Wintergreen holiday rentals

We found 918 holiday rentals — enter your dates for availability
Select from 226 houses, 314 flats and other holiday rentals to find the perfect place for your stay in Wintergreen. Holiday homes provide the best amenities for you and your friends, family or even pets, such as Wi-Fi and a washer and dryer. At the end of the day, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Wintergreen

Showing deals for:18 Dec - 25 Dec

Living Room opening on to porch and fire pit beyond.
Cozy log cabin porch with rocking chairs, warm interior glow, and forest views. Perfect for relaxing evenings in a peaceful, secluded woodland setting.
Elegant rustic living room featuring a grand stone fireplace, wood-burning stove, rich antique-style furnishings, and serene forest views through expansive glass doors.
Dining Area.
Exceptional
(243 reviews)

Restored Double Log Cabin on 400 Mountain Acres

Covesville

8% off
AU$7,369
for 7 nights, 1 cabin
AU$1,053 per night
includes taxes & fees
Restored Double Log Cabin on 400 Mountain Acres
Private well-lit walkway to your private entrance on home's main floor.
Wall-to-wall windows creating a backdrop of treetops & mountain views.
The kitchen opens directly to the living room with beautiful views.
Main living floor contains dining, kitchen, living room, and half bath.
Exceptional
(57 reviews)

Spacious + Serene Mtn Top Escape, 4 En Suites

Wintergreen Resort

8% off
AU$7,906
for 7 nights, 1 home
AU$1,129 per night
includes taxes & fees
Spacious + Serene Mtn Top Escape, 4 En Suites
Property grounds
Interior
Living area
Dining
Exceptional
(22 reviews)

Fire pit with MTN views! Book for fall! Nelson 151!

Roseland

8% off
AU$8,042
for 7 nights, 1 home
AU$1,149 per night
includes taxes & fees
Fire pit with MTN views! Book for fall! Nelson 151!
Downstairs living room with seating for 12+.
Enjoy some wine by the fire pit.
The kitchen features seating for two at the bar top.
Dine on the screened in deck.
Exceptional
(10 reviews)

Extreme privacy/Acreage/Hot Tub/Mountain Views/Central!!

Afton

8% off
AU$6,818
for 7 nights, 1 home
AU$974 per night
includes taxes & fees
Extreme privacy/Acreage/Hot Tub/Mountain Views/Central!!
Master Bedroom, King Bed, private bathroom
58" flat screen, basic cable.  Living Room
Kitchen.  Open to dining area and living room.
Front of House
Exceptional
(111 reviews)

Wintergreen Family Retreat- Each Br With Its Own Sliding Doors To A Deck

Wintergreen Resort

12% off
AU$2,704
for 7 nights, 1 home
AU$386 per night
includes taxes & fees
Wintergreen Family Retreat- Each Br With Its Own Sliding Doors To A Deck
Primary bedroom with King bed
Enter into spacious great room
Kitchen opens to great room
Perfect spot to sit with a cup of coffee or watch the sunset from inside
Exceptional
(33 reviews)

Mountain Season Lodge

Nellysford

12% off
AU$8,984
for 7 nights, 1 room
AU$1,283 per night
includes taxes & fees
Mountain Season Lodge
Fire pit with accessories to use as grill
Exterior
Private kitchen
Interior
Exceptional
(73 reviews)

Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

Montebello

12% off
AU$1,571
for 7 nights, 1 cabin
AU$224 per night
includes taxes & fees
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA
Open kitchen island area
Front entrance
Dining area view to nature's beauty.
The spacious living room opens in to the dining area.
Exceptional
(20 reviews)

Relax in Nature's Beauty: Private Log Cabin w/ two Spacious, Open Living Areas

Shipman

12% off
AU$3,079
for 7 nights, 1 cabin
AU$440 per night
includes taxes & fees
Relax in Nature's Beauty: Private Log Cabin w/ two Spacious, Open Living Areas
The downstairs full bathroom with shower/tub combo and washer/dryer.
The propane fire pit provides intimacy and warmth!
Our private home.
Enjoy a home cooked meal in our fully stocked kitchen.
Exceptional
(26 reviews)

Secluded 20+ Acre Retreat Near Brew & Wine Trails

Afton

8% off
AU$3,244
for 7 nights, 1 home
AU$463 per night
includes taxes & fees
Secluded 20+ Acre Retreat Near Brew & Wine Trails
Exterior
Living area
Private kitchen
Living area
Exceptional
(22 reviews)

Above the Clouds! Perfect Escape for Families!

