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Our top choices for Highland hotels

Ramada by Wyndham Richland Center

Ramada by Wyndham Richland Center
3.0 star property
Richland Center
8.2 out of 10, Very Good, (650)
"The room was comfortable and clean. The breakfast was definitely lacking. Basically the only hot meal options were microwave burritos and pancakes. "
United States
Aaron
$85 nightly
The price is $96
Jan 4 - Jan 5, 2026
Total with taxes and fees
Ramada by Wyndham Richland Center

AmericInn by Wyndham Boscobel

AmericInn by Wyndham Boscobel
2.5 star property
Boscobel
8.6 out of 10, Excellent, (464)
"The breakfast, pool, and pet policy are the highlights and quite outstanding for Wyndham Boscobel, the rest of the property is meh. We didn't book the hot tub room to use it but for the square footage gained, room was musty. Room needs a deep cleaning - wiping all the walls, kitchenette and bathroom with some elbow grease."
United States
Alejandra
$74 nightly
The price is $82
Jan 1 - Jan 2, 2026
Total with taxes and fees
AmericInn by Wyndham Boscobel

Sleep Inn & Suites Lancaster-Platteville

Sleep Inn & Suites Lancaster-Platteville
2.5 star property
Lancaster
9.2 out of 10, Wonderful, (274)
"Front desk employee at check-in was amazing! Friendly funny & very competent!"
United States
Rachel
$88 nightly
The price is $93
Jan 18 - Jan 19, 2026
Total with taxes and fees
Sleep Inn & Suites Lancaster-Platteville

Best Western Dodgeville Inn & Suites

Best Western Dodgeville Inn & Suites
2.5 star property
Dodgeville
8.4 out of 10, Very Good, (645)
"Friendly staff. Clean and quiet room. Comfortable beds. Pool area was clean and comfortable. Nice place to stay."
United States
Ronda
$74 nightly
The price is $84
Dec 31 - Jan 1, 2026
Total with taxes and fees
Best Western Dodgeville Inn & Suites

Don Q Inn

Don Q Inn
2.5 star property
Dodgeville
8.2 out of 10, Very Good, (1001)
"The place is amazing! I definitely will be going back!!"
United States
Stephanie
$63 nightly
The price is $71
Dec 28 - Dec 29
Total with taxes and fees
Don Q Inn

Quality Inn & Suites Belmont - Platteville

Quality Inn & Suites Belmont - Platteville
2.5 star property
Belmont
8.4 out of 10, Very Good, (277)
"We stayed here for our son's UWP graduation. It was clean, comfortable and friendly. Our younger kids enjoyed the pool and we appreciated the clean, comfortable rooms with breakfast on site. All the staff was warm and kind and helpful. Definitely recommend!"
United States
Heidi
$63 nightly
The price is $69
Jan 18 - Jan 19, 2026
Total with taxes and fees
Quality Inn & Suites Belmont - Platteville

Holiday Inn Express and Suites-Platteville by IHG

Holiday Inn Express and Suites-Platteville by IHG
2.5 star property
Platteville
9.6 out of 10, Exceptional, (566)
"awesome staff at check in!"
United States
joshaua
$107 nightly
The price is $118
Jan 11 - Jan 12, 2026
Total with taxes and fees
Holiday Inn Express and Suites-Platteville by IHG

Pine Ridge Motel

Pine Ridge Motel
2.0 star property
Dodgeville
8.2 out of 10, Very Good, (370)
"Room was very clean and bed was super comfortable."
United States
Patricia
$60 nightly
The price is $68
Dec 25 - Dec 26
Total with taxes and fees
Pine Ridge Motel

Super 8 by Wyndham Dodgeville

Super 8 by Wyndham Dodgeville
2.0 star property
Dodgeville
7.6 out of 10, Good, (838)
"It would have been nice to mention where & hours of hot tub and breakfast. Outlets were all loose, hard to charge cell phones and get cpaps connected. It was unnerving that first floor back entrance wasn't locked during the day. connected. phan"
United States
Janet
$67 nightly
The price is $76
Dec 31 - Jan 1, 2026
Total with taxes and fees
Super 8 by Wyndham Dodgeville

Fenway House Hotel

Fenway House Hotel
2.5 star property
Fennimore
9.2 out of 10, Wonderful, (75)
"Very cool old downtown hotel "
United States
Jeff
$95 nightly
The price is $100
Dec 25 - Dec 26
Total with taxes and fees
Fenway House Hotel

