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Top Holiday Rentals in Winterset

LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!

9.8 out of 10, Exceptional, (61)
"Good space and size for larger groups."
The price is £490
includes taxes & fees
20 Aug - 21 Aug
LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!

Luxury 4 bedroom and 2.5 bath home

8.0 out of 10, Very good, (12)
"I was impressed by the entire stay. We had a small problem on the first day and they got it fixed immediately, it was everything I was hoping it was. I would definitely stay here again."
The price is £385
includes taxes & fees
16 Aug - 17 Aug
Luxury 4 bedroom and 2.5 bath home

Comfortable and Spacious 3 Bedroom Home

9.8 out of 10, Exceptional, (55)
"Overall, nice stay. Abundant, clean linens were available, back deck super.nice and Keurig coffee maker with plenty of coffee and tea. "
Comfortable and Spacious 3 Bedroom Home

Walnut Place a Charming Home in Historic Valley Junction area of West Des Moines

9.6 out of 10, Exceptional, (175)
"Beautiful home! Great owners! Ample parking. A few blocks away from the Valley Junction business district. Will stay again. "
Walnut Place a Charming Home in Historic Valley Junction area of West Des Moines

Close to Drake/Downtown - Filled With Amenities, Pet Friendly, Hot Tub, Theater!

9.6 out of 10, Exceptional, (23)
"Grand Daughters 14 Birthday, her friends loved the hot tubtub and Movie Theater. Big stormed rolled through day before, out host sent someone over to get hot top checked and cleaned. Very responsive, and much appreciated "
The price is £435
includes taxes & fees
18 Aug - 19 Aug
Close to Drake/Downtown - Filled With Amenities, Pet Friendly, Hot Tub, Theater!

Recently Remodeled! Charming 2-bedroom bungalow in terrific DSM neighborhood

9.6 out of 10, Exceptional, (4)
"This house and the host were fabulous! Great location and great decor."
Recently Remodeled! Charming 2-bedroom bungalow in terrific DSM neighborhood

Beautiful Clive 3BR Duplex w/Fireplace

7.0 out of 10, Good, (9)
"Great clean "
The price is £351
includes taxes & fees
17 Aug - 18 Aug
Beautiful Clive 3BR Duplex w/Fireplace

NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOLS..WE HAVE IT ALL!

9.4 out of 10, Exceptional, (62)
"Very nice place, great size for our work team in town for training. "
The price is £349
includes taxes & fees
24 Aug - 25 Aug
NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOLS..WE HAVE IT ALL!

The Love Shack: Spacious Family Getaway, 5 bed/3 bath, 10 Minutes from Downtown

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great house for our family to stay and gather between weddings events! Easy to get to and had lots of space to hang out. "
The price is £363
includes taxes & fees
19 Aug - 20 Aug
The Love Shack: Spacious Family Getaway, 5 bed/3 bath, 10 Minutes from Downtown

Bright and Spacious Historic Kingman Blvd 3Bdr #1

7.8 out of 10, Good, (6)
"We had a great stay here. The host was very responsive and was willing to make some accomadations for us. House was clean and a nice space for multiple couples traveling for a weekend wedding."
The price is £185
includes taxes & fees
20 Aug - 21 Aug
Bright and Spacious Historic Kingman Blvd 3Bdr #1

Beautiful remodeled historic Drake Univ home minutes from downtown and all metro

9.8 out of 10, Exceptional, (47)
"Everything was great. Anything we needed was there only thing we had a problem was there were ants in the kitchen and bathrooms, But other than that the stay was comfortable and great. "
The price is £626
includes taxes & fees
17 Aug - 18 Aug
Beautiful remodeled historic Drake Univ home minutes from downtown and all metro

Vibrant Downtown Condo with Skywalk Access #1

9.0 out of 10, Wonderful, (4)
"Place was very neat & tidy. Quiet apartment building. Great location! "
The price is £125
includes taxes & fees
25 Aug - 26 Aug
Vibrant Downtown Condo with Skywalk Access #1

Vibrant Downtown Condo with Skywalk Access #5

8.0 out of 10, Very good, (9)
"Love staying here"
The price is £126
includes taxes & fees
26 Aug - 27 Aug
Vibrant Downtown Condo with Skywalk Access #5

Beautiful home minutes from downtown!

