Highland Holidays

Book a Hotel + Flight or Car together to unlock savings

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 2.133.680 ₫ per night from 26 Aug to 27 Aug
2.133.680 ₫
2.421.773 ₫ total
26 Aug - 27 Aug
includes taxes & fees
8/10 Very Good! (1,002 reviews)
"Good just tv small and not functioning so had to go to lobby"

Reviewed on 21 Aug 2025

Don Q Inn
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 2.873.022 ₫ per night from 25 Aug to 26 Aug
2.873.022 ₫
3.031.170 ₫ total
25 Aug - 26 Aug
includes taxes & fees
8.6/10 Excellent! (644 reviews)
"Deer Valley Lodge was a great place to stay with our two kids. We loved that there was a bar with food options available, as well as a little shop with things we may need. Our kids enjoyed the pool and water features! The staff were very friendly and accommodating. The grounds were beautiful with ..."

Reviewed on 20 Aug 2025

Deer Valley Lodge & Golf
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 3.083.886 ₫ per night from 26 Aug to 27 Aug
3.083.886 ₫
3.500.342 ₫ total
26 Aug - 27 Aug
includes taxes & fees
8.2/10 Very Good! (537 reviews)
"When i did the pre check-in, it didnt check in both of my adjoining rooms. Caused a hassle."

Reviewed on 19 Aug 2025

AmericInn by Wyndham Dodgeville
See all 126 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.

Popular places to visit

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.

Blackhawk Lake Recreation Area

Spurgeon Vineyards & Winery

You can enjoy a tasting or tour at Spurgeon Vineyards & Winery during your travels to Highland. While you're in the area, wander around the natural setting.

Spurgeon Vineyards & Winery

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.