Highland Holiday Rentals, Wisconsin: Private House Rentals

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Our top choices for Highland hotels

A hotel room with two beds, a wall-mounted light fixture, a window with curtains, and a view of the outdoors.

An indoor swimming pool with wooden walls and ceiling, a seating area with chairs, and a view into adjacent rooms.

A modern living area with a dining table, blue sofa, and a kitchen area with a refrigerator and microwave.

A vending machine with snacks and drinks, a seating area with chairs, and a window with a view.

1. AmericInn by Wyndham Dodgeville

Dodgeville

Christine

2.567.466 ₫

2.914.204 ₫ total

includes taxes & fees

4 Nov - 5 Nov

A wooden cabin with a glass-enclosed shower area, a visible towel, and a tiled floor.

A log cabin-style restaurant with wooden walls, a fireplace, and multiple tables and chairs.

A large indoor pool with clear blue water, surrounded by lounge chairs and a seating area with a sofa and table.

A hotel room with two beds, a TV, a desk, and a chair.

2. Best Western Dodgeville Inn & Suites

Dodgeville

Colleen

2.567.207 ₫

2.913.780 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A room with a bed, a small table, and a chair, all set in a cave-like environment with textured walls and a stone floor.

A circular bed in a cave-like room with a small desk and chair.

A room with a colorful hot air balloon decoration, a staircase with a rocky wall, and a mural of mountains.

A cave-themed bedroom with a bed, a television, and a small table with a telephone.

3. Don Q Inn

Dodgeville

Deborah

1.931.435 ₫

2.192.179 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A cozy room with a piano, green walls, and a brick fireplace.

A bar area with a bookshelf, stools, and a window with a view of the street.

A kitchen with a checkered countertop, a refrigerator, a microwave, and bar stools.

4. Fenway House Hotel

Fennimore

Rickey

2.853.777 ₫

3.010.678 ₫ total

includes taxes & fees

11 Oct - 12 Oct

A hotel room with a large bed, a separate bathroom with a bathtub, a large mirror, and a television in the corner.

An indoor swimming pool with a hexagonal tile floor, wooden walls, and large windows.

A bar area with arcade games, a counter, and bar stools.

A living room with a fireplace, a flat-screen TV, a ceiling fan, and a dining area with chairs and a table.

5. Ramada by Wyndham Richland Center

Richland Center

Rachel

2.428.870 ₫

2.732.479 ₫ total

includes taxes & fees

18 Oct - 19 Oct

An indoor swimming pool with a wooden ceiling and surrounding seating areas.

A wedding reception with round tables, white tablecloths, and floral centerpieces.

A pool table in a room with a checkered carpet, a billiards table, and a sofa with colorful cushions.

A reception area with a fireplace, a desk with a computer, a red telephone, and a sign with the hotel's name.

6. The Round Barn Lodge

Spring Green

colleen

2.904.608 ₫

3.064.361 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A hotel room with a bed, a desk, a lamp, a painting, and a bathtub.

A living room with two sofas, a coffee table, and a dining area with chairs and a table.

A gym with treadmills, a mirrored wall, and a door leading to a pool area.

A hotel hallway with carpeted floors, dark doors, and wall-mounted light fixtures.

7. Dodgeville inn and suites

Dodgeville

Tonia

1.750.545 ₫

1.987.063 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A Pine Ridge Motel sign with amenities like clean rooms, phones, new owners, and television.

A compact kitchenette with a microwave and a small refrigerator on a wooden stand.

A Pine Ridge Motel with a clear sign, parking lot, and a grassy area with shrubs.

A hotel room with a bed, a desk with a chair, a television, a microwave, and a small kitchenette.

8. Pine Ridge Motel

Dodgeville

John

1.685.451 ₫

1.912.892 ₫ total

includes taxes & fees

11 Oct - 12 Oct

A spacious room with large windows, a table with chairs, and a rug.

A room with two beds, a table, and chairs. There are two lamps, a window with curtains, and two framed pictures on the wall.

A building with a stone facade and a metal roof, featuring a sign that reads "Welcome Office".

A bedroom with a large bed, a chair, a bedside table with a lamp, and a wall-mounted air conditioner.

9. Napps Motel

Fennimore

Robert

1.610.501 ₫

1.755.472 ₫ total

includes taxes & fees

12 Oct - 13 Oct

A modern lobby with a reception desk, seating area, and a large window providing natural light.

A laundry room with two white washers and dryers, a gray countertop, a wooden table, and black chairs.

