Vacation rentals in Sherando, VA

Best vacation rentals and Airbnb offers in Sherando, VA

Wintergreen Resort Vacation Rental w/ Balcony!

Holiday Home, Sherando

Wintergreen Resort Vacation Rental w/ Balcony! is a holiday home in Sherando, with pet-friendly space, pool access, and outdoor space. This stay gives travelers a comfortable base for…

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About Wintergreen Resort Vacation Rental w/ Balcony!

Wintergreen Resort Vacation Rental w/ Balcony! is a holiday home in Sherando, with pet-friendly space, pool access, and outdoor 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, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,177.

From$110/night

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Blair's Vintage Apartment Nestled in Wine Country

Apartment, Sherando

Blair's Vintage Apartment Nestled in Wine Country is a apartment in Sherando, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Blair's Vintage Apartment Nestled in Wine Country

Blair's Vintage Apartment Nestled in Wine Country is a apartment in Sherando, 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, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $788.

From$113/night

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Top of Mountain 2 BR Condo, Short Walk to scenic overlooks and nearby trails.

Condo, Sherando

Top of Mountain 2 BR Condo, Short Walk to scenic overlooks and nearby trails. is a condo in Sherando, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Top of Mountain 2 BR Condo, Short Walk to scenic overlooks and nearby trails.

Top of Mountain 2 BR Condo, Short Walk to scenic overlooks and nearby trails. is a condo in Sherando, with parking, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $820.

From$117/night

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Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

Condo, Sherando

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course is a condo in Sherando, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base…

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About Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course is a condo in Sherando, with pet-friendly space, pool access, 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, pool, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $824.

From$118/night

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Vacation rentals with a pool in Sherando, VA

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

100 yards to Tyro slope Nestled in the woods

Holiday Home, Sherando

100 yards to Tyro slope Nestled in the woods is a holiday home in Sherando, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About 100 yards to Tyro slope Nestled in the woods

100 yards to Tyro slope Nestled in the woods is a holiday home in Sherando, with pool access, 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, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,135.

From$162/night

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Devil's Knob Mtn. condo on golf course with views of Shenandoah Valley

Condo, Sherando

Devil's Knob Mtn. condo on golf course with views of Shenandoah Valley is a condo in Sherando, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base…

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About Devil's Knob Mtn. condo on golf course with views of Shenandoah Valley

Devil's Knob Mtn. condo on golf course with views of Shenandoah Valley is a condo in Sherando, with pool access, 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, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,208.

From$173/night

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Serene haven \"The Nest\" in Wintergreen, close to activities and restaurants.

Condo, Sherando

Serene haven \"The Nest\" in Wintergreen, close to activities and restaurants. is a condo in Sherando, with pool access, parking, and kitchen access. This stay gives travelers a comfortable…

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About Serene haven \"The Nest\" in Wintergreen, close to activities and restaurants.

Serene haven \"The Nest\" in Wintergreen, close to activities and restaurants. is a condo in Sherando, with pool access, 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, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,221.

From$174/night

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Wintergreen Resort Vacation Rental w/ Pool Access!

Condo, Sherando

Wintergreen Resort Vacation Rental w/ Pool Access! is a condo in Sherando, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for…

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About Wintergreen Resort Vacation Rental w/ Pool Access!

Wintergreen Resort Vacation Rental w/ Pool Access! is a condo in Sherando, with pet-friendly space, pool access, 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, pool, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,371.

From$196/night

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Vacation rentals with parking in Sherando, VA

Find vacation rentals that make arriving by car easier.

Wintergreen Resort Condo: Deck & Golf Course Views

Condo, Sherando

Wintergreen Resort Condo: Deck & Golf Course Views is a condo in Sherando, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Wintergreen Resort Condo: Deck & Golf Course Views

Wintergreen Resort Condo: Deck & Golf Course Views is a condo in Sherando, 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,145.

From$164/night

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Shenandoah Valley Atelier: NEW Waynesboro Loft

Apartment, Sherando

Shenandoah Valley Atelier: NEW Waynesboro Loft is a apartment in Sherando, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Shenandoah Valley Atelier: NEW Waynesboro Loft

Shenandoah Valley Atelier: NEW Waynesboro Loft is a apartment in Sherando, 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 $1,154.

From$165/night

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Cozy 2-bedroom Condo in Wintergreen Resort with Full Kitchen & Beautiful Balcony

Condo, Sherando

Cozy 2-bedroom Condo in Wintergreen Resort with Full Kitchen & Beautiful Balcony is a condo in Sherando, with outdoor space, parking, and kitchen access. This stay gives travelers a…

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About Cozy 2-bedroom Condo in Wintergreen Resort with Full Kitchen & Beautiful Balcony

Cozy 2-bedroom Condo in Wintergreen Resort with Full Kitchen & Beautiful Balcony is a condo in Sherando, 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 $1,287.

