Holiday rentals in Winterset

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Top-rated holiday rentals in Winterset

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

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Superhost

Cabin in Rockbridge

4.86 out of 5 average rating, 205 reviews

Private Modern Cabin | Hot Tub, Dogs, April Deals!

JenRating, 5 stars4 days ago

Pat & Chelsea were great hosts. We had a few minor instances, but they responded very quickly and got everything resolved. The house is nicely decorated and clean. The only way to enter the house is by climbing stairs and the stairs inside are steep and narrow, something we were not expecting so if you have issues climbing, it may be a problem. The deck is very large and a great hang out spot, but the deck needs some love. There are boards popping up, even under the rug which caused some tripping hazards. An umbrella on the outdoor table would be nice and the string lights made it feel cozy but not all of them worked. There is an eye sore house across the street so a privacy screen of some sort on the deck would be nice. With a little TLC, the deck will be the spotlight of the house!! We thoroughly enjoyed the fire pit each night, but there are no lights on the outside stairs, so bring a lantern. There are no hammocks like the picture displays. Overall, we enjoyed our stay!

Top guest favourite

Flat in Howard

4.97 out of 5 average rating, 58 reviews

Woodside Hideaway.

SheilaRating, 5 stars2 months ago

Mr. Frank came out to greet us on arrival and directed us to where we were staying. The B and B was exactly like pictures/discription and stocked with tea, coffee, ice, and lots of soaps/shampoo/conditioner, etc. When my son locked the bathroom door by mistake, Mr. Frank fixed it right away. They were very welcoming and the Band B was inexcellent condition. I will definitely use them in the future!

Top guest favourite

Cabin in New Plymouth

5 out of 5 average rating, 19 reviews

Havenbrook-Hocking Hills Luxury, 10 Acres, Hot Tub

SarahRating, 5 stars2 weeks ago

We went to Havenbrook for a girls weekend and getaway and had a great time. The home was incredibly clean and as described in the listing. It was so cozy and a lovely place to spend quality time with friends. Despite the fact that the weather wasn't great, we had no shortage of things to do, cooking in the kitchen, enjoying the hot tub, playing games, and taking a trip to the Inn and Spa at Cedar Falls for massages (about 15 minutes away). We had a wonderful time!

Guest favourite

Villa in Jeromesville

4.93 out of 5 average rating, 301 reviews

Whispering Pines Retreat by Private Lake/ Villa #1

DanielleRating, 5 stars3 weeks ago

Overall we had a wonderful stay. We got to enjoy being disconnected from the world while not being completely lost. We stayed for two nights and we utilized everything this retreat had to offer. The hot tub, shower, and fishing in the lake were what stood out the most to us and there are a few fish in the pond!

Guest favourite

Home in Rockbridge

4.93 out of 5 average rating, 14 reviews

The Yosemite-A Parkside Retreat - with Party Barn!

GregoryRating, 5 stars2 days ago

We had a fantastic guy’s trip to The Yosemite. The amenities and things to do at the house were plentiful and kept us busy the whole weekend. Several great hikes within 30 minutes. There were also several restaurants, breweries, and wineries close by. Great weekend, thank you!

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Popular amenities for Winterset holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Winterset

Superhost

Home in Logan

4.92 out of 5 average rating, 72 reviews

Peaceful 3 Bedroom Getaway Home

JeannetteRating, 5 stars6 months ago

The house was clean and conviently located. The neighborhood was a little sketchy. We were on a tight budget so it met our needs.

Guest favourite

Home in Carrollton

4.91 out of 5 average rating, 11 reviews

Oak Haven Retreat: Tranquil Stay w/King bed

ErinRating, 5 stars2 weeks ago

Had a great stay at Christine’s!! Beautiful surroundings, big beautiful space in the apartment, and everything was so CLEAN! Nice and relaxing getaway, and I highly recommend!

Guest favourite

Home in Marietta

4.84 out of 5 average rating, 107 reviews

Cole Coffman Garden

BrendaRating, 5 stars3 months ago

Chaos house did not disappoint. Beautiful house with a beautiful view. The deer walking through the yard in the evening was a bonus. It was winter with snow but Chao made sure the driveway was clear and salted so it was not slick. Pictures did not do it justice. Chao went above and beyond to accommodate us. Cant wait to come back, hopeful in the spring!

Guest favourite

Cabin in Rockbridge

4.95 out of 5 average rating, 40 reviews

The Ellwood Box Hop

MirandaRating, 5 stars1 week ago

Beautiful place with everything that you need. Hosts were great and gave plenty of clear instructions and recommendations.

Top guest favourite

Home in Creola

5 out of 5 average rating, 71 reviews

Cozy Home (1 Mile from Ash Cave) in Hocking Hills!

KellyRating, 5 stars6 months ago

Even more amazing than last year! We noticed several renovations / improvements around the property. Everything was well-stocked, clearly-labeled, so well-organized! Kitchen/bathrooms/ linens/kitchen PRISTINE. Fall foliage on-point (last year we were a few weeks too late). The gas grill and solo fire pit are amazing! Thank you Devon for another AMAZING stay and break from the pressures day-to-day life!

Guest favourite