Vacation rentals in Wintergreen, VA

200 available vacation rental offers

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Best vacation rentals and Airbnb offers in Wintergreen, VA

Idyllic Wintergreen Condo w/ Resort Amenities - Wintergreen, VA

Idyllic Wintergreen Condo w/ Resort Amenities

Holiday Home, Wintergreen

Idyllic Wintergreen Condo w/ Resort Amenities is a holiday home in Wintergreen, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Idyllic Wintergreen Condo w/ Resort Amenities

Idyllic Wintergreen Condo w/ Resort Amenities is a holiday home in Wintergreen, 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 wifi, parking, paid parking, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,063.

From$97/night
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Wintergreen Resort Condo w/ Deck, 0.3 Mi to Slopes - Wintergreen, VA

Wintergreen Resort Condo w/ Deck, 0.3 Mi to Slopes

Holiday Home, Wintergreen

Wintergreen Resort Condo w/ Deck, 0.3 Mi to Slopes is a holiday home in Wintergreen, with pool access, outdoor space, and parking. This stay gives travelers a comfortable base for exploring…

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About Wintergreen Resort Condo w/ Deck, 0.3 Mi to Slopes

Wintergreen Resort Condo w/ Deck, 0.3 Mi to Slopes is a holiday home in Wintergreen, with pool access, 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, pool, free wifi, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,062.

From$98/night
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Wintergreen Resort Vacation Rental w/ Balcony! - Wintergreen, VA

Wintergreen Resort Vacation Rental w/ Balcony!

Holiday Home, Wintergreen

Wintergreen Resort Vacation Rental w/ Balcony! is a holiday home in Wintergreen, 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 Wintergreen, 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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Top of Mountain 2 BR Condo, Short Walk to scenic overlooks and nearby trails. - Wintergreen, VA

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

Condo, Wintergreen

Top of Mountain 2 BR Condo, Short Walk to scenic overlooks and nearby trails. is a condo in Wintergreen, 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 Wintergreen, 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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Vacation rentals with a pool in Wintergreen, VA

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

Idyllic Wintergreen Condo w/ Resort Amenities - Wintergreen, VA

Idyllic Wintergreen Condo w/ Resort Amenities

Condo, Wintergreen

Idyllic Wintergreen Condo w/ Resort Amenities is a condo in Wintergreen, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Idyllic Wintergreen Condo w/ Resort Amenities

Idyllic Wintergreen Condo w/ Resort Amenities is a condo in Wintergreen, 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 $929.

From$133/night
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Walk to Slopes and Restaurants - Cozy 1 Bedroom Condo - Wintergreen, VA

Walk to Slopes and Restaurants - Cozy 1 Bedroom Condo

Condo, Wintergreen

Walk to Slopes and Restaurants - Cozy 1 Bedroom Condo is a condo in Wintergreen, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Walk to Slopes and Restaurants - Cozy 1 Bedroom Condo

Walk to Slopes and Restaurants - Cozy 1 Bedroom Condo is a condo in Wintergreen, 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 $1,051.

From$150/night
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Wintergreen Condo w/ Pool: Near Hike & Market! - Wintergreen, VA

Wintergreen Condo w/ Pool: Near Hike & Market!

Apartment, Wintergreen

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

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

Wintergreen Condo w/ Pool: Near Hike & Market! is a apartment in Wintergreen, 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 $1,403.

From$154/night
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100 yards to Tyro slope Nestled in the woods - Wintergreen, VA

100 yards to Tyro slope Nestled in the woods

Holiday Home, Wintergreen

100 yards to Tyro slope Nestled in the woods is a holiday home in Wintergreen, 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 Wintergreen, 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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Vacation rentals with parking in Wintergreen, VA

Find vacation rentals that make arriving by car easier.

Renovated Wintergreen Condo with Pool Access, and more! - Wintergreen, VA

Renovated Wintergreen Condo with Pool Access, and more!

Condo, Wintergreen

Renovated Wintergreen Condo with Pool Access, and more! is a condo in Wintergreen, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Renovated Wintergreen Condo with Pool Access, and more!

Renovated Wintergreen Condo with Pool Access, and more! is a condo in Wintergreen, 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 $986.

From$141/night
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Cozy Lux Condo at Wintergreen Resort - Wintergreen, VA

Cozy Lux Condo at Wintergreen Resort

Condo, Wintergreen

Cozy Lux Condo at Wintergreen Resort is a condo in Wintergreen, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Cozy Lux Condo at Wintergreen Resort

Cozy Lux Condo at Wintergreen Resort is a condo in Wintergreen, 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 $1,038.

From$148/night
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Cozy Studio Overlooking 18 Hole - Wintergreen, VA

Cozy Studio Overlooking 18 Hole

Condo, Wintergreen

Cozy Studio Overlooking 18 Hole is a condo in Wintergreen, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Cozy Studio Overlooking 18 Hole

Cozy Studio Overlooking 18 Hole is a condo in Wintergreen, 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,077.

