Winterset Holiday Homes from €157: Search Top House Rentals

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

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Our top choices for Winterset holiday homes

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

A single-story house with a garage, a front porch, and a stone foundation.

A modern kitchen with white cabinets, a central island with bar stools, and a dining area with wooden chairs and a table.

A modern kitchen with a central island, bar stools, and a dining area with a view.

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)

10/10

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."

Nickay M.

The price is €280

€280

includes taxes & fees

20 Oct - 21 Oct

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

A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

A modern kitchen with white cabinetry, a central island, and a view to the dining area.

A spacious living area with a large island, dark green sofas, and a flat-screen TV mounted on the wall.

2. 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)

10/10

Exceptional

(16 reviews)

"Great place to stay!"

Elizabeth V.

The price is €425

€425

includes taxes & fees

13 Oct - 14 Oct

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

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

A well-maintained garden with a variety of plants and a stone wall.

A spacious attic room with a brown leather couch, a plaid sofa, a dining table with chairs, and a ceiling fan.

A compact kitchen with a built-in refrigerator and freezer, a window with a view of trees, and a countertop with a coffee maker and a toy car.

3. 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)

9.2/10

Wonderful

(15 reviews)

"Beautiful place to stay and very accommodating host."

Amy K.

The price is €159

€159

includes taxes & fees

1 Nov - 2 Nov

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

A garden with a stream, rocks, and flowers.

A log cabin interior with a sofa, armchairs, a coffee table, and a fireplace.

A white tent-like structure with a clear sky and a calm body of water in the foreground.

A stone fireplace with a fire, surrounded by decorative foliage and ornaments.

4. 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)

10/10

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!!"

Genevieve P.

The price is €189

€189

includes taxes & fees

11 Oct - 12 Oct

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

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

A two-story house with a garage, a covered porch, and a well-maintained lawn.

A living room with a stone fireplace, a flat-screen TV, a wooden coffee table, a gray sofa, and a white armchair.

A living room with a sectional sofa, a coffee table, and a door leading to another room.

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

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

Adel

8.0 out of 10, Very good, (4 reviews)

8.0/10

Very good

(4 reviews)

"The house itself was beautiful. It was very clean and was decorated really cute. There were three bathrooms to go with the four bedrooms, so everyone had their own private space which was really nice. House was in a nice, quiet neighborhood. Would definitely stay here again if we are in the area."

Darla F.

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

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

A hallway with a wooden staircase, a checkered bed, a bathtub, and a framed picture on the wall.

A kitchen with a central island, wooden bar stools, a ceiling fan, and a window with a view.

A covered porch with wicker furniture, columns, and a view of the outdoors.

6. 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)

10/10

Exceptional

(21 reviews)

"Very nice place to stay."

Todd W.

The price is €202

€202

includes taxes & fees

11 Oct - 12 Oct

Spacious Farmhouse beautifully decorated waiting for laughs and memories

A single-story house with a front yard, a mailbox, and a tree.

A wooden deck with a wicker chair and a hot tub.

A modern kitchen with dark cabinets, stainless steel appliances, and a dining area with a marble table and chairs.

A bedroom with a bed, nightstands, a dresser, a window with curtains, and a ceiling light.

7. Farmhouse Oasis

Farmhouse Oasis

Dallas Center

10.0 out of 10, Exceptional, (31 reviews)

10/10

Exceptional

(31 reviews)

"The property was great and would stay again and recommend to family and friends if ciming into town."

Michael D.

The price is €160

€160

includes taxes & fees

12 Oct - 13 Oct

Farmhouse Oasis

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

A bedroom with a bed, a nightstand, a lamp, and two windows with curtains.

A living room with a floral sofa, a wooden coffee table, a patterned rug, a staircase, and a flat-screen TV mounted on the wall.

A house with a covered porch, two bicycles, and a door with a window.

8. 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)

10/10

Exceptional

(19 reviews)

"Loved it, every thing was awesome."

Adam b.

The price is €173

€173

includes taxes & fees

11 Oct - 12 Oct

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

A living room with a sofa, a coffee table, a TV, and a dining area with chairs and a table.

A living room with a dark sofa, a coffee table, and a small side table. There is a kitchen area with white cabinets and a dining table.

A concrete-walled, unfinished basement with a door and a small window.

A kitchen with white cabinets, a stove, and a dishwasher.

9. Adair Hideaway : Quiet Neighborhood - Fenced Yard

Adair Hideaway : Quiet Neighborhood - Fenced Yard

Creston

10.0 out of 10, Exceptional, (11 reviews)

10/10

Exceptional

(11 reviews)

"Nice place"

Dale T.

The price is €205

€205

includes taxes & fees

12 Oct - 13 Oct

Adair Hideaway : Quiet Neighborhood - Fenced Yard

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

A grassy outdoor area with a metal fence, a tree, and a wooden bench.

A bedroom with a bed, a nightstand, a chair, a dresser, and a ceiling fan.

A living room with a red leather sofa, a fireplace, a ceiling fan, and a TV mounted on the wall.

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

•Delightful 5b stay in Paradise!!•

Waukee

9.8 out of 10, Exceptional, (21 reviews)

9.8/10

Exceptional

(21 reviews)

"It was perfect for our family getaway!"

justine p.

