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
7 Feb - 9 Feb
In two weeks
14 Feb - 16 Feb
In one month
28 Feb - 2 Mar
In two months
28 Mar - 30 Mar

Compare 13 Cottages in Winterset with updated reviews, rates, and availability.

Family-friendly Des Moines Retreat w/ Patio!
Living area

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
Exterior

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!
Property grounds

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!
Exterior

Raccoon River Retreat: Indoor Pool & Outdoor Fun!

3.0 star property
Raccoon River Retreat: Indoor Pool & Outdoor Fun!
Pet-friendly Urbandale Home ~ 8 Mi to Des Moines!
Exterior

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

3.0 star property
Pet-friendly Urbandale Home ~ 8 Mi to Des Moines!
'the Barn' Secluded Home 7 Mi to Afton Lake!
Exterior

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

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

'the Lodge' Spacious Afton Cabin Near Fishing!

2.0 star property
'the Lodge' Spacious Afton Cabin Near Fishing!
Pet-friendly Des Moines Home w/ Fenced Yard!
Living area

Pet-friendly Des Moines Home w/ Fenced Yard!

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

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

3.0 star property
15 Mi to Dtwn Des Moines: Pet-friendly Waukee Home
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!
5-acre Graceland Family Home in West Des Moines
Outdoor spa tub

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
Property grounds

1 Mi to Valley Junction: Pet-friendly Iowa Home

3.0 star property
1 Mi to Valley Junction: Pet-friendly Iowa Home
Cozy Home w/ Fireplace, Walk to Dining & Shopping
Living area

Cozy Home w/ Fireplace, Walk to Dining & Shopping

3.0 star property
Cozy Home w/ Fireplace, Walk to Dining & Shopping
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

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

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 AED 1,282
AED 2,575 total
includes taxes & fees
3 Mar - 4 Mar
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!!
Game room

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 AED 1,025
AED 2,246 total
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!
Game room

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

10.0 out of 10, Exceptional, (55)
" Bedrooms, bathrooms, and living space were perfect for a large family get together. House is stocked with little extras to help make your stay perfect. The hot tub was not working and the sink in the party barn was out of order, but otherwise fantastic!"
The price is AED 1,465
AED 3,521 total
includes taxes & fees
2 Mar - 3 Mar
SPACIOUS LUXURY- PARTY BARN… PL TBl, PNG PNG, ARCADE, PATIOS. 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.

Frequently asked questions

Why book your cottage in Winterset with Expedia?
We think that vacays should be simple, so if you’re chasing cottages in Winterset at a competitive price, Expedia delivers. Keep the budget in check and select a cheap option surrounded by wilderness, or splurge on an upmarket cottage to pamper your loved ones.
How can I find cheap cottages in Winterset?
With Expedia’s useful filter tool, comparing cheap cottages in Winterset is a breeze. To find accommodations that are very pocket friendly, narrow down your search by amenities, budget and star rating.