From$184/night

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Secluded 20+ Acre Retreat Near Brew & Wine Trails

Holiday Home, Sherando

Secluded 20+ Acre Retreat Near Brew & Wine Trails is a holiday home in Sherando, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Secluded 20+ Acre Retreat Near Brew & Wine Trails

Secluded 20+ Acre Retreat Near Brew & Wine Trails is a holiday home in Sherando, 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: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,379.

From$197/night

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Pet-friendly vacation rentals in Sherando, VA

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

Afton escape centrally located on the brew trail

Holiday Home, Sherando

Afton escape centrally located on the brew trail is a holiday home in Sherando, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Afton escape centrally located on the brew trail

Afton escape centrally located on the brew trail is a holiday home in Sherando, 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 $1,100.

From$157/night

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Wintergreen Resort Vacation Rental w/ Pool Access!

Apartment, Sherando

Wintergreen Resort Vacation Rental w/ Pool Access! is a apartment in Sherando, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area,…

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About Wintergreen Resort Vacation Rental w/ Pool Access!

Wintergreen Resort Vacation Rental w/ Pool Access! is a apartment in Sherando, 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, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,725.

From$184/night

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Lovely home in quaint rolling hills near Afton wineries

Holiday Home, Sherando

Lovely home in quaint rolling hills near Afton wineries is a holiday home in Sherando, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Lovely home in quaint rolling hills near Afton wineries

Lovely home in quaint rolling hills near Afton wineries is a holiday home in Sherando, 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 $1,326.

From$189/night

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Hansel 'n Gretel: Wood Stove Grill Firepit Dogs OK

Chalet, Sherando

Hansel 'n Gretel: Wood Stove Grill Firepit Dogs OK is a chalet in Sherando, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for…

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About Hansel 'n Gretel: Wood Stove Grill Firepit Dogs OK

Hansel 'n Gretel: Wood Stove Grill Firepit Dogs OK is a chalet in Sherando, with pet-friendly space, pool access, 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: pool, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,275.

From$182/night

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Vacation rentals with a kitchen in Sherando, VA

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

Close to Skyliine Drive Wintergreen Cozy and Private

Apartment, Sherando

Close to Skyliine Drive Wintergreen Cozy and Private is a apartment in Sherando, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Close to Skyliine Drive Wintergreen Cozy and Private

Close to Skyliine Drive Wintergreen Cozy and Private is a apartment in Sherando, 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $793.

From$113/night

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Blue Rivers Loft on the Brew Ridge Trail

Apartment, Sherando

Blue Rivers Loft on the Brew Ridge Trail is a apartment in Sherando, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Blue Rivers Loft on the Brew Ridge Trail

Blue Rivers Loft on the Brew Ridge Trail is a apartment in Sherando, 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, free wifi, kitchen, with kitchen, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $898.

From$128/night

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Smoky Bear Cabin

Cabin, Sherando

Smoky Bear Cabin is a cabin in Sherando, with kitchen access. 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 Smoky Bear Cabin

Smoky Bear Cabin is a cabin in Sherando, 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, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,082.

From$155/night

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Murphy’s Place 2-bedroom apartment near hiking skiing wineries and breweries.

Apartment, Sherando

Murphy’s Place 2-bedroom apartment near hiking skiing wineries and breweries. is a apartment in Sherando, with pool access, kitchen access, and room for a group. This stay gives travelers a…

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About Murphy’s Place 2-bedroom apartment near hiking skiing wineries and breweries.

Murphy’s Place 2-bedroom apartment near hiking skiing wineries and breweries. is a apartment in Sherando, 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 $1,187.

From$170/night

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Family-friendly vacation rentals in Sherando, VA

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

Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat

Cottage, Sherando

Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat is a cottage in Sherando, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat

Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat is a cottage in Sherando, 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 $898.

From$128/night

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Nona's Cottage-Waynesboro/Shenandoah Valley, VA

Holiday Home, Sherando

Nona's Cottage-Waynesboro/Shenandoah Valley, VA is a holiday home in Sherando, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Nona's Cottage-Waynesboro/Shenandoah Valley, VA

Nona's Cottage-Waynesboro/Shenandoah Valley, VA is a holiday home in Sherando, 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 $1,001.

From$143/night

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Afton Mountain Inn

Guest House, Sherando

Afton Mountain Inn is a guest house in Sherando, with pool access, parking, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Afton Mountain Inn

Afton Mountain Inn is a guest house in Sherando, with pool access, 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: pool, parking, free parking, family friendly, and game room.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,604.

From$197/night

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Buck's Cabin: Cozy retreat with hot tub. Pet- & kid-friendly!

Holiday Home, Sherando

Buck's Cabin: Cozy retreat with hot tub. Pet- & kid-friendly! is a holiday home in Sherando, with pet-friendly space, pool access, and a quieter setting. This stay gives travelers a…

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About Buck's Cabin: Cozy retreat with hot tub. Pet- & kid-friendly!

Buck's Cabin: Cozy retreat with hot tub. Pet- & kid-friendly! is a holiday home in Sherando, with pet-friendly space, pool 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, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,625.

From$232/night

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