Ashland vacation rentals

We found 48 vacation rentals — enter your dates for availability

Discover a selection of 11 homes and other vacation rentals in Ashland that are perfect for your trip. Vacation homes offer the best amenities for you and your friends, family, or even pets, such as parking and a hot tub. At the end of the day, you'll be sure to find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Ashland

Why visit Ashland

  • Outdoor adventures: Ashland is a haven for outdoor enthusiasts, offering activities like hiking, fishing, and boating on beautiful lakes.
  • Scenic beauty: Enjoy picturesque lakeside views and unwind on private beaches, perfect for relaxation and family fun.
  • Cultural experiences: Explore local history museums and cultural attractions that showcase Ashland's rich heritage.
  • Charming neighborhoods: Discover warm and welcoming neighborhoods, ideal for leisurely strolls and community engagement.
  • Diverse accommodations: Choose from a variety of vacation rentals, including cozy cabins and condos with essential amenities.

Popular types of accommodation in Ashland

Planning a getaway to Ashland? Discover the perfect place to stay with a range of vacation rentals that cater to your needs. From cozy houses and charming cabins to convenient condos, Ashland offers a variety of accommodations. Many of these rentals feature essential amenities like laundry facilities, ensuring a comfortable and hassle-free stay. Explore your options and find the ideal holiday cottage for your next adventure.

  • Houses: The top choice for visitors in Ashland, these spacious homes offer a comfortable retreat for families and groups, providing amenities that make you feel at home.
  • Cabins: A popular option for those seeking a rustic experience, these cozy cabins allow you to immerse yourself in nature while enjoying modern conveniences.
  • Condos: Ideal for travelers wanting a blend of comfort and convenience, these well-equipped condos provide easy access to local attractions.
  • Cottages: Charming and inviting, these quaint cottages are perfect for a peaceful getaway, often located near the water.
  • Apartments: A practical choice for solo travelers or couples, these apartments offer a cozy and convenient place to unwind after a day of exploration.**

Top attractions in and around Ashland

Ashland, Wisconsin, is perfect for outdoor and adventure lovers, offering stunning scenery and a rich cultural experience. Explore local attractions such as history museums, marinas, and parks that cater to families and solo travelers alike. For those planning a longer stay, consider looking into vacation rentals in Ashland to fully enjoy all that this charming destination has to offer.

  • Ashland Historical Museum: Dive into local history with engaging exhibits showcasing Ashland's rich culture and heritage. This museum is a perfect spot for history enthusiasts to explore artifacts and stories that shaped the community.
  • Bayview Park: A beautiful outdoor setting just 1 mile from Ashland, Bayview Park is ideal for families and nature lovers. Enjoy walking trails, picnic areas, and eco-friendly activities amidst stunning views of the surrounding landscape.
  • Maslowski Beach: Located 2 miles from Ashland, this beach offers a relaxing atmosphere with sandy shores and clear waters. Perfect for sunbathing, swimming, or enjoying a peaceful day by the lake.

Things to do recommended for couples

For a romantic getaway in Ashland, embark on an adventure at Mount Ashwabay Ski and Recreation Area, just 13 miles away. For a unique experience, try sailing with AnimAashi Sailing Company, 15 miles from town, or enjoy outdoor thrills with Living Adventure, located 18 miles from Ashland.

Things to do recommended for families

Families will appreciate the Northern Great Lakes Visitor Center in Ashland, where they can explore nature trails and exhibits while enjoying the serene atmosphere. This recreational area offers a perfect blend of relaxation and outdoor adventure for all ages.

Things to do recommended for groups

Enjoy a round of golf with friends at Chequamegon Bay Golf Course, soak in the arts at StageNorth theater, or catch a show at the iconic Big Top Chautauqua for a memorable group experience in Ashland.

