
Southwest Illinois Romantic Vacations
Book a Romantic Hotel + Flight or Car together to unlock savings
Photo by Southernmost Illinois Tourism Bureau
- Plan, book, travel with confidence
Better together
Save up to ¥45,448 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top Romantic Southwest Illinois Hotels

Cozy Cottage On The Shawnee Hills Wine Trail
Cobden
Love is in the air at this romantic cottage, featuring a garden and a hot tub. Couples will appreciate the in-room fireplaces.
9.8/10 Exceptional! (156 reviews)
Couples like: hot tub, fireplace
Great weekend stay!
"Perfect spot for S I wine country. Front porch coffee in the morning with peaceful views was the best. Hosts we great. We will be back."
Reviewed on Jun 25, 2025

Great Shawnee Wine Trail Cabin in Relaxing Setting
Alto Pass
If you're looking for a special getaway, consider a stay at this romantic cabin where there's in-room fireplaces and much more for you and your partner to ...
10/10 Exceptional! (39 reviews)
Perfect for us
"We were as comfortable in the cabin as we are in our own home. It was great having laundry machines (we were staying with 4 kids ages 5 to 12). The kitchen was equipped with everything we needed. Be careful the water out of the faucet can get steaming hot. We enjoyed the fire pit. Would recommend ..."
Reviewed on Mar 29, 2025

Relaxing Unique Cave Creek Cabin 2 in Shawnee near Alto Pass and Bald Knob Cross
Alto Pass
If you're looking for a special getaway, consider a stay at this romantic cabin where there's in-room fireplaces and much more for you and your partner to ...
10/10 Exceptional! (44 reviews)
Amazing cabin nestled in the woods but close to everything!
"We very much enjoyed our weekend stay at this amazing cabin! The hosts thought of every detail. Be ready for a stress free, relaxing stay!"
Reviewed on Jul 9, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.