Winterset Vacation Rentals from $164: Search Short-Term Rentals

A red covered bridge over a calm river, surrounded by lush greenery and trees.

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Our top choices for Winterset vacation rentals

A deck with a table and chairs, surrounded by a wooden deck and a white railing.

1. Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset

Winterset

Nickay M.

$271 nightly

Nov 30 - Dec 1

Total with taxes and fees

2. Middlebrook Retreat, "Luxurious Retreat in Iowa's First Agrihood: Minutes to Des Moines & Steps to C...

Cumming

Elizabeth V.

$395 nightly

Nov 15 - Nov 16

Total with taxes and fees

A multi-story residential building with a stone facade, a small porch, and a garage.

3. The Cascades at Jordan Creek WDSM/Pool/Tanning/Gym

West Des Moines

Janell R.

$215 nightly

Nov 16 - Nov 17

Total with taxes and fees

A modern building with a reflective pool in front.

4. No Stairs! Upgraded Executive Suite with Garage

West Des Moines

Jon C.

$213 nightly

Nov 30 - Dec 1

Total with taxes and fees

A garden with a stream, rocks, and flowers.

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

NEW VIRGINIA

Genevieve P.

$191 nightly

Nov 16 - Nov 17

Total with taxes and fees

A kitchen with wooden cabinets, a stove, and various kitchen appliances.

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

Indianola

Adam b.

$173 nightly

Nov 15 - Nov 16

Total with taxes and fees

A residential house with a well-maintained lawn, a stone pathway, and a variety of trees and shrubs.

7. 1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU

West Des Moines

Amy K.

$147 nightly

Nov 30 - Dec 1

Total with taxes and fees

A modern kitchen with dark wooden cabinets, a stainless steel stove, and a granite countertop.

8. Adel 4BR/Game Room, Park Nearby & Sleeps 12

Adel

Lisa R.

$328 nightly

Nov 16 - Nov 17

Total with taxes and fees

A spacious living room with a sofa, a dining table, and a large window offering a view of the outdoors.

9. Modern Luxury West Des Moines Condo

West Des Moines

Melissa H.

$292 nightly

Nov 30 - Dec 1

Total with taxes and fees

A modern kitchen with a dining area, wooden flooring, and a large window offering a view of the backyard.

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

Waukee

Steven B.

$333 nightly

Nov 21 - Nov 22

Total with taxes and fees

A modern living room with a glass coffee table, a sofa, a TV, and a view of the outdoors.

11. Good Vibes 2-Bedroom Apartment in Waukee - Central Location & Modern Comforts

Waukee

Amy P.

$210 nightly

Nov 13 - Nov 14

Total with taxes and fees

A house with a swimming pool, a covered patio, and a stone chimney.

12. Wooded Views | King Bed | No Stairs

West Des Moines

Emily R.

$212 nightly

Nov 30 - Dec 1

Total with taxes and fees

A modern kitchen with stainless steel appliances, dark cabinetry, and a granite countertop.

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

Waukee

Jenny B.

$569 nightly

Nov 15 - Nov 16

Total with taxes and fees

A two-story residential building with a front porch, a street lamp, and a well-maintained lawn.

14. 3-bedroom End-Unit Townhome in beautiful West Des Moines

West Des Moines

Kyan L.

$277 nightly

Nov 13 - Nov 14

Total with taxes and fees

A spacious kitchen with white cabinetry, a granite countertop, and a large island.

15. AMAZING & A PARTY BARN… HOT TUB, PL TBl, PNG PNG, & ARCADE! ACCESS TO POOLS!

West Des Moines

Cindy H.

$786 nightly

Nov 16 - Nov 17

Total with taxes and fees

A modern house with a stone pillar, a front door with a glass panel, a bench, and a small garden.

16. Convenient functional quiet 5 bedroom 3 bath home in Clive.

Clive

Anonymous traveler

$652 nightly

Nov 13 - Nov 14

Total with taxes and fees

A dining room with a wooden table, chairs, a bench, a chandelier, and a potted plant.

17. •Delightful 5b stay in Paradise!!•

Waukee

justine p.

$379 nightly

Nov 22 - Nov 23

Total with taxes and fees

A two-story house with a front porch, a red garage door, and a brick wall with a star emblem.

18. Spacious Farmhouse beautifully decorated waiting for laughs and memories

New Virginia

Todd W.

$191 nightly

Nov 13 - Nov 14

Total with taxes and fees

A modern kitchen with white cabinets, stainless steel appliances, and a central island.

19. Peaceful Modern Studio in Prime Location

Waukee

$155 nightly

Nov 16 - Nov 17

Total with taxes and fees

A residential complex with multiple apartment buildings, a swimming pool, and outdoor seating areas.

20. Luxe Executive Suite with Attached, Private Garage

West Des Moines

Amber T.

