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Check Highland hotel prices

Tonight
May 21 - May 22
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May 22 - May 23
This weekend
May 24 - May 26
Next weekend
May 31 - Jun 2

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Top hotels and accommodation in Highland

Exterior
The Guest House
10.0 out of 10, Exceptional, (21)
"We found the property clean and perfect for our needs. The host was gracious and the loft was well supplied. They sell farm fresh beef and eggs. We had the eggs for breakfast each morning, what a treat. We would recommend Hollow Rule to anyone staying in the area."
The price is AU$208
per night
10 June - 11 June
The Guest House
2 bedrooms, iron/ironing board, free WiFi, bed sheets
Unique! A renovated old railroad depot turned into a cozy cottage.
10.0 out of 10, Exceptional, (92)
"We enjoyed our stay at your lovely, beautifully decorated depot. The pictures online do not do it justice. The nature path nearby was ideal for morning walks. It was the perfect peaceful getaway."
Unique! A renovated old railroad depot turned into a cozy cottage.
Dining
River's Edge Cabin, LLC
10.0 out of 10, Exceptional, (58)
"Great cabin on the river. Beautiful and peaceful play to stay!"
River's Edge Cabin, LLC
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Fridge, microwave, oven, stovetop
Amish-Built Cabin in the Driftless Area
10.0 out of 10, Exceptional, (47)
"Had a great time in SW Wisconsin!"
Amish-Built Cabin in the Driftless Area
TV, fireplace, DVD player, books
The Driftless Escape! Modern, large cabin/57 private acres in WI drift less area
10.0 out of 10, Exceptional, (118)
"A beautiful cabin on a beautiful piece of land. As described in the listing and absolutely peaceful. This is our second time staying here and we will be back."
The Driftless Escape! Modern, large cabin/57 private acres in WI drift less area
Fridge, microwave, oven, stovetop
Cozy hillside retreat near trout stream, public forest and UTV trails.
10.0 out of 10, Exceptional, (2)
"Great cabin in a great location. So peaceful and relaxing. We loved our time there and are looking forward to returning!"
Cozy hillside retreat near trout stream, public forest and UTV trails.
Fridge, microwave, oven, stovetop
Newly remodeled log cabin next to beautiful Wisconsin River- Rivers Edge Cabin
10.0 out of 10, Exceptional, (17)
"We came to enjoy a weekend away from worries and we very much accomplished it! We enjoyed some local food and walked along the river in between playing games at the cabin. The cabin itself was very clean and cozy!"
Newly remodeled log cabin next to beautiful Wisconsin River- Rivers Edge Cabin
Fridge, microwave, oven, stovetop
Pine Trails Escape
10.0 out of 10, Exceptional, (3)
"Very clean, welcoming, and well furnished. Great info on checking in and using the rental. We very likely utilize this rental again."
Pine Trails Escape
Fridge, microwave, oven, stovetop
Relax with beautiful views overlooking the Wisconsin River
10.0 out of 10, Exceptional, (29)
"What a charming home! It was just as beautiful as the pictures, loved the view of the river, close to our daughter, loved cooking meals in the spacious kitchen & we loved ordering our food from The Port which was just up the road. The host (Holly) was very responsive and helpful. Hope to come back again!"
Relax with beautiful views overlooking the Wisconsin River
Property grounds
Spacious Cabin on the Wisconsin River!
10.0 out of 10, Exceptional, (23)
"Plenty of room inside and out. Clean. Easy to communicate with owners. Beautiful view. Near groceries and places to eat."
Spacious Cabin on the Wisconsin River!
Property grounds
Room for a crowd at Akey Valley in southwest Wisconsin
10.0 out of 10, Exceptional, (57)
"This was our fourth stay at the Akey House. It is a fine place for a family gathering; we had five adults and two dogs. We enjoyed sitting on the front porch watching deer, listening to birds and coyotes, reading and just relaxing. The house is ideal location for those who wish to canoe, hike, and bicycle. It is modern (kitchen is great) yet retains that old-time feel in the dining room, porch, parlor and bedrooms. Very comfortable for large or small gatherings."
Room for a crowd at Akey Valley in southwest Wisconsin
Property grounds
Serenity awaits at this secluded riverfront property
10.0 out of 10, Exceptional, (32)
"My partner and I spent a long weekend here and completely enjoyed ourselves. The house is serene and perfectly tidy. We spent a lot of time on the screened-in porch watching birds on the water. This property is also a great home base for exploring other interesting towns in the area: Boscobel, Viroqua, Spring Green, etc. We will definitely be back!"
Serenity awaits at this secluded riverfront property
Exterior
Riverside Chalet, LLC
10.0 out of 10, Exceptional, (32)
"We had a wonderful time at the riverside chalet! The view from the living room is fantastic, you are literally a stone's throw away from the river when you're on the deck, a nice fire pit area with wood available for purchase, and the chalet itself is cozy and charming! Would stay again!"
Riverside Chalet, LLC
Property grounds
Rustic, small and primitive cabin - Riverview Cabin, LLC
9.8 out of 10, Exceptional, (34)
"Sandy is a great host, checks in to make sure everything is good. Place is beautiful and perfect place to unwind. We will definitely be staying again! Thanks Sandy!"
Rustic, small and primitive cabin - Riverview Cabin, LLC
Balcony
Upper Place Vacation Cottage
9.6 out of 10, Exceptional, (26)
"Nice place with a great fire pit and plenty of wood. We enjoyed our stay and it had everything we wanted."
Upper Place Vacation Cottage
Property grounds
English Run Rental House
9.6 out of 10, Exceptional, (9)
"Nice little house which fit our needs, beautiful setting…"
The price is AU$392
per night
2 June - 3 June
English Run Rental House
View from property
Heaven on the Hill Sleeps up to 25, prices based on 12 guests, events welcomed
9.0 out of 10, Wonderful, (2)
"Excellent communication from owner and location was private"
Heaven on the Hill Sleeps up to 25, prices based on 12 guests, events welcomed
Reception
AmericInn by Wyndham Boscobel
2.5 star property
8.8 out of 10, Excellent, (346)
"Property was great!"
The price is AU$139
per night
27 May - 28 May
AmericInn by Wyndham Boscobel
Exterior
River Road Retreat
8.4 out of 10, Very good, (5)
"This was a beautiful new log house across the street from a spacious park and across the street from the Wisconsin River. It’d be a great staging spot for starting or ending a canoe/kayak trip on the river. The house is essentially new construction and made (entirely) of pine. The smell is fantastic. The check-in process was easy and the property manager made sure to let us know they were available if we had any needs. We enjoyed our stay. Just wish we could have adjusted our schedule to stay...
The price is AU$365
per night
22 May - 23 May
River Road Retreat
Bar (on property)
Ramada by Wyndham Richland Center
3.0 star property
8.2 out of 10, Very good, (490)
"Our room was very clean. Bathroom lighting was excellent. The whole facility was very clean and maintained very well. Pool was a great temperature. On-site restaurant had excellent food and service.. We will return. .have to get"
The price is AU$143
per night
2 June - 3 June
Ramada by Wyndham Richland Center
Don't see what you're looking for?
See all available 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 top Highland attractions

