1. USA
  2. Wisconsin
  3. Ashland
  4. Ski Chalets

Ashland Ski Chalets

House
Map-icon
like-icon10.0
Exceptional
(46 Reviews)
3 Bedrooms 1 Bath 6 Guests 1 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Ocean View
    Ocean View
More amenities
US $270/Night 7 Nights - US $1,889
star-icons-3
Resort
Map-icon
like-icon9.6
Exceptional
(56 Reviews)
5 Baths 21 Guests 908.47 ft²
  • Private Beach
    Private Beach
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $154/Night 7 Nights - US $1,078
star-icons-3
House
Map-icon
like-icon9.6
Exceptional
(100 Reviews)
1 Bedroom 1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $192/Night 7 Nights - US $1,344
Apartment
Map-icon
like-icon10.0
Exceptional
(43 Reviews)
1 Bedroom 1 Bath 6 Guests 700 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
US $217/Night 7 Nights - US $1,517
Hotel
Map-icon
like-icon10.0
Exceptional
(11 Reviews)
1 Bath 779.31 ft²
  • Skiing
    Skiing
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $140/Night 7 Nights - US $980
House
Map-icon
like-icon10.0
Exceptional
(18 Reviews)
2 Bedrooms 1 Bath 4 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $236/Night 7 Nights - US $1,652
star-icons-4
Hotel
Map-icon
like-icon8.5
Fabulous
(382 Reviews)
1 Bath 275.83 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
US $197/Night 7 Nights - US $1,376
Apartment
Map-icon
like-icon9.8
Exceptional
(23 Reviews)
1 Bedroom 1 Bath 4 Guests 650 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
US $206/Night 7 Nights - US $1,441
Hotel
Map-icon
like-icon8.4
Excellent
(136 Reviews)
3 Baths 375.84 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
US $235/Night 7 Nights - US $1,645
Apartment
Map-icon
like-icon9.8
Exceptional
(12 Reviews)
1 Bedroom 1 Bath 2 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Air Conditioner
    Air Conditioner
More amenities
US $124/Night 7 Nights - US $870
star-icons-3
Hotel
Map-icon
like-icon7.9
Very Good
(180 Reviews)
20 Baths 280.4 ft²
  • Private Pool
    Private Pool
  • Private Beach
    Private Beach
More amenities
US $173/Night 7 Nights - US $1,209
House
Map-icon
like-icon9.6
Exceptional
(4 Reviews)
2 Bedrooms 2 Baths 7 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Ocean View
    Ocean View
More amenities
US $298/Night 7 Nights - US $2,085

Discover & compare premier experiences around Ashland

We understand the importance of quality and reliability in your travel experiences. That's why we've curated options from the most reputable tour and activity providers globally, ensuring you have access to top-tier adventures.

Why Choose Rent By Owner for your Ashland Ski Chalets?

What makes our Ski Chalets special?

image
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
image
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
image
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Ashland

When should you plan your Ski Chalets stay?

Choosing the right time to visit here ensures you experience optimal conditions for enjoying your stay in this destination, whether you're seeking winter snow or the region's scenic seasonal charm.

Peak Season Highlights

winter
Winter (December to February)

During the peak winter months, you can experience ideal conditions for snow sports and outdoor activities in this region, making it a perfect time to stay in cozy ski chalets.

Average Temperature Daytime: -2°C to 2°C - Nighttime: -10°C to -5°C
spring
Spring Break (March to April)

As spring approaches, the area sees increased visitors seeking a late-season winter getaway while enjoying the scenic beauty around the slopes and charming surroundings.

Average Temperature Daytime: 2°C to 8°C - Nighttime: -4°C to 0°C

Off-Season Highlights

image
Late Spring (May to June)

In late spring, fewer travelers visit, allowing you to enjoy more tranquil accommodations and the natural serenity of the region before summer crowds arrive.

Average Temperature Daytime: 10°C to 18°C - Nighttime: 2°C to 8°C
image
Fall (September to November)

During fall, the area offers a peaceful retreat with colorful foliage and fewer visitors, providing an excellent opportunity for a quiet stay in welcoming ski chalets.

Average Temperature Daytime: 12°C to 16°C - Nighttime: 3°C to 7°C

Weekly Weather Forecast for Ashland

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy a spacious outdoor patio or deck ideal for relaxing after a day on the slopes.
  • Take advantage of private outdoor fire pits to gather with friends and family during cool evenings.
  • Benefit from well-maintained outdoor grills perfect for preparing hearty meals in this ski-friendly area.
  • Explore scenic nature trails and pathways surrounding your rental, offering opportunities for winter hikes or snowshoeing.
  • Make use of ample parking spaces designed to accommodate vehicles heading to nearby ski resorts.
  • Relax in outdoor hot tubs with mountain views, a popular feature in this winter retreat destination.
  • Utilize designated outdoor storage areas for skis, snowboards, and other winter gear to keep your space organized.
image
image

Family Activities

  • South Shore Brewery Tour Experience a family-friendly tour at this local brewery, offering insights into the brewing process and tasting sessions for all ages.
  • Ashland Lighthouse Tour Discover the historic lighthouses that line the coast, providing scenic views and educational opportunities about the area's maritime heritage.
  • Bayfield Maritime Museum Explore exhibits on the region's rich shipping history, perfect for engaging children and adults alike in this seaside town.
  • Hiking at Copper Falls State Park Enjoy outdoor adventures with scenic trails, waterfalls, and picnic areas that create memorable family outings in this natural setting.
image

Adult Activities

  • Exploring the Ashland Lighthouse Discover stunning panoramic views of Lake Superior from this iconic lighthouse, perfect for a peaceful afternoon escape.
  • Walking along the Ashland Waterfront Trail Enjoy a scenic stroll along the shoreline, taking in the fresh lake air and the natural beauty of the surrounding region.
  • Visiting the Bayfield Maritime Museum Gain insight into the area's rich maritime history through engaging exhibits and artifacts that showcase this destination's seafaring heritage.
  • Attending local cultural events and festivals Immerse yourself in Ashland’s vibrant community spirit by participating in seasonal festivities and live performances held throughout the year.

