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Winterset Holiday Rentals

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Holiday Rentals in Winterset

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

9.8 out of 10, Exceptional, (47)
"This property was perfect for our family christmas- plenty of things on the property for everyone to do, and close proximity to so many options for all ages"
The price is AU$1,268
includes taxes & fees
13 Feb - 14 Feb
LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!

SO MUCH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!

9.4 out of 10, Exceptional, (46)
"Everything was great and really fun!"
The price is AU$1,088
includes taxes & fees
16 Feb - 17 Feb
SO MUCH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!

SPACIOUS LUXURY- PARTY BARN… PL TBl, PNG PNG, ARCADE, PATIOS. ACCESS TO POOLS!

10.0 out of 10, Exceptional, (56)
"The property was just as described. Perfect place for our staff of over 20 ladies to hang out and reconnect outside the busy office environment. A few of us enjoyed the hot tub and the younger girls really enjoyed the shed! Thank you!! "
The price is AU$1,524
includes taxes & fees
16 Feb - 17 Feb
SPACIOUS LUXURY- PARTY BARN… PL TBl, PNG PNG, ARCADE, PATIOS. ACCESS TO POOLS!

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

9.6 out of 10, Exceptional, (51)
"Our large family had a great stay here! There was something for everyone to do! "
The price is AU$715
includes taxes & fees
10 Feb - 11 Feb
NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOLS..WE HAVE IT ALL!

Comfortable and Spacious 3 Bedroom Home

9.8 out of 10, Exceptional, (36)
"We were in town for a funeral and the location of the property was perfect for our location of activities. House was good in person, as advertised in the pictures. "
Comfortable and Spacious 3 Bedroom Home

Hot Tub, Fenced Yard, Games, Office/Gym + Pets Ok!

9.4 out of 10, Exceptional, (22)
"This property was the best VRBO we've ever stayed at.so far.We came to town for the holidays and found the house comfortable, with plenty of room to relax between gatherings. Every bedroom has a TV, plenty of pillows, room for your things, and a comfortable bed. The only drawback to the house was the stairs. There are stairs everywhere. We will definitely book this house again. As long as no one is on crutches. "
Hot Tub, Fenced Yard, Games, Office/Gym + Pets Ok!

Suburban Oasis with Hot Tub Spa

10.0 out of 10, Exceptional, (14)
"The home was inviting, clean, and the check in and check out process were smooth. I’d definitely recommend this place to others and would stay here again. Thanks for being a great host!! "
Suburban Oasis with Hot Tub Spa

Charming 3-bedroom house with WiFi and fitness room and hot tub, playground

2.0 star property
9.4 out of 10, Exceptional, (10)
"This property has plenty of space. The living room, dinning room and kitchen can accommodate a larger group. Comfortable beds in all the bedrooms. We would book this property again."
The price is AU$445
includes taxes & fees
12 Feb - 13 Feb
Charming 3-bedroom house with WiFi and fitness room and hot tub, playground

Family-Friendly Home Near Airport and Downtown with Plenty of Quality Amenities

10.0 out of 10, Exceptional, (24)
"We came to Des Moines to put on a baby shower. This house was perfect for our family!! Our host communicated with us before, during and after our stay. The house was exactly as described. So many extra touches throughout the entire house. We highly recommend! "
The price is AU$861
includes taxes & fees
9 Feb - 10 Feb
Family-Friendly Home Near Airport and Downtown with Plenty of Quality Amenities

Executive Living 2min to Jordan Creek 6 bed/5 bath near Jordan Creek Mall!

10.0 out of 10, Exceptional, (33)
"Family Christmas for a large group, worked out perfectly. Great communication with owner."
Executive Living 2min to Jordan Creek 6 bed/5 bath near Jordan Creek Mall!

Beautiful home minutes from downtown!

9.2 out of 10, Wonderful, (7)
"This house had everything we needed. The location was within 20 minutes of everything we needed and wanted to do. There’s plenty of room so you’re not on top of each other. The owner was responsive and friendly. We will stay here again when we need to see family. "
The price is AU$465
includes taxes & fees
10 Feb - 11 Feb
Beautiful home minutes from downtown!

The CORN CRIB: Spa - Game Room - BBQ - Office - DOWNTOWN - Sleeps 14

10.0 out of 10, Exceptional, (17)
"Three families came together to enjoy a couple days of togetherness here, and we couldn't have asked for better accommodations. So cozy and comfortable! Hot tub, huge dining room table, game zone, well stocked kitcgen and comfy beds were favorites. Definitely recommend!!"
The price is AU$618
includes taxes & fees
11 Feb - 12 Feb
The CORN CRIB: Spa - Game Room - BBQ - Office - DOWNTOWN - Sleeps 14

Beautiful Rustic Barn just waiting for you to kick back and relax.

