Holiday Homes in Monona

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Featured Holiday Homes in Monona

Cottage on Main, Monona, Iowa, is right in the middle of the driftless area. ♥️

9.8 out of 10, Exceptional, (92)
"The house was perfect for us! We were attending a wedding nearby and wanted a place where our grandbaby could have her own room. This"
Cottage on Main, Monona, Iowa, is right in the middle of the driftless area. ♥️

Luxurious home with hot tub, electric fireplace, and stunning views

2.0 star property
10.0 out of 10, Exceptional, (9)
"Great place for fall getaway. One of the nicest places we’ve ever stayed, thanks for wonderful time!"
Luxurious home with hot tub, electric fireplace, and stunning views

Prairie du Chien Home w/ Yard: 3 Mi to River!

10.0 out of 10, Exceptional, (3)
"The perfect house in a quiet rural neighborhood with great hosts!"
Prairie du Chien Home w/ Yard: 3 Mi to River!

Copper Roof Cottage

10.0 out of 10, Exceptional, (38)
"Very clean, excellent amenities "
Copper Roof Cottage

Newly updated historical home

9.8 out of 10, Exceptional, (46)
"Our stay at this recently updated historical home in PdC was very enjoyable! This home was conveniently located to the activities we did, and you can walk to many places. Communication from the owner was also fabulous. We choose VRBO over hotels for the extra space and privacy, and this historic home did not disappoint."
Newly updated historical home

Elkader Jailhouse Inn (Entire Inn)

10.0 out of 10, Exceptional, (16)
"Would have been helpful to have a manual on how to operate the ac system, the whirlpool tub, Wolf range. The refrigerator had not been cleaned. Had a Murder mystery dinner and the Inn was part of the setting. People in town were friendly with the exception of the brewery. It was handy to have restaurants menus available to review. Kids want to come back."
The price is AU$1,721
includes taxes & fees
2 Dec - 3 Dec
Elkader Jailhouse Inn (Entire Inn)

Scenic Valley Lodge

9.6 out of 10, Exceptional, (7)
"Three floors of spaced out bedrooms and huge kitchen/dining/livingroom space where all can gather. Great price for all of the room and location near the river and town for nightlife and grocery odds and ends. Will book again no doubt. "
The price is AU$545
includes taxes & fees
1 Dec - 2 Dec
Scenic Valley Lodge

Tiny House on Upper Iowa River w/ hot tub

8.8 out of 10, Excellent, (30)
"We had a great night away in the tiny house. A couple of tight fits if you’re over 6 feet tall, but if you don’t see that coming with a tiny home, well, that’s on you. Great experience! "
The price is AU$378
includes taxes & fees
10 Dec - 11 Dec
Tiny House on Upper Iowa River w/ hot tub

Hot Tub! Cowboy Retreat! SW Wisconsin Driftless Region on UTV Route

9.2 out of 10, Wonderful, (20)
"My husband and I had a great weekend. We wish we could stayed longer! Ed was so nice and accommodating."
Hot Tub! Cowboy Retreat! SW Wisconsin Driftless Region on UTV Route

Newly remodeled cozy retreat. Pet friendly & 3 minute walk to the river!

10.0 out of 10, Exceptional, (26)
"Cozy spot with all the little amenities you might want! We loved our stay here and how close we were to the river. Very comfortable and they've thought of everything!"
The price is AU$190
includes taxes & fees
1 Dec - 2 Dec
Newly remodeled cozy retreat. Pet friendly & 3 minute walk to the river!

Winter special HALF OFF!!!

10.0 out of 10, Exceptional, (45)
"Very comfortable. Nice deck on the back. Few sheep wandering around across femce from neigjbor a bonus. Very quiet"
Winter special HALF OFF!!!

