Wintergreen Vacation Rentals

PRICE PER NIGHT

ACCOMMODATION TYPES

Top-Rated Vacation Rentals in Wintergreen, VA

Book a vacation rental in Wintergreen that has the highest visitor rating. Here are 6 of the best vacation rentals in Wintergreen.
Renovated Studio on 5 Acres - Near Vineyards!
10

Excellent

·
Apartment
·
1 br
·
Sleeps 4
·
Kitchen · Ceiling Fan · Workspace ·
From
$117/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Ceiling Fan
Wifi
Free Parking
Assigned Parking
Dishwasher
Toiletries
Tv
Oven
Other spaces
Kitchen, Workspace
Yogi’s Paradise w/ Deck ~ 1 Mi to Yogaville!
10

Excellent

·
House
·
4 br
·
Sleeps 6
·
Cable · Microwave · Air Conditioning ·
From
$75/night
Check availability
Property
House · 4 Beds · 2 baths
Amenities
Cable
Microwave
Air Conditioning
Oven
Free Parking
Dishwasher
Wifi
Fireplace
Other spaces
Kitchen, Garden
Wintergreen Cabin w/ Hot Tub: Golf & Relax!
10

Excellent

·
House
·
3 br
·
Sleeps 7
·
Free Parking · Fireplace · Assigned Parking ·
From
$249/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Free Parking
Fireplace
Assigned Parking
Fitness Center
Ceiling Fan
Swimming Pool
Pool
On Site Laundry
Other spaces
Balcony, Kitchen, Workspace
Serene Hideaway with Views, 1 Mi to Hike & Ski!
9.7

Excellent

·
House
·
3 br
·
Sleeps 8
·
Mountains · Free Parking · Air Conditioning ·
From
$180/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Mountains
Free Parking
Air Conditioning
Wifi
Fireplace
Oven
Cable
Pool
Other spaces
Garden, Kitchen
Mountaintop Wintergreen Resort Home w/ Deck+Views!
9.6

Excellent

·
House
·
4 br
·
Sleeps 10
·
Air Conditioning · Ceiling Fan · Fitness Center ·
From
$125/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Air Conditioning
Ceiling Fan
Fitness Center
Central Heat
Swimming Pool
Dishwasher
Oven
On Site Laundry
Other spaces
Kitchen
Cozy Getaway in Wintergreen Resort: Deck & Hot Tub
9.6

Excellent

·
House
·
4 br
·
Sleeps 10
·
Balcony · Free Parking · Fireplace ·
From
$350/night
Check availability
Property
House · 4 Beds · 5 baths
Amenities
Free Parking
Fireplace
Cable
Wifi
Air Conditioning
Ceiling Fan
Dishwasher
Central Heat
Other spaces
Balcony, Kitchen

Budget-Friendly Vacation Rentals in Wintergreen, VA

Traveling on a budget? We've got you covered. Find a great deal on a vacation rental in Wintergreen starting at $35. Use the price filter at the top of the page to search for more specific prices.
Snug Wintergreen Resort Studio: Ski In & Out!
10

Excellent

·
Apartment
·
1 br
·
Sleeps 5
·
Cable · Oven · Assigned Parking ·
From
$35/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Cable
Oven
Assigned Parking
Air Conditioning
Tv
Microwave
Wifi
Free Parking
Other spaces
Kitchen
Studio One Bedroom and Two bedroom Furnished

No rating

·
Condo
·
2 br
·
On Site Laundry · Cable · Furnished ·
From
$47/night
Min stay: 30 nights
Property
Condo · 2 Beds · 1 bath
Amenities
On Site Laundry
Cable
Furnished
Microwave
In Unit Laundry
Quality Inn Waynesboro
7

Very good

·
Hotel
·
1 br
·
Sleeps 4
·
Pool · Air Conditioning · On Site Laundry ·
From
$54/night
Check availability
Property
Hotel · 1 Bed
Amenities
Pool
Air Conditioning
On Site Laundry
Carpet
Smoking Allowed
Swimming Pool
Assigned Parking
Free Parking
Other spaces
Balcony, Workspace
Price drop
Snug Wintergreen Resort Studio: Ski In & Out!
10

