Highland Holidays

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Your Highland Holiday

Memorable adventures await when you reserve a holiday package to Highland. Whether you're a foodie, history enthusiast or just a traveller who loves to experience new places, there's something for everyone in this interesting city. If sightseeing is on the cards during your trip to Highland, visit popular attractions like Blackhawk Lake Recreation Area, Beach at Black Hawk Lake Recreation Area and Spurgeon Vineyards & Winery. Whoever you're going away with and whatever the size of your budget, your ultimate Highland holiday is just a few clicks away with Expedia.

Highland Essential Information

Language
English
Currency
U.S dollars
Population
840
Max Temp Winter
-3.89ºC
Max Temp Summer
27ºC
Top Sights
Beach at Black Hawk Lake Recreation Area, Spurgeon Vineyards & Winery and Blackhawk Lake Recreation Area

Our pick of the best Highland Hotel Deals

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 coffee maker. Popular attractions Spurgeon Vineyards & Winery and Blackhawk ...
10/10 Exceptional! (1 review)
"Great property. Had everything we needed. Highly recommend."

Reviewed on 27 May 2025

Highland: Driftless Fun Awaits
Don Q Inn
Don Q Inn
2.5 out of 5
3658 State Road 23, Dodgeville, WI
Stay at this hotel in Dodgeville. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their reviews. ...
8/10 Very Good! (1,000 reviews)
"We stayed here because we were going to house on the rock. This hotel adds a fun element and charm to your trip in between visiting there! The staff is readily available and super kind. We stayed in a basic room but it was really nice and clean. The price for staying for three days is pretty affordable. ..."

Reviewed on 23 Jun 2025

Don Q Inn
Deer Valley Lodge & Golf
Deer Valley Lodge & Golf
2.5 out of 5
401 West Industrial Drive, Barneveld, WI
Stay at this golf hotel in Barneveld. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms in their reviews. ...
8.8/10 Excellent! (605 reviews)
"Beautiful property located adjacent to the golf course and njce views .Attached water park looked fun but didn't use. Breakfast was good"

Reviewed on 20 Jun 2025

Deer Valley Lodge & Golf
See all 119 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Highland travel package cost?
Get your credit card ready, because a trip to Highland starts from just . When you bundle your flights, hotels and car rentals into a travel package, you'll land the best bargains.
If I'm not able to travel, can I cancel my Highland travel package?
You sure can, and we'll help you every step of the way. You may be able to cancel or amend your Highland travel package at no cost if you booked in the last 24 hours. However, you may incur a fee from your airline, hotel or car rental company if your booking is older than that. If life gets in the way of your holiday, visit our Customer Service Portal for more information.
How do I get a cheap travel package to Highland?
One word: bundle. Flights, rental cars and hotels --- combine whatever you need into a Highland travel package to save a pile of cash. Score even more discounts when you add extras such as tours or experiences to your booking. But that's not the only good part. You have the flexibility to put together your trip your own way. We offer over 550 air carriers and 1,000,000 hotels across the world, so that everyone has a chance to travel and fulfil those holiday dreams.
Does Expedia offer Book Now, Pay Later Highland holidays?
Expedia has partnered with online lender Klarna to make your next break easier on your bank balance. Paying in instalments means you can spread the costs of your next adventure, leaving you with more cash to splash while you're travelling. Klarna has several payment plans to choose from, so you're sure to find one that works with your budget. Browse these flexible payment options:

  • Pay monthly holidays: Jet off on that dream holiday sooner with Klarna's convenient monthly instalment plans. If making small repayments each month sounds right for you, pick this option during the checkout process.
  • Pay in instalments holidays: Into the idea of paying for your holiday in multiple transactions? Then go for this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: When you stumble on an unbeatable deal but don't have the full amount yet, Klarna's low deposit holiday plan will help you lock in your escape.

What are the top hotels in Highland?
Get your trip off to an excellent start by booking a room at Don Q Inn. It's one of most popular properties in Highland. Another cosy option is AmericInn by Wyndham Dodgeville.
How far in advance should I book my Highland holiday?
It depends on the air carrier, but you can generally browse through international airfares on Expedia nearly a year in advance. While it's a good idea to book ahead of time, lucky customers will occasionally nab a cheaper seat only weeks before departure dates.
What does an Expedia Highland travel package include?
With Expedia, you can select a combination of car rentals, hotels and flights to create your perfect Highland package. Once you've made your booking, you can add on all the fun stuff like activities and tours. Remember, the more you bundle, the greater the savings!
What should I know before booking a Highland travel package?
You'll land big savings when you bundle your hotels, flights and rental cars into a travel package. Plus, booking everything together makes trip planning easier. So why waste time or money? Whether you're putting together a ritzy city getaway or a budget family adventure, explore our travel packages today.
Can I choose my airline with a Highland Expedia travel package?
Yes --- and it's easy too. Expedia has access to more than 550 partner airlines globally. Our packages give you the flexibility to pick from available flight, hotel or activity options that suit you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.