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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.

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Top guest favorite
A cozy cabin is nestled on a grassy hillside, surrounded by trees. A wooden deck wraps around the cabin, providing outdoor space. Stone steps, lined with potted flowers, lead up to the cabin entrance, enhancing the natural setting.
Cabin in Benton
4.96 out of 5 average rating, 136 reviews

Our cabin's a win-win

In 1834, it was a chicken coop nestled between the house and barn. Today, it's a cozy cabin just a stone's throw away from the villa and venue. From the private, rural setting to the rustic decor, you'll feel as though you've traveled back to simpler times. It's unique, refreshing and oh-so tranquil. If you're looking for a little hush and a lot less rush, you're going to fall in love with this little home away from home. While you're visiting, get the scoop on how we transformed this coop.

Top guest favorite
A well-maintained home exterior is surrounded by a lush garden, featuring a variety of plants and shrubs. The entrance is framed by a decorative archway, and a large tree provides shade. An inviting walkway leads up to the front door, enhancing the overall charm of the property.
Guest suite in Spring Green
4.91 out of 5 average rating, 172 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.

Top guest favorite
The bedroom features a queen size bed adorned with a patterned blanket and several decorative pillows. A bedside lamp sits on a nightstand, providing soft lighting. A dresser is visible, complementing the warm tones of the room.
Apartment in Dodgeville
4.97 out of 5 average rating, 119 reviews

Private, and everything you need to feel at home.

Welcome, with this unique key-less entry, you have privacy. Walk into the fully loaded kitchen and living room. The living room has a desk to work at or watch TV. The bathroom has a walk in shower; use the fan or heat lamp. The Bedroom has a queen size bed, a dresser, night stand with lamp. Along with a spacious closet, it includes a washer and dryer. Feel free to do your laundry and hang your items up. Working, relaxing, and living. Our space have all the essentials you need for your stay.

Superhost
A spacious living area features a dark sectional sofa adorned with decorative pillows. A small white table holds a decorative vase, and large windows allow natural light to fill the room. A sliding glass door provides access to the private patio, showcasing a view of the outdoors.
Guest suite in Spring Green
4.79 out of 5 average rating, 214 reviews

River Valley Retreat

Enjoy your stay in the Spring Green Area! This private apartment in the lower level of our home is located on the edge of town - close to everything you're here to see! This space provides a home-like feel while you tour the area. Offering a one bedroom (queen bed) with the ability to sleep up to 4 more people (2 on sectional sofa and 2 on air mattress), plus a loaded kitchenette (no stove), dining area, bathroom, extra space for gaming (includes a free arcade and foosball) and private patio.

Top guest favorite
Guest suite in Dubuque
4.95 out of 5 average rating, 323 reviews

Private entrance/space. Peaceful. Close to events.

Private entrance. You have a completely updated/ remodeled private space on the walk-out level of my home. Open floor plan, a carpeted bedroom with KING bed, a full-size memory foam sleeper sofa, a living room, mini-kitchen, laundry and bath. The mini-kitchen has a mini-fridge, microwave, coffee maker, crock pot, toaster, table/chairs. The desk, with woods view, is a perfect place to reflect, read, and write. Many extras. Snacks. Quiet residential area of Dubuque. I live upstairs with my dog.

Top guest favorite
A charming farmhouse is nestled among lush greenery, surrounded by tall trees. The two-story structure features a gabled roof and a covered front porch. Natural landscaping, including shrubs and grass, frames the house, creating a serene and private atmosphere amidst the forested hills.
Cabin in Gays Mills
4.98 out of 5 average rating, 368 reviews

Driftless Region Cabin/ Stream and Sauna

Settle into a quaint farmhouse nestled in a valley in the rolling, forested hills of the Driftless Region. Start your day with a cup of local coffee on the front porch. Go on a long walk or bike ride, then return to the cottage to cook, play board games, listen the record collection or visit Viroqua (25 minutes) for a farm-to-table 5-star dinner, or check out local music. Build a warm fire outdoors/ warm up by the gas stove indoors, or go down to the stream for a sauna by the cool water creek.