Wintergreen Resort

11% off
AU$5,277
for 7 nights, 1 home
AU$754 per night
includes taxes & fees
Above the Clouds! Perfect Escape for Families!
Interior
Exterior
Property grounds
Interior
Exceptional
(30 reviews)

5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries

Montebello

12% off
AU$1,571
for 7 nights, 1 cabin
AU$224 per night
includes taxes & fees
5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries
Interior
Exterior
Interior
Property grounds
Exceptional
(23 reviews)

New Blue RIdge Mountains Montebello, Virginia with stary stary skies

Montebello

12% off
AU$1,571
for 7 nights, 1 cabin
AU$224 per night
includes taxes & fees
New Blue RIdge Mountains Montebello, Virginia with stary stary skies
Exterior detail
Private kitchen
Interior
Private kitchen
Exceptional
(62 reviews)

Rockfish Farmhouse - Home In the heart of The Rockfish Valley

Afton

8% off
AU$3,509
for 7 nights, 1 home
AU$501 per night
includes taxes & fees
Rockfish Farmhouse - Home In the heart of The Rockfish Valley
Top of the stairs
Dining
Interior
Living area
Exceptional
(59 reviews)

Spectacular mountain home perfect for multiple families! Just added deck firepit

Roseland

8% off
AU$3,565
for 7 nights, 1 home
AU$509 per night
includes taxes & fees
Spectacular mountain home perfect for multiple families! Just added deck firepit
Imported 100-year old door to deck with incredible glasswork that dazzles!
Gas grill, Adirondacks chairs with custom-dimmable patio lights & firepit
Living Room with fireplace & beautiful 100-year old door w intricate glasswork
Dining Room table for all your friends & family in front of bay windows w views
Exceptional
(12 reviews)

5 BR Wintergreen House w/ Game Room, 75” TV, Ping Pong, Foosball, Wet Bar & Deck

Nellysford

8% off
AU$10,105
for 7 nights, 1 home
AU$1,444 per night
includes taxes & fees
5 BR Wintergreen House w/ Game Room, 75” TV, Ping Pong, Foosball, Wet Bar & Deck
kitchen
Property grounds
master bedroom
wintergreen cottage...ski slope is to the lower right of photo
Exceptional
(94 reviews)

COZY SKI COTTAGE--SKI IN SKI OUT

Roseland

8% off
AU$5,364
for 7 nights, 1 home
AU$766 per night
includes taxes & fees
COZY SKI COTTAGE--SKI IN SKI OUT
Games room
Living area
Living area
Fully Equiped Kitchen
Exceptional
(129 reviews)

Eagles Court Slopeside Condo, Wifi, Walk to everything!

Wintergreen Resort

11% off
AU$1,921
for 7 nights, 1 apartment
AU$274 per night
includes taxes & fees
Eagles Court Slopeside Condo, Wifi, Walk to everything!
Open plan living and flexible seating!
Let's go back outside!
Drone view of Black Bear Lodge!
Dining
Exceptional
(34 reviews)

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

Wintergreen Resort

8% off
AU$10,626
for 7 nights, 1 home
AU$1,518 per night
includes taxes & fees
Luxury Black Bear Lodge: Stunning 4 Season Mountain Views! Perfect for Families.
Living area
Private kitchen
Exterior detail
Private kitchen
Exceptional
(22 reviews)

Cozy Farmhouse W/Mountain Views

Roseland

7% off
AU$2,982
for 7 nights, 1 home
AU$426 per night
includes taxes & fees
Cozy Farmhouse W/Mountain Views
New Double Oven and Microwave (Jan 2021)
Living/Dinning Room (Table Expands to seat 6).
Private Pool just steps away and only for Laurelwood Guests
Deck
Exceptional
(107 reviews)

Laurelwood Condo, Walk to Slopes, The Market & Restaurants + NFL Sunday Ticket

Roseland

12% off
AU$4,206
for 7 nights, 1 apartment
AU$601 per night
includes taxes & fees
Laurelwood Condo, Walk to Slopes, The Market & Restaurants + NFL Sunday Ticket
Private kitchen
Living area
Living area
Living area
Exceptional
(28 reviews)

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

Wintergreen Resort

12% off
AU$2,938
for 7 nights, 1 home
AU$420 per night
includes taxes & fees
Condo at Fairway Woods, perfect home base for ski season! ☃️🏂
The master suite is a joy to hang out in.
Enjoy a morning coffee with some of the world's best sunrises!
Enjoy the mountain views while preparing a home cooked meal.
The open floor plan makes visiting with family and friends easy.
Exceptional
(44 reviews)

Luxury Condo in the Sky! Finest in Wintergreen!

