Holiday rentals near Big Sky Drive-In

We found 1,273 holiday rentals — enter your dates for availability

Where to?

Dates

Calendar
Flexible dates

August 2025

September 2025

Scroll through and discover private holiday rentals within easy reach of Big Sky Drive-In that provide the perfect home base for your trip. Whether you're travelling with your children or with friends, holiday rentals have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a pool. You'll be able to choose a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Big Sky Drive-In

Showing deals for:14 Nov - 21 Nov

Exceptional

(7 reviews)

Cozy A-Frame near Wisconsin Dells and river access l Dogs Welcome

Lyndon Station, WI

8% off

S$302 per night

includes taxes & fees

Relax with family and friends on our large front porch!

Exceptional

(31 reviews)

Cozy Country Historic Home - Clean,Spacious,Scenic - near Devil's Lake ,WI Dells

Mauston, WI

8% off

S$318 per night

includes taxes & fees

Front of home: porch with 4 wicker chairs, end tables, swing, 2 garage spots

Exceptional

(43 reviews)

Pet-Friendly 5BR 3.5BA Cabin on 6-acres Sleeps 15, Game Room, Deck, Dells 10min

Lyndon Station, WI

9% off

S$774 per night

includes taxes & fees

Exceptional

(42 reviews)

Dells Secret Cottage - Huge Private Yard, Minutes to downtown Wisconsin Dells

Wisconsin Dells, WI

8% off

S$476 per night

includes taxes & fees

Wisconsin Dells Vacation Rental | 2BR | 1BA | 2 Steps to Enter | 1,500 Sq Ft

Exceptional

(34 reviews)

Riverfront Home w/ Private Dock in Wisconsin Dells

Wisconsin Dells, WI

15% off

S$623 per night

includes taxes & fees

Exceptional

(33 reviews)

Arbor Acres Cottage! Bright, cheery, cozy and ready for you right by Wis Dells!

Lyndon Station, WI

8% off

S$313 per night

includes taxes & fees

Exceptional

(104 reviews)

🏞New Log CabinPerfect Location by Devil's LakeClose to DellsSkiFireplace*🏕

Baraboo, WI

8% off

S$731 per night

includes taxes & fees

Exceptional

(29 reviews)

Rustic Cabin with Sandstone Canyon & Dock on the WI River in Wisconsin Dells

Wisconsin Dells, WI

8% off

S$271 per night

includes taxes & fees

Exceptional

(181 reviews)

Making memories at the lake house, dogs alwd Dells 30 min away TRH Lic 9368

Oxford, WI

8% off

S$483 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Big Sky Drive-In

Charming cottage in lovely Merrimac next to Ski/Golf/Hiking/Breweries

Sleeps 8 · 1 bedroom · 1 bathroom

Top rated rentals - Big Sky Drive-In

Soaring ceilings welcome you into the great room of Turkey Run

Premier Host

Christmas Cabin Celebration

Our family thoroughly enjoyed celebrating Christmas at Turkey Run Cabin. We appreciated that they had put up a tree for the holidays and created a festive atmosphere. The Kitchen was well stocked for us to prepare holiday meals. The Whirlpool tub was enjoyed by 6 out of 8 of us and was very relaxing. We woke up to enjoy the views and saw a flock of wild turkeys as we had our morning coffee and later enjoying a lovely outdoor fire in the pit. Sondra was very hospitable and offered us tips for hiking trails and addressed all our questions. We highly recommend Turkey Run for a relaxing family retreat. Thank you!

Pam F.

Stayed Dec 2022

Premier Host

Olya’s Cabin. 5761 Coleman Baraboo, WI

Nice and close; walking distance to the Pub and Brewery. Very nice home.

Mike C.

Stayed Jan 2020

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value