Highland Holidays

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Top hotels in Highland

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 S$123 per night from 14 Jul to 15 Jul
S$123
14 Jul - 15 Jul
includes taxes & fees
8/10 Very good! (1,009 reviews)
"We did not know what to expect from this hotel but were very surprised by the cool vibe of the hotel. We knew we had arrived due to the big plane in the front of the property, with a Q on the tail. The front desk greeted us, looked up our reservation and offered to show us some other rooms. Some ..."

Reviewed on 4 Jul, 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 S$103 per night from 20 Jul to 21 Jul
S$103
20 Jul - 21 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 Jul, 2026

Dodgeville inn and suites
Deer Valley Lodge & Golf

Deer Valley Lodge & Golf

2.5 out of 5
401 West Industrial Drive Barneveld WI
Fully refundableReserve now, pay when you stay
The price is S$176 per night from 14 Jul to 15 Jul
S$176
14 Jul - 15 Jul
includes taxes & fees
8.8/10 Excellent! (712 reviews)
"Cute watermark for kids and stunning golf course!"

Reviewed on 5 Jul, 2026

Deer Valley Lodge & Golf
See all 128 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 holiday package cost?
You can grab a holiday package to this top destination on Expedia. However, how much your holiday to Highland costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Highland?
You're likely to find reduced prices and greater availability in January, February and April. Explore our cheap Highland holiday packages and you could score some great off-season discounts.
How many days is enough for Highland?
Usually, a handful of days is enough to explore the main attractions during your Highland holiday. However, if you'd like to have more time to relax or take day tours, think about extending your trip.
How to find the best Highland package deals?
Start your search for a Highland package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select some filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Highland package deal right away, simply change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Highland adventure off to a flying start.
Is it cheaper to book a Highland holiday as a package?
You can enjoy significant savings on your Highland retreat by booking a tailored holiday package. Check the "Package" heading, then select your travel dates and destination to view some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Highland?
If you're considering a spur-of-the-moment Highland adventure, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Highland?

  1. Pick your travel dates: The things you'd like to do in Highland and your preferred season will help you decide when to get away.
  2. Work out your budget: Make sure you have enough money to pay for everything from food and transportation to flights and activities. Your hotel will probably be the largest expense during your trip to Highland.
  3. Decide how long to go for: Now that you're up to speed on Highland, you can figure out the perfect length of your break. Create a draft plan and allocate enough time to cover everything you want to see.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to choose a Highland holiday package that brings all your bookings together.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.