The Riverside Retreat! cozy, newly remodeled home

8.8 out of 10, Excellent, (14)
"The home was cute. Neighborhood was quiet. "
The Riverside Retreat! cozy, newly remodeled home

The Farmhouse- country charm, room for family visiting, relaxing, or gathering

10.0 out of 10, Exceptional, (35)
"Wonderful home with a beautiful property. Very comfortable beds. We all wish we would have had an extra day to use the game room (skeeball is a favorite) and explore the creek/woods at the end of the property. It is at the top of the list when we go visit family in the area again! "
The Farmhouse- country charm, room for family visiting, relaxing, or gathering

Enjoy the top floor of this victorian house With two suites & a bonus bedroom

9.6 out of 10, Exceptional, (5)
"The house is beautiful, clean and felt homey/comfortable. Thank you "
Enjoy the top floor of this victorian house With two suites & a bonus bedroom

Harstad Suite at Elkader Jailhouse Inn

10.0 out of 10, Exceptional, (6)
"The Inn is beautiful! My husband I spent 2 nights in the Harstad Suite. It was spacious and comfortable and I loved the big bath tub. Highly recommended."
The price is AU$372
includes taxes & fees
30 Nov - 1 Dec
Harstad Suite at Elkader Jailhouse Inn

Hydro-Massage Tub! Wrangler Outlaw Suite! Horses!

9.6 out of 10, Exceptional, (54)
"Wonderful location, beautiful bathroom, relaxing. Definitely would visit again. "
The price is AU$277
includes taxes & fees
1 Dec - 2 Dec
Hydro-Massage Tub! Wrangler Outlaw Suite! Horses!

Beautiful Riverfront Home on the Mississippi!

10.0 out of 10, Exceptional, (1)
"Awesome little place on the river. Fishing was good, quiet and really enjoyed the fire pit. Located next to train tracks and trains rolled through a couple times in the early morning, didn’t really bother us though as we knew the tracks were there when we booked it. Overall, great place!"
Beautiful Riverfront Home on the Mississippi!

River Valley Cabin

10.0 out of 10, Exceptional, (75)
"This was a perfect place for our family Fall trip! It was peaceful and the scenery was absolutely beautiful. So many things to do in Lansing and surrounding towns. I highly recommend."
River Valley Cabin

Pet Friendly River Bottom Oasis - Bagley

10.0 out of 10, Exceptional, (16)
"We loved our stay! We got holed up with the heat for a few days.. but thank goodness for that game room!!! The only reason I gave one less star on location is that the property is right on the road, and the gameroom is across that road, although the traffic is not bad at all as far as amount of traffic :) - Everything was very clean, and it was so nice to be able to bring our dogs! The host was incredibly responsive- Wyalusing park up the road approximately 9 miles is such a treat as well-...
Pet Friendly River Bottom Oasis - Bagley

Ohio Street Retreat-hot tub, massage chair, pool

10.0 out of 10, Exceptional, (43)
"Everything was great, beautiful little home! "
The price is AU$304
includes taxes & fees
1 Dec - 2 Dec
Ohio Street Retreat-hot tub, massage chair, pool
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.
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Other property types in Monona

Walnut Ridge Cabin w/ Hot Tub

9.2 out of 10, Wonderful, (20)
"Beautiful, and well kept cabin! Loved the hot tub!"
The price is AU$348
includes taxes & fees
1 Dec - 2 Dec
Walnut Ridge Cabin w/ Hot Tub

Paint Creek Lodge w/ Hot Tub & Swimming Pond... 5 Bedroom Cabin

9.0 out of 10, Wonderful, (11)
"We just wanted to get away somewhere quite and this place fit the bill! Highly recommend!"
The price is AU$439
includes taxes & fees
1 Dec - 2 Dec
Paint Creek Lodge w/ Hot Tub & Swimming Pond... 5 Bedroom Cabin

Thornwood Cottage is the perfect little get away

10.0 out of 10, Exceptional, (101)
"It's a really nice property out in the country. It is well taken care of. It would be great for a husband and wife with 2 kids. A group of 4 friends, you'd have to share beds or figure something else out. The bathroom is detached but it is a very nice bathroom. It's a nice comfortable place to stay."
Thornwood Cottage is the perfect little get away
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.