Wintergreen Resort

8% off
AU$5,169
for 7 nights, 1 apartment
AU$738 per night
includes taxes & fees
Luxury Condo in the Sky! Finest in Wintergreen!
Exterior
Interior
Exterior detail
Living area
Exceptional
(228 reviews)

Come and enjoy a beautiful view and relaxing time at Windy Knoll....

Afton

8% off
AU$3,027
for 7 nights, 1 home
AU$432 per night
includes taxes & fees
Come and enjoy a beautiful view and relaxing time at Windy Knoll....
Morning coffee from Keurig  on the deck!
Private kitchen
Master bedroom TV and chest of drawers
Living area
Exceptional
(91 reviews)

Location, location, location mountain side in Wintergreen Mountain Village

Wintergeen

16% off
AU$2,174
for 7 nights, 1 apartment
AU$311 per night
includes taxes & fees
Location, location, location mountain side in Wintergreen Mountain Village
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Wintergreen

  • Adventurous skiing and outdoor pursuits: Wintergreen offers thrilling ski slopes and a host of adventure sports set against the majestic Blue Ridge Mountains.
  • Stunning natural landscapes: Revel in the breathtaking valley views and explore the surrounding national and state parks.
  • Cultural attractions: Discover local history through museums and historic houses that capture the charm of the area.
  • Family-friendly excursions: Enjoy a variety of recreational activities suitable for visitors of all ages.
  • Tranquil holiday living: Embrace a peaceful retreat with cosy and comfortable accommodation options in a picturesque setting.

Popular types of accommodation in Wintergreen

Welcome to Wintergreen, Virginia, where scenic beauty meets tranquil holiday living. Renowned for its Private Holiday Homes, Condos and Cabins, Wintergreen offers a variety of accommodation options including wintergreen homesites, wintergreen va homes, next home at wintergreen resort, holiday home, and homes within wintergreen resort. Explore local attractions, enjoy breathtaking landscapes, and experience the charm of this picturesque city.

  • Private Holiday Homes: A favourite choice for visitors, these spacious residences offer a home-like experience with all the comforts you need for a delightful stay.
  • Condos: Ideal for those seeking modern amenities, condos provide a blend of comfort and convenience in a vibrant community setting.
  • Cabins: Embrace nature in these charming retreats, perfect for a cosy getaway surrounded by the beautiful Virginia landscape.
  • Apartments: Offering a practical and central option, apartments are great for short stays while enjoying easy access to local attractions.
  • Cottages: Quaint and often tucked away, cottages provide a peaceful escape, perfect for a romantic getaway or family retreat.**

Top attractions near Wintergreen

Wintergreen, Virginia, is a charming destination perfect for skiing and adventure sports enthusiasts. Visitors can explore a variety of attractions, including museums and historic houses, as well as the stunning landscapes of nearby national and state parks. Whether seeking cultural experiences or outdoor adventures, Wintergreen offers a delightful blend of activities that cater to all interests, making it an ideal spot for a memorable holiday.

  • Walton's Mountain Museum: Located 21km from Wintergreen, this museum offers a rich cultural experience, displaying local artefacts and historical narratives that capture the spirit of the region.
  • Oak Ridge Estate: Situated 19km away, this historic house exudes cultural heritage with its well-preserved architecture and period furnishings, offering a glimpse into the past.
  • Rockfish Gap Entrance Shenandoah: Positioned 18km from Wintergreen, this national state park invites outdoor enthusiasts to explore scenic landscapes and partake in adventurous pursuits.

Things to do recommended for couples

Wintergreen offers a magical retreat for couples. Enjoy a scenic hike through the Blue Ridge Mountains, followed by a cosy evening by the fireplace at a local lodge. Don't miss a romantic stargazing session; the clear night skies provide a perfect backdrop for love.

Things to do recommended for families

Families visiting Wintergreen can enjoy skiing or snowboarding at the local slopes, take scenic hikes through the Blue Ridge Mountains, and explore the fun-filled activities at the Wintergreen Nature Foundation, offering educational programs for children of all ages.

Things to do recommended for groups

Explore the stunning Blue Ridge Mountains with a group hike along the Appalachian Trail or enjoy a day of skiing at Wintergreen Resort. For a unique experience, consider a guided wine tour of local vineyards, perfect for tasting Virginia's finest offerings together.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Wintergreen

If you’re travelling with a group, family, or pets, or if you’re seeking longer stays, it’s important to use the appropriate filters to match your priorities. Here are some helpful Stayz booking tips for you.

