Highland Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AEDĀ 5,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Highland Vacation Packages

Highland Hotel Deals

Cheese Wedge Cabin Idyllic Farm

Cheese Wedge Cabin Idyllic Farm

Highland WI
10/10 Exceptional! (1 review)
"If you are looking for a unconventional place to unplug and unwind, the Cheese Wedge Cabin is a charming getway. Etienne is a lovely host who made us feel welcome and comfortable on her farm. We got up close and personal with the sheep, chickens, and Phoenix the sheepdog (who is the gentlest giant ..."

Reviewed on 28 July 2025

Get rates
Cheese Wedge Cabin Idyllic Farm
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 AEDĀ 308 per night from Jul 19 to Jul 20
AEDĀ 308
AEDĀ 349 total
19 Jul - 20 Jul
includes taxes & fees
8/10 Very Good! (1,002 reviews)
"The room was damp and musty smelling. Pool was great! Breakfast was average."

Reviewed on 17 July 2026

Don Q Inn
Dodgeville inn and suites

Dodgeville inn and suites

2.5 out of 5
1308 n johns st Dodgeville WI
Fully refundableReserve now, pay when you stay
The price is AEDĀ 256 per night from Jul 28 to Jul 29
AEDĀ 256
AEDĀ 291 total
28 Jul - 29 Jul
includes taxes & fees
7.4/10 Good! (62 reviews)
"Only stayed here for a few hours to sleep. Stayed during an extreme heat warning. There was no AC in the room. It stayed above 80 degrees the whole night. We profusely sweated. Could not wait to leave the next morning. Aside from the lack of AC and the strong odor in the hotel, it was OK, I guess. ..."

Reviewed on 9 July 2026

Dodgeville inn and suites
See all 125 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

How much does a Highland vacation package cost?
Offering excellent value package deals 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 ā€” ideal for budget-conscious travelers.
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 traveling on a whim.
How to plan a trip to Highland?

  1. Pick your dates: What you want to do in Highland and your favorite 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.