Vacation rentals in Sherando, VA

200 available vacation rental offers

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Best vacation rentals and Airbnb offers in Sherando, VA

Wintergreen Resort Vacation Rental w/ Balcony! - 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 $1,176.

From$110/night
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Top of Mountain 2 BR Condo, Short Walk to scenic overlooks and nearby trails. - Sherando, VA

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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Beautiful 2BR/2BA - DOG FRIENDLY -- Great LOW Rates - Sherando, VA

Beautiful 2BR/2BA - DOG FRIENDLY -- Great LOW Rates

Condo, Sherando

Beautiful 2BR/2BA - DOG FRIENDLY -- Great LOW Rates is a condo in Sherando, with pet-friendly space, pool access, and room for a group. This stay gives travelers a comfortable base for…

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About Beautiful 2BR/2BA - DOG FRIENDLY -- Great LOW Rates

Beautiful 2BR/2BA - DOG FRIENDLY -- Great LOW Rates is a condo in Sherando, with pet-friendly space, pool 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, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $839.

From$120/night
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Updated! Cozy and clean two bedroom condo. - Sherando, VA

Updated! Cozy and clean two bedroom condo.

Condo, Sherando

Updated! Cozy and clean two bedroom condo. is a condo in Sherando, with pet-friendly space, pool access, and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Updated! Cozy and clean two bedroom condo.

Updated! Cozy and clean two bedroom condo. is a condo in Sherando, with pet-friendly space, pool 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, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $949.

From$136/night
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Waterfront vacation rentals in Sherando, VA

Discover vacation rentals close to the coast, water, and beach areas around Sherando, VA.

Blue Rivers Loft on the Brew Ridge Trail - Sherando, VA

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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Stoney Creek Cottage: Waterfront Hot Tub, Fire Pit - Sherando, VA

Stoney Creek Cottage: Waterfront Hot Tub, Fire Pit

Holiday Home, Sherando

Stoney Creek Cottage: Waterfront Hot Tub, Fire Pit is a holiday home in Sherando, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Stoney Creek Cottage: Waterfront Hot Tub, Fire Pit

Stoney Creek Cottage: Waterfront Hot Tub, Fire Pit is a holiday home in Sherando, with easy beach access 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, hot tub, free wifi, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,281.

From$238/night
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Condo at Fairway Woods, perfect home base for ski season! ☃️🏂 - Sherando, VA

Condo at Fairway Woods, perfect home base for ski season! ☃️🏂

Holiday Home, Sherando

Condo at Fairway Woods, perfect home base for ski season! ☃️🏂 is a holiday home in Sherando, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Condo at Fairway Woods, perfect home base for ski season! ☃️🏂

Condo at Fairway Woods, perfect home base for ski season! ☃️🏂 is a holiday home in Sherando, 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 $1,924.

From$275/night
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Stoney Creek Cottage: Waterfront Hot Tub, Fire Pit - Sherando, VA

Stoney Creek Cottage: Waterfront Hot Tub, Fire Pit

Cottage, Sherando

Stoney Creek Cottage: Waterfront Hot Tub, Fire Pit is a cottage in Sherando, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Stoney Creek Cottage: Waterfront Hot Tub, Fire Pit

Stoney Creek Cottage: Waterfront Hot Tub, Fire Pit is a cottage in Sherando, with easy beach 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, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,369.

From$275/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.

Wintergreen Condo w/ Pool: Near Hike & Market! - Sherando, VA

Wintergreen Condo w/ Pool: Near Hike & Market!

Apartment, Sherando

Wintergreen Condo w/ Pool: Near Hike & Market! is a apartment in Sherando, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Wintergreen Condo w/ Pool: Near Hike & Market!

Wintergreen Condo w/ Pool: Near Hike & Market! is a apartment in Sherando, with 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,398.

From$153/night
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Devil's Knob Mtn. condo on golf course with views of Shenandoah Valley - Sherando, VA

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. - Sherando, VA

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: Weeping Rock Retreat - Sherando, VA

Wintergreen Resort: Weeping Rock Retreat

Holiday Home, Sherando

Wintergreen Resort: Weeping Rock Retreat is a holiday home in Sherando, with pet-friendly space, pool access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Wintergreen Resort: Weeping Rock Retreat

Wintergreen Resort: Weeping Rock Retreat 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, 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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Vacation rentals with parking in Sherando, VA

Find vacation rentals that make arriving by car easier.

Afton escape centrally located on the brew trail - Sherando, VA

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 $1,096.

From$157/night
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100 yards to Tyro slope Nestled in the woods - Sherando, VA

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

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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Lovely home in quaint rolling hills near Afton wineries - Sherando, VA

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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Pet-friendly vacation rentals in Sherando, VA

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

Wintergreen Resort Vacation Rental w/ Pool Access! - Sherando, VA

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 $1,722.

From$184/night
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Location, location, location mountain side in Wintergreen Mountain Village - Sherando, VA

Location, location, location mountain side in Wintergreen Mountain Village

Condo, Sherando

Location, location, location mountain side in Wintergreen Mountain Village is a condo in Sherando, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Location, location, location mountain side in Wintergreen Mountain Village

Location, location, location mountain side in Wintergreen Mountain Village is a condo 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 $1,323.

From$189/night
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Wintergreen Resort Vacation Rental w/ Pool Access! - Sherando, VA

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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Hansel 'n Gretel: Wood Stove Grill Firepit Dogs OK - Sherando, VA

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 $1,280.

From$183/night
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Vacation rentals with a kitchen in Sherando, VA

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

Secluded 20+ Acre Retreat Near Brew & Wine Trails - Sherando, VA

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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Private One Bedroom by Mountain Stream - Sherando, VA

Private One Bedroom by Mountain Stream

Cabin, Sherando

Private One Bedroom by Mountain Stream is a cabin in Sherando, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Private One Bedroom by Mountain Stream

Private One Bedroom by Mountain Stream is a cabin in Sherando, with pet-friendly space, 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,393.

From$199/night
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Golf, Spa, Wine,or just a quiet getaway - Sherando, VA

Golf, Spa, Wine,or just a quiet getaway

Condo, Sherando

Golf, Spa, Wine,or just a quiet getaway is a condo in Sherando, with pool access, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area,…

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About Golf, Spa, Wine,or just a quiet getaway

Golf, Spa, Wine,or just a quiet getaway is a condo in Sherando, with pool access, 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: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,534.

From$219/night
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Golf Course Views Golden Tee Pool Tennis Golf Hike - Sherando, VA

Golf Course Views Golden Tee Pool Tennis Golf Hike

Holiday Home, Sherando

Golf Course Views Golden Tee Pool Tennis Golf Hike is a holiday home in Sherando, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Golf Course Views Golden Tee Pool Tennis Golf Hike

Golf Course Views Golden Tee Pool Tennis Golf Hike is a holiday home in Sherando, with 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,582.

From$226/night
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