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Wintergreen Holiday Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
476 rentals in Wintergreen.
Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!, holiday rental in Wintergreen
Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!, holiday rental in Wintergreen
Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!, holiday rental in Wintergreen

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

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery, holiday rental in Wintergreen
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery, holiday rental in Wintergreen
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery, holiday rental in Wintergreen

Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Wintergreen Condo w/ Balcony + Mountain Views!, holiday rental in Wintergreen
Wintergreen Condo w/ Balcony + Mountain Views!, holiday rental in Wintergreen
Wintergreen Condo w/ Balcony + Mountain Views!, holiday rental in Wintergreen

Wintergreen Condo w/ Balcony + Mountain Views!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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SPECIAL CRAZY WEATHER SPECIAL $175 for FRI and Sat $125 Mon-Thur, holiday rental in Wintergreen
SPECIAL CRAZY WEATHER SPECIAL $175 for FRI and Sat $125 Mon-Thur, holiday rental in Wintergreen
SPECIAL CRAZY WEATHER SPECIAL $175 for FRI and Sat $125 Mon-Thur, holiday rental in Wintergreen

SPECIAL CRAZY WEATHER SPECIAL $175 for FRI and Sat $125 Mon-Thur

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Ski In & Out Mountain & Firework Views Studio, holiday rental in Wintergreen
Ski In & Out Mountain & Firework Views Studio, holiday rental in Wintergreen
Ski In & Out Mountain & Firework Views Studio, holiday rental in Wintergreen

Ski In & Out Mountain & Firework Views Studio

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Wintergreen Resort Studio w/ Deck & Ski-Out Access, holiday rental in Wintergreen
Wintergreen Resort Studio w/ Deck & Ski-Out Access, holiday rental in Wintergreen
Wintergreen Resort Studio w/ Deck & Ski-Out Access, holiday rental in Wintergreen

Wintergreen Resort Studio w/ Deck & Ski-Out Access

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Highlands Condo LOTS OF DETAILED INFO LISTED☺️ Views for days!, holiday rental in Wintergreen
Highlands Condo LOTS OF DETAILED INFO LISTED☺️ Views for days!, holiday rental in Wintergreen
Highlands Condo LOTS OF DETAILED INFO LISTED☺️ Views for days!, holiday rental in Wintergreen

Highlands Condo LOTS OF DETAILED INFO LISTED☺️ Views for days!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ski In & Ski Out Condo - Heart of Wintergreen, holiday rental in Wintergreen
Ski In & Ski Out Condo - Heart of Wintergreen, holiday rental in Wintergreen
Ski In & Ski Out Condo - Heart of Wintergreen, holiday rental in Wintergreen

Ski In & Ski Out Condo - Heart of Wintergreen

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Travelers' Rest--Your Wintergreen Retreat in the Center of it All!, holiday rental in Wintergreen
Travelers' Rest--Your Wintergreen Retreat in the Center of it All!, holiday rental in Wintergreen
Travelers' Rest--Your Wintergreen Retreat in the Center of it All!, holiday rental in Wintergreen

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

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Wintergreen. Mountain view's for miles Sunset Vista Villa - Sea of Mountains, holiday rental in Wintergreen
Wintergreen. Mountain view's for miles Sunset Vista Villa - Sea of Mountains, holiday rental in Wintergreen
Wintergreen. Mountain view's for miles Sunset Vista Villa - Sea of Mountains, holiday rental in Wintergreen

Wintergreen. Mountain view's for miles Sunset Vista Villa - Sea of Mountains

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Private creek, 5 minutes to slopes, under new management, pet friendly, hot tub!, holiday rental in Wintergreen
Private creek, 5 minutes to slopes, under new management, pet friendly, hot tub!, holiday rental in Wintergreen
Private creek, 5 minutes to slopes, under new management, pet friendly, hot tub!, holiday rental in Wintergreen

Private creek, 5 minutes to slopes, under new management, pet friendly, hot tub!

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Wintergreen Resort Vacation Rental w/ Pool Access!, holiday rental in Wintergreen
Wintergreen Resort Vacation Rental w/ Pool Access!, holiday rental in Wintergreen
Wintergreen Resort Vacation Rental w/ Pool Access!, holiday rental in Wintergreen

Wintergreen Resort Vacation Rental w/ Pool Access!

