Vacation rentals in Darlington

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Top-rated vacation rentals in Darlington

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

Guest favorite

Home in Cuba City

4.95 out of 5 average rating, 187 reviews

Recharge your soul at “The Church”!

This historic 1867 Church was meticulously remodeled into a quaint and quiet escape from the constant buzz of todays world. The Church boasts beautiful sunrises, a giant wrap around accessible deck, stone firepit, new kitchen and bath area and a large open space to unwind and truly unplug. Set upon a hill in a small rural community in SouthWest WI just minutes from the mighty Mississippi near Dubuque IA, Galena IL. and Platteville Wi. The Church is a perfect quiet safe haven from everything.

Apr 25 – May 2

ﺩ.ﺇ411 per night
Guest favorite

Cabin in Durango

5.0 out of 5 average rating, 234 reviews

Cozy Cabin by the Pond

Quiet, private country location to relax and unwind. 9 miles west of Dubuque, close to Wineries, Heritage Trail, Sundown Mountain Resort. Cozy cabin and quarter acre pond. Sun yourself on the patio, or nap in the shade of the covered porch. We're sure you will love this space as much as we do. Not suitable for children under 12, we strictly enforce no children and no pets. Outdoor relaxing space, gas grill. Fully stocked cabin, with the essentials such as coffee, tea, spices and condiments.

Nov 11 – 18

ﺩ.ﺇ470 per night
Guest favorite

Loft in Monroe

4.99 out of 5 average rating, 121 reviews

Loft 3 - On The Historic Monroe Square

Loft 3 is 40 steps (2 flights of stairs) above the Monroe Square. It's a climb, but the view is totally worth it! Newly remodeled in 2021, and reminiscent of the 1859 character of the building, this space is cute, cozy, and truly one of a kind. Literally a couple steps away from your entryway is Sunrise Donut Cafe, featuring customized donuts and a full menu of excellent coffee items. From there, explore the rest of the Square for food, drinks, and shopping in a quaint Main Street atmosphere.

Dec 26 – Jan 2

ﺩ.ﺇ422 per night

Popular amenities for Darlington vacation rentals

Other great vacation rentals in Darlington

Guest favorite

Cabin in Darlington

5.0 out of 5 average rating, 13 reviews

Hilltop Hideaway. Relax, unwind, and getaway!

Sep 14 – 21

ﺩ.ﺇ380 per night
Guest favorite

Home in Darlington

4.95 out of 5 average rating, 80 reviews

Hamilton Goebel House

Jul 16 – 23

ﺩ.ﺇ386 per night
Guest favorite

Home in Darlington

4.94 out of 5 average rating, 17 reviews

Fayette Getaway: No cleaning fee!

Sep 14 – 21

ﺩ.ﺇ1,158 per night
Guest favorite

Home in Shullsburg

5.0 out of 5 average rating, 83 reviews

The Car Wash Inn A Unique Stay

Dec 2 – 9

ﺩ.ﺇ429 per night
Guest favorite

Home in Darlington

4.84 out of 5 average rating, 57 reviews

Destination Driftless Winter Rec Trailside Retreat

Mar 14 – 21

ﺩ.ﺇ948 per night
Guest favorite

Home in South Wayne

5.0 out of 5 average rating, 40 reviews

Welcome to the "Bat Cave"!

Aug 17 – 24

ﺩ.ﺇ577 per night
Superhost

Home in Argyle

5.0 out of 5 average rating, 4 reviews

The Old Church in Woodford-1 bed

Apr 15 – 22

ﺩ.ﺇ377 per night
Guest favorite

Apartment in Shullsburg

5.0 out of 5 average rating, 75 reviews

Water Street Apartment

Aug 7 – 14

ﺩ.ﺇ403 per night
Superhost

Place to stay in Shullsburg

5.0 out of 5 average rating, 3 reviews

Historic Shullsburg Suites, Suite 202

Oct 7 – 14

ﺩ.ﺇ352 per night
Guest favorite

Home in Dubuque

5.0 out of 5 average rating, 48 reviews

Home by the River

Jun 9 – 16

ﺩ.ﺇ496 per night
Guest favorite

Cabin in Blanchardville

5.0 out of 5 average rating, 46 reviews

Quiet Farmhouse-Style Cabin w/ Front Porch!

Oct 6 – 13

ﺩ.ﺇ729 per night
Guest favorite

Guesthouse in Blanchardville

4.94 out of 5 average rating, 78 reviews

Rural Driftless Region Stay with Pastoral View

Jun 6 – 13

ﺩ.ﺇ393 per night

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