From$154/night
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Tucked Inn: Lower Unit - NEW Nelson Co Getaway - Wintergreen, VA

Tucked Inn: Lower Unit - NEW Nelson Co Getaway

Holiday Home, Wintergreen

Tucked Inn: Lower Unit - NEW Nelson Co Getaway is a holiday home in Wintergreen, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Tucked Inn: Lower Unit - NEW Nelson Co Getaway

Tucked Inn: Lower Unit - NEW Nelson Co Getaway is a holiday home in Wintergreen, 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,138.

From$163/night
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Pet-friendly vacation rentals in Wintergreen, VA

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

Updated! Cozy and clean two bedroom condo. - Wintergreen, VA

Updated! Cozy and clean two bedroom condo.

Condo, Wintergreen

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

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About Updated! Cozy and clean two bedroom condo.

Updated! Cozy and clean two bedroom condo. is a condo in Wintergreen, 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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Wintergreen Resort Vacation Rental w/ Pool Access! - Wintergreen, VA

Wintergreen Resort Vacation Rental w/ Pool Access!

Holiday Home, Wintergreen

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

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About Wintergreen Resort Vacation Rental w/ Pool Access!

Wintergreen Resort Vacation Rental w/ Pool Access! is a holiday home in Wintergreen, 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 $1,663.

From$151/night
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Prime WTG Location - Summer Fun at Swoopside Hideaway - Outdoor Pools - Wintergreen, VA

Prime WTG Location - Summer Fun at Swoopside Hideaway - Outdoor Pools

Apartment, Wintergreen

Prime WTG Location - Summer Fun at Swoopside Hideaway - Outdoor Pools is a apartment in Wintergreen, with pool access and kitchen access. This stay gives travelers a comfortable base for…

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About Prime WTG Location - Summer Fun at Swoopside Hideaway - Outdoor Pools

Prime WTG Location - Summer Fun at Swoopside Hideaway - Outdoor Pools is a apartment in Wintergreen, 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 $1,099.

From$157/night
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Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views! - Wintergreen, VA

Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!

Condo, Wintergreen

Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views! is a condo in Wintergreen, with pet-friendly space and pool access. This stay gives travelers a comfortable base…

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About Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!

Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views! is a condo in Wintergreen, 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 $1,185.

From$169/night
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Vacation rentals with a kitchen in Wintergreen, VA

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

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

Blue Rivers Loft on the Brew Ridge Trail

Apartment, Wintergreen

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

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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 Wintergreen, 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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Wintergreen Resort Vacation Rental w/ Balcony! - Wintergreen, VA

Wintergreen Resort Vacation Rental w/ Balcony!

Condo, Wintergreen

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

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About Wintergreen Resort Vacation Rental w/ Balcony!

Wintergreen Resort Vacation Rental w/ Balcony! is a condo in Wintergreen, 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,097.

From$157/night
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Travelers' Rest--Your Wintergreen Retreat in the Center of it All! - Wintergreen, VA

Travelers' Rest--Your Wintergreen Retreat in the Center of it All!

Condo, Wintergreen

Travelers' Rest--Your Wintergreen Retreat in the Center of it All! is a condo in Wintergreen, with pool access, kitchen access, and a quieter setting. This stay gives travelers a…

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About Travelers' Rest--Your Wintergreen Retreat in the Center of it All!

Travelers' Rest--Your Wintergreen Retreat in the Center of it All! is a condo in Wintergreen, 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: free cancellation, pool, kitchen, with kitchen, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,155.

From$165/night
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Wintergreen Condo w/ Pool: Near Hike & Market! - Wintergreen, VA

Wintergreen Condo w/ Pool: Near Hike & Market!

Condo, Wintergreen

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

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

Wintergreen Condo w/ Pool: Near Hike & Market! is a condo in Wintergreen, 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 $1,174.

From$168/night
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Family-friendly vacation rentals in Wintergreen, VA

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

Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat - Wintergreen, VA

Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat

Cottage, Wintergreen

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

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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 Wintergreen, 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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Bluebird Cottage: Near 151 + Appalachian Trail - Wintergreen, VA

Bluebird Cottage: Near 151 + Appalachian Trail

Cottage, Wintergreen

Bluebird Cottage: Near 151 + Appalachian Trail is a cottage in Wintergreen, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Bluebird Cottage: Near 151 + Appalachian Trail

Bluebird Cottage: Near 151 + Appalachian Trail is a cottage in Wintergreen, 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 $1,183.

From$169/night
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Walk to Ski Slopes: Wintergreen Resort Treehouse - Wintergreen, VA

Walk to Ski Slopes: Wintergreen Resort Treehouse

Cottage, Wintergreen

Walk to Ski Slopes: Wintergreen Resort Treehouse is a cottage in Wintergreen, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Walk to Ski Slopes: Wintergreen Resort Treehouse

Walk to Ski Slopes: Wintergreen Resort Treehouse is a cottage in Wintergreen, 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 $1,955.

From$224/night
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Stoney Creek Cottage: Waterfront Hot Tub, Fire Pit - Wintergreen, VA

Stoney Creek Cottage: Waterfront Hot Tub, Fire Pit

Holiday Home, Wintergreen

Stoney Creek Cottage: Waterfront Hot Tub, Fire Pit is a holiday home in Wintergreen, 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 Wintergreen, 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 $2,284.

From$238/night
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