A modern reception desk with a wooden accent, a large window with a view, and a geometric patterned wall.

A hotel room with two beds, a large window, a wall-mounted heater, and a bedside table with a lamp.

10. Holiday Inn Express and Suites-Platteville by IHG

Platteville

2.567.466 ₫

2.837.050 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A wooden cabin with a swimming pool, large windows, and a patio area.

A hotel room with a large bed, a sofa, a small table, a desk, a chair, a lamp, a painting, and a bathroom with a bathtub.

A bar area with multiple tables and chairs, a counter with a neon sign, and a display of liquor bottles.

A compact hotel room with a kitchenette, a small refrigerator, a microwave, a sink, and a sofa.

11. AmericInn by Wyndham Boscobel

Boscobel

Robert

2.402.785 ₫

2.655.077 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A hotel with a modern design, featuring a prominent sign and a covered entrance.

A modern restaurant with wooden flooring, multiple seating areas including booths and tables, and a bar area with stools.

An outdoor patio with seating and a view of a golf course.

A modern lounge area with a sofa set, a blue armchair, a small table, and a potted plant.

12. Sleep Inn & Suites Lancaster-Platteville

Lancaster

adebayo

2.459.062 ₫

2.594.310 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A room with two beds, a kitchenette, a mirror, and a door.

A large industrial building with a flat roof, a parking lot, and a small green area with a sign.

A long, narrow hotel corridor with wooden doors on both sides, carpeted flooring, and a ceiling light.

A hotel room with two beds, a desk, a chair, a TV, a window with curtains, and a lamp.

13. SANDS MOTEL

Boscobel

1.475.304 ₫

1.630.211 ₫ total

includes taxes & fees

11 Oct - 12 Oct

14. Quality Inn Mineral Point

Mineral Point

Jeanne

2.340.544 ₫

2.586.303 ₫ total

includes taxes & fees

2 Nov - 3 Nov

An indoor swimming pool with a slide and a small pool area.

An indoor archway with white drapery and greenery, leading to a room with a wooden floor and a dining area in the background.

A lodge interior with wooden furniture, a stone fireplace, and Christmas decorations.

A stone building with a balcony overlooking a golf course.

15. Deer Valley Lodge & Golf

Barneveld

Baylie

3.345.486 ₫

3.529.617 ₫ total

includes taxes & fees

20 Oct - 21 Oct

A bathroom with a bathtub, a shower curtain, and a towel rack.

16. Mound View Inn & Suites

Platteville

Michael

2.567.207 ₫

2.836.763 ₫ total

includes taxes & fees

19 Oct - 20 Oct

A Victorian-style house with a prominent tower, a front porch, and a green awning.

A traditional dining room with a wooden table, chairs, a fireplace, and a patterned rug.

A living room with two sofas, a coffee table, a clock, and a chandelier.

A dining room with a wooden table, green chairs, a chandelier, and a patterned rug.

17. Maon House Bed and Breakfast

Richland Center

Kathy Z

4.318.011 ₫

4.857.762 ₫ total

includes taxes & fees

21 Oct - 22 Oct

A reception area with a wooden reception desk, a digital screen, and a staircase leading to upper floors.

A long table set with white chairs, gold chargers, and clear glassware.

An indoor swimming pool with a wooden deck, a small balcony, and a reception area with a counter and chairs.

A hotel lobby with a sofa, armchairs, a fireplace, a vending machine, and large windows with a view of the outside.

18. Quality Inn & Suites Belmont - Platteville

Belmont

joe

1.741.468 ₫

1.906.908 ₫ total

includes taxes & fees

29 Oct - 30 Oct

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Stay near popular Highland attractions

Blackhawk Lake Recreation Area

10.0/10 (2 reviews)

Explore the great outdoors at Blackhawk Lake Recreation Area, a lovely green space in Highland. Stroll along the lakeside or discover the area's waterfalls.

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Beach at Black Hawk Lake Recreation Area

Why not spend a lazy afternoon at Beach at Black Hawk Lake Recreation Area during your trip to Highland? While you're in the area, wander around the parks.

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Spurgeon Vineyards & Winery

9.0/10 (2 reviews)

You can enjoy a tasting or tour at Spurgeon Vineyards & Winery during your travels to Highland. While you're in the area, wander around the natural setting.

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Top Highland Hotel Reviews

AmericInn by Wyndham Boscobel

10/10 Excellent

"Had a great stay."

