Winterset Vacation Packages 2026 from $490

Winterset flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Sonesta Simply Suites Des Moines

$490

per person

Oct 29 - Nov 1

found 1 hour ago

Roundtrip non-stop flight included

Boston (BOS) to Des Moines (DSM)

A 24-hour gym, free self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. A terrace, a snack bar/deli, and a grocery/convenience store are also on offer.

Wildwood Lodge

$570

per person

Oct 29 - Nov 1

found 1 hour ago

Roundtrip non-stop flight included

Boston (BOS) to Des Moines (DSM)

This hotel features an indoor pool and a gym. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. A business center, a lobby fireplace, and express check-out are also on offer.

Renaissance Des Moines Savery Hotel

Downtown Des Moines

$602

per person

Oct 29 - Nov 1

found 1 hour ago

Roundtrip non-stop flight included

Boston (BOS) to Des Moines (DSM)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Valet parking, a snack bar/deli, and express check-in are also offered.

Hotel Fort Des Moines, Curio Collection by Hilton

Downtown Des Moines

$679

per person

Oct 29 - Nov 1

found 1 hour ago

Roundtrip non-stop flight included

Boston (BOS) to Des Moines (DSM)

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A coffee shop, a snack bar/deli, and a library are also on offer.

Quality Inn & Suites Des Moines - Merle Hay Road

Lovington

$509

per person

Oct 29 - Nov 1

found 1 hour ago

Roundtrip non-stop flight included

Boston (BOS) to Des Moines (DSM)

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. There's an indoor pool on site, and a 24-hour front desk and express check-out are also provided.

Top Winterset hotels deals

Cobblestone Inn & Suites - Winterset, IA

1304 North 4th Avenue Winterset IA

Free Cancellation

Reserve now, pay when you stay

$151 nightly

$170 total

Aug 18 - Aug 19

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like self-serve breakfast and free self parking.

Breakfast included

Pet friendly

Covered Bridge Inn

1312 Cedar Bridge Rd. Winterset IA

Free Cancellation

Reserve now, pay when you stay

$113 nightly

$126 total

Aug 17 - Aug 18

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace and a picnic area are also provided.

Fairfield Inn and Suites by Marriott Des Moines West

7225 Vista Dr West Des Moines IA

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$114 total

Aug 23 - Aug 24

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Breakfast included

Days Inn & Suites by Wyndham Des Moines Airport

1901 Hackley Ave Des Moines IA

Free Cancellation

Reserve now, pay when you stay

$69 nightly

$77 total

Sep 7 - Sep 8

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

Hotel Fort Des Moines, Curio Collection by Hilton

1000 Walnut St Des Moines IA

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$146 total

Sep 6 - Sep 7

Total with taxes and fees

Free WiFi

Restaurant

Stoney Creek Hotel Des Moines - Johnston

5291 Stoney Creek Court Johnston IA

Free Cancellation

Reserve now, pay when you stay

$109 nightly

$122 total

Aug 23 - Aug 24

Total with taxes and fees

This hotel features an outdoor pool and an indoor pool. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Enjoy the gym and free perks like continental breakfast and free self parking.

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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.

Stay near popular Winterset attractions

A red bridge over a calm river with greenery around.

Roseman Bridge

9.6/10 (75 reviews)

You can learn about the history of Winterset with a stop at Roseman Bridge. Make some time to visit the monuments while you're in the area.

See properties

Frequently asked questions

How much are vacation packages to Winterset?

Your travel dreams can all come true in Winterset for only $490. Packages include flights and hotels, so organizing everything should be a cinch. The only thing you'll need to worry about is what amazing attraction you'll head to first.

How long should my Winterset vacation be?

Many people book a hotel for 2 nights in Winterset. But that doesn't mean you're limited to that. How long you hang around comes down to what you want to do during your vacation. If you'd love to discover every part of this impressive place, treat yourself to another couple of nights (or even an extra week!).

Where can I get the best vacation package deals for Winterset?

You can score awesome Winterset package deals with Travelocity. Pick from 400 airlines and 1,000,000 worldwide properties and turn those vacation daydreams into reality.

Why should I purchase my Winterset vacation bundle with Travelocity?

From our 24/7 customer support to our range of fantastic destinations, we're dedicated to fulfilling your travel dreams. All you need to do is to click and book — our Price Match Guarantee will make sure you score the best price.

Will I save money on my Winterset car rental if I book it with my hotel or flight?

You sure can — combine your hotel, car and flight into a Winterset vacation package and you can save plenty. With so much to see and do in and around Winterset, having your own wheels will make exploring a joy. Once you've buckled yourself in, turn up the tunes and make tracks to Adventureland, a well-known attraction roughly 35 mi from Winterset.

Which airport is best for Winterset?

You'll find Des Moines Intl. Airport (DSM) 25 mi northeast of the center of Winterset.

What is there to do in Winterset?

Winterset is overflowing with places to discover, such as The Winterset Stage and Clark Tower. These two popular attractions are on most tourists' itineraries.

Where should I stay when visiting Winterset?

If you're after someplace comfortable to base yourself, consider the Covered Bridge Inn. It's the top pick for many travelers.