Highland Vacation Packages

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Your Highland Vacation

Memorable adventures await when you reserve a vacation package to Highland. Whether you're a foodie, history enthusiast or just a traveler 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 vacation is just a few clicks away with Expedia.

Top Highland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Dubuque

Super 8 by Wyndham Dubuque

2 out of 5
per person
Sep 24 - Sep 29
found 13 hours ago
Roundtrip flight included
Vancouver (YVR) to Dubuque (DBQ)
7/10 Good! (1,004 reviews)
Great place to stay felt safe and the room was very clean.

Reviewed on Jul. 1, 2025

Ready to book your vacation to Highland?

 

Choose your dates

Highland Hotel Deals

AmericInn by Wyndham Dodgeville

AmericInn by Wyndham Dodgeville

2.5 out of 5
3637 State Road 23, Dodgeville, WI
Fully refundableReserve now, pay when you stay
The price is CA $145 per night from Aug 10 to Aug 11
CA $145
CA $164 total
Aug 10 - Aug 11
includes taxes & fees
8.2/10 Very Good! (509 reviews)
"Friendly staff. Property is well maintained and clean"

Reviewed on Jul. 13, 2025

AmericInn by Wyndham Dodgeville
Don Q Inn

Don Q Inn

2.5 out of 5
3658 State Road 23, Dodgeville, WI
Fully refundableReserve now, pay when you stay
The price is CA $99 per night from Jul 20 to Jul 21
CA $99
CA $112 total
Jul 20 - Jul 21
includes taxes & fees
8/10 Very Good! (1,000 reviews)
"The rooms were clean and the lounge was unique with barber chairs. The plane outside looked neat too."

Reviewed on Jul. 13, 2025

Don Q Inn
Deer Valley Lodge & Golf

Deer Valley Lodge & Golf

2.5 out of 5
401 West Industrial Drive, Barneveld, WI
The price is CA $150 per night from Jul 17 to Jul 18
CA $150
CA $158 total
Jul 17 - Jul 18
includes taxes & fees
8.8/10 Excellent! (614 reviews)
"The property was very nice and clean. The lobby staff at check in and check out were so nice and helpful."

Reviewed on Jul. 14, 2025

Deer Valley Lodge & Golf
See all 121 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 Vacations

All Inclusive Vacations

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Frequently asked questions

How much does a Highland vacation package cost?
Offering excellent value package deals from CA $635 on Expedia, you'll be thrilled with how little a vacation to Highland costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Highland?
If you're looking to score a cheap Highland vacation package, consider visiting in January, February and April. You'll generally find lower rates on accommodations and flights during these months --- ideal for budget-conscious travellers.
How many days is enough for Highland?
Typically, a handful of days is enough to explore the main sights during your Highland vacation. But if you prefer to have time to unwind or take day trips, think about extending your itinerary.
How to find the best Highland package deals?
Finding a cheap Highland package deal is easy with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget range, apply a few filters and browse what's available. You can customize your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Highland package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Highland vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging accommodations and flights individually. Better still, you can personalize your Highland escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Highland?
If you have your Highland travel dates confirmed, book as soon as you can to score some incredible deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are great for travelling on a whim.
How to plan a trip to Highland?

  1. Pick your dates: What you want to do in Highland and your favourite season will help you decide when to travel.
  2. Set a budget: Factor in expenses like flights, meals and transportation when calculating how much to put aside for your trip to Highland. Then, select a property that matches your budget, whether that's an economical option or a deluxe retreat.
  3. Decide how long to go away for: Now that you know more about Highland, you can work out the perfect length of your break. Put together a draft itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a customized Highland vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.