*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 Ashland

If you're planning a trip with friends, family, pets, or need extended accommodations, be sure to refine your search based on your key priorities. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Ashland with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Ashland with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Ashland: For many families, a vacation wouldn’t be the same without their furry companions. If you can relate, explore Vrbo listings that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Ashland: If you're in search of vacation rentals that offer great deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search for the perfect getaway.

Where to stay in and around Ashland

Ashland, Wisconsin, offers a perfect blend of outdoor adventure and scenic beauty, making it an ideal vacation spot. Explore picturesque lakeside views, unwind on private beaches, and enjoy a beachside getaway with family-friendly vibes. Nearby neighborhoods exude warmth and hospitality, providing a welcoming atmosphere for all travelers. Whether you're seeking excursions or simply relaxing in a large yard, Ashland promises memorable experiences in a charming setting.

  • Washburn: Located 6 miles from Ashland, Washburn is a charming city that beckons outdoor enthusiasts and adventure seekers. Known for its stunning scenery, Washburn offers a variety of recreational activities, including skiing in the winter and water sports in the summer. The local marina and proximity to the national state park and beautiful lakes make it an ideal destination for fishing, boating, and hiking. Don't miss the breathtaking views along the shores of Lake Superior, which provide perfect photo opportunities and serene spots for relaxation.
  • White River: Nestled in the Ashland area, the village of White River is a haven for those who love nature and adventure. Here, visitors can explore scenic landscapes while enjoying activities like skiing at the local ski resort or hiking through the stunning national state park. The nearby river and picturesque waterfalls offer tranquil settings for picnics and photography. With its inviting atmosphere and abundance of outdoor activities, White River is a great place to immerse yourself in the beauty of northern Wisconsin.
  • Moquah: This quaint village, located near Ashland, is perfect for travelers seeking outdoor adventures and scenic beauty. Moquah is known for its extensive trail access, ideal for hiking enthusiasts looking to explore the natural surroundings. The area is home to a serene lake and offers historic sites as well as mountain views, making it a great spot for both relaxation and exploration. Enjoy the peaceful ambiance while hiking the trails, and experience the diverse wildlife and natural beauty that Moquah has to offer.

Best time to go to Ashland

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January14.7°F (-9.6°C)No Rain (Dry)Very CloudyModerately LowAverage
February15.4°F (-9.2°C)No Rain (Dry)Mostly CloudyAverageAverage
March28.0°F (-2.2°C)Light RainMostly CloudyAverageSlightly Low
April38.1°F (3.4°C)Light RainMostly CloudyAverageSlightly Low
May51.6°F (10.9°C)Light RainMostly SunnyAverageAverage
June61.5°F (16.4°C)Light RainMostly SunnyModerately HighSlightly High
July68.0°F (20.0°C)Light RainMostly SunnyModerately HighSlightly High
August66.9°F (19.4°C)Light RainMostly SunnyModerately HighSlightly High
September59.7°F (15.4°C)Light RainMostly SunnyAverageAverage
October46.2°F (7.9°C)Light RainMostly SunnyAverageAverage
November33.3°F (0.7°C)Light RainMostly CloudyModerately LowSlightly Low
December21.7°F (-5.7°C)Light RainMostly CloudyModerately LowAverage

Booking with Vrbo is simple

Planning your next getaway? Consider being flexible with your travel dates, as this can lead to better prices. Additionally, booking a longer stay often brings considerable savings. To discover a Vrbo property that suits your budget, make use of our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect fit for your trip.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a user-friendly area for you to design new trips, continue planning from where you last stopped, or review and manage your itineraries. Here, you can easily access your saved or booked properties, sorted into categories like Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Cozy Ashland will entice you

Enjoy the architecture and other features of Ashland. This city is well-known for its lake and hiking. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Sightseeing in and around Ashland