  • Traveling to Wintergreen with a group: Consider how many bedrooms you will require, along with facilities like a fully equipped kitchen or an outdoor area for social gatherings. Thankfully, on Stayz, you can refine your search to include all these options and many others.
  • Traveling to Wintergreen with young kids: Travelling with young children can present some challenges. It's important to prioritise their comfort and safety, along with ensuring access to suitable amenities, such as a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Wintergreen: For many, a family holiday isn’t truly complete without their furry companion by their side. If this resonates with you, explore Stayz accommodations that welcome pets. The majority of pet-friendly properties offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Wintergreen: If you're seeking holiday lets offering special rates for stays of a month or more, you've come to the right place. With the appropriate filter, you can effortlessly find and secure savings on monthly rentals. You may also want to consider including a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay in Wintergreen

Wintergreen, Virginia, is a delightful village perfect for an adventurous holiday. Nestled among the stunning Blue Ridge Mountains, it offers thrilling skiing and outdoor activities for nature lovers. Enjoy family-friendly excursions and recreational opportunities, all while soaking in the breathtaking valley views. Whether you seek a winter getaway or a peaceful retreat, Wintergreen provides a unique blend of relaxation and excitement, making it an ideal destination for all types of travellers.

  • Nellysford: Nestled in the heart of Virginia, Nellysford is a charming city that serves as the gateway to Wintergreen. Renowned for its exhilarating skiing and adventure sports, this area attracts outdoor enthusiasts year-round. Visitors can indulge in a variety of activities such as skiing on well-maintained slopes at nearby ski resorts. The scenic surroundings boast stunning natural landmarks, including the expansive national state park and picturesque lakes, making it an ideal spot for both relaxation and exploration.
  • Chestnut Springs: Located closely to Wintergreen, Chestnut Springs is a delightful neighbourhood known for its adventurous spirit. It offers a similar allure to its neighbouring city, drawing visitors keen on skiing and outdoor sports. The area is surrounded by breathtaking landscapes, including lakes and national parks, which provide ample opportunities for hiking and nature walks. Chestnut Springs is a perfect base for travellers looking to immerse themselves in the local natural beauty while enjoying a variety of recreational activities.
  • Three Ridges Wilderness: Just a short drive from Wintergreen, Three Ridges Wilderness is a stunning natural park that beckons those seeking adventure and captivating scenery. This wilderness area is characterised by dramatic landscapes, dense forests, and panoramic views, making it a haven for hikers and outdoor enthusiasts. Popular activities here include skiing and exploring the nearby national state park and nature reserves. Whether you’re trekking through the forests or simply soaking in the tranquil environment, Three Ridges Wilderness promises an unforgettable experience in nature.

Best time to go to Wintergreen

If you're planning a trip to Wintergreen, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from December to February, while off-peak times, like May to June and August tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January33.4°F (0.8°C)Light RainMostly SunnyModerately HighSlightly High
February37.2°F (2.9°C)Light RainMostly SunnyModerately HighSlightly High
March44.6°F (7.0°C)Light RainMostly SunnyAverageSlightly Low
April54.9°F (12.7°C)Light RainMostly SunnyAverageSlightly Low
May64.0°F (17.8°C)Light RainMostly SunnyModerately LowAverage
June72.1°F (22.3°C)Light RainMostly SunnyModerately LowAverage
July76.6°F (24.8°C)Light RainMostly SunnyAverageSlightly Low
August74.3°F (23.5°C)Light RainMostly SunnyModerately LowAverage
September68.0°F (20.0°C)Light RainMostly SunnyAverageAverage
October56.8°F (13.8°C)Light RainMostly SunnyAverageAverage
November44.8°F (7.1°C)Light RainMostly SunnyAverageAverage
December38.5°F (3.6°C)Light RainMostly SunnyModerately HighSlightly High

Booking with Stayz is a breeze

Are you hoping to make your next trip more affordable? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you might enjoy considerable savings by opting for a longer stay. To discover a Stayz property that suits your budget, feel free to utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Effortless planning

Stayz’s Trip Board provides a convenient area for you to craft new journeys, carry on with your plans, or review and manage your bookings. The properties you've either saved or reserved are now organised into categories: Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

Why people love visiting scenic Wintergreen

Enjoy the wineries and other features of Wintergreen. Travellers to this scenic city praise the mountain views, skiing and hiking. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in and around Wintergreen

