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

Winterset Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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

Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
Winterset
10.0 out of 10, Exceptional, (15 reviews)
"The house in Winterset was perfect in every way. It was beautifully furnished and extremely comfortable. We are so glad we stayed there."
United States
Nickay M.
$279 nightly
The price is $313
Nov 2 - Nov 3
Total with taxes and fees
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
A residential house with a well-maintained lawn, a stone pathway, and a variety of trees and shrubs.

2. 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
9.2 out of 10, Wonderful, (15 reviews)
"Beautiful place to stay and very accommodating host."
United States
Amy K.
$155 nightly
The price is $174
Nov 30 - Dec 1
Total with taxes and fees
1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU
A modern building with a reflective pool in front.

3. No Stairs! Upgraded Executive Suite with Garage

No Stairs! Upgraded Executive Suite with Garage
West Des Moines
9.6 out of 10, Exceptional, (22 reviews)
"Modern new and like a bedroom suite at a hotel but cheaper."
United States
Jon C.
$215 nightly
The price is $241
Nov 1 - Nov 2
Total with taxes and fees
No Stairs! Upgraded Executive Suite with Garage
A bar area with a large 'M' logo on the wall, shelves with bottles, and a counter with bar tools.

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

Middlebrook Retreat, "Luxurious Retreat in Iowa's First Agrihood: Minutes to Des Moines & Steps to C...
Cumming
10.0 out of 10, Exceptional, (16 reviews)
"Great place to stay!"
United States
Elizabeth V.
$360 nightly
The price is $403
Nov 2 - Nov 3
Total with taxes and fees
Middlebrook Retreat, "Luxurious Retreat in Iowa's First Agrihood: Minutes to Des Moines & Steps to C...
A multi-story residential building with a stone facade, a small porch, and a garage.

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

The Cascades at Jordan Creek WDSM/Pool/Tanning/Gym
West Des Moines
10.0 out of 10, Exceptional, (32 reviews)
"Great place to stay! So much better than a hotel room!!"
United States
Janell R.
$219 nightly
The price is $246
Nov 2 - Nov 3
Total with taxes and fees
The Cascades at Jordan Creek WDSM/Pool/Tanning/Gym
A modern kitchen with dark wooden cabinets, a stainless steel stove, and a granite countertop.

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

Adel 4BR/Game Room, Park Nearby & Sleeps 12
Adel
8.4 out of 10, Very good, (5 reviews)
"This suited our needs in preparation of our daughter’s wedding so our immediate family could all be together. Maybe the lawn could’ve been freshly mowed for easier outside games. The house was clean and nice and fit our needs. Thank you."
United States
Anna C.
$493 nightly
The price is $552
Nov 3 - Nov 4
Total with taxes and fees
Adel 4BR/Game Room, Park Nearby & Sleeps 12
A garden with a stream, rocks, and flowers.

7. 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, (415 reviews)
"This place was so incredibly cute. We loved our little getaway for our first anniversary and we had everything we needed and more. Thank you for providing such a great place, we’ll definitely be back!!"
United States
Genevieve P.
$186 nightly
The price is $196
Nov 2 - Nov 3
Total with taxes and fees
Beautiful Rustic Barn just waiting for you to kick back and relax.
A house by a lake with a covered porch and a satellite dish.

8. Cozy pond house nestled in nature waiting for you to enjoy

Cozy pond house nestled in nature waiting for you to enjoy
Osceola
9.8 out of 10, Exceptional, (6 reviews)
"It was more than we expected, a perfect place to get away for some peace and quiet. Super clean and very well equipped with everything we needed. Can't wait to stay again!"
United States
Eric F.
$167 nightly
The price is $175
Nov 2 - Nov 3
Total with taxes and fees
Cozy pond house nestled in nature waiting for you to enjoy
A modern living room with a glass coffee table, a sofa, a TV, and a view of the outdoors.

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

Good Vibes 2-Bedroom Apartment in Waukee - Central Location & Modern Comforts
Waukee
10.0 out of 10, Exceptional, (15 reviews)
"Perfect location, very clean, would definitely stay again! "
United States
Amy P.
$222 nightly
The price is $248
Nov 1 - Nov 2
Total with taxes and fees
Good Vibes 2-Bedroom Apartment in Waukee - Central Location & Modern Comforts
A two-story house with a front porch, a red garage door, and a brick wall with a star emblem.

10. Spacious Farmhouse beautifully decorated waiting for laughs and memories

Spacious Farmhouse beautifully decorated waiting for laughs and memories
New Virginia
10.0 out of 10, Exceptional, (21 reviews)
"Very nice place to stay."
United States
Todd W.
$200 nightly
The price is $210
Nov 1 - Nov 2
Total with taxes and fees
Spacious Farmhouse beautifully decorated waiting for laughs and memories
A single-story house with a front yard, a mailbox, and a tree.

11. Farmhouse Oasis

Farmhouse Oasis
Dallas Center
10.0 out of 10, Exceptional, (32 reviews)
"The property was great and would stay again and recommend to family and friends if ciming into town."
United States
Michael D.
$166 nightly
The price is $174
Nov 2 - Nov 3
Total with taxes and fees
Farmhouse Oasis
A kitchen with wooden cabinets, a stove, and various kitchen appliances.