Are you hoping to find things to do while you're in the area? Venture out of your cozy vacation rental and check out everything that makes Ashland a one-of-a-kind vacation spot. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Mount Ashwabay Ski and Recreation Area (12.7 mi / 20.5 km)
  • Whitecap Mountains (26.2 mi / 42.2 km)
  • Ashland Mural Walk (0.3 mi / 0.4 km)
  • Chequamegon Bay Golf Course (2.1 mi / 3.4 km)
  • Apostle Highlands Golf Course (15.2 mi / 24.5 km)

Exploring the natural features in Ashland

Whether you're looking for adventure or just want to spend some time taking in the scenery, Ashland is a great place to get outside. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Chequamegon Bay (5.6 mi / 9 km)
  • Copper Falls State Park (20 mi / 32.3 km)
  • Spider Lake (24.8 mi / 39.9 km)
  • Whitecap Mountains (26.2 mi / 42.2 km)
  • Lake Namakagon (28.2 mi / 45.4 km)
  • Chequamegon National Forest (29.8 mi / 48 km)

Traveling to and around Ashland

The nearest airport is in Ironwood, MI (IWD-Gogebic County), located 35.9 mi (57.7 km) from the city center.

Frequently asked questions

What is the best area to stay in Ashland, Wisconsin, United States of America when booking a vacation rental?
When considering a vacation rental in Ashland, Wisconsin, the downtown area stands out as a fantastic option. This vibrant neighborhood not only offers a variety of rental properties but also places you in close proximity to some of the city's top attractions. Just a short stroll away, you'll find the Ashland Historical Museum, where you can delve into the region's rich history, and the scenic Bayview Park, superb for enjoying the stunning views of Lake Superior.

Another appealing area to explore is the Lakeshore neighborhood, which features a mix of charming homes and rentals with easy access to the waterfront. Visitors here can enjoy outdoor activities such as hiking or biking along the shoreline, and the nearby Chequamegon National Forest offers a beautiful backdrop for nature lovers.
How much does it cost to rent a vacation home in Ashland?
Prices for vacation rentals in Ashland 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Ashland to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Ashland vacation house rentals?
You can find great discounts on house rentals in Ashland on Vrbo, 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.
Where are the best areas for renting a beach house in Ashland?
For renting a beach house in Ashland, consider the scenic shoreline along Lake Superior. The area near Chequamegon Bay offers a variety of vacation rentals, many of which come with stunning views of the water and access to sandy beaches. Properties here often feature amenities such as spacious decks, outdoor grills, and fire pits, providing a ideal setting for evening gatherings after a day of enjoying the lake.

In addition, the Ashland Marina area is another excellent choice, where visitors can find charming cottages and larger homes equipped with modern kitchens and comfortable living spaces. Many of these rentals are situated close to local attractions, including the nearby Apostle Islands National Lakeshore, which is famous for its breathtaking scenery and outdoor activities like kayaking and hiking. Rentals in this region often come with additional conveniences, such as laundry facilities and Wi-Fi, ensuring a comfortable stay for families or groups.
Where are the best Ashland ski resort rentals?
For the best ski resort rentals near Ashland, Wisconsin, travelers should focus on the nearby area of Mount Ashwabay, which offers a variety of winter sports activities. In the vicinity of this ski area, visitors can find cozy cabins and lodges that cater to both families and groups. Many of these properties feature essential amenities such as fireplaces, fully equipped kitchens, and easy access to ski slopes, ensuring a comfortable stay after a day of skiing.

Additionally, the town of Ashland itself provides several rental options, including charming homes and apartments that are a short drive from the ski area. These accommodations often come with features like outdoor decks, hot tubs, and scenic views of the surrounding landscape, great for unwinding in the evenings. The town also boasts local dining options and shops, adding to the convenience for travelers.