The Round Barn Lodge

The Round Barn Lodge
2.5 star property
Spring Green
8.6 out of 10, Excellent, (617)
"Friendly staff, nice pool to swim & clean room. Comfortable sleeping bed. "
United States
Renee
$91 nightly
The price is $95
Dec 29 - Dec 30
Total with taxes and fees
The Round Barn Lodge

AmericInn by Wyndham Dodgeville

AmericInn by Wyndham Dodgeville
2.5 star property
Dodgeville
8.4 out of 10, Very Good, (569)
"Was a great stay!"
United States
Kathryn
$78 nightly
The price is $89
Dec 25 - Dec 26
Total with taxes and fees
AmericInn by Wyndham Dodgeville

Deer Valley Lodge & Golf

Deer Valley Lodge & Golf
2.5 star property
Barneveld
8.8 out of 10, Excellent, (676)
"We love it here!! The pool is WARM the staff is great!"
United States
Bailey
$129 nightly
The price is $136
Dec 28 - Dec 29
Total with taxes and fees
Deer Valley Lodge & Golf

Napps Motel

Napps Motel
2.0 star property
Fennimore
7.2 out of 10, Good, (33)
"Good budget motel."
United States
ken
$71 nightly
The price is $75
Dec 25 - Dec 26
Total with taxes and fees
Napps Motel

Maon House Bed and Breakfast

Maon House Bed and Breakfast
2.0 star property
Richland Center
9.4 out of 10, Exceptional, (12)
"Wonderful place to stay and a very nice host that cooked an amazing breakfast."
United States
Matt
$122 nightly
The price is $138
Jan 5 - Jan 6, 2026
Total with taxes and fees
Maon House Bed and Breakfast
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.
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Stay near popular Highland attractions

Top Highland Hotel Reviews

More cheap stays in Highland

Hotels in Highland with star-rating

Find out more about Highland

Top reasons to visit Highland

  • Outdoor Adventures: Highland is a haven for outdoor enthusiasts, offering activities like hiking and beach days in beautiful natural settings.
  • Family-Friendly Atmosphere: The town caters to families with a variety of recreational options and safe, welcoming neighborhoods.
  • Scenic Campgrounds: Relax at picturesque campgrounds that provide a perfect backdrop for a peaceful getaway.
  • Local Golf Course: Enjoy a round of golf at the local course, which blends recreation with stunning views.
  • Rich Community Culture: Immerse yourself in the warm community vibe and explore local history during your stay.

Find great hotels near Highland

Discover the charm of Highland, Wisconsin, with a range of hotel accommodations tailored for every type of traveler. From pet-friendly options to family-oriented stays, you'll find the perfect place to relax. Enjoy luxury amenities, complimentary parking, and business-friendly facilities, ensuring a comfortable experience whether you're here for leisure or work. Dive into local hotel reviews to guide your choice for a memorable visit.

  • Don Q Inn: Experience a unique blend of comfort and charm at Don Q Inn, located 13 miles from Highland. This hotel offers a distinctive theme with its cozy, home-like atmosphere and themed rooms. Guests can enjoy complimentary amenities such as daily breakfast options, including continental choices and wrapped food. For entertainment, the property features LCD and cable TVs, ensuring you stay connected and entertained during your visit. Nature enthusiasts will appreciate the proximity to local attractions, including nearby national and state parks, perfect for outdoor adventures.
  • AmericInn by Wyndham Dodgeville: Ideal for families and business travelers, AmericInn by Wyndham Dodgeville, situated 13 miles from Highland, provides a pet-friendly environment with amenities designed to cater to various needs. This hotel features essential business services and is equipped with free cribs for families traveling with young children. The pet policy allows certain pets on-site, making it a great choice for those who want to bring their furry friends along. With a welcoming atmosphere and a focus on family-friendly activities, this hotel ensures a comfortable and enjoyable stay.
  • Best Western Dodgeville Inn & Suites: Located 14 miles from Highland, Best Western Dodgeville Inn & Suites is a pet-friendly haven for travelers. This hotel is designed with comfort in mind, offering a warm and inviting atmosphere. Pets are allowed with some restrictions, ensuring that your four-legged companions can join you on your vacation. Guests appreciate the spacious accommodations and convenient amenities that make for a relaxing stay. Whether you’re traveling for leisure or business, this hotel provides a comfortable base from which to explore the surrounding area.