Top guest favorite
A cozy cabin is perched on large boulders, surrounded by lush greenery. It features a spacious deck with railing and multiple seating areas, offering a serene view of the wooded area. The stone chimney adds character to the rustic design of the cabin.
Cabin in Avoca
5 out of 5 average rating, 221 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.

Top guest favorite
A winding stone path leads to the retreat, nestled among tall trees. The modern structure features large glass windows, blending with the surrounding greenery. Outdoor seating is provided on a patio, while a grill is positioned nearby for outdoor cooking.
Cabin in Richland Center
4.93 out of 5 average rating, 112 reviews

The Spring Water Retreat -@MillCreekCabinsWI

After crossing a narrow path along the lake you will find the entrance to the Spring Water Retreat at Mill Creek Cabins. The remains of an old farmhouse now welcome our guests to a warm, secure, escape from the everyday. This secluded space is the perfect place to relax in the woods.​ With no TV and large windows looking out over the lake, the focus is on the outdoors. Despite the remote location, a high-speed internet connection is available to keep you connected throughout your stay. ​

Superhost
A single-story farmhouse is set against a backdrop of greenery, showcasing a combination of stone and wooden exterior. The well-maintained lawn is complemented by surrounding trees, with a pathway leading towards the entrance. A spacious deck is visible to the side, enhancing the outdoor appeal.
Farm stay in Wauzeka
4.81 out of 5 average rating, 312 reviews

Larsen Farm Secluded Farmhouse with Hotub

Secluded farmhouse with glass hot tub room 600 acres of private trails to hike and explore the cave. Bring your UTV and ride the trails for $30 per driver and $10 per passenger or rent a UTV for $300. Close to trout fishing stream or Mississippi for fishing. Approx 15 miles from Prairie Du Chein, close to canoeing for the Kickapoo, Wisconsin river. Has a gas & charcoal grill, pool table, firepit, Smart TV. Private trails closed Oct 15th thru mid Feb There is Access to public UTV trails.

Top guest favorite
A blue A-frame house is showcased, surrounded by greenery. The brick walkway leads to a cedar deck, framed by landscaping. Windows are visible on the sides, allowing natural light to fill the interior.
Chalet in Elizabeth
4.92 out of 5 average rating, 372 reviews

Galena Country Getaway

Brick walkway leads to the cedar deck with Adirondack chairs overlooking the large backyard. Enjoy dinner out on the deck and roast marshmallows over a bonfire at the firepit. The dark sky provides excellent stargazing. Kitchen features full-sized refrigerator, cooking utensils and a variety of spices. Spacious bathroom with a waterfall-style shower. Carpeted loft includes a sleep number queen sized bed and two twin beds. Close to Historic Galena & Apple Canyon State Park

Top guest favorite
A recently renovated cabin is surrounded by a serene snow-covered landscape, featuring natural wood siding and large windows. In the foreground, a hot tub bubbles gently, while tall pine trees provide a wooded backdrop.
Cabin in Muscoda
4.99 out of 5 average rating, 110 reviews

Unwind at Driftless Pines Cabin

Kick back and relax in this calm, stylish, and recently renovated space. Driftless Pines was completely updated (including a brand new hot tub) with one thing in mind, to create an amazing cabin experience with all the proper luxuries & amenities our guests could want or need. Spend a day on the breathtaking Wisconsin River (just down the road), visit a local favorite in Vickie's Cafe or partake in a wine tasting session at the gorgeous & scenic nearby Wild Hills Winery.

Top guest favorite
A cabin exterior is showcased, featuring dark wood siding and a steeply pitched roof. A spacious deck with chairs and potted plants invites relaxation. Large windows allow for natural light, and a balcony is visible above the entrance, enhancing the overall charm of the space.
Cabin in Viola
5 out of 5 average rating, 141 reviews

River Valley Cabin

Very private on-the-grid cabin overlooking the Kickapoo River. Kitchen & bath, dining room, one bedroom and futon in the large living room. TV and internet, laundry and cooking. Bring your own phone. Two additional cots provided. Stunning views for every season, a unique and colorful experience in nature any day of the year. The best hunting and fishing, canoeing and horse riding, nature trails, morels and foraging.

Popular amenities for Highland vacation rentals

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Iowa County
  5. Highland