$201 nightly

Nov 30 - Dec 1

Total with taxes and fees

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Find vacation rentals that suit your style

Top Winterset Hotel Reviews

A hotel entrance with a stone facade, a sign above the entrance, and a covered walkway.

Cobblestone Inn & Suites - Winterset, IA

Winterset

10/10 Excellent

Anonymous traveler

A covered outdoor area with a wooden ceiling and brick pillars, overlooking a parking lot with cars and a distant landscape.

Covered Bridge Inn

Winterset

10/10 Excellent

We didn't arrive till nearly 1am but they came right up to the desk when we rang the bell. Very friendly. The room was clean and larger than many Hamptons I've been in. The beds were comfortable, there was a coffee pot, shampoo and blow dryer, desk, side chair, and even a free breakfast which I don't always expect to see in a Super 8. It just felt very comfortable. We were there to go to the State Fair and the drive from Winterset to Des Moines was through pretty countryside.

An indoor swimming pool with a 30 ft depth sign, a reception area, and a 'No Lifeguard' warning sign.

Drury Inn & Suites West Des Moines

West Des Moines

10/10 Excellent

Ann

A modern lobby with a sofa, chairs, a lamp, and a wall with a floral pattern.

Sleep Inn Waukee-West Des Moines

Waukee

10/10 Excellent

Janet

A modern hotel with a glass facade, a covered entrance, and a landscaped area.

Hyatt Place West Des Moines Jordan Creek

West Des Moines

10/10 Excellent

The room was excellent…clean, spacious, and modern. It was nice to have a little sectional for our family to lounge on instead of always being on the beds. Beds were comfortable…down pillows and comforter. Rooms were nice and quiet! I couldn't ever hear other doors closing or people above us. The breakfast was complimentary and was delicious! My kids loved the French toast! It’s too bad there wasn’t a hot tub but the pool area was nice and warm. The kids swam forever because the water was...

Melissa

A sunroom with a glass ceiling, wicker furniture, and potted plants.

Baymont by Wyndham Des Moines Airport

Southwestern Hills

10/10 Excellent

Andrew

An outdoor seating area with yellow chairs and a colorful sofa, a fire pit, and a wooden ceiling with hanging lights.

Home2 Suites by Hilton Des Moines at Drake University

Drake

10/10 Excellent

Tricia

A hotel lobby with a bar area, seating, and a television.

Hampton Inn & Suites West Des Moines/SW Mall Area

West Des Moines

10/10 Excellent

Roger

A modern lounge area with a grey sofa, red chairs, and round tables.

Tru By Hilton Grimes Des Moines

Grimes

10/10 Excellent

Kelly

A spacious indoor area with multiple seating arrangements, including tables and chairs, and a large window providing a view of the outdoors.

MainStay Suites Waukee - West Des Moines

Waukee

10/10 Excellent

James

A spacious lobby with high ceilings, large windows, and a chandelier.

Hotel Fort Des Moines, Curio Collection by Hilton

Downtown Des Moines

10/10 Excellent

This is one of the nicest hotels I’ve ever stayed at. Absolutely beautiful historic building with a grand scale and fully updated modern rooms. The design and comfort is impeccable. Large room and bathroom, but not so large that it isn’t cozy. Perfect in my opinion. The onsite dining options are fantastic for world class breakfast lunch and dinner at very reasonable prices. And the coffee is amazing. There were a couple of quirks in the room—the sound of trickling water whenever the ac turned...

David Morrow

A small, single-story building with a flat roof and a large glass door. There are two potted plants on either side of the entrance, and a small trash can to the right.

Stuart Motor Lodge

Stuart

10/10 Excellent

This was a hidden gem on our cross country travels. Weather forced us off the interstate and most of the rooms in the area were full. We took a chance and were very pleased with our stay. It’s not fancy but it was very clean, updated with a large bathroom. While there wasn’t a breakfast the McDonalds was right across the street so we could grab our smoothies and morning latte on our way out of town. We wouldn’t hesitate to stay again.

Anonymous traveler

A modern hotel lobby with a round coffee table, sofas, and a TV mounted on the wall.

Homewood Suites by Hilton Des Moines Airport

Des Moines

10/10 Excellent

Theodore

Find out more about Winterset

Everything you need to know about Winterset vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winterset vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winterset vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winterset vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winterset. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winterset in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $164 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winterset rentals

At Expedia, we put the best Winterset vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winterset rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winterset vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winterset. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find vacation rentals in Winterset?

Yes, you can find vacation rentals in Winterset close to Rotary Hedge Maze, or you can choose a secluded option if you want 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 vacation rentals in Winterset?

SO MUCH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!: Visitors like this Winterset vacation home rental. It offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Winterset?

With 5 Expedia vacation rentals, you're sure 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, Clark Tower and Cedar Bridge are other places worth a visit.

What are vacation rentals like in Winterset?

Vacation rentals are private properties you can stay in for several days or longer in Winterset. Vacation rentals feature amenities like laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for family trips or small group gatherings.

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