12. 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, (19 reviews)
"Loved it, every thing was awesome."
United States
Adam b.
$181 nightly
The price is $190
Nov 8 - Nov 9
Total with taxes and fees
The Hen House Country Living with Farm Life Appeal Indianola, IA
A residential complex with multiple apartment buildings, a swimming pool, and outdoor seating areas.

13. Luxe Executive Suite with Attached, Private Garage

Luxe Executive Suite with Attached, Private Garage
West Des Moines
10.0 out of 10, Exceptional, (1 review)
"Great quiet community, close to shopping and restaurants. A nice place to stay with great communication! Will most definitely stay here again in the future. "
United States
Amber T.
$200 nightly
The price is $224
Nov 1 - Nov 2
Total with taxes and fees
Luxe Executive Suite with Attached, Private Garage
A staircase with white railings and a potted plant at the bottom.

14. 2-bedroom apartment close to uptown Creston with WiFi and off street parking.

2-bedroom apartment close to uptown Creston with WiFi and off street parking.
Creston
10.0 out of 10, Exceptional, (10 reviews)
"Great little apartment-like spot for stays on Creston. Easy checkin, clean spot, easy checkout."
United States
Samuel
$170 nightly
The price is $190
Nov 4 - Nov 5
Total with taxes and fees
2-bedroom apartment close to uptown Creston with WiFi and off street parking.
A modern kitchen with a dining area, wooden flooring, and a large window offering a view of the backyard.

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

Spacious 4BR Home • WiFi • Family-Friendly • Waukee
Waukee
10.0 out of 10, Exceptional, (43 reviews)
"A very nice place! Throughly enjoyed my stay there!"
United States
Steven B.
$394 nightly
The price is $441
Nov 21 - Nov 22
Total with taxes and fees
Spacious 4BR Home • WiFi • Family-Friendly • Waukee
A modern building with a reflective pool in front.

16. Updated, Top Floor Suite with Private Garage

Updated, Top Floor Suite with Private Garage
West Des Moines
8.0 out of 10, Very good, (4 reviews)
"We were here to help our daughter move. The apartment is in the same complex which was very helpful. There is plenty to do if here for vacation. The two state parks we went to were fairly close and nice. There are many stores, a mall, and plenty of restaurants within a ten minute drive. Des Moines is 20-30 minutes."
United States
H and P H.
$213 nightly
The price is $239
Nov 1 - Nov 2
Total with taxes and fees
Updated, Top Floor Suite with Private Garage
A breakfast buffet area with a sign indicating free daily breakfast, stainless steel food containers, a coffee machine, and a toaster.

17. Accessible Studio w/ Roll-In Shwr | Free Breakfast

Accessible Studio w/ Roll-In Shwr | Free Breakfast
West Des Moines
$151 nightly
The price is $170
Nov 29 - Nov 30
Total with taxes and fees
Accessible Studio w/ Roll-In Shwr | Free Breakfast
A compact kitchen with a central island, a dining area with a sofa and chairs, and a living room with a couch and a coffee table.

18. Sherman Hill Hide-a-way

Sherman Hill Hide-a-way
Downtown Des Moines
10.0 out of 10, Exceptional, (5 reviews)
"Good stay."
United States
Nick & Heather W.
$154 nightly
The price is $172
Nov 30 - Dec 1
Total with taxes and fees
Sherman Hill Hide-a-way
A residential neighborhood with a house featuring a stone foundation, a sloped roof, and a front yard with a tree and a small garden.

19. Beautiful home minutes from downtown!

Beautiful home minutes from downtown!
Des Moines
9.2 out of 10, Wonderful, (49 reviews)
"Very clean and spacious. Good location to downtown. Very comfortable home. Would recommend and would stay again!!"
United States
Melissa W.
$247 nightly
The price is $277
Nov 6 - Nov 7
Total with taxes and fees
Beautiful home minutes from downtown!
A swimming pool with lounge chairs, a covered seating area, and a multi-story building with balconies.

20. The Carmel/Bold/Massage /Chair Spacious / 3D Wall / Pool / Gym / Tanning Bed

The Carmel/Bold/Massage /Chair Spacious / 3D Wall / Pool / Gym / Tanning Bed
West Des Moines
9.8 out of 10, Exceptional, (31 reviews)
"This VRBO is located in a safe, clean area. The unit itself was clean and comfortable, Everything was as described and communication was great. It was nice to have a private garage. Definitely would stay there again."
United States
Colleen N.
$204 nightly
The price is $228
Nov 1 - Nov 2
Total with taxes and fees
The Carmel/Bold/Massage /Chair Spacious / 3D Wall / Pool / Gym / Tanning Bed
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winterset Hotel Reviews

Wildwood Lodge

Wildwood Lodge

10/10 Excellent
"Clean room. Good bed. Friendly staff."
Lori 1-night trip
Posted 3 hours ago
Wildwood Lodge

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 $276 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.

Explore a world of travel with Expedia

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.