Highland Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Our top choices for Highland holiday rentals

1. Highland: Driftless Fun Awaits

Highland: Driftless Fun Awaits
Highland
10.0 out of 10, Exceptional, (1 review)
"Great property. Had everything we needed. Highly recommend. "
United States
Joshua
The price is NZ$361
includes taxes & fees
8 Dec - 9 Dec
Highland: Driftless Fun Awaits

2. Crooked Creek - Relaxation Cabin

Crooked Creek - Relaxation Cabin
Boscobel
9.8 out of 10, Exceptional, (13 reviews)
"Nice location quiet and relaxing)."
United States
Nick N.
The price is NZ$256
includes taxes & fees
15 Nov - 16 Nov
Crooked Creek - Relaxation Cabin

3. River Road Retreat

River Road Retreat
Muscoda
9.8 out of 10, Exceptional, (32 reviews)
"We had a great stay"
United States
Robert S.
The price is NZ$367
includes taxes & fees
10 Nov - 11 Nov
River Road Retreat

4. Crooked Creek - Serenity Cabin

Crooked Creek - Serenity Cabin
Boscobel
10.0 out of 10, Exceptional, (16 reviews)
"Worked well for our 2-day stay. "
United States
John V.
The price is NZ$329
includes taxes & fees
10 Nov - 11 Nov
Crooked Creek - Serenity Cabin

5. Crooked Creek - Rustic Cabin

Crooked Creek - Rustic Cabin
Boscobel
9.6 out of 10, Exceptional, (13 reviews)
"very nice and quiet place to hang your hat."
United States
reuben n.
The price is NZ$295
includes taxes & fees
10 Nov - 11 Nov
Crooked Creek - Rustic Cabin

6. River Road Getaway

River Road Getaway
Muscoda
9.6 out of 10, Exceptional, (42 reviews)
"Had everything we needed."
United States
Tawnia
The price is NZ$367
includes taxes & fees
10 Nov - 11 Nov
River Road Getaway

7. Charming 3-bedroom upstairs apartment in welcoming Fennimore.

Charming 3-bedroom upstairs apartment in welcoming Fennimore.
Fennimore
9.4 out of 10, Exceptional, (6 reviews)
"The property was exactly as described. The decor was super cute and the beds were very comfortable! Highly recommend this property!"
United States
Christina
The price is NZ$301
includes taxes & fees
11 Nov - 12 Nov
Charming 3-bedroom upstairs apartment in welcoming Fennimore.

8. Close to Local Opera House - On the main drag

Close to Local Opera House - On the main drag
Downtown Mineral Point
9.8 out of 10, Exceptional, (45 reviews)
"Great spot in town. Very nice space."
United States
Rebecca S.
The price is NZ$403
includes taxes & fees
10 Nov - 11 Nov
Close to Local Opera House - On the main drag

9. A Comfy Cozy Cottage on Clowney

A Comfy Cozy Cottage on Clowney
Mineral Point
9.8 out of 10, Exceptional, (142 reviews)
"This is such a charming and unique old place, and right next to downtown. What a perfect location in one of the most charming and welcoming towns you'll ever visit!"
United States
Cindy P.
The price is NZ$420
includes taxes & fees
10 Nov - 11 Nov
A Comfy Cozy Cottage on Clowney

10. Serenity Cottage at Mineral Point

Serenity Cottage at Mineral Point
Mineral Point
10.0 out of 10, Exceptional, (126 reviews)
"Super cute and cozy place - perfect for our getaway. "
United States
Katie K.
The price is NZ$435
includes taxes & fees
1 Dec - 2 Dec
Serenity Cottage at Mineral Point

11. Escape to this amazing 3 bedroom home just 5 minutes from Historic Mineral Point

Escape to this amazing 3 bedroom home just 5 minutes from Historic Mineral Point
Mineral Point
9.4 out of 10, Exceptional, (18 reviews)
"Awesome views, clean and Perfect for our 3 couples!"
United States
Cathleen T.
The price is NZ$719
includes taxes & fees
10 Nov - 11 Nov
Escape to this amazing 3 bedroom home just 5 minutes from Historic Mineral Point

12. Downtown Spring Green Oasis | Hot Tub & Fire Pit

Downtown Spring Green Oasis | Hot Tub & Fire Pit
Spring Green
9.8 out of 10, Exceptional, (29 reviews)
"Kids loved all the board games and comfy seating options in the living room! Very comfortable stay."
United States
Elizabeth N.
The price is NZ$567
includes taxes & fees
15 Nov - 16 Nov
Downtown Spring Green Oasis | Hot Tub & Fire Pit
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.

Find holiday rentals that suit your style

Find out more about Highland

Everything you need to know about Highland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Highland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Highland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Highland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Highland. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Highland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Highland holiday rentals we have selected for you start as low as NZ$255 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Highland rentals

At Expedia, we put the best Highland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Highland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Highland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Highland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find a holiday rental in Highland?

Yes, there are holiday rentals close to the most popular sights in Highland, or you can select a more secluded option if you're looking for a relaxing stay. Highland is known for its parks.

What are some of the best holiday rentals that Highland has to offer?

Elegant country retreat near Spring Green w expansive views of Driftless Region: This holiday home rental outside of Highland is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What’s there to see and do in Highland?

Blackhawk Lake Recreation Area and Beach at Black Hawk Lake Recreation Area are a couple of lovely local spots to get outside and enjoy nature. Spurgeon Vineyards & Winery and The House on the Rock are a couple of places you'll find in the wider area.

What’s a holiday rental in Highland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Highland. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.