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Wintergreen Home w/ Hot Tub, Deck & Mountain Views, holiday rental in Wintergreen
Wintergreen Home w/ Hot Tub, Deck & Mountain Views, holiday rental in Wintergreen
Wintergreen Home w/ Hot Tub, Deck & Mountain Views, holiday rental in Wintergreen

Wintergreen Home w/ Hot Tub, Deck & Mountain Views

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Breathtaking views!! Overlooking the slopes, holiday rental in Wintergreen
Breathtaking views!! Overlooking the slopes, holiday rental in Wintergreen
Breathtaking views!! Overlooking the slopes, holiday rental in Wintergreen

Breathtaking views!! Overlooking the slopes

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cozy Wintergreen Condo! Walk to slopes and hiking! Dogs ok!, holiday rental in Wintergreen
Cozy Wintergreen Condo! Walk to slopes and hiking! Dogs ok!, holiday rental in Wintergreen
Cozy Wintergreen Condo! Walk to slopes and hiking! Dogs ok!, holiday rental in Wintergreen

Cozy Wintergreen Condo! Walk to slopes and hiking! Dogs ok!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Peak Views!, holiday rental in Wintergreen
Peak Views!, holiday rental in Wintergreen
Peak Views!, holiday rental in Wintergreen

Peak Views!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Leaf-Peeping at Oak Ledge! Trails+Tastings+Peace, holiday rental in Wintergreen
Leaf-Peeping at Oak Ledge! Trails+Tastings+Peace, holiday rental in Wintergreen
Leaf-Peeping at Oak Ledge! Trails+Tastings+Peace, holiday rental in Wintergreen

Leaf-Peeping at Oak Ledge! Trails+Tastings+Peace

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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True Ski-in/out Condo! Step off the deck onto the beginner slopes!, holiday rental in Wintergreen
True Ski-in/out Condo! Step off the deck onto the beginner slopes!, holiday rental in Wintergreen
True Ski-in/out Condo! Step off the deck onto the beginner slopes!, holiday rental in Wintergreen

True Ski-in/out Condo! Step off the deck onto the beginner slopes!

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Custom Builder just completely  remodeled this Mountain Chalet! ...with Hot Tub!, holiday rental in Wintergreen
Custom Builder just completely  remodeled this Mountain Chalet! ...with Hot Tub!, holiday rental in Wintergreen
Custom Builder just completely  remodeled this Mountain Chalet! ...with Hot Tub!, holiday rental in Wintergreen

Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Mountain View Wintergreen Condo - Sleeps up to 4, holiday rental in Wintergreen
Mountain View Wintergreen Condo - Sleeps up to 4, holiday rental in Wintergreen
Mountain View Wintergreen Condo - Sleeps up to 4, holiday rental in Wintergreen

Mountain View Wintergreen Condo - Sleeps up to 4

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Dobie condo, renovated top to bottom! LOTS OF DETAILED INFO LISTED ☺️, holiday rental in Wintergreen
Dobie condo, renovated top to bottom! LOTS OF DETAILED INFO LISTED ☺️, holiday rental in Wintergreen
Dobie condo, renovated top to bottom! LOTS OF DETAILED INFO LISTED ☺️, holiday rental in Wintergreen

Dobie condo, renovated top to bottom! LOTS OF DETAILED INFO LISTED ☺️

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Serene Hideaway with Views, 1 Mi to Hike & Ski!, holiday rental in Wintergreen
Serene Hideaway with Views, 1 Mi to Hike & Ski!, holiday rental in Wintergreen
Serene Hideaway with Views, 1 Mi to Hike & Ski!, holiday rental in Wintergreen

Serene Hideaway with Views, 1 Mi to Hike & Ski!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Idyllic Wintergreen Condo w/ Resort Amenities, holiday rental in Wintergreen
Idyllic Wintergreen Condo w/ Resort Amenities, holiday rental in Wintergreen
Idyllic Wintergreen Condo w/ Resort Amenities, holiday rental in Wintergreen

Idyllic Wintergreen Condo w/ Resort Amenities

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS, holiday rental in Wintergreen
WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS, holiday rental in Wintergreen
WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS, holiday rental in Wintergreen

WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Diamond Adventure at Wintergreen Resort *FULLY UPDATED*, holiday rental in Wintergreen
Diamond Adventure at Wintergreen Resort *FULLY UPDATED*, holiday rental in Wintergreen
Diamond Adventure at Wintergreen Resort *FULLY UPDATED*, holiday rental in Wintergreen

Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Find peace at Dove's Landing at Wintergreen resort - 
family- and pet-friendly!, holiday rental in Wintergreen
Find peace at Dove's Landing at Wintergreen resort - 
family- and pet-friendly!, holiday rental in Wintergreen
Find peace at Dove's Landing at Wintergreen resort - 
family- and pet-friendly!, holiday rental in Wintergreen

Find peace at Dove's Landing at Wintergreen resort - family- and pet-friendly!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Mountain Hideaway Cabin Near Wintergreen and Rt 151 Nelson County, VA, holiday rental in Wintergreen
Mountain Hideaway Cabin Near Wintergreen and Rt 151 Nelson County, VA, holiday rental in Wintergreen
Mountain Hideaway Cabin Near Wintergreen and Rt 151 Nelson County, VA, holiday rental in Wintergreen

Mountain Hideaway Cabin Near Wintergreen and Rt 151 Nelson County, VA

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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An All Season Resort- Serenity Above the Clouds, holiday rental in Wintergreen
An All Season Resort- Serenity Above the Clouds, holiday rental in Wintergreen
An All Season Resort- Serenity Above the Clouds, holiday rental in Wintergreen

An All Season Resort- Serenity Above the Clouds

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Incredible Mountain Views - Modern Four Bedroom Home - Five Minute Walk to Slope, holiday rental in Wintergreen
Incredible Mountain Views - Modern Four Bedroom Home - Five Minute Walk to Slope, holiday rental in Wintergreen
Incredible Mountain Views - Modern Four Bedroom Home - Five Minute Walk to Slope, holiday rental in Wintergreen

Incredible Mountain Views - Modern Four Bedroom Home - Five Minute Walk to Slope

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Unbeatable Views Atop Wintergreen 4min to Skiing, holiday rental in Wintergreen
Unbeatable Views Atop Wintergreen 4min to Skiing, holiday rental in Wintergreen
Unbeatable Views Atop Wintergreen 4min to Skiing, holiday rental in Wintergreen

Unbeatable Views Atop Wintergreen 4min to Skiing

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Wintergreen Resort Home w/ 2 Decks + Ski Access!, holiday rental in Wintergreen
Wintergreen Resort Home w/ 2 Decks + Ski Access!, holiday rental in Wintergreen
Wintergreen Resort Home w/ 2 Decks + Ski Access!, holiday rental in Wintergreen

Wintergreen Resort Home w/ 2 Decks + Ski Access!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Modern Wintergreen Cabin with Hot Tub, Sauna, holiday rental in Wintergreen
Modern Wintergreen Cabin with Hot Tub, Sauna, holiday rental in Wintergreen
Modern Wintergreen Cabin with Hot Tub, Sauna, holiday rental in Wintergreen

Modern Wintergreen Cabin with Hot Tub, Sauna

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Beautiful 4-season Mountain Home- New Listing, holiday rental in Wintergreen
Beautiful 4-season Mountain Home- New Listing, holiday rental in Wintergreen
Beautiful 4-season Mountain Home- New Listing, holiday rental in Wintergreen

Beautiful 4-season Mountain Home- New Listing

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Remodeled 3BR/2BA Ski Chalet off Tyro Slope, holiday rental in Wintergreen
Remodeled 3BR/2BA Ski Chalet off Tyro Slope, holiday rental in Wintergreen
Remodeled 3BR/2BA Ski Chalet off Tyro Slope, holiday rental in Wintergreen

Remodeled 3BR/2BA Ski Chalet off Tyro Slope

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Endless Mountain Top Views from All The Way Up!, holiday rental in Wintergreen
Endless Mountain Top Views from All The Way Up!, holiday rental in Wintergreen
Endless Mountain Top Views from All The Way Up!, holiday rental in Wintergreen

Endless Mountain Top Views from All The Way Up!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK, holiday rental in Wintergreen
Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK, holiday rental in Wintergreen
Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK, holiday rental in Wintergreen

Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Luxury Black Bear Lodge: Stunning 4 Season Mountain Views! Perfect for Families., holiday rental in Wintergreen
Luxury Black Bear Lodge: Stunning 4 Season Mountain Views! Perfect for Families., holiday rental in Wintergreen
Luxury Black Bear Lodge: Stunning 4 Season Mountain Views! Perfect for Families., holiday rental in Wintergreen

Luxury Black Bear Lodge: Stunning 4 Season Mountain Views! Perfect for Families.

