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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Winterset holiday homes

Fridge, microwave, oven, stovetop

The Hen House Country Living with Farm Life Appeal Indianola, IA

The Hen House Country Living with Farm Life Appeal Indianola, IA
Indianola
10.0 out of 10, Exceptional, (13 reviews)
"This house has everything you can need along with amazing hosts! The house is cozy and comfortable with plenty of space to spread out and relax. Lori does a great job communicating with you and is so friendly! We will be staying again!"
United States
Krissy M.
The price is £143
includes taxes & fees
20 Apr - 21 Apr
The Hen House Country Living with Farm Life Appeal Indianola, IA
Property grounds

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

Beautiful Rustic Barn just waiting for you to kick back and relax.
NEW VIRGINIA
10.0 out of 10, Exceptional, (408 reviews)
"Everything was wonderful "
United States
Don and Kris M.
The price is £129
includes taxes & fees
21 Apr - 22 Apr
Beautiful Rustic Barn just waiting for you to kick back and relax.
Exterior

1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU

1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU
West Des Moines
8.8 out of 10, Excellent, (6 reviews)
"The location was absolutely perfect being on the very edge of Des Moines. It was quiet, no city distractions and very private. The space was very clean and Clayton was very friendly and personable. We definitely would stay again!"
United States
Melissa C.
The price is £134
includes taxes & fees
22 Apr - 23 Apr
1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU
Property grounds

Farmhouse Oasis

Farmhouse Oasis
Dallas Center
10.0 out of 10, Exceptional, (21 reviews)
"This was a beautiful rural setting. We enjoyed our stay very much. "
United States
Norman Z.
The price is £129
includes taxes & fees
20 Apr - 21 Apr
Farmhouse Oasis
Fridge, microwave, oven, stovetop

The Love Shack | Spacious Family Getaway • 5BR/3BA • 10 Mins to Downtown

The Love Shack | Spacious Family Getaway • 5BR/3BA • 10 Mins to Downtown
Windsor Heights
10.0 out of 10, Exceptional, (21 reviews)
"The Love Shack was a wonderful place for our family to gather for the weekend and wedding plan! The home was spotless, all the beds were comfy and it had everything you needed for a nice stay. Highly recommend! "
United States
Missy
The price is £344
includes taxes & fees
20 Apr - 21 Apr
The Love Shack | Spacious Family Getaway • 5BR/3BA • 10 Mins to Downtown
Exterior

Beautiful home minutes from downtown!

Beautiful home minutes from downtown!
Des Moines
9.2 out of 10, Wonderful, (31 reviews)
"What a great place to stay! "
United States
Annie P.
The price is £202
includes taxes & fees
21 Apr - 22 Apr
Beautiful home minutes from downtown!
Interior

Spacious 4BR Home • WiFi • Family-Friendly • Waukee

Spacious 4BR Home • WiFi • Family-Friendly • Waukee
Waukee
10.0 out of 10, Exceptional, (28 reviews)
"Enjoyed our stay. Especially appreciated the snow removal! Will stay here again! "
United States
Meredith B.
The price is £293
includes taxes & fees
20 Apr - 21 Apr
Spacious 4BR Home • WiFi • Family-Friendly • Waukee
Fridge, microwave, oven, stovetop

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

LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!
Waukee
9.6 out of 10, Exceptional, (83 reviews)
"Great house for a weekend of family get togethers! Had something for all ages and was so well stocked with everything we could have needed! "
United States
Keri R.
The price is £376
includes taxes & fees
20 Apr - 21 Apr
LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!
Interior

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

NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOL. WE HAVE IT ALL!
Urbandale
9.4 out of 10, Exceptional, (78 reviews)
"Excellent communication lots of amenities. We were very happy with our stay."
United States
Shannon W.
The price is £335
includes taxes & fees
20 Apr - 21 Apr
NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOL. WE HAVE IT ALL!
Dining

•Delightful 5b stay in Paradise!!•

•Delightful 5b stay in Paradise!!•
Waukee
9.8 out of 10, Exceptional, (21 reviews)
"It was perfect for our family getaway!"
United States
justine p.
The price is £216
includes taxes & fees
20 Apr - 21 Apr
•Delightful 5b stay in Paradise!!•
Smart TV