Other Places to Stay in Ashland, WI

Northern Great Lakes Visitor Center
Ashland Historical Museum
Maslowski Beach
Chequamegon Bay Golf Course

Ashland Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Winter Activities Early: Secure your preferred ski chalets in the area in advance to enjoy a stress-free experience during the peak season.
  • Explore Local Snowshoe Trails: Take advantage of the region's scenic snowshoe routes for a peaceful way to embrace the winter landscape around your accommodation.
  • Visit During Off-Peak Times: Consider planning your trip during less busy periods to maximize privacy and enjoy more personalized service in your Ashland, Wisconsin stay.
  • Discover Nearby Dining Options: Sample local cuisine at nearby restaurants to complement your outdoor adventures and make the most of your visit here.

Transportation Options

  • Local Bus Services: This region offers reliable local bus options that can conveniently connect you to key areas around Ashland, making it easy to reach your chosen ski chalets without hassle.
  • Rental Car Services: Renting a vehicle provides the flexibility to explore the area at your own pace, especially useful for accessing remote or scenic spots near your accommodations.
  • Taxi and Ride-Sharing: Taxis and ride-sharing services are available for quick trips within the region, offering a convenient way to travel to nearby ski slopes or dining options.
  • Airport Transfers: For travelers arriving by plane, dedicated airport transfer services ensure a comfortable and punctual journey from the regional airports directly to your ski chalets.

Local Customs Options

  • Native American Traditions: You can experience respectful acknowledgment of the area's rich Native American heritage through local powwows and cultural events that honor the region’s original inhabitants.
  • Seasonal Festivals: The community hosts seasonal festivals celebrating its natural beauty, where you might witness traditional music, dance, and local crafts during your stay.
  • Local Dining Customs: Enjoy the region's culinary traditions by trying locally sourced dishes at eateries that emphasize fresh, regional ingredients, offering an authentic taste of here.
  • Outdoor Etiquette: When exploring the scenic landscapes, it’s customary to follow Leave No Trace principles to preserve the pristine environment for future visitors.

Ashland Ski Chalets Frequently Asked Questions

1. What are the top Ski Chalets in Ashland?

There are a lot of options in Ashland. If you plan on staying in the Ashland area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Ski Chalets in Ashland:

2. How many Ski Chalets are available in Ashland?

Currently, the total number of properties listed by RBO in 2026 is over 46 in the Ashland area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Ski Chalets in Ashland. 

3. What is the cancellation policy for booking a ski chalet in this region?

The cancellation policy varies depending on the specific property listing. It is recommended to review the property's cancellation terms directly on the listing or contact the owner for detailed information.

4. Are there any specific amenities included with the ski chalets in this area?

Amenities can differ between properties, so it's best to check each listing for details such as heating, kitchen facilities, Wi-Fi, and other features that suit your needs.

5. What is the process for confirming my booking at a ski chalet here?

Booking confirmation typically involves selecting your dates, completing payment, and receiving a confirmation email. For precise steps, refer to the booking instructions on the listing or reach out to the property owner.

6. Is there a minimum or maximum stay requirement for these ski chalets?

Stay requirements vary by property. Please review the individual listing details or contact the owner to confirm any minimum or maximum night policies.

7. How do I find out about local restrictions or guidelines during my stay?

Local restrictions or guidelines are often outlined in the property listing or provided upon booking. For additional questions, contacting the owner directly ensures you receive accurate and current information.

More Rentals You May Like Near Ashland

star-icons-3
Hotel
Map-icon
like-icon7.5
Very Good
(321 Reviews)
1 Bath
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $219/Night 7 Nights - US $1,534
House
Map-icon
like-icon9.2
Exceptional
(10 Reviews)
2 Bedrooms 2 Baths 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $246/Night 7 Nights - US $1,723
New
House
Map-icon
1 Bedroom 2 Baths 5 Guests
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $582/Night 7 Nights - US $4,077
Cabin
Map-icon
1 Bedroom 1 Bath 4 Guests
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $327/Night 7 Nights - US $2,289
Apartment
Map-icon
1 Bedroom 1 Bath 2 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
US $54/Night 7 Nights - US $378
New
Other
Map-icon
2 Bedrooms 1 Bath 7 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $152/Night 7 Nights - US $1,066
Cabin
Map-icon
like-icon10.0
Exceptional
(105 Reviews)
4 Bedrooms 2 Baths 14 Guests
  • Spa
    Spa
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $528/Night 7 Nights - US $3,693
Cabin
Map-icon
like-icon10.0
Exceptional
(105 Reviews)
3 Bedrooms 2 Baths 8 Guests 1800 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $500/Night 7 Nights - US $3,500
House
Map-icon
like-icon10.0
Exceptional
(18 Reviews)
4 Bedrooms 2 Baths 12 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Ocean View
    Ocean View
More amenities
US $723/Night 7 Nights - US $5,059
House
Map-icon
like-icon10.0
Exceptional
(1 Review)
3 Bedrooms 1 Bath 5 Guests 1400 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $108/Night 7 Nights - US $758
House
Map-icon
like-icon9.8
Exceptional
(34 Reviews)
3 Bedrooms 1 Bath 6 Guests 1300 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $252/Night 7 Nights - US $1,767
Apartment
Map-icon
1 Bedroom 1 Bath 2 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Child Friendly
    Child Friendly
More amenities
US $228/Night 7 Nights - US $1,599