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Highland Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Highland vacation rentals

A bedroom with a large window, a bed, and a view of the outdoors.

1. Cheese Wedge Cabin Idyllic Farm

Cheese Wedge Cabin Idyllic Farm
Highland
10.0 out of 10, Exceptional, (1 review)
"If you are looking for a unconventional place to unplug and unwind, the Cheese Wedge Cabin is a charming getway. Etienne is a lovely host who made us feel welcome and comfortable on her farm. We got up close and personal with the sheep, chickens, and Phoenix the sheepdog (who is the gentlest giant and steadfast companion). We had plenty of privacy in the cabin while still being close enough to get anything we needed from the private guest kitchen & bath connected to the main house. Another...
United States
Annie
The price is ￥34,602
￥40,280 total
includes taxes & fees
Sep 28 - Sep 29
Cheese Wedge Cabin Idyllic Farm
A wooden cabin with a porch, two windows, and a star decoration on the wall.

2. 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 ￥28,310
￥33,186 total
includes taxes & fees
Sep 30 - Oct 1
River Road Retreat
A playground with various play structures, including a slide, swings, and climbing frames, surrounded by grass and trees.

3. River Road Getaway

River Road Getaway
Muscoda
9.6 out of 10, Exceptional, (36 reviews)
"Nice clean place to stay for weekend vacation:) would stay again if in the area"
United States
Anonymous traveler
The price is ￥28,310
￥33,186 total
includes taxes & fees
Sep 28 - Sep 29
River Road Getaway
A log cabin interior with a leather armchair, a sofa, a table with a lamp, and a wood-burning stove.

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 ￥16,801
￥30,088 total
includes taxes & fees
Sep 29 - Sep 30
Crooked Creek - Serenity Cabin
A rustic cabin with a wooden exterior and a red roof, surrounded by a well-maintained grassy area and trees.

5. 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 ￥13,715
￥24,119 total
includes taxes & fees
Sep 28 - Sep 29
Crooked Creek - Relaxation Cabin
A cozy room with a wooden floor, a blue sofa, a door with windows, and a lamp on a table.

6. A Comfy Cozy Cottage on Clowney

A Comfy Cozy Cottage on Clowney
Mineral Point
9.8 out of 10, Exceptional, (138 reviews)
"The cottage was very quaint and comfortable. Great location for exploring downtown Mineral Point on foot. Had a fun stay."
United States
Rick C.
The price is ￥26,187
￥37,628 total
includes taxes & fees
Sep 29 - Sep 30
A Comfy Cozy Cottage on Clowney

7. Serenity Cottage at Mineral Point

Serenity Cottage at Mineral Point
Mineral Point
10.0 out of 10, Exceptional, (123 reviews)
"Super cute and cozy place - perfect for our getaway. "
United States
Katie K.
The price is ￥24,205
￥35,438 total
includes taxes & fees
Sep 28 - Sep 29
Serenity Cottage at Mineral Point
A cozy cabin interior with a wooden TV stand, bookshelves, a sofa, and a dining area with chairs.

8. Crooked Creek - Rustic Cabin

Crooked Creek - Rustic Cabin
Boscobel
9.6 out of 10, Exceptional, (11 reviews)
"very nice and quiet place to hang your hat."
United States
reuben n.
The price is ￥15,429
￥26,832 total
includes taxes & fees
Oct 7 - Oct 8
Crooked Creek - Rustic Cabin
A hallway with wooden flooring, a dark door, and a small table with a vase.

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

Charming 3-bedroom upstairs apartment in welcoming Fennimore.
Fennimore
9.2 out of 10, Wonderful, (5 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 ￥15,099
￥27,545 total
includes taxes & fees
Sep 28 - Sep 29
Charming 3-bedroom upstairs apartment in welcoming Fennimore.
A cozy living room with a sofa, a patterned rug, and a coffee table. There are three windows with curtains, a lamp, and a door labeled "PRIVATE".

10. 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 ￥10,223
￥36,325 total
includes taxes & fees
Oct 11 - Oct 12
Close to Local Opera House - On the main drag
A spacious living room with a fireplace, wooden flooring, and a large window.

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
9.6 out of 10, Exceptional, (7 reviews)
"Awesome views, clean and Perfect for our 3 couples!"
United States
Cathleen T.
The price is ￥39,635
￥58,243 total
includes taxes & fees
Sep 29 - Sep 30
Escape to this amazing 3 bedroom home just 5 minutes from Historic Mineral Point
A bedroom with a bed, a wooden dresser, and a mirror.

12. Cozy 1-bedroom apartment in peaceful Boscobel with AC

Cozy 1-bedroom apartment in peaceful Boscobel with AC
Boscobel
The price is ￥13,164
￥18,024 total
includes taxes & fees
Sep 29 - Sep 30
Cozy 1-bedroom apartment in peaceful Boscobel with AC
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

Sleep Inn & Suites Lancaster-Platteville

Sleep Inn & Suites Lancaster-Platteville

10/10 Excellent
"This was a nice play to stay. The room and bathroom were clean. The beds were comfortable and we slept very well. The breakfast was very good."
Harry 1-night trip
Posted 4 hours ago
Sleep Inn & Suites Lancaster-Platteville

Find out more about Highland

Search for holiday rentals in Highland on Expedia! You can easily find your home rentals, villas, holiday apartments in Highland using one of the methods below:

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Look no further and take a look at our great range of rental properties in Highland!

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?

Elegant country retreat near Spring Green w expansive views of Driftless Region: This vacation home rental near Highland is located on a river and has a fireplace, a patio, and a barbecue grill 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 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 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.