Moreover, for those looking to explore the natural beauty of the Chequamegon National Forest, many rentals offer proximity to trails for snowshoeing and cross-country skiing.
What is the most popular type of vacation rental accomodation in Ashland?
In Ashland, vacation houses are quite popular, with several available throughout the area. These rentals often provide spacious rooms, featuring multiple bedrooms, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups. Additionally, cabins and cottages are also prevalent, allowing visitors to immerse themselves in the natural beauty of the surroundings. Many of these properties come with outdoor spaces, such as decks or fire pits, great for enjoying evenings under the stars.
Are there any family house rentals in Ashland?
In Ashland, Wisconsin, there are some family-friendly house rentals available, with around 12 options to choose from. Visitors can find spacious homes equipped with amenities such as full kitchens, cozy living areas, and outdoor patios superb for family gatherings. Many properties are situated close to the beautiful shores of Lake Superior, offering easy access to beaches and parks where children can enjoy outdoor activities.

Additionally, families can explore the nearby Chequamegon National Forest, which provides ample opportunities for hiking, biking, and appreciating the region's natural beauty. Ashland's charming downtown area features local shops and restaurants that cater to families, making it a delightful destination for all ages.
Can I find long-stay vacation rentals in Ashland?
A long-stay vacation rental in Ashland is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Ashland?
In Ashland, there are several pet-friendly house rentals available, providing a friendly setting for travelers with furry companions. Many of these vacation homes are equipped with essential amenities such as fully stocked kitchens, comfortable living spaces, and outdoor areas where pets can enjoy the fresh air.

The area around Ashland is known for its natural beauty, with nearby parks and access to the shores of Lake Superior, where you can explore scenic trails and enjoy various outdoor activities. The Chequamegon National Forest is not far, offering additional opportunities for hiking and scenic walks that are great for pet owners looking to enjoy the great outdoors.
Are there any remote work vacation rentals in Ashland?
In Ashland, Wisconsin, there are some remote work-friendly vacation rentals available, with approximately 13 options for travelers to choose from. Many of these properties are equipped with essential amenities like high-speed Wi-Fi, dedicated workspaces, and comfortable living areas, making them suitable for those looking to balance work and leisure.

Situated along the beautiful shores of Lake Superior, Ashland offers a charming blend of natural beauty and small-town hospitality. While staying here, guests can enjoy the scenic views and outdoor activities, such as hiking and biking in nearby Chequamegon National Forest. The town also features local attractions like the Ashland Historical Museum and the picturesque Apostle Islands, providing ample opportunities for exploration during downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Ashland vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Ashland with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo 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.
What are popular rental amenities in Ashland?
In Ashland, popular vacation rental amenities include fully equipped kitchens, allowing guests to prepare their own meals during their stay. Many rentals also feature decks or patios, providing outdoor space for relaxation and enjoying the scenic views of Lake Superior and the surrounding landscapes. Additionally, travelers can expect amenities like blenders and coffee/tea makers for convenience, as well as onsite parking to make their stay straightforward.
How early should I book a Ashland vacation rental?
Book your Ashland vacation rental 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 Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Ashland, Wisconsin, United States of America?
In Ashland, visitors can explore a range of attractions that highlight the area's natural beauty and cultural heritage. The city is situated on the shores of Lake Superior, making the waterfront a prime spot for scenic views and outdoor activities. The Chequamegon National Forest nearby offers endless opportunities for hiking, biking, and wildlife watching, with trails suited for all skill levels.

In the downtown area, the Ashland Historical Museum provides insights into the region's history and its significance as a center for fishing and lumber industries. Art enthusiasts can enjoy the local art scene, with galleries featuring works by regional artists, particularly along Main Street.

The Apostle Islands National Lakeshore, a short drive from Ashland, is a must-visit, famous for its stunning sea caves and pristine wilderness. During winter, the area is popular for ice fishing and snowshoeing, while summer activities include kayaking and sailing around the islands.

For those interested in local culture, the annual Bayfield Apple Festival and other community events offer a taste of Ashland's vibrant local traditions.
Can I change or cancel my Ashland home rental booking on Vrbo?
To find Ashland vacation rentals with free cancellation, just use Vrbo'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". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Ashland vacation rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing 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 favorites, and build the perfect itinerary together.

More Vacation Ideas