• Lively Cottage 2 King Beds 4 Bed 2 Bath •

• Lively Cottage 2 King Beds 4 Bed 2 Bath •
Indianola
9.4 out of 10, Exceptional, (18 reviews)
"Had a great stay, will come back!"
United States
Spring A.
The price is £182
includes taxes & fees
6 May - 7 May
• Lively Cottage 2 King Beds 4 Bed 2 Bath •
Smart TV, fireplace, video games, ping pong

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

SO MUCH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!
Woodland Heights
9.4 out of 10, Exceptional, (75 reviews)
"The place was great for our family Christmas. Plenty of beds and all were comfortable. The teens loved the game area and having their bedroom there was perfect. We cooked all meals there and had plenty of kitchen supplies to use. Very well stocked for anything we needed. We even utilized the pool that was available- it was warm and comfortable even in the cold weather. "
United States
Julie H.
The price is £376
includes taxes & fees
20 Apr - 21 Apr
SO MUCH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!
TV

Beautiful 3-bedroom house with AC in adorable Des Moines

Beautiful 3-bedroom house with AC in adorable Des Moines
Beaverdale
9.6 out of 10, Exceptional, (7 reviews)
"Great location close to friends. Hosts were great with awesome communication. "
United States
Karen G.
The price is £198
includes taxes & fees
10 May - 11 May
Beautiful 3-bedroom house with AC in adorable Des Moines
Outdoor dining

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

The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10
Woodland Heights
10.0 out of 10, Exceptional, (73 reviews)
"Clean, comfortable, responsive host! Will stay again."
United States
Paul R.
The price is £258
includes taxes & fees
3 May - 4 May
The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10
Smart TV, offices

Roomy 4BR by Drake Sleeps 13 HUGE yard

Roomy 4BR by Drake Sleeps 13 HUGE yard
Drake
7.0 out of 10, Good, (9 reviews)
"Good"
United States
Laurie P.
The price is £223
includes taxes & fees
20 Apr - 21 Apr
Roomy 4BR by Drake Sleeps 13 HUGE yard
Terrace/patio

Urban Farmer House

Urban Farmer House
Greater South Side
8.4 out of 10, Very good, (38 reviews)
"Nice place for the family! "
United States
Brandon G.
The price is £257
includes taxes & fees
20 Apr - 21 Apr
Urban Farmer House
Terrace/patio

Spacious 4-bedroom house central to Des Moines near Drake Univ. Fenced yard

Spacious 4-bedroom house central to Des Moines near Drake Univ. Fenced yard
Drake
9.8 out of 10, Exceptional, (10 reviews)
"Loved your place RyanThanks for adding to a wonderful family get together"
United States
Dan V.
The price is £355
includes taxes & fees
20 Apr - 21 Apr
Spacious 4-bedroom house central to Des Moines near Drake Univ. Fenced yard
3 bedrooms, desk, iron/ironing board, travel cot

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

Serenity Heights - Peaceful Country Acres with beautiful view in every direction
Osceola
10.0 out of 10, Exceptional, (84 reviews)
"The property was clean, cozy and well appointed. Heather was very accommodating when we arrived a day late due to the weather. The views were spectacular as well, even in the winter. This was the best VRBO I've had the pleasure to stay at and we will be back next hunting season."
United States
Patricia S.
The price is £240
includes taxes & fees
30 Apr - 1 May
Serenity Heights - Peaceful Country Acres with beautiful view in every direction
Smart TV

The Cactus House: A Boho Western Single Family Home Just South of Downtown DSM

The Cactus House: A Boho Western Single Family Home Just South of Downtown DSM
Des Moines
The price is £176
includes taxes & fees
29 Apr - 30 Apr
The Cactus House: A Boho Western Single Family Home Just South of Downtown DSM
TV

Cozy Bungalow Retreat

Cozy Bungalow Retreat
Greater South Side
The price is £156
includes taxes & fees
27 Apr - 28 Apr
Cozy Bungalow Retreat
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

Sonesta Simply Suites Des Moines

Sonesta Simply Suites Des Moines

10/10 Excellent
"Great as always. Would highly recommended. Simply but comfortably posch. Perfect combo of value for your money. Staff is exceptional"
Lennard 1-night trip
Posted 15 hours ago
Sonesta Simply Suites Des Moines

Find out more about Winterset

Winterset Holiday Homes information

Number of reviews
962
Accommodation
172 Holiday Homes
Lowest Price
£129
Highest Price
£376