Vacation rentals in Winterset

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Top-rated vacation rentals in Winterset

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

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Top guest favorite

Apartment 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 favorite

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 favorite

Villa in Jeromesville

4.93 out of 5 average rating, 301 reviews

Whispering Pines Retreat by Private Lake/ Villa #1

DanielleRating, 5 stars2 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 favorite

Home in South Columbus

4.92 out of 5 average rating, 12 reviews

AG Family Vacation Home

DevonRating, 5 stars1 week ago

I thought the listing was great until the 'ants'... There was water coming up from the floor in the basement, we kept having to mop up the water... The ceiling fan was really wobbly and loud, could not run because we were afraid that it was going to fall from the ceiling Amanuel was a great host, but this was not worth over $1,100.

Top guest favorite

Cabin in Rockbridge

4.98 out of 5 average rating, 193 reviews

Cozy Cottage Escape

AshleighRating, 5 stars1 week ago

This spot was great for our family visit to Hocking Hills. It was clean and had a well equipped kitchen. It was super cute. The kids loved the swing inside and the nearby mini golf course. The property was nice and tucked away. I would definitely stay again in the future!

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What guests are saying

Premier Destination in New Phily - Deerwood Cabin

4.85 out of 5 average rating, 62 reviews1 month ago

Fantastic place to stay! Cristina’s clear instructions and warm, friendly messages made the space feel incredibly welcoming and homey. The living room was much more spacious than I had expected, adding to the overall comfort. I absolutely loved my stay and will definitely be returning!

Cabin in New Philadelphia

What guests are saying

Almas Retreat

4.95 out of 5 average rating, 62 reviews2 weeks ago

I can’t give this place and the host enough stars! I don’t think 5 stars properly covers it. She was always friendly and fast to respond. It was my girls and I anniversary and she set out flowers for her that were beautiful. Now the place, inside is super cute, clean and well setup. We loved that there were board games and movies there. Outside was breathtaking and just what you want for a peaceful getaway. It’s now going to be our go to place when we need a weekend to disconnect from the hustle of everyday life. Truly has beautiful views and relaxing atmosphere.

Tiny home in Logan

What guests are saying

The country cottage: with hot tub!!

4.98 out of 5 average rating, 54 reviews5 months ago

The entire experience from check in to check out was flawless. The Cottage was very clean and comfortable. The kitchen had every thing you could possibly need to cook any meal The gas gril was top quality with even heat distribution and a large cooking surface . The hot tub was a real bonus and enjoyed by all. Rebecca was a very gracious host. She did a great job communicating before and during our stay. She also provided an amazing assortment of snacks and candy that we really enjoyed . We hope to visit the Cottage again next fall. I would highly recommend Rebecca's Cottage for a fun and relaxing get away

Cottage in Quaker City

What guests are saying

Lake Front Paradise - Dock, Lake, & The Views

5 out of 5 average rating, 17 reviews4 months ago

Such a beautiful house. Very well furnished, comfortable and very clean. The surrounding area is peaceful with great view of the lake. The owners are very responsive and communicated with no delay. During our stay, there was a problem with the water and the owners worked tirelessly and spared no expense to solve the issue quickly.

Home in Apple Valley

What guests are saying

Summer’s Breeze Lake House

5 out of 5 average rating, 68 reviews1 week ago

We loved this house. My kids entertained themselves for hours with the pool table, arcade games and jacuzzi. The fire pit was nice to roast marshmallows and relax around. The only thing we could really have a problem with, was the beds had plastic mattress covers under the sheets which made for sweaty, slightly uncomfortable sleeping. ( but we totally understand why they would have them on the mattresses)

Home in Thornville

What guests are saying

The Retreat at Barrs Pond

4.94 out of 5 average rating, 93 reviewstoday

I would highly recommend staying here if you are in the area. Very impressed with the cleanliness and relaxing atmosphere. Beds were very comfortable. Loved drinking my coffee on the front porch swing in the morning. Then was pleasantly surprised by the delicious homemade muffins that were left upon our arrival. I will definitely be back!😊

Cottage in Massillon

What guests are saying

The Mary Cabin

4.87 out of 5 average rating, 39 reviews4 months ago

We had such an amazing stay! We enjoy coming to town quite frequently, and this was our first time staying at Mary’s cabin. I have nothing but excellent things to say, and we will most likely be staying here every single time we come! The hospitality was amazing and everything item we had forgotten was provided. The cleanliness was exceptional as well as the comfort. We cannot wait to come back!

Cabin in Brinkhaven

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Popular amenities for Winterset vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation 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 favorite

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 favorite

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 favorite

Cabin in Rockbridge

4.95 out of 5 average rating, 40 reviews

The Ellwood Box Hop

MirandaRating, 5 stars5 days ago

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

Superhost

Home in Canton

4.91 out of 5 average rating, 11 reviews

Immaculate Home | Private Pool | Pro Football HOF

DanielleRating, 5 stars2 weeks ago

Everything was well accommodating, and we loved the house!!

Top guest favorite

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 favorite