Photo by Tonette Pineda✈⛵🚌🚉🚃🚅🚀

Search Cottages in Winterset

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
28 Rab. I - 30 Rab. I
In two weeks
4 Rab. II - 6 Rab. II
In one month
18 Rab. II - 20 Rab. II
In two months
16 Jum. I - 18 Jum. I

Compare 12 Cottages in Winterset with updated reviews, rates, and availability.

Family-friendly Des Moines Retreat w/ Patio!
Interior

Family-friendly Des Moines Retreat w/ Patio!

3.0 star property
Family-friendly Des Moines Retreat w/ Patio!
Charming Winterset Vacation Rental w/ Yard & Patio
Interior

Charming Winterset Vacation Rental w/ Yard & Patio

3.0 star property
10.0 out of 10, Exceptional, (1)
"We stayed here on a trip for the Knoxville Nationals. Went to the John Wayne Museum, seen the bridges. The house is a nice house, met many locals at the pharmacy-resturaunt in the square downtown, very friendly, ate at several other local spots, all good service and food. The area is quiet and the house in great shape, clean, had plenty of towels and comfortable beds. Would definitely recommend if you need a place in this area. "
Charming Winterset Vacation Rental w/ Yard & Patio
Secluded St Charles Cabin w/ Gas Grill + Fire Pit!
Interior

Secluded St Charles Cabin w/ Gas Grill + Fire Pit!

2.0 star property
Secluded St Charles Cabin w/ Gas Grill + Fire Pit!
Raccoon River Retreat: Indoor Pool & Outdoor Fun!
Interior

Raccoon River Retreat: Indoor Pool & Outdoor Fun!

3.0 star property
Raccoon River Retreat: Indoor Pool & Outdoor Fun!
15 Mi to Dtwn Des Moines: Pet-friendly Waukee Home
Interior

15 Mi to Dtwn Des Moines: Pet-friendly Waukee Home

3.0 star property
15 Mi to Dtwn Des Moines: Pet-friendly Waukee Home
Pet-friendly Des Moines Home w/ Fenced Yard!
Outdoor dining

Pet-friendly Des Moines Home w/ Fenced Yard!

3.0 star property
Pet-friendly Des Moines Home w/ Fenced Yard!
Pet-friendly Urbandale Home ~ 8 Mi to Des Moines!
Interior

Pet-friendly Urbandale Home ~ 8 Mi to Des Moines!

3.0 star property
Pet-friendly Urbandale Home ~ 8 Mi to Des Moines!
1 Mi to Golf: Quiet Waukee Home w/ Fireplace!
Interior

1 Mi to Golf: Quiet Waukee Home w/ Fireplace!

3.0 star property
1 Mi to Golf: Quiet Waukee Home w/ Fireplace!
'the Lodge' Spacious Afton Cabin Near Fishing!
Interior

'the Lodge' Spacious Afton Cabin Near Fishing!

2.0 star property
'the Lodge' Spacious Afton Cabin Near Fishing!
'the Barn' Secluded Home 7 Mi to Afton Lake!
Fireplace

'the Barn' Secluded Home 7 Mi to Afton Lake!

2.0 star property
'the Barn' Secluded Home 7 Mi to Afton Lake!
5-acre Graceland Family Home in West Des Moines
Property grounds

5-acre Graceland Family Home in West Des Moines

3.0 star property
5-acre Graceland Family Home in West Des Moines
1 Mi to Valley Junction: Pet-friendly Iowa Home
Microwave, oven, stovetop, dishwasher

1 Mi to Valley Junction: Pet-friendly Iowa Home

3.0 star property
1 Mi to Valley Junction: Pet-friendly Iowa Home
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.
Don't see what you're looking for?
See all available properties in Winterset
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Winterset

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

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

2.0 star property
9.4 out of 10, Exceptional, (13)
"Good. Close to many places we needed to go"
The price is SAR 375
SAR 1,054 total
includes taxes & fees
7 Apr - 8 Apr
Charming 3-bedroom house with WiFi and fitness room and hot tub, playground
LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!
Fridge, microwave, oven, stovetop

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 SAR 746
SAR 2,155 total
includes taxes & fees
18 Mar - 19 Mar
LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!
NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOLS..WE HAVE IT ALL!
Smart TV, video games, table tennis

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

9.4 out of 10, Exceptional, (52)
"Our large family had a great stay here! There was something for everyone to do! "
The price is SAR 559
SAR 1,655 total
includes taxes & fees
23 Mar - 24 Mar
NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOLS..WE HAVE IT ALL!
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

Why book your cottage in Winterset with Expedia?
Expedia has some wonderful cottages in Winterset, so get set for an unforgettable stay on nature’s doorstep. If you have a budget, choose how much you want to spend and the preferred star rating of your property. Or, use our handy filters to search for cottages with a pool or a hot tub. We’ll help you find the right digs whatever your escape looks like.
How can I find cheap cottages in Winterset?
The quickest way to uncover cheap cottages in Winterset is with Expedia’s handy filter tool. Narrow your search by budget, star rating and amenities to discover awesome rates in a few clicks.