tripforth is a holiday home in Simmons Gap, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Massanutten's Woodstone Meadows by Tripforth

Massanutten's Woodstone Meadows by Tripforth is a holiday home in Simmons Gap, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,499.

From$156/night
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The Summit at Massanutten Resort by Tripforth - Simmons Gap, VA

The Summit at Massanutten Resort by Tripforth

Holiday Home, Simmons Gap

The Summit at Massanutten Resort by Tripforth is a holiday home in Simmons Gap, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About The Summit at Massanutten Resort by Tripforth

The Summit at Massanutten Resort by Tripforth is a holiday home in Simmons Gap, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,661.

From$176/night
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Vacation rentals with parking in Simmons Gap, VA

Find vacation rentals that make arriving by car easier.

Hike,Massanutten Resort,LurayCaverns,Skyline Drive, Snow Tube/Ski - Simmons Gap, VA

Hike,Massanutten Resort,LurayCaverns,Skyline Drive, Snow Tube/Ski

Cabin, Simmons Gap

Hike,Massanutten Resort,LurayCaverns,Skyline Drive, Snow Tube/Ski is a cabin in Simmons Gap, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Hike,Massanutten Resort,LurayCaverns,Skyline Drive, Snow Tube/Ski

Hike,Massanutten Resort,LurayCaverns,Skyline Drive, Snow Tube/Ski is a cabin in Simmons Gap, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,166.

From$167/night
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Triquetra: A Shenandoah Farmstay Retreat - Simmons Gap, VA

Triquetra: A Shenandoah Farmstay Retreat

Apartment, Simmons Gap

Triquetra: A Shenandoah Farmstay Retreat is a apartment in Simmons Gap, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the…

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About Triquetra: A Shenandoah Farmstay Retreat

Triquetra: A Shenandoah Farmstay Retreat is a apartment in Simmons Gap, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,237.

From$177/night
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Massanutten Retreat w/ Double Deck & Mtn View! - Simmons Gap, VA

Massanutten Retreat w/ Double Deck & Mtn View!

Holiday Home, Simmons Gap

Massanutten Retreat w/ Double Deck & Mtn View! is a holiday home in Simmons Gap, with outdoor space, parking, and a quieter setting. This stay gives travelers a comfortable base for…

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About Massanutten Retreat w/ Double Deck & Mtn View!

Massanutten Retreat w/ Double Deck & Mtn View! is a holiday home in Simmons Gap, with outdoor space, parking, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, gym, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,892.

From$193/night
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Cave Hill Farm Bed & Breakfast - Simmons Gap, VA

Cave Hill Farm Bed & Breakfast

B & B, Simmons Gap

Cave Hill Farm Bed & Breakfast is a b & b in Simmons Gap, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Cave Hill Farm Bed & Breakfast

Cave Hill Farm Bed & Breakfast is a b & b in Simmons Gap, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free breakfast, free wifi, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,180.

From$153/night
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Pet-friendly vacation rentals in Simmons Gap, VA

Bring your pet along with stays that welcome four-legged travelers.

Home 14 Mi to Shenandoah Natl Park! Fenced Yard - Simmons Gap, VA

Home 14 Mi to Shenandoah Natl Park! Fenced Yard

Cottage, Simmons Gap

Home 14 Mi to Shenandoah Natl Park! Fenced Yard is a cottage in Simmons Gap, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Home 14 Mi to Shenandoah Natl Park! Fenced Yard

Home 14 Mi to Shenandoah Natl Park! Fenced Yard is a cottage in Simmons Gap, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,489.

From$162/night
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Elkton, Va. Modernized Farmhouse! Great location in the Shenandoah Valley. - Simmons Gap, VA

Elkton, Va. Modernized Farmhouse! Great location in the Shenandoah Valley.

Country House, Simmons Gap

Elkton, Va. Modernized Farmhouse! Great location in the Shenandoah Valley. is a country house in Simmons Gap, with parking and kitchen access. This stay gives travelers a comfortable base…

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About Elkton, Va. Modernized Farmhouse! Great location in the Shenandoah Valley.

Elkton, Va. Modernized Farmhouse! Great location in the Shenandoah Valley. is a country house in Simmons Gap, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,227.

From$175/night
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Large Hot Tub – Outdoor Fireplace – Propane Grill – Pet Friendly - WIFI! - Simmons Gap, VA

Large Hot Tub – Outdoor Fireplace – Propane Grill – Pet Friendly - WIFI!

Holiday Home, Simmons Gap

Large Hot Tub – Outdoor Fireplace – Propane Grill – Pet Friendly - WIFI! is a holiday home in Simmons Gap, with pet-friendly space and pool access. This stay gives travelers a comfortable…

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About Large Hot Tub – Outdoor Fireplace – Propane Grill – Pet Friendly - WIFI!

Large Hot Tub – Outdoor Fireplace – Propane Grill – Pet Friendly - WIFI! is a holiday home in Simmons Gap, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,341.

From$192/night
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Cozy Cabin located close to Shenandoah National Park, Wineries, and Breweries. - Simmons Gap, VA

Cozy Cabin located close to Shenandoah National Park, Wineries, and Breweries.

