Deals on vacations and trips to Highland

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Highland flight + hotel vacation packages

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

Baymont by Wyndham Dubuque

2.5 out of 5
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Dubuque (DBQ)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the sauna and free perks like continental breakfast and free self parking.
Hotel Galena

Hotel Galena

2 out of 5
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Dubuque (DBQ)
This hotel features free WiFi in public areas, concierge services, and free self parking. Enjoy the free continental breakfast each morning. A garden, express check-out, and luggage storage are also on offer.
Irish Cottage Inn & Suites

Irish Cottage Inn & Suites

3.5 out of 5
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Dubuque (DBQ)
A full-service spa, an indoor pool, and a restaurant are all featured at this traditional hotel. Enjoy the gym and free perks like buffet breakfast and free self parking. Relax with a drink at the bar/lounge and enjoy the hot tub.
Country Inn & Suites by Radisson, Galena, IL

Country Inn & Suites by Radisson, Galena, IL

2.5 out of 5
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Dubuque (DBQ)
2 indoor pools, a hot tub, and a gym are all featured at this hotel. There's fun for all ages with a children's pool and a waterslide, and families will appreciate the onsite laundry facilities. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking.
Quality Inn & Suites Belmont Route 151

Quality Inn & Suites Belmont Route 151

2.5 out of 5
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Dubuque (DBQ)
This hotel features an indoor pool and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Top Highland hotels deals

Highland: Driftless Fun Awaits

Highland: Driftless Fun Awaits

$233 nightly
The price is $243 total per night
$243 total
Sep 1 - Sep 2
Total includes taxes and fees
This apartment includes a garden and laundry facilities.
Kitchen
Washer
Don Q Inn

Don Q Inn

2.5 out of 5
3658 State Road 23, Dodgeville, WI
Free Cancellation
Reserve now, pay when you stay
$80 nightly
The price is $91 total per night
$91 total
Sep 1 - Sep 2
Total includes taxes and fees
This hotel features an indoor pool and a seasonal outdoor pool. Enjoy the hot tub and free perks like continental breakfast and free self parking. A business center, free WiFi in public areas, and a lobby fireplace are also on offer.
Pool
Hot Tub
Deer Valley Lodge & Golf

Deer Valley Lodge & Golf

2.5 out of 5
401 West Industrial Drive, Barneveld, WI
Free Cancellation
Reserve now, pay when you stay
$109 nightly
The price is $115 total per night
$115 total
Aug 20 - Aug 21
Total includes taxes and fees
The golf course and water park are among the highlights at this hotel. There's fun for all ages with a children's pool and a waterslide, and families will appreciate the picnic area. Enjoy the indoor pool and free perks like continental breakfast and free self parking.
Pool
Hot Tub
AmericInn by Wyndham Dodgeville

AmericInn by Wyndham Dodgeville

2.5 out of 5
3637 State Road 23, Dodgeville, WI
Free Cancellation
Reserve now, pay when you stay
$119 nightly
The price is $135 total per night
$135 total
Sep 7 - Sep 8
Total includes taxes and fees
This hotel features an indoor pool and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the hot tub and free perks like self-serve breakfast and free self parking.
Pool
Hot Tub
Holiday Inn Express and Suites-Platteville by IHG

Holiday Inn Express and Suites-Platteville by IHG

2.5 out of 5
55 S ELM ST, Platteville, WI
Free Cancellation
$112 nightly
The price is $124 total per night
$124 total
Sep 2 - Sep 3
Total includes taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
The Round Barn Lodge

The Round Barn Lodge

2.5 out of 5
E4830 Us Highway 14, Spring Green, WI
Free Cancellation
Reserve now, pay when you stay
$109 nightly
The price is $115 total per night
$115 total
Sep 2 - Sep 3
Total includes taxes and fees
This lodge doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.
Parking included
Free WiFi
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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

Beach at Black Hawk Lake Recreation Area

Why not spend a lazy afternoon at Beach at Black Hawk Lake Recreation Area during your trip to Highland? While you're in the area, wander around the parks.

Beach at Black Hawk Lake Recreation Area

Blackhawk Lake Recreation Area

5/5(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.

Blackhawk Lake Recreation Area

Spurgeon Vineyards & Winery

4.5/5(2 reviews)

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 are vacation packages to Highland?
With vacation packages available from as little as $392, there's no need to blow out the credit card to travel to Highland. Travelocity is here to help. Combine hotels, flights and experiences into a package and land some impressive discounts. The more you book, the greater the savings.
Where can I get the best vacation package deals for Highland?
Travelocity can help you find an awesome Highland package deal. With no less than 400 partner airlines and 1,000,000 properties across the world, you're sure to find the perfect combination.
Why should I purchase my Highland vacation bundle via Travelocity?
Whether you're searching for the ultimate unplugged getaway or you crave the fun and excitement of the big city, booking everything with Travelocity saves you time, money and hassle. No need to sift through hundreds of websites to find the best deal — our Price Match Guarantee ensures you'll always get the lowest price, and our professional customer service experts are available for you round-the-clock.
Will I save money on my Highland car rental if I bundle it with my hotel or flight?
Absolutely — and booking one of our Highland vacation packages is the ideal way to do this. Bundle any combination of a hotel, car, flight and experience and land great discounts. The more you book, the more you'll save. There are plenty of exciting sights in Highland to add to your itinerary, including University of Wisconsin-Madison (50 mi from Highland). Nothing tops discovering amazing places like this with the freedom of your own set of wheels.
What is there to do in Highland?
Grab your travel schedule and make time for Beach at Black Hawk Lake Recreation Area and Spurgeon Vineyards & Winery. They are two of the most interesting sights in Highland.

Photos of local treasures

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