Where to stay near Highland

Highland, Wisconsin, offers a delightful blend of outdoor adventures and rich history, making it perfect for family vacations. Nearby cities like Hudson Valley invite you to explore charming neighborhoods with family-friendly atmospheres. Enjoy the scenic beauty and affordable accommodations that Highland has to offer, while immersing yourself in the local culture. Experience the warmth of community and the allure of history as you create unforgettable memories on your getaway.

  • Dodgeville: Located 14 miles from Highland, Dodgeville is a charming city that attracts visitors year-round, with peak travel from June to August. Known for its stunning outdoor experiences, families flock here to enjoy recreational areas and campgrounds. The nearby national state park and picturesque lake offer breathtaking scenery and ample opportunities for hiking, fishing, and picnicking. Dodgeville's blend of natural beauty and family-friendly activities makes it a perfect getaway for adventure seekers and nature lovers alike.
  • Montfort: Just 6 miles from Highland, Montfort is a delightful city that invites travelers throughout the year, with peak visits occurring in April to May and September. This destination is perfect for couples looking for a romantic escape, as well as families eager to enjoy its scenic beauty. Popular venues include local campgrounds and resorts, while the nearby lake and national state park provide excellent opportunities for relaxation and outdoor fun. Montfort’s welcoming atmosphere and natural surroundings make it a lovely stop on your journey.
  • Cobb: A mere 6 miles from Highland, Cobb is a vibrant city that offers an entertainment-themed experience perfect for families and adventure enthusiasts. Visitor numbers peak during the summer months of June to August, with a variety of attractions including a water park and recreational areas. Families can enjoy engaging educational experiences alongside thrilling adventures at the nearby theme park and national state park. Cobb's lively atmosphere and array of activities ensure a fun-filled visit for everyone.

Things to do in and around Highland

Highland, Wisconsin, offers a perfect blend of outdoor adventures and family-friendly activities, making it an ideal vacation spot. Visitors can enjoy the scenic recreational area, relax at the campground, or hit the greens at the local golf course. For those seeking excitement after sunset, the nightlife provides a unique experience, while fun day trips can enhance your stay, showcasing the beauty and charm of this picturesque region.

Shopping

In Highland, you can shop at local favorites like the Carr Valley Cheese store, known for its delicious cheeses. If you're up for a drive, explore the WI River Outings and Spring Green General Store, both offering unique gifts and souvenirs, located 15 and 18 miles away, respectively.

Recreation

At Blackhawk Lake Recreation Area, immerse yourself in nature with hiking, fishing, and picnicking, promoting relaxation and wellness. Fireman's Park, a short drive away, offers serene walking trails and peaceful green spaces for unwinding. For golf enthusiasts, Spring Green Golf Course provides an invigorating outdoor experience amidst beautiful landscapes.

Adventure

Explore the Meadow Valley Trailhead, a scenic hiking trail located 13 miles from Highland, where you can enjoy breathtaking views and immerse yourself in nature. Additionally, venture to Miner Hill Trails Park, 20 miles away, for more outdoor adventure and stunning landscapes to experience.

Nightlife

In Highland, the American Players Theatre, located 18 miles away, offers a romantic and cultural experience with captivating performances. Similarly, the Alley Stage, 16 miles from Highland, provides a charming atmosphere perfect for families and couples looking for entertainment and unique theatrical experiences.

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

Booking tips and Expedia advantages for Highland

To save money on your trip to Highland, visit between January and March for lower accommodation rates, and consider staying on a Tuesday for the best prices. Use Expedia’s search tool to sort hotels by price and filter by eco-certified options. Look for package deals that combine flights and activities for additional savings. Joining Expedia's One Key membership can unlock exclusive discounts and allow you to earn OneKeyCash for future bookings. Enjoy free local activities and explore the area on foot to minimize transport costs.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Highland are January to March, where the prices are slightly lower. This is in comparison to August to October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Highland is Tuesday. The most expensive day to stay in Highland is Saturday.
  • Find cheap hotels on Expedia: Expedia's search tool enables you to set your budget, choose your ideal location, and much more. You can easily sort the results to display hotels from the lowest to the highest price, ensuring you find the most affordable options first. Additionally, you have the option to refine your search by hotel type. For instance, if you select the Eco-certified filter, you'll be shown sustainable and environmentally friendly hotels that are available for booking.
  • Consider bundling your trip: You can potentially save money by combining your hotel stay in Highland with your flights and activities through an Expedia package deal.
  • Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions in and around Highland

Highland, Wisconsin, offers a perfect getaway for outdoor enthusiasts and families alike. Visitors can explore beautiful beaches, scenic landscapes, and the nearby national state park, providing ample opportunities for adventure and relaxation. Whether you're looking for a day at the beach or a hike in nature, Highland has a variety of attractions that cater to all types of travelers seeking an unforgettable experience.

