Highland, WI

Travel Guide

Cheese Wedge Cabin Idyllic Farm

Cheese Wedge Cabin Idyllic Farm

Highland WI
Stay at this cabin in Highland. Enjoy a garden, laundry facilities, and an in-room coffeemaker. Popular attractions Beach at Black Hawk Lake Recreation Area ...
8.8/10 Excellent! (3 reviews)
"Wonderful experience! Host is amazing! Really hoping to come back soon! Words cannot describe how lovely our time there was!"

Reviewed on Sep 18, 2026

Get rates
Cheese Wedge Cabin Idyllic Farm
Don Q Inn

Don Q Inn

2.5 out of 5
3658 State Road 23 Dodgeville WI
$90 nightly
The price is $102 total per night from Oct 4 to Oct 5
$102 total
Oct 4 - Oct 5
Total with taxes and fees
Stay at this hotel in Dodgeville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8/10 Very Good! (1,001 reviews)
"It was a cute lil hotel and the room was great! It is outdated, and the mattress definitely needs to be upgraded. It was sagging in the middle but you couldn’t really sleep on the outside because it was almost like you’d roll out otherwise. The tub was a nice addition to the room, but not sure how ..."

Reviewed on Oct 2, 2026

Don Q Inn
Sleep Inn & Suites Lancaster-Platteville

Sleep Inn & Suites Lancaster-Platteville

2.5 out of 5
1600 S Madison Street Lancaster WI
$94 nightly
The price is $99 total per night from Oct 25 to Oct 26
$99 total
Oct 25 - Oct 26
Total with taxes and fees
Book a stay at this golf hotel in Lancaster. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
9.4/10 Exceptional! (380 reviews)
"The staff was very friendly, easy to talk to. We enjoyed the breakfast and the pride the staff showed to provide the selection of food."

Reviewed on Sep 30, 2026

Sleep Inn & Suites Lancaster-Platteville
See all 129 properties in Highland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Cheese Wedge Cabin Idyllic Farm

Cheese Wedge Cabin Idyllic Farm

Highland WI
Stay at this cabin in Highland. Enjoy a garden, laundry facilities, and an in-room coffeemaker. Popular attractions Beach at Black Hawk Lake Recreation Area ...
8.8/10 Excellent! (3 reviews)
"Wonderful experience! Host is amazing! Really hoping to come back soon! Words cannot describe how lovely our time there was!"

Reviewed on Sep 18, 2026

Cheese Wedge Cabin Idyllic Farm
Highland: Driftless Fun Awaits

Highland: Driftless Fun Awaits

Highland WI
Stay at this apartment in Highland. Enjoy a garden, laundry facilities, and an in-room coffeemaker. Popular attractions Spurgeon Vineyards & Winery and Blackhawk ...
10/10 Exceptional! (1 review)
"Great property. Had everything we needed. Highly recommend."

Reviewed on May 27, 2025

Highland: Driftless Fun Awaits
The Driftless Escape! Modern, large cabin/57 private acres in WI drift less area

The Driftless Escape! Modern, large cabin/57 private acres in WI drift less area

Richland Center WI
Stay at this cabin in Richland Center. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Richland Museum & Visitor's Center and A.D. German ...
10/10 Exceptional! (182 reviews)
"The house was very clean and was a great place to getaway for the weekend. And there is so much to do in the area"

Reviewed on Sep 22, 2026

The Driftless Escape! Modern, large cabin/57 private acres in WI drift less area
See all properties in Highland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Highland attractions

Blackhawk Lake Recreation Area

10.0/10 (2 reviews)
Explore the great outdoors at Blackhawk Lake Recreation Area, a lovely green space in Highland. Stroll along the lakeside or discover the area's waterfalls.
See properties

Frequently asked questions

Is Highland worth visiting?
Highland is worth visiting for its diverse Italian and North American dining experiences. Travelers can also explore the Blackhawk Lake Recreation Area, which offers outdoor activities and a popular beach perfect for relaxation and enjoying the water.
When is the best time to visit Highland?
The best time to visit Highland is from May through September, when the climate is most favorable. For travelers seeking fewer crowds and better value, the quieter months of November through February are a good option, offering a different experience with cooler weather.
What is Highland known for?
Highland is known for Blackhawk Lake Recreation Area, which includes the Beach at Black Hawk Lake Recreation Area, offering travelers opportunities for outdoor activities. The area also features Spurgeon Vineyards & Winery, and you can find a local Italian food culture to explore.
What is a good itinerary length for Highland?
A good itinerary length for Highland is one to two days to explore highlights like Blackhawk Lake Recreation Area and Spurgeon Vineyards & Winery. For a more relaxed trip, consider three to four days, allowing extra time to enjoy the beach at Black Hawk Lake Recreation Area and sample the local Italian, North American, and Latin American dining options.
What are the top things to do in and around Highland?
Highland offers natural beauty, including a lake and beach, plus a local winery to explore:


How do I plan a trip to Highland?
When planning your trip to Highland, search for places to stay and book flights and rental cars early. Explore activities like Blackhawk Lake Recreation Area, its beach, and Spurgeon Vineyards & Winery. For weather flexibility, consider pairing your outdoor plans with indoor options.
What cuisines can you find in Highland?
In Highland you can find German cuisine, with dishes like bratwurst, schnitzel, and pretzels. Travelers can also enjoy Italian, North American, and Latin American options, including Mexican tacos. Asian choices like Chinese, Japanese, and Vietnamese food are also available, alongside Mediterranean dishes.
Can I book a refundable hotel in Highland?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Highland by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Highland with Expedia?
Expedia makes it easier to plan your Highland trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Highland?
The best choice depends on your travel style. Hotels in Highland can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Highland trip on Expedia?
Once you've booked your Highland trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Highland trip?
Expedia offers customer support before, during, and after your Highland trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Highland?
If it's your first trip to Highland, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Highland hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Highland hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Highland

A park with a picnic table, trees with autumn foliage, and a grassy area.

Dodgeville

A wooden pier extending into calm water with a forested shoreline reflecting in the water.

Muscoda

Explore a world of travel with Expedia