Photo by Erin Hansen

Holiday Homes in McGregor

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Featured Holiday Homes in McGregor

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

9.8 out of 10, Exceptional, (93)
"Easy peasy, comfy and sweet"
Cottage on Main, Monona, Iowa, is right in the middle of the driftless area. ♥️

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!

Hydro-Massage Tub! Wrangler Outlaw Suite! Horses!

9.6 out of 10, Exceptional, (55)
"Wonderful location, beautiful bathroom, relaxing. Definitely would visit again. "
The price is AU$294
includes taxes & fees
19 Feb - 20 Feb
Hydro-Massage Tub! Wrangler Outlaw Suite! Horses!

Ohio Street Retreat-hot tub, massage chair, pool

10.0 out of 10, Exceptional, (47)
"Immaculate with great extras like the outdoor hot tub and inside massage chair. Plenty of hot water. Comfy beds. Felt safe as a female traveling alone. For sure a retreat experience for me."
The price is AU$313
includes taxes & fees
19 Feb - 20 Feb
Ohio Street Retreat-hot tub, massage chair, pool

Hygge Hideaway. Pet friendly, cozy retreat & 3 minute walk to the river!

10.0 out of 10, Exceptional, (35)
"Perfect in every way. Cozy, quiet and everything you need. We will definitely go back to this little hideaway "
The price is AU$201
includes taxes & fees
2 Mar - 3 Mar
Hygge Hideaway. Pet friendly, cozy retreat & 3 minute walk to the river!

Pet Friendly River Bottom Oasis - Bagley

10.0 out of 10, Exceptional, (18)
"Just what we were looking for to spend Christmas when we come from all over. Enough room for all of us. Host were easy to work with and very responsive. Thank you for everything!"
Pet Friendly River Bottom Oasis - Bagley

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$1,762
includes taxes & fees
2 Mar - 3 Mar
Elkader Jailhouse Inn (Entire Inn)

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

9.2 out of 10, Wonderful, (22)
"This was a great location for our women's weekend away. Plenty of room for the 5 of us. Property tour, hike and living quarters were as advertised. Ed was an attentive manager and addressed our requests in a timely manner. Fire ban kept us from enjoying a campfire. If you're a light sleeper - consider earplugs if on the lower level (some noise/movement heard) overnight which is expected in a shared lodge. "
Hot Tub! Cowboy Retreat! SW Wisconsin Driftless Region on UTV Route

Copper Roof Cottage

10.0 out of 10, Exceptional, (42)
"Great space for our large group and well stocked with kitchen items, bedding and towels. I have given it 4 stars because the driveway, sidewalks and porch were not shoveled when we arrived. A good few inches of snow came in a day before we arrived so I feel like it should have been done. We couldn’t find a shovel so we had to use a dust pan to make a path out the front of the house otherwise we would’ve tracked an insane amount of snow into the home. Besides this issue, we greatly enjoyed our...
The price is AU$635
includes taxes & fees
28 Feb - 1 Mar
Copper Roof Cottage

Winter special HALF OFF!!!

10.0 out of 10, Exceptional, (48)
"We had a great stay for a family ice fishing trip"
Winter special HALF OFF!!!

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

2.0 star property
10.0 out of 10, Exceptional, (10)
"The property was exactly as stated in the listing. Everything was very clean. The kitchen was well-equipped with everything you need for cooking and baking. This is an excellent property if you have kids because they have everything you need including kids games, toys, pack-n-play, baby gates, kids dishes, and more! It was the small touches that made all the difference, like having extra toothpaste and toothbrushes if you forgot yours, a basket of snacks, special makeup towels, and much more! We...
Luxurious home with hot tub, electric fireplace, and stunning views

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

Harstad Suite at Elkader Jailhouse Inn

10.0 out of 10, Exceptional, (7)
"We have stayed at the Elkader Jail House many times and the Harstad Suite is a great room for the 4 of us. The large kitchen and family space on the first floor provide plenty of space for everyone to get together and relax. Its nearby my family and takes the stress off anyone needing to make space for all of us to sleep. Its comfortable, clean and an easy to walk downtown. We'll be back soon!"
The price is AU$379
includes taxes & fees
21 Feb - 22 Feb
Harstad Suite at Elkader Jailhouse Inn

River Valley Cabin

10.0 out of 10, Exceptional, (78)
"Everything was exactly as described. Beautiful house and beautiful views. If there were 100 stars for communication with the owner, Jane would get 100 everytime. We would definitely stay again. Alreadplann"
River Valley Cabin

Fritz’s Farmhouse.. Country getaway.

10.0 out of 10, Exceptional, (70)
"Cozy, comfortable, and clean. Hosts were extremely nice and great communicators. Planning on returning next year!"
The price is AU$577
includes taxes & fees
19 Feb - 20 Feb
Fritz’s Farmhouse.. Country getaway.

Newly updated historical home

9.8 out of 10, Exceptional, (47)
"Splendid return visit to the Copper Roof. We will be back"
Newly updated historical home

Becwar House . . . at the Mississippi River

10.0 out of 10, Exceptional, (22)
"Beautiful & comfortable home. So many details that make all the difference. It's apparent that the house is loved & owner wants to make you feel comfortable and welcomed.Thank you for sharing your beautiful home! We'd love to come back! "
Becwar House . . . at the Mississippi River

Cozy Cottage w/ private patio just 1 block to downtown. Packed with charm!

10.0 out of 10, Exceptional, (4)
"I was really impressed by the decor of the interior of the house and its location in proximity to the Villa Louie grounds was just about perfect. It worked perfectly for myself and guess where we could actually walk and or bike. To the horse show grounds. It worked perfectly!"
Cozy Cottage w/ private patio just 1 block to downtown. Packed with charm!

Clayton Savings Bank - One Block To Might Mississippi River!

2.0 star property
9.4 out of 10, Exceptional, (6)
"Perfect location to visit pikes peak, the river restaurant pub was convenient & very good. The view from the bedroom window was beautiful. Thank you!"
Clayton Savings Bank - One Block To Might Mississippi River!

Centrally located in the NE Iowa Driftless Area!

10.0 out of 10, Exceptional, (48)
"We enjoyed the stay and loved the amenities. Very clean and nice touches to make the stay enjoyable!"
Centrally located in the NE Iowa Driftless Area!
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 McGregor

The Riverside Brickhouse- 6 Bedrooms, 2 Bathroom, Riverviews, Grill, AC/Wifi

The Riverside Brickhouse- 6 Bedrooms, 2 Bathroom, Riverviews, Grill, AC/Wifi

SereniTree Cabin - Modern Rustic Getaway tucked in the trees

10.0 out of 10, Exceptional, (81)
"This place was super cozy and had plenty of amenities to choose from. Everything was very clean and welcoming"
SereniTree Cabin - Modern Rustic Getaway tucked in the trees

Chestnut 3 Bed / 2 Bath cabin with Hot Tub Jacuzzi

9.0 out of 10, Wonderful, (6)
"It was a great stay! Only downside to the cabin was that there was no hot water in the kitchen to clean dishes, we did a lot of cooking at the cabin. Other than that it was a great experience! "
Chestnut 3 Bed / 2 Bath cabin with Hot Tub Jacuzzi
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.