Excellent

·
Apartment
·
Studio
·
Sleeps 5
·
Wifi · Kitchen · Oven ·
From
$61/night
Check availability
Property
Apartment · Studio · 1 bath
Amenities
Wifi
Oven
Air Conditioning
Furnished
In Unit Laundry
Other spaces
Kitchen
Price drop
Super 8 by Wyndham Waynesboro
7.2

Very good

·
Hotel
·
1 br
·
Sleeps 10
·
Furnished · On Site Laundry · Business Center ·
From
$64/night
Check availability
Property
Hotel · 1 Bed
Amenities
Furnished
On Site Laundry
Business Center
Free Parking
Air Conditioning
Wifi
Carpet
Other spaces
Workspace

Furnished Vacation Rentals in Wintergreen, VA

We've collected furnished vacation rentals in Wintergreen so you can spend more time relaxing and enjoying your trip.
Price drop
Afton Bliss
10

Excellent

·
Apartment
·
3 br
·
Sleeps 9
·
Dishwasher · On Site Laundry · Workspace ·
From
$359/night
Check availability
Property
Apartment · 3 Beds · 2 baths
Amenities
Dishwasher
On Site Laundry
Air Conditioning
Wifi
Fireplace
Furnished
Oven
In Unit Laundry
Other spaces
Workspace, Kitchen
Price drop
Afton Clubhouse

No rating

·
Apartment
·
3 br
·
Sleeps 8
·
In Unit Laundry · Hot Tub · Outdoor Space ·
From
$531/night
Check availability
Property
Apartment · 3 Beds · 2 baths
Amenities
In Unit Laundry
Hot Tub
On Site Laundry
Dishwasher
Free Parking
Oven
Furnished
Wifi
Other spaces
Kitchen
Price drop
Afton Farmhouse

No rating

·
Apartment
·
4 br
·
Sleeps 10
·
Outdoor Space · Furnished · Air Conditioning ·
From
$709/night
Check availability
Property
Apartment · 4 Beds · 2 baths
Amenities
Furnished
Air Conditioning
Free Parking
Dishwasher
Fireplace
On Site Laundry
Wifi
Hardwood Floor
Other spaces
Kitchen

Pet-Friendly Vacation Rentals in Wintergreen, VA

Pets are part of the family, so instead of leaving them at home, book one of these pet-friendly vacation rentals in Wintergreen. Read the details of each rental more closely for specific pet policies.
Cozy 'Hillside Hideaway' in Wintergreen Resort!
9.3

Excellent

·
House
·
3 br
·
Sleeps 10
·
Oven · Cable · Walk In Closets ·
From
$144/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Oven
Cable
Walk In Closets
Central Heat
Ceiling Fan
Tv
Fireplace
Toiletries
Other spaces
Workspace, Balcony, Garden, Kitchen
Price drop
Wintergreen Resort Retreat with Skiing Access!

No rating

·
Apartment
·
3 br
·
Sleeps 6
·
Oven · Furnished · Wifi ·
From
$288/night
Check availability
Property
Apartment · 3 Beds · 3 baths
Amenities
Oven
Furnished
Wifi
Pool
Fireplace
Dishwasher
Free Parking
Swimming Pool
Other spaces
Balcony, Kitchen
Price drop
Wintergreen Condo with Mtn Views and Shuttle to Resort

No rating

·
Apartment
·
3 br
·
Sleeps 8
·
Fireplace · Free Parking · Kitchen ·
From
$231/night
Check availability
Property
Apartment · 3 Beds · 3 baths
Amenities
Fireplace
Free Parking
Wifi
In Unit Laundry
Furnished
Oven
Dishwasher
Other spaces
Kitchen
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Updated: September 6, 2023