Vacation rentals in Wintergreen Resort, VA

200 available vacation rental offers

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Best vacation rentals and Airbnb offers in Wintergreen Resort, VA

Idyllic Wintergreen Condo w/ Resort Amenities - Wintergreen Resort, VA

Idyllic Wintergreen Condo w/ Resort Amenities

Holiday Home, Wintergreen Resort

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

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About Idyllic Wintergreen Condo w/ Resort Amenities

Idyllic Wintergreen Condo w/ Resort Amenities is a holiday home in Wintergreen Resort, 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 $1,062.

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

Wintergreen Resort Condo w/ Deck, 0.3 Mi to Slopes

Holiday Home, Wintergreen Resort

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

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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 Resort, 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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Snug Wintergreen Resort Studio: Ski In & Out! - Wintergreen Resort, VA

Snug Wintergreen Resort Studio: Ski In & Out!

Apartment, Wintergreen Resort

Snug Wintergreen Resort Studio: Ski In & Out! is a apartment in Wintergreen Resort, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Snug Wintergreen Resort Studio: Ski In & Out!

Snug Wintergreen Resort Studio: Ski In & Out! is a apartment in Wintergreen Resort, 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 non smoking::room.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,139.

From$103/night
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Walking Distance to Ski Slopes! Cozy Condo that sleeps 4! - Wintergreen Resort, VA

Walking Distance to Ski Slopes! Cozy Condo that sleeps 4!

Condo, Wintergreen Resort

Walking Distance to Ski Slopes! Cozy Condo that sleeps 4! is a condo in Wintergreen Resort, with pool access, parking, and room for a group. This stay gives travelers a comfortable base for…

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About Walking Distance to Ski Slopes! Cozy Condo that sleeps 4!

Walking Distance to Ski Slopes! Cozy Condo that sleeps 4! is a condo in Wintergreen Resort, 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: free cancellation, pool, free wifi, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $748.

From$107/night
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Vacation rentals with a pool in Wintergreen Resort, 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 Resort, VA

Idyllic Wintergreen Condo w/ Resort Amenities

Condo, Wintergreen Resort

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

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About Idyllic Wintergreen Condo w/ Resort Amenities

Idyllic Wintergreen Condo w/ Resort Amenities is a condo in Wintergreen Resort, 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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Wintergreen Resort Condo w/ Deck, 0.3 Mi to Slopes - Wintergreen Resort, VA

Wintergreen Resort Condo w/ Deck, 0.3 Mi to Slopes

Condo, Wintergreen Resort

Wintergreen Resort Condo w/ Deck, 0.3 Mi to Slopes is a condo in Wintergreen Resort, 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 condo in Wintergreen Resort, 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, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $997.

From$142/night
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Walk to Slopes and Restaurants - Cozy 1 Bedroom Condo - Wintergreen Resort, VA

Walk to Slopes and Restaurants - Cozy 1 Bedroom Condo

Condo, Wintergreen Resort

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

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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 Resort, 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 Resort, VA

Wintergreen Condo w/ Pool: Near Hike & Market!

Apartment, Wintergreen Resort

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

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

Wintergreen Condo w/ Pool: Near Hike & Market! is a apartment in Wintergreen Resort, 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 $1,402.

From$154/night
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Vacation rentals with parking in Wintergreen Resort, VA

Find vacation rentals that make arriving by car easier.

2 minutes from the shops and activities; Cozy 1 bedroom end unit. - Wintergreen Resort, VA

2 minutes from the shops and activities; Cozy 1 bedroom end unit.

Condo, Wintergreen Resort

2 minutes from the shops and activities; Cozy 1 bedroom end unit. is a condo in Wintergreen Resort, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About 2 minutes from the shops and activities; Cozy 1 bedroom end unit.

2 minutes from the shops and activities; Cozy 1 bedroom end unit. is a condo in Wintergreen Resort, 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $971.

From$139/night
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Snug Wintergreen Resort Studio: Ski In & Out! - Wintergreen Resort, VA

Snug Wintergreen Resort Studio: Ski In & Out!

Apartment, Wintergreen Resort

Snug Wintergreen Resort Studio: Ski In & Out! is a apartment in Wintergreen Resort, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Snug Wintergreen Resort Studio: Ski In & Out!

Snug Wintergreen Resort Studio: Ski In & Out! is a apartment in Wintergreen Resort, 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 $992.

From$142/night
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Ski In & Out Mountain & Firework Views Studio - Wintergreen Resort, VA

Ski In & Out Mountain & Firework Views Studio

Condo, Wintergreen Resort

Ski In & Out Mountain & Firework Views Studio is a condo in Wintergreen Resort, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Ski In & Out Mountain & Firework Views Studio

Ski In & Out Mountain & Firework Views Studio is a condo in Wintergreen Resort, 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 ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,027.

