Highland Holiday Rentals

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Holiday Rentals in Highland

Highland: Driftless Fun Awaits
10.0 out of 10, Exceptional, (1)
"Great property. Had everything we needed. Highly recommend. "
United States
Joshua
The price is NZ$443
includes taxes & fees
18 Nov - 19 Nov
Highland: Driftless Fun Awaits
A Comfy Cozy Cottage on Clowney
9.6 out of 10, Exceptional, (117)
"Comfortable, easy stay for a weekend. "
United States
Kelly
The price is NZ$362
includes taxes & fees
2 Nov - 3 Nov
A Comfy Cozy Cottage on Clowney
Hot Tub/Golfing/King Bed @ The Hemlock
9.8 out of 10, Exceptional, (19)
"The Hemlock was perfect for our family. We were visiting Spring Green for a family wedding and enjoyed all the clean space and fully equipped kitchen. We also had fun riding the electric bikes. Will definitely stay here on our next visit!"
United States
Charla S.
The price is NZ$569
includes taxes & fees
26 Oct - 27 Oct
Hot Tub/Golfing/King Bed @ The Hemlock
Close to Local Opera House - On the main drag
9.8 out of 10, Exceptional, (39)
"Short stay, but nice place."
United States
Kirstin S.
The price is NZ$308
includes taxes & fees
27 Oct - 28 Oct
Close to Local Opera House - On the main drag
Serenity Cottage at Mineral Point
10.0 out of 10, Exceptional, (98)
"What a wonderful place to stay. So much better than a hotel."
United States
Sharon L R.
The price is NZ$308
includes taxes & fees
26 Oct - 27 Oct
Serenity Cottage at Mineral Point
Suite in the heart of the center of spring green
9.8 out of 10, Exceptional, (93)
"Wonderful place to stay! Clean, welcoming, comfortable--the perfect place to overnight when seeing plays at American Players Theatre."
United States
Jessica L.
The price is NZ$223
includes taxes & fees
26 Oct - 27 Oct
Suite in the heart of the center of spring green
Rustic Cabin at Crooked Creek
9.6 out of 10, Exceptional, (8)
"very nice and quiet place to hang your hat."
United States
reuben n.
The price is NZ$268
includes taxes & fees
2 Nov - 3 Nov
Rustic Cabin at Crooked Creek
River Road Retreat
9.6 out of 10, Exceptional, (18)
"Relaxing trip with family- lived the cabin and the kids loved the basement"
United States
Nora M.
The price is NZ$415
includes taxes & fees
23 Oct - 24 Oct
River Road Retreat
Historic District, Charming Cottage, Sleeps 10
2.0 star property
10.0 out of 10, Exceptional, (1)
The price is NZ$605
includes taxes & fees
27 Oct - 28 Oct
Historic District, Charming Cottage, Sleeps 10
River Road Getaway
9.6 out of 10, Exceptional, (26)
"Property just as advertised nice place to stay. "
United States
Alison S.
The price is NZ$415
includes taxes & fees
23 Oct - 24 Oct
River Road Getaway
Serenity cabin at Crooked Creek
10.0 out of 10, Exceptional, (9)
"the place was peacefull and cozy, had everything we needed for our short stay, we enjoyed the outdoor fire pit a lot, seating outside in the porch with a morning coffee and enjoying the scenery was my highlight."
United States
Monica R.
The price is NZ$294
includes taxes & fees
30 Oct - 31 Oct
Serenity cabin at Crooked Creek
Relaxation cabin at Crooked Creek
9.8 out of 10, Exceptional, (7)
"Everything smooth and the cabin was very good "
United States
david h.
The price is NZ$268
includes taxes & fees
4 Nov - 5 Nov
Relaxation cabin at Crooked Creek
Quaint & Quiet 2 bed 1 bath
10.0 out of 10, Exceptional, (1)
"the location was convinience for us considering my brother lives one block away.They were very nice to accommodate a very late check in."
United States
Monica R.
The price is NZ$266
includes taxes & fees
4 Nov - 5 Nov
Quaint & Quiet 2 bed 1 bath
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.
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Top Highland Hotel Reviews

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$223 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?

Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!: This holiday home rental outside of Highland is located on a river, and has an indoor pool, a patio and air conditioning to put you at ease in your new surroundings. It has 6 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?

Beach at Black Hawk Lake Recreation Area and Blackhawk 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.