Image for Blackhawk Lake Recreation Area

Blackhawk Lake Recreation Area

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
Blackhawk Lake Recreation Area

Highland Travel Info

Number of reviews
1,427
Accommodation
113 hotels
Highest price
AU$392
Lowest price
AU$139

Frequently asked questions

Where is the best place for a stay in Highland?

Don Q Inn, located 12.6 mi (20.3 km) from the heart of Highland, is a top choice for your stay, based on our traveller data. Two other options for your stay in the area are Deer Valley Lodge & Golf and AmericInn by Wyndham Dodgeville. See all available top hotels, or vacation rentals in Highland.

What are some of the best holiday rentals that Highland has to offer?

Stunning, serene, rustic house in the woods near Spring Green, Wisconsin: This holiday home rental outside of Highland is located on a river, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of books. See all vacation rentals in Highland.

If I need to cancel my hotel reservation in Highland, will I receive a refund?

Yes, you'll find most hotel reservations are fully refundable if you cancel prior to the hotel's cancellation deadline, which is usually within 24-48 hours of your scheduled arrival. If you have a non-refundable reservation, you might still have the option to cancel and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Highland.

What are some hotels with pools in Highland?

AmericInn by Wyndham Boscobel: Offers free breakfast, an indoor pool and free self-parking. Don Q Inn and Deer Valley Lodge & Golf are a couple of other choices that offer an on-site pool. View all hotels with pools in Highland.

How is it to stay in Highland?

Visitors can enjoy all that Highland has to offer, including its parks. There are 111 hotels and other accommodation options in the surrounding area. Find out more about Highland.

What should I see while I'm in Highland?

The picturesque setting of Blackhawk Lake Recreation Area and Beach at Black Hawk Lake Recreation Area exemplify the area's natural beauty. Additionally, you might want to add Spurgeon Vineyards & Winery to your itinerary. Take a look at what more there is to see and do in Expedia's Highland guide.

What's the weather like in Highland?

The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Highland are January, April, March and December, with each month seeing an average of 21 cm of snowfall.

Recent Reviews in Highland
Expedia verified reviews

Don Q Inn

Don Q Inn

5/5 Excellent
One night get-away
"We enjoyed our stay here immensely with a private in-room whirlpool. While the room was showing its age somewhat and could use a few updates, overall it was quite comfy. We stayed in the Paradise Cove suite as we were looking for a tropical vacation theme to escape from the cold. Breakfast was more than adequate and had good variety."
A verified traveller stayed at Don Q Inn
Posted 2 months ago
Don Q Inn