Vacation rentals in Highland

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Top-rated vacation rentals in Highland

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Home in Muscoda

4.96 out of 5 average rating, 261 reviews

Century Old Charming Farmhouse Atop Rolling Hills

Summertime fun! A place to get out in the fresh air, sit by the campfire, & gaze at the stars. Fish the many TROUT streams nearby. Hike, bike, and horseback trails at Ash Creek Forest. WI River-4 miles away. Wild Hills Winery - right next door! Drive-in theatre, Pine River Trails & Kayaking, beautiful parks, aquatic center, 18 hole disc golf course, coffee house, Ocooch Books & Libations, & FLW-A.D. German Warehouse, Richland Center- 6 miles. Eagle Cave is an awesome, brief, tour -10 miles away.

Dec 25 – Jan 1

$89 per night
Guest favorite

Guest suite in Spring Green

4.9 out of 5 average rating, 112 reviews

Spring Green River Pines

Spend a few days in the beautiful countryside. A private entrance to the lower level of home (completely separate from our home) that includes a central room, 2 bedrooms with kitchenette, & 1 lg bath. WiFi >500 Mbps speed. Smart 60" TV, Bluetooth Airplay/stream compatible. Parking on sight. Great location 5 min from beautiful downtown Spring Green. Close to APT, Taliesin/Frank Lloyd Wrights Home/School, House on the Rock, WI River, Gov. Dodge State Park and 1/2 hr to Devils Lake State Park.

Oct 7 – 14

$113 per night
Guest favorite

Cabin in Avoca

4.99 out of 5 average rating, 149 reviews

Cool quiet country cabin on boulders and 120 acres

Funky, tidy 23 year old country cabin on 120 acres of farmland & woods in a private, quiet rural setting. It's cozy, 950 sq ft, built with stone and wood. Open concept with a two story fireplace, porch fireplace, firepit, and open loft for sleeping (1 bed), with spiral stairs, lots of windows, walnut floors and trim, oak beams and pine kitchen tops. Shower is big and open, with doors opening to a back deck for outdoor showering. Beautiful covered porch overlooking rolling meadows and woods.

Aug 21 – 28

$197 per night

Popular amenities for Highland vacation rentals

Other great vacation rentals in Highland

Guest favorite

Cabin in Hill Point

4.96 out of 5 average rating, 455 reviews

Big R's Retreat Secluded and located in Nature

Mar 18 – 25

$183 per night
Guest favorite

Home in Cuba City

4.95 out of 5 average rating, 187 reviews

Recharge your soul at “The Church”!

Apr 25 – May 2

$98 per night
Superhost

Cabin in Readstown

4.86 out of 5 average rating, 214 reviews

Romantic Getaway in the Woods

Nov 30 – Dec 7

$81 per night
Guest favorite

Farm stay in Viola

4.99 out of 5 average rating, 164 reviews

Guesthouse at Griff Run - Tiny House, Sleeps 2

Jun 6 – 13

$94 per night
Guest favorite

Apartment in Spring Green

4.91 out of 5 average rating, 142 reviews

Suite in Heart of Downtown Spring Green

Nov 3 – 10

$80 per night
Guest favorite

Cottage in Gays Mills

4.98 out of 5 average rating, 267 reviews

Remote Driftless Gem Stream and Sauna near Viroqua

Dec 26 – Jan 2

$159 per night
Superhost

Apartment in Highland

5.0 out of 5 average rating, 3 reviews

Highland: Driftless Fun Awaits

Oct 25 – Nov 1

$138 per night
Guest favorite

Cottage in Boscobel

4.88 out of 5 average rating, 33 reviews

Unwind in the spacious 1 bedroom Relaxation cabin

Jul 4 – 11

$77 per night
Guest favorite

Apartment in Dodgeville

4.97 out of 5 average rating, 68 reviews

Private, and everything you need to feel at home.

Jun 25 – Jul 2

$84 per night
Guest favorite

Guesthouse in Boscobel

5.0 out of 5 average rating, 34 reviews

The Guest House

Aug 8 – 15

$73 per night
Guest favorite

Cabin in Muscoda

4.97 out of 5 average rating, 36 reviews

Rivers Edge Cabin

Apr 15 – 22

$138 per night
Guest favorite

Cabin in Boscobel

5.0 out of 5 average rating, 13 reviews

Navy Cabin at Bailey Hollow

Aug 29 – Sep 5

$119 per night

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