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Restored Vintage Airstream at Craft Brewery, holiday rental in Wintergreen
Restored Vintage Airstream at Craft Brewery, holiday rental in Wintergreen
Restored Vintage Airstream at Craft Brewery, holiday rental in Wintergreen

Restored Vintage Airstream at Craft Brewery

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Creek Dogs OK PacMan Pool Tennis Golf Pack 'n Play, holiday rental in Wintergreen
Creek Dogs OK PacMan Pool Tennis Golf Pack 'n Play, holiday rental in Wintergreen
Creek Dogs OK PacMan Pool Tennis Golf Pack 'n Play, holiday rental in Wintergreen

Creek Dogs OK PacMan Pool Tennis Golf Pack 'n Play

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Walk to  Market/Private community outdoor pool!, holiday rental in Wintergreen
Walk to  Market/Private community outdoor pool!, holiday rental in Wintergreen
Walk to  Market/Private community outdoor pool!, holiday rental in Wintergreen

Walk to Market/Private community outdoor pool!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cozy Wintergreen Resort Condo: Walk to Ski Lifts!, holiday rental in Wintergreen
Cozy Wintergreen Resort Condo: Walk to Ski Lifts!, holiday rental in Wintergreen
Cozy Wintergreen Resort Condo: Walk to Ski Lifts!, holiday rental in Wintergreen

Cozy Wintergreen Resort Condo: Walk to Ski Lifts!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Luxury Mountain House - November Fall Dates still available, holiday rental in Wintergreen
Luxury Mountain House - November Fall Dates still available, holiday rental in Wintergreen
Luxury Mountain House - November Fall Dates still available, holiday rental in Wintergreen

Luxury Mountain House - November Fall Dates still available

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Wintergreen Resort Mountain Condo w/ Pool Access!, holiday rental in Wintergreen
Wintergreen Resort Mountain Condo w/ Pool Access!, holiday rental in Wintergreen
Wintergreen Resort Mountain Condo w/ Pool Access!, holiday rental in Wintergreen

Wintergreen Resort Mountain Condo w/ Pool Access!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Snug Wintergreen Resort Studio: Ski In & Out!, holiday rental in Wintergreen
Snug Wintergreen Resort Studio: Ski In & Out!, holiday rental in Wintergreen
Snug Wintergreen Resort Studio: Ski In & Out!, holiday rental in Wintergreen

Snug Wintergreen Resort Studio: Ski In & Out!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Spacious + Serene Mtn Top Escape, 4 En Suites, holiday rental in Wintergreen
Spacious + Serene Mtn Top Escape, 4 En Suites, holiday rental in Wintergreen
Spacious + Serene Mtn Top Escape, 4 En Suites, holiday rental in Wintergreen

Spacious + Serene Mtn Top Escape, 4 En Suites

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Marley's Cabin - a five star getaway on Wintergreen mountain, holiday rental in Wintergreen
Marley's Cabin - a five star getaway on Wintergreen mountain, holiday rental in Wintergreen
Marley's Cabin - a five star getaway on Wintergreen mountain, holiday rental in Wintergreen

Marley's Cabin - a five star getaway on Wintergreen mountain

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Walking Distance to Ski Slopes! Cozy Condo that sleeps 4!, holiday rental in Wintergreen
Walking Distance to Ski Slopes! Cozy Condo that sleeps 4!, holiday rental in Wintergreen
Walking Distance to Ski Slopes! Cozy Condo that sleeps 4!, holiday rental in Wintergreen

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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View from the Top, holiday rental in Wintergreen
View from the Top, holiday rental in Wintergreen
View from the Top, holiday rental in Wintergreen

View from the Top

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New listing- Five minute walk to slopes and village!, holiday rental in Wintergreen
New listing- Five minute walk to slopes and village!, holiday rental in Wintergreen
New listing- Five minute walk to slopes and village!, holiday rental in Wintergreen

New listing- Five minute walk to slopes and village!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Renovated, dog friendly, summer pool access and beautiful views!, holiday rental in Wintergreen
Renovated, dog friendly, summer pool access and beautiful views!, holiday rental in Wintergreen
Renovated, dog friendly, summer pool access and beautiful views!, holiday rental in Wintergreen

Renovated, dog friendly, summer pool access and beautiful views!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Showing results 1-50 of 476
Frequently Asked Questions about Wintergreen