Cabin, Simmons Gap

Cozy Cabin located close to Shenandoah National Park, Wineries, and Breweries. is a cabin in Simmons Gap, with pet-friendly space. This stay gives travelers a comfortable base for exploring…

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About Cozy Cabin located close to Shenandoah National Park, Wineries, and Breweries.

Cozy Cabin located close to Shenandoah National Park, Wineries, and Breweries. is a cabin in Simmons Gap, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,555.

From$222/night
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Vacation rentals with a kitchen in Simmons Gap, VA

Compare stays with kitchen access for longer trips and easier meals.

Massanutten Resort's Eagle Trace 1 Bedroom Condo w/Full Kitchen - Simmons Gap, VA

Massanutten Resort's Eagle Trace 1 Bedroom Condo w/Full Kitchen

Condo, Simmons Gap

Massanutten Resort's Eagle Trace 1 Bedroom Condo w/Full Kitchen is a condo in Simmons Gap, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Massanutten Resort's Eagle Trace 1 Bedroom Condo w/Full Kitchen

Massanutten Resort's Eagle Trace 1 Bedroom Condo w/Full Kitchen is a condo in Simmons Gap, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,382.

From$197/night
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Massanutten Retreat w/ Double Deck & Mtn View! - Simmons Gap, VA

Massanutten Retreat w/ Double Deck & Mtn View!

Cottage, Simmons Gap

Massanutten Retreat w/ Double Deck & Mtn View! is a cottage in Simmons Gap, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Massanutten Retreat w/ Double Deck & Mtn View!

Massanutten Retreat w/ Double Deck & Mtn View! is a cottage in Simmons Gap, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,964.

From$228/night
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A Den for all four seasons, visit the Bear's Den and create lasting memories. - Simmons Gap, VA

A Den for all four seasons, visit the Bear's Den and create lasting memories.

Holiday Home, Simmons Gap

A Den for all four seasons, visit the Bear's Den and create lasting memories. is a holiday home in Simmons Gap, with parking and kitchen access. This stay gives travelers a comfortable base…

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About A Den for all four seasons, visit the Bear's Den and create lasting memories.

A Den for all four seasons, visit the Bear's Den and create lasting memories. is a holiday home in Simmons Gap, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,608.

From$230/night
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Mountain cabin by Shenandoah National Park - Simmons Gap, VA

Mountain cabin by Shenandoah National Park

Cabin, Simmons Gap

Mountain cabin by Shenandoah National Park is a cabin in Simmons Gap, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Mountain cabin by Shenandoah National Park

Mountain cabin by Shenandoah National Park is a cabin in Simmons Gap, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, fireplace, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,835.

From$262/night
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Family-friendly vacation rentals in Simmons Gap, VA

Plan a trip with stays that give families more room to spread out.

Red Brush Cottage Property - Simmons Gap, VA

Red Brush Cottage Property

Holiday Home, Simmons Gap

Red Brush Cottage Property is a holiday home in Simmons Gap, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Red Brush Cottage Property

Red Brush Cottage Property is a holiday home in Simmons Gap, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,053.

From$150/night
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Family Getaway; Skiing, Wineries; Skyline Dr; Sleeps 4; Short Stays; EV+ - Simmons Gap, VA

Family Getaway; Skiing, Wineries; Skyline Dr; Sleeps 4; Short Stays; EV+

Holiday Home, Simmons Gap

Family Getaway; Skiing, Wineries; Skyline Dr; Sleeps 4; Short Stays; EV+ is a holiday home in Simmons Gap, with parking and room for a group. This stay gives travelers a comfortable base…

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About Family Getaway; Skiing, Wineries; Skyline Dr; Sleeps 4; Short Stays; EV+

Family Getaway; Skiing, Wineries; Skyline Dr; Sleeps 4; Short Stays; EV+ is a holiday home in Simmons Gap, with parking and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, gym, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,070.

From$153/night
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60 acre farm with mountain views & trails. 15 min from Shenandoah National Park - Simmons Gap, VA

60 acre farm with mountain views & trails. 15 min from Shenandoah National Park

Cottage, Simmons Gap

60 acre farm with mountain views & trails. 15 min from Shenandoah National Park is a cottage in Simmons Gap, with pet-friendly space, parking, and kitchen access. This stay gives travelers…

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About 60 acre farm with mountain views & trails. 15 min from Shenandoah National Park

60 acre farm with mountain views & trails. 15 min from Shenandoah National Park is a cottage in Simmons Gap, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,216.

From$174/night
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Quiet, clean, jacuzzi hot tub. hidden gem, families. Skyline Park & Massanutten. - Simmons Gap, VA

Quiet, clean, jacuzzi hot tub. hidden gem, families. Skyline Park & Massanutten.

Cottage, Simmons Gap

Quiet, clean, jacuzzi hot tub. hidden gem, families. Skyline Park & Massanutten. is a cottage in Simmons Gap, with pet-friendly space and a quieter setting. This stay gives travelers a…

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About Quiet, clean, jacuzzi hot tub. hidden gem, families. Skyline Park & Massanutten.

Quiet, clean, jacuzzi hot tub. hidden gem, families. Skyline Park & Massanutten. is a cottage in Simmons Gap, with pet-friendly space and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,521.

From$217/night
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