Highland Vacation Rentals

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Vacation Rentals in Highland

Our top choices for Highland vacation rentals

Highland: Driftless Fun Awaits

10.0 out of 10, Exceptional, (1)
"Great property. Had everything we needed. Highly recommend. "
The price is CA $177
CA $334 total
includes taxes & fees
Sep 22 - Sep 23
Highland: Driftless Fun Awaits

Stunning, serene, rustic house in the woods near Spring Green, Wisconsin

10.0 out of 10, Exceptional, (483)
"it was a very relaxing serene location. The home had everything we needed. "
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin

A Comfy Cozy Cottage on Clowney

9.6 out of 10, Exceptional, (110)
"Comfortable, easy stay for a weekend. "
The price is CA $186
CA $286 total
includes taxes & fees
Sep 11 - Sep 12
A Comfy Cozy Cottage on Clowney

The Driftless Escape! Modern, large cabin/57 private acres in WI drift less area

10.0 out of 10, Exceptional, (151)
"Great stay with lovely scenery and beautiful cabin. Would highly recommend to anyone."
The Driftless Escape! Modern, large cabin/57 private acres in WI drift less area

Elegant country retreat near Spring Green w expansive views of Driftless Region

10.0 out of 10, Exceptional, (56)
"The property and house are breathtaking. We particularly loved the Tea House. Gorgeous, clean and the host was wonderful and responsive. A great place to stay!"
Elegant country retreat near Spring Green w expansive views of Driftless Region

Serenity Cottage at Mineral Point

10.0 out of 10, Exceptional, (89)
"What a wonderful place to stay. So much better than a hotel."
The price is CA $186
CA $243 total
includes taxes & fees
Sep 9 - Sep 10
Serenity Cottage at Mineral Point

Unique! A renovated old railroad depot turned into a cozy cottage.

10.0 out of 10, Exceptional, (118)
"This is a cozy, delightful little spot in the middle of Wisconsin. We had a nice 3 day stay with no issues at all. The Depot was always nice and warm and welcoming. "
Unique! A renovated old railroad depot turned into a cozy cottage.

Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym

10.0 out of 10, Exceptional, (21)
"Barn was beautiful, clean & fun amenities."
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym

Newly remodeled log cabin next to beautiful Wisconsin River- Rivers Edge Cabin

10.0 out of 10, Exceptional, (45)
"Was a wonderful Valentine’s Day weekend very quiet cozy stay will definitely be staying there again "
Newly remodeled log cabin next to beautiful Wisconsin River- Rivers Edge Cabin

Private Isle-side, Waterfront Retreat with Stunning Views/Pet Friendly

10.0 out of 10, Exceptional, (36)
"We enjoyed fishing and the kayaks!"
Private Isle-side, Waterfront Retreat with Stunning Views/Pet Friendly

Suite in the heart of the center of spring green

9.8 out of 10, Exceptional, (86)
"Very nice and cozy, we will be renting again if available."
The price is CA $105
CA $177 total
includes taxes & fees
Sep 14 - Sep 15
Suite in the heart of the center of spring green

Charming Historic Getaway: Unwind in Lancaster's Timeless Elegance

10.0 out of 10, Exceptional, (7)
"Thank you for the wonderful stay. Will definitely stay again!"
Charming Historic Getaway: Unwind in Lancaster's Timeless Elegance

Serenity cabin at Crooked Creek

10.0 out of 10, Exceptional, (8)
"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."
The price is CA $118
CA $226 total
includes taxes & fees
Sep 10 - Sep 11
Serenity cabin at Crooked Creek

Wildwood Retreat - Newly remodeled

9.6 out of 10, Exceptional, (8)
"It was perfect for us for the weekend!"
Wildwood Retreat - Newly remodeled

Luxury Retreat in Prime Downtown Spring Green Location

10.0 out of 10, Exceptional, (54)
"We stayed here for our wedding weekend, and it was absolutely perfect. They gave us a bottle of champagne and flowers, and let us check out late the day after the wedding. Wonderful hosts, beautiful apartment. The best VRBO we’ve ever stayed in! "
Luxury Retreat in Prime Downtown Spring Green Location

Charming 1-bedroom apartment in the historic Hotel Royal.

Charming 1-bedroom apartment in the historic Hotel Royal.

The Guest House

10.0 out of 10, Exceptional, (30)
"Great property and location. Easy access and comfortable hospitality."
The Guest House

Amish-Built Cabin in the Driftless Area

10.0 out of 10, Exceptional, (67)
"Wonderful cabin. Had everything we needed plus everything we might of wanted. "
Amish-Built Cabin in the Driftless Area

150 Year Old Home Situated in the Picturesque Rolling Hills of Southwest WI

9.6 out of 10, Exceptional, (85)
"We had the best time! We came for a little weekend getaway with the whole family and agreed that we'd all love to be back for a longer time. The House was everything we were looking for and absolutely lovely. It was the perfect fit all around. "
150 Year Old Home Situated in the Picturesque Rolling Hills of Southwest WI

Relax & Recharge: Mid-Century Modern Home with Sauna in Spring Green

10.0 out of 10, Exceptional, (29)
"Had a wonderful stay"
Relax & Recharge: Mid-Century Modern Home with Sauna in Spring Green
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

Find out more about Highland

Everything you need to know about Highland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Highland vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Highland vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Highland vacation rentals we have selected for you start as low as CA $105 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 vacation 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 vacation.

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 vacation rental in Highland?

Yes, we have vacation rentals near well known local attractions in Highland, or you can go with a more secluded option if you want a relaxing place to stay. Highland is known for its parks.

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

Stunning, serene, rustic house in the woods near Spring Green, Wisconsin: This vacation home rental near Highland is located on a river and has a patio, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of books.

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 larger area.

What’s a vacation rental in Highland like?

Vacation rentals are privately owned properties you can stay in for a couple of days or more in Highland. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from public hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for a small group gathering.