9.2 out of 10, Wonderful, (15)
"My family and I had a nice stay. The house was spot on to the description, and you can tell the host goes above and beyond to make guests feel comfortable. "
The price is £206
includes taxes & fees
17 Aug - 18 Aug
Beautiful home minutes from downtown!

Lovely 2-bedroom apartment in Sherman Hill-4

8.2 out of 10, Very good, (16)
"Clean and worked well for our stay in Des Moines"
The price is £134
includes taxes & fees
17 Aug - 18 Aug
Lovely 2-bedroom apartment in Sherman Hill-4

Nice 2 bedroom in Sherman Hill-8

9.0 out of 10, Wonderful, (16)
"We wanted a quick getaway to see a show at Hoyt Sherman and visit our favorite brewery, Lua for dinner and drinks and this couldn’t have been a more perfect location at an affordable rate! So many great places nearby and nice to be able to walk and not worry about parking for the show. Highly recommend for a small group wanting to take in Sherman Hill area."
The price is £134
includes taxes & fees
24 Aug - 25 Aug
Nice 2 bedroom in Sherman Hill-8

Upscale 1BR Downtown apt with Hot tub!!

8.8 out of 10, Excellent, (9)
"We were very surprised and impressed by this place! Absolutely incredible value for the location. Check in and out was a breeze too! Highly recommended..."
The price is £750
includes taxes & fees
24 Aug - 25 Aug
Upscale 1BR Downtown apt with Hot tub!!

Downtown Skyline Views in Modern Townhome with Rooftop Patios

10.0 out of 10, Exceptional, (31)
"We had a great time and an easy stay walking distance from several great spots."
The price is £240
includes taxes & fees
24 Aug - 25 Aug
Downtown Skyline Views in Modern Townhome with Rooftop Patios

Serenity Heights - Peaceful Country Acres with beautiful view in every direction

10.0 out of 10, Exceptional, (79)
"Beautiful property that worked perfectly for our family (ranging in age for newborn to 65 yrs old)! We will definitely book again!"
Serenity Heights - Peaceful Country Acres with beautiful view in every direction

AMAZING & A PARTY BARN… HOT TUB, PL TBl, PNG PNG, & ARCADE! ACCESS TO POOLS!

9.8 out of 10, Exceptional, (63)
"Our stay was an amazing experience and the host was very helpful with any and all questions we had. I would recommend this host/property to any of my family or friends!"
The price is £664
includes taxes & fees
17 Aug - 18 Aug
AMAZING & A PARTY BARN… HOT TUB, PL TBl, PNG PNG, & ARCADE! ACCESS TO POOLS!
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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Top Winterset Hotel Reviews

Frequently asked questions

Can I find holiday rentals in Winterset?

Yes, there are holiday rentals close to the most popular sights in Winterset, or you can select a more secluded option if you're looking for a relaxing stay. Winterset is known for its shopping and restaurants. Make sure you have time to check out the bars while you're in the area.

What are some of the best holiday rentals that Winterset has to offer?

LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!: This holiday home rental outside of Winterset is located next to a golf course, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Winterset?

With 4 Expedia holiday rentals, you're guaranteed to find just the right place for your Winterset stay.

What can I see and do in Winterset?

Cultural attractions include John Wayne Birthplace Museum and The Winterset Stage, whereas Pammel State Park is one spot to enjoy nature. While here, Madison County Courthouse and Cedar Bridge are other places worth a visit.

What are holiday rentals like in Winterset?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winterset. Holiday rentals feature extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for family trips or small group gatherings.