  • The House on the Rock: Located 13 miles from Highland, this unique attraction features a stunning collection of architecture and art, including the famous Infinity Room. Enjoy a whimsical blend of nature and creativity, with family-friendly outdoor vibes that make it a memorable experience for all ages.
  • Beach at Black Hawk Lake Recreation Area: Situated within Highland, this serene beach offers a perfect spot for relaxation and recreation. Enjoy sunbathing, swimming, or picnicking with family and friends while soaking in the beautiful lakeside atmosphere.
  • Governor Dodge State Park: Just 14 miles away, this national state park boasts breathtaking scenery and a variety of outdoor adventures. Hike scenic trails, explore picturesque landscapes, or enjoy picnicking in nature, making it an ideal destination for outdoor enthusiasts.

Best time to go to Highland

The best time to visit Highland is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are moderately low and weather is mostly cloudy with no rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January18.0°F (-7.8°C)No RainMostly CloudyModerately LowSlightly Low
February20.5°F (-6.4°C)No RainMostly CloudyModerately LowSlightly Low
March34.9°F (1.6°C)Light RainMostly CloudyAverageSlightly Low
April45.5°F (7.5°C)Light RainMostly CloudyAverageAverage
May57.9°F (14.4°C)Light RainMostly SunnyAverageAverage
June67.8°F (19.9°C)Light RainMostly SunnyAverageAverage
July71.8°F (22.1°C)Light RainMostly SunnyModerately HighAverage
August70.2°F (21.2°C)Light RainMostly SunnyModerately HighSlightly High
September63.0°F (17.2°C)Light RainMostly SunnyAverageSlightly High
October49.6°F (9.8°C)Light RainMostly SunnyModerately HighSlightly High
November36.7°F (2.6°C)Light RainMostly SunnyAverageAverage
December25.5°F (-3.6°C)Light RainMostly CloudyModerately LowAverage

The nearest major airports for your trip to Highland

When visiting Highland, Wisconsin, you can fly into two major airports: Madison, WI (MSN-Dane County Regional), located 53 miles away, and Dubuque, IA (DBQ-Dubuque Regional), situated 47 miles away. Near Madison Airport, you can stay at The Edgewater, a 4.5-star hotel 5 miles from the airport, offering free airport transportation. The DoubleTree by Hilton Madison East and Downtown are both 4-star options, 2 and 5 miles away respectively. For Dubuque Airport, Hotel Julien Dubuque, Grand Harbor Resort and Waterpark, and The Hancock House, a charming bed and breakfast, are all excellent 3.5-star choices, each 7 miles from the airport.

Frequently asked questions

What is the best area to stay in Highland?
The best area to stay in Highland is near the main square, particularly along Main Street, for convenient access to local amenities and a central experience.

This area serves as the modest downtown of Highland. Main Street is where you'll find the majority of the town's businesses, including local eateries and a few shops. It's a straightforward layout, making it easy to navigate on foot.

Couples looking for a quiet retreat will appreciate staying near the main square. It offers a relaxed pace, with opportunities for strolls and enjoying the local dining options without the hustle and bustle of larger towns.
When is the best time to go to Highland?
The best time to visit Highland, Wisconsin, is during the summer months, from June to August, when the weather is warm and conducive to outdoor activities, or in the fall, from September to October, for the striking autumn foliage.

Summer in Highland brings average temperatures in the 70s, making it ideal for exploring the area's natural beauty. You can enjoy hiking and biking on trails like those found in the Governor Dodge State Park, or spend time on the water at Blackhawk Lake. This season is particularly good for families looking for an active vacation.

For those who appreciate scenic beauty, the fall offers cooler temperatures, typically in the 50s and 60s, and a spectacular display of changing leaves. This period is superb for couples seeking a peaceful getaway and picturesque drives through the Wisconsin Driftless Area.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Highland.
How can I save on a Highland hotel booking with Expedia?
With Expedia, you earn OneKeyCash™* on eligible Highland hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
How much is the nightly rate at a Highland hotel?
Prices for hotels in Highland often vary, but you can find a great deal from $68 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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