10.0 out of 10, Exceptional, (392)
"I can’t say enough good things! This place was everything I was looking for and expecting and more! Cabin was spotless. Linens were provided and fresh. Every box was checked. We had the relaxing weekend we were looking for and are already planning our next trip back to this place! Love love love it!!"
The price is AU$304
includes taxes & fees
10 Feb - 11 Feb
Beautiful Rustic Barn just waiting for you to kick back and relax.

Cozy Waterbury VRBO next to Willow on Grand Events Center and Val Air Ballroom

10.0 out of 10, Exceptional, (11)
"Large modern house, great space both inside and out. Nice fixtures and fittings (couple of minor things need a touch up) but overall wonderful! Comfy living room, beds comfy too. Garden and decking area great space to relax in. Host friendly and super responsive....also able to accommodate extra nights stay."
Cozy Waterbury VRBO next to Willow on Grand Events Center and Val Air Ballroom

Good Vibes 2 Bed Home Centrally Located on Quiet St.

10.0 out of 10, Exceptional, (35)
"Nicely decorated & Clean property. Bathroom needs newer tub surround. Hooks for hanging clothes, towels, & coats, which was nice. Quiet neighborhood. We would stay here again."
Good Vibes 2 Bed Home Centrally Located on Quiet St.

Downtown Skyline Views in Modern Townhome with Rooftop Patios

9.8 out of 10, Exceptional, (17)
"Clean and comfortable. A wonderfully responsive host."
The price is AU$369
includes taxes & fees
9 Feb - 10 Feb
Downtown Skyline Views in Modern Townhome with Rooftop Patios

The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10

10.0 out of 10, Exceptional, (55)
"Stayed 4 nights in town for our daughter’s wedding. Great location. Very nice and clean property. Everything went very smoothly. Highly recommend."
The price is AU$594
includes taxes & fees
17 Feb - 18 Feb
The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10

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

9.8 out of 10, Exceptional, (15)
"We had nice relaxing stay. Watched movies In the theater area and relaxed in the hot tub. Definitely be going back"
The price is AU$704
includes taxes & fees
10 Feb - 11 Feb
Close to Drake/Downtown - Filled With Amenities, Pet Friendly, Hot Tub, Theater!

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

10.0 out of 10, Exceptional, (39)
"We loved this property! It was a lovely, big house for our sports team. The location was great and the neighbors were super friendly. "
The price is AU$869
includes taxes & fees
11 Feb - 12 Feb
Beautiful remodeled historic Drake Univ home minutes from downtown and all metro

Historic Valley Junction Loft

10.0 out of 10, Exceptional, (14)
"This place was so beautiful and the area was very nice, the loft is so quiet and have everything you need in more. The host was very nice and friendly 10/10 for me will be be back soon"
The price is AU$213
includes taxes & fees
2 Mar - 3 Mar
Historic Valley Junction Loft
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 types of properties in Winterset you may be interested in

Covered Bridge Inn

2.5 star property
9.2 out of 10, Wonderful, (648)
"Updates made at Covered Bridge Inn are very welcoming. . Entrance with nice morning coffee,snacks area led to new carpeting in hallway and refreshed room with new bathtub comb, new flooring & decor Hosts provided any request or assistance we needed quickly."
The price is AU$103
includes taxes & fees
10 Feb - 11 Feb
Covered Bridge Inn

Cobblestone Inn & Suites - Winterset, IA

2.5 star property
9.2 out of 10, Wonderful, (607)
"This hotel was amazing. All staff welcome you with a smile and help with any detail. The room was very cozy as well. Breakfast eggs were cold already at 7:15 or so but the food itself tasted great. Winterset ,the surroundings and the people here are so calm and inviting."
The price is AU$161
includes taxes & fees
22 Feb - 23 Feb
Cobblestone Inn & Suites - Winterset, IA

Stoney Creek Hotel Des Moines - Johnston

2.5 star property
9.0 out of 10, Wonderful, (1578)
"The room was a very good balance of comfort, style, and function. The whirlpool was pleasant and it was so quiet and a great environment to relax and unwind in peace"
The price is AU$164
includes taxes & fees
16 Feb - 17 Feb
Stoney Creek Hotel Des Moines - Johnston
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.

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 3 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 Clark Tower 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.