Are you hoping to find attractions to see during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Wintergreen has to offer. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Wintergreen Resort (3.2 mi / 5.1 km)
  • Afton Mountain Vineyards (8.9 mi / 14.3 km)
  • Veritas Vineyard and Winery (9.5 mi / 15.4 km)
  • Lovingston Winery (11.5 mi / 18.5 km)
  • Pippin Hill Farm & Vineyards (14 mi / 22.6 km)
  • King Family Vineyards (15.4 mi / 24.7 km)

Exploring the natural landscape of Wintergreen

Whether you're an adventurous traveller or just want to appreciate the scenery, Wintergreen is a great place to get out in nature. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Sherando Lake Recreation Area (6.5 mi / 10.5 km)
  • Crabtree Falls (10.1 mi / 16.3 km)
  • Blue Ridge Parkway North Entrance (10.3 mi / 16.6 km)
  • Rockfish Gap Entrance Shenandoah (10.8 mi / 17.4 km)
  • Reids Gap Trailhead (4.8 mi / 7.8 km)
  • Humpback Rocks (5.3 mi / 8.5 km)

Seasonal weather averages in Wintergreen

Travellers enjoy Wintergreen for its skiing. If you've planned your trip around snowy activities, consider visiting in January, December, February or March, when snowfall averages 3 cm and temperatures average 4°C.

Travelling to and around Wintergreen

The nearest airport is in Weyers Cave, VA (SHD-Shenandoah Valley Regional), located 26.2 mi (42.1 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into Charlottesville, VA (CHO-Charlottesville-Albemarle), which is 30.3 mi (48.8 km) away.

Frequently asked questions

What is the best area to stay in Wintergreen when booking a holiday rental?
When considering a holiday rental in Wintergreen, Virginia, the area around the Wintergreen Resort is an excellent choice. This picturesque neighbourhood offers a range of properties, from charming cabins to modern condos, suiting various preferences and budgets. Staying here places you in close proximity to the resort's top attractions, including the stunning hiking trails that wind through the Blue Ridge Mountains and the popular ski slopes during the winter months.Another appealing aspect of this area is its access to the nearby Appalachian Trail, which is superb for outdoor enthusiasts looking to explore the natural beauty of the region. Additionally, the resort features amenities such as a golf course and spa, providing plenty of opportunities for relaxation and recreation.
When is the best time to visit Wintergreen for a holiday rental?
January is the most popular time to visit Wintergreen, Virginia, as it falls within the peak season from December to February. This is when winter enthusiasts flock to the area to enjoy fantastic skiing, snowboarding, and other winter sports. With temperatures typically ranging from -5 to 5 degrees Celsius, visitors can take advantage of the crisp, invigorating climate while engaging in outdoor adventures.During January, the slopes are in prime condition, and the resort buzzes with energy, making it an ideal time for those seeking an active holiday. The stunning views of the Blue Ridge Mountains blanketed in snow create a picturesque setting, superb for both adrenaline seekers and those looking to relax by a warm fire after a day on the slopes.For travellers who prefer a quieter experience, May is an excellent time to consider. This month often sees fewer visitors, allowing for a more peaceful retreat. The weather begins to warm up, making it superb for hiking and enjoying the blooming flora of the region without the crowds.Ultimately, the best time to book a holiday rental in Wintergreen depends on your preferences—whether you are drawn to the thrill of winter sports in the peak season or prefer the tranquility of spring's arrival.
What are the top attractions in Wintergreen?
In Wintergreen, Virginia, visitors can explore a variety of attractions that cater to both nature enthusiasts and those seeking outdoor adventure. The Wintergreen Resort is a major highlight, offering a range of activities such as skiing in the winter and hiking or mountain biking during the warmer months. The resort features scenic views of the Blue Ridge Mountains, making it a superb spot for outdoor lovers.For those interested in natural beauty, the nearby Shenandoah National Park provides stunning landscapes, with opportunities for hiking along the Appalachian Trail and enjoying breathtaking vistas at various overlooks. The park is ideal for wildlife viewing and immersing oneself in the tranquility of nature.In addition, the local area boasts charming wineries and breweries that offer tastings and tours, allowing visitors to sample the region's best beverages while enjoying the picturesque countryside.
Are all fees included in the Wintergreen holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Wintergreen holiday homes with parking?
Stayz offers a wide selection of holiday homes in Wintergreen with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Wintergreen holiday homes?
You can find great discounts on holiday homes in Wintergreen on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Wintergreen holiday home booking on Stayz?
To find Wintergreen holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Wintergreen?
A long-stay holiday home in Wintergreen is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Wintergreen holiday home?
Book your Wintergreen holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Wintergreen?
Prices for holiday homes in Wintergreen vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Wintergreen to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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