From$147/night
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Cozy Studio Overlooking 18 Hole - Wintergreen Resort, VA

Cozy Studio Overlooking 18 Hole

Condo, Wintergreen Resort

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

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About Cozy Studio Overlooking 18 Hole

Cozy Studio Overlooking 18 Hole is a condo in Wintergreen Resort, 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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Pet-friendly vacation rentals in Wintergreen Resort, VA

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

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

Wintergreen Resort Vacation Rental w/ Pool Access!

Holiday Home, Wintergreen Resort

Wintergreen Resort Vacation Rental w/ Pool Access! is a holiday home in Wintergreen Resort, with pet-friendly space and pool 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 holiday home in Wintergreen Resort, 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 Resort, VA

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

Apartment, Wintergreen Resort

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

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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 Resort, 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 Resort, VA

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

Condo, Wintergreen Resort

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

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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 Resort, 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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Newly Updated Cozy Condo in the Heart of Wintergreen! Pet friendly. - Wintergreen Resort, VA

Newly Updated Cozy Condo in the Heart of Wintergreen! Pet friendly.

Condo, Wintergreen Resort

Newly Updated Cozy Condo in the Heart of Wintergreen! Pet friendly. is a condo in Wintergreen Resort, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a…

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About Newly Updated Cozy Condo in the Heart of Wintergreen! Pet friendly.

Newly Updated Cozy Condo in the Heart of Wintergreen! Pet friendly. is a condo in Wintergreen Resort, 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 $1,217.

From$174/night
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Vacation rentals with a kitchen in Wintergreen Resort, VA

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

Smoky Bear Cabin - Wintergreen Resort, VA

Smoky Bear Cabin

Cabin, Wintergreen Resort

Smoky Bear Cabin is a cabin in Wintergreen Resort, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Smoky Bear Cabin

Smoky Bear Cabin is a cabin in Wintergreen Resort, 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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100 yards to Tyro slope Nestled in the woods - Wintergreen Resort, VA

100 yards to Tyro slope Nestled in the woods

Holiday Home, Wintergreen Resort

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

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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 Resort, 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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Wintergreen Resort Condo: Deck & Golf Course Views - Wintergreen Resort, VA

Wintergreen Resort Condo: Deck & Golf Course Views

Condo, Wintergreen Resort

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

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About Wintergreen Resort Condo: Deck & Golf Course Views

Wintergreen Resort Condo: Deck & Golf Course Views is a condo in Wintergreen Resort, 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 $1,144.

From$163/night
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Wintergreen Condo w/ Pool: Near Hike & Market! - Wintergreen Resort, VA

Wintergreen Condo w/ Pool: Near Hike & Market!

Condo, Wintergreen Resort

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

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

Wintergreen Condo w/ Pool: Near Hike & Market! is a condo in Wintergreen Resort, 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 $1,172.

From$167/night
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Family-friendly vacation rentals in Wintergreen Resort, VA

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

Walk to Ski Slopes: Wintergreen Resort Treehouse - Wintergreen Resort, VA

Walk to Ski Slopes: Wintergreen Resort Treehouse

Cottage, Wintergreen Resort

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

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About Walk to Ski Slopes: Wintergreen Resort Treehouse

Walk to Ski Slopes: Wintergreen Resort Treehouse is a cottage in Wintergreen Resort, 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 $1,954.

From$224/night
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Wintergreen Resort Home w/ 2 Decks + Ski Access! - Wintergreen Resort, VA

Wintergreen Resort Home w/ 2 Decks + Ski Access!

Cottage, Wintergreen Resort

Wintergreen Resort Home w/ 2 Decks + Ski Access! is a cottage in Wintergreen Resort, with pool access, outdoor space, and kitchen access. This stay gives travelers a comfortable base for…

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About Wintergreen Resort Home w/ 2 Decks + Ski Access!

Wintergreen Resort Home w/ 2 Decks + Ski Access! is a cottage in Wintergreen Resort, with pool access, outdoor 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, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,119.

From$239/night
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Beautiful Mountain Getaway - Walk to Everything at Wintergreen! - Wintergreen Resort, VA

Beautiful Mountain Getaway - Walk to Everything at Wintergreen!

Condo, Wintergreen Resort

Beautiful Mountain Getaway - Walk to Everything at Wintergreen! is a condo in Wintergreen Resort, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base…

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About Beautiful Mountain Getaway - Walk to Everything at Wintergreen!

Beautiful Mountain Getaway - Walk to Everything at Wintergreen! is a condo in Wintergreen Resort, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,690.

From$241/night
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Cozy 'hillside Hideaway' in Wintergreen Resort! - Wintergreen Resort, VA

Cozy 'hillside Hideaway' in Wintergreen Resort!

Cottage, Wintergreen Resort

Cozy 'hillside Hideaway' in Wintergreen Resort! is a cottage in Wintergreen Resort, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Cozy 'hillside Hideaway' in Wintergreen Resort!

Cozy 'hillside Hideaway' in Wintergreen Resort! is a cottage in Wintergreen Resort, 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 $2,372.

From$270/night
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