AmericInn by Wyndham Dodgeville

10/10 Excellent

"Staff so friendly. Hot tub was great. Very quiet."

Sleep Inn & Suites Lancaster-Platteville

10/10 Excellent

"This hotel is an excellent value! Super clean and very friendly staff. Breakfast was good with waffle maker, eggs, sausage, etc…"

Quality Inn Mineral Point

8/10 Good

"It is decent and near a cute, historic town."

The Round Barn Lodge

8/10 Good

"Staff was very helpful and pleasant! Hotel value was excellent! Great location"

Deer Valley Lodge & Golf

10/10 Excellent

"Perfect family friendly place"

Best Western Dodgeville Inn & Suites

10/10 Excellent

"We come every year in October for House on the Rock Darkside. This is the perfect hotel for that. Close drive but near some food and stores. Always friendly staff, clean rooms, and comfy beds. Breakfast is very basic but free . Great to have a mini fridge and microwave in the room. We will be back next year!"

Maon House Bed and Breakfast

10/10 Excellent

"Mary was very accommodating. Breakfast earlier so I could start my day on time menu changed and just a nice calm start to the day."

Napps Motel

10/10 Excellent

"Pleasingly large accommodations."

More cheap stays in Highland

Quality Inn & Suites Belmont - Platteville

103 W Mound View Avenue Belmont WI

1.741.468 ₫

1.906.908 ₫ total

29 Oct - 30 Oct

includes taxes & fees

8.4/10 Very good! (326 reviews)

Dodgeville inn and suites

1308 n johns st Dodgeville WI

1.750.545 ₫

1.987.063 ₫ total

2 Nov - 3 Nov

includes taxes & fees

7.2/10 Good! (121 reviews)

Don Q Inn

3658 State Road 23 Dodgeville WI

1.931.435 ₫

2.192.179 ₫ total

1 Nov - 2 Nov

includes taxes & fees

Sleep Inn & Suites Lancaster-Platteville

1600 S Madison Street Lancaster WI

2.459.062 ₫

2.594.310 ₫ total

1 Nov - 2 Nov

includes taxes & fees

9.4/10 Exceptional! (381 reviews)

Holiday Inn Express and Suites-Platteville by IHG

55 S ELM ST Platteville WI

2.567.466 ₫

2.837.050 ₫ total

8 Nov - 9 Nov

includes taxes & fees

The Round Barn Lodge

E4830 Us Highway 14 Spring Green WI

2.904.608 ₫

3.064.361 ₫ total

2 Nov - 3 Nov

includes taxes & fees

8.6/10 Excellent! (696 reviews)

Hotels in Highland with star rating

Frequently asked questions

What's the weather like in Highland?

The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Highland are January, April, March and December, with each month seeing an average of 21 cm of snowfall.

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Find hotels in Highland, WI from 1.630.211 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Highland

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Highland hotels

1. AmericInn by Wyndham Dodgeville

2. Best Western Dodgeville Inn & Suites

3. Don Q Inn

4. Fenway House Hotel

5. Ramada by Wyndham Richland Center

6. The Round Barn Lodge

7. Dodgeville inn and suites

8. Pine Ridge Motel

9. Napps Motel

10. Holiday Inn Express and Suites-Platteville by IHG

11. AmericInn by Wyndham Boscobel

12. Sleep Inn & Suites Lancaster-Platteville

13. SANDS MOTEL

14. Quality Inn Mineral Point

15. Deer Valley Lodge & Golf

16. Mound View Inn & Suites

17. Maon House Bed and Breakfast

18. Quality Inn & Suites Belmont - Platteville

Stay near popular Highland attractions

Blackhawk Lake Recreation Area

Beach at Black Hawk Lake Recreation Area

Spurgeon Vineyards & Winery

Top Highland Hotel Reviews

AmericInn by Wyndham Boscobel

AmericInn by Wyndham Dodgeville

Sleep Inn & Suites Lancaster-Platteville

Quality Inn Mineral Point

The Round Barn Lodge

Deer Valley Lodge & Golf

Best Western Dodgeville Inn & Suites

Maon House Bed and Breakfast

Napps Motel

More cheap stays in Highland

Quality Inn & Suites Belmont - Platteville

Dodgeville inn and suites

Don Q Inn

Sleep Inn & Suites Lancaster-Platteville

Holiday Inn Express and Suites-Platteville by IHG

The Round Barn Lodge

Hotels in Highland with star rating

Frequently asked questions

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