The price is €376

€376

includes taxes & fees

25 Oct - 26 Oct

•Delightful 5b stay in Paradise!!•

A bedroom with a bed, curtains, a lamp, and a view of the outdoors.

A dining area with a red table, yellow chairs, and a patterned rug. There are shelves with dishes and a window with a view of trees.

A room with a large window, a white shelf with a potted plant, and a view of a backyard with trees and a wooden fence.

A garden with various plants and a metal structure.

11. • Iconic Lustron home with 2 king beds •

• Iconic Lustron home with 2 king beds •

Windsor Heights

9.2 out of 10, Wonderful, (7 reviews)

9.2/10

Wonderful

(7 reviews)

"We had a week packed full of fun visiting several locations in and around Windsor Heights, Iowa. The place was perfect for our sleeping needs. "

Martina G.

The price is €187

€187

includes taxes & fees

22 Oct - 23 Oct

• Iconic Lustron home with 2 king beds •

A residential neighborhood with a house featuring a stone foundation, a sloped roof, and a front yard with a tree and a small garden.

A kitchen with wooden cabinets, a white stove, and a dining table with chairs.

A single-story house with a front porch, a small attached garage, and a visible chimney.

A room with a foosball table, a bar area with a galaxy-themed mural, and a cityscape painting.

12. Beautiful home minutes from downtown!

Beautiful home minutes from downtown!

Des Moines

9.4 out of 10, Exceptional, (47 reviews)

9.4/10

Exceptional

(47 reviews)

"Very clean and spacious. Good location to downtown. Very comfortable home. Would recommend and would stay again!!"

Melissa W.

The price is €244

€244

includes taxes & fees

14 Oct - 15 Oct

Beautiful home minutes from downtown!

A Staybridge hotel with a brick facade, multiple windows, and a covered entrance.

A hotel room with a bed, bedside tables, a desk, a mirror, a wardrobe, and a bathroom.

A modern office with two desks, computers, and chairs.

A conference room with multiple tables and chairs, large windows, and ceiling lights.

13. Studio Suite w/ Jetted Tub | Free Breakfast!

Studio Suite w/ Jetted Tub | Free Breakfast!

West Des Moines

The price is €157

€157

includes taxes & fees

1 Nov - 2 Nov

Studio Suite w/ Jetted Tub | Free Breakfast!

A modern living room with a grey sectional sofa, a small white table, and a large round rug. There are two windows with floral curtains, a wooden door, and a white ceiling.

A laundry room with a washing machine, dryer, and sink.

A living room with a sofa, TV, and dining area.

A bedroom with a bed, a ceiling fan, and curtains.

14. Beautiful 3-bedroom house with AC in adorable Des Moines

Beautiful 3-bedroom house with AC in adorable Des Moines

Beaverdale

9.6 out of 10, Exceptional, (22 reviews)

9.6/10

Exceptional

(22 reviews)

"Perfect for our needs. The host was very communicative during our stay and check-in and check-out was simple and smooth. Great value and we would stay here again!"

Michael G.

Beautiful 3-bedroom house with AC in adorable Des Moines

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

A two-story house with a stone facade, a large front lawn, and a driveway.

A modern kitchen with dark cabinets, granite countertops, and pendant lighting.

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

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

Waukee

9.6 out of 10, Exceptional, (99 reviews)

9.6/10

Exceptional

(99 reviews)

"Such a fabulous property and located perfected by lots of fun things to do."

Landon B.

The price is €610

€610

includes taxes & fees

19 Oct - 20 Oct

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

A two-story brick house with a front porch, a small garden, and a clear sky.

A bed with a headboard, pillows, and a lamp.

A brick house with a patio, outdoor seating, and a garden.

A modern living room with a flat-screen TV, wooden furniture, a coffee table, and a sofa.

16. Walnut Row, Walk to Valley Junction, Sleeps 10+

Walnut Row, Walk to Valley Junction, Sleeps 10+

West Des Moines

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"I can't say enough about our stay at Walnut place. Very cozy and comfortable. we had more room than we needed. Comfortable beds, close to dining and shopping and most importantly it was CLEAN! If were in the area again, we will certainly stay here again and again!"

Tracie F.

The price is €415

€415

includes taxes & fees

11 Oct - 12 Oct

Walnut Row, Walk to Valley Junction, Sleeps 10+

A two-story house with a garage, a covered porch, and a small attached shed.

A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a coffee maker.

A bedroom with a bed, a large mirror, a framed picture on the wall, and a window with an air conditioning unit.

A modern living room with a grey sofa, a black coffee table, a flat-screen TV, and a wooden floor.

17. Near Downtown ~ 2BDR & Fun Backyard ~ Pet Friendly

Near Downtown ~ 2BDR & Fun Backyard ~ Pet Friendly

Drake

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"It was well organized and clean. The on site parking was super convenient. Host was very response, which I really appreciated. Would stay here again!"

Elvis G.

Near Downtown ~ 2BDR & Fun Backyard ~ Pet Friendly

A hot tub with a purple light, surrounded by outdoor furniture and string lights.

A living room with a TV, wooden flooring, a dining area with chairs and a table, and a hallway with a door leading to another room.

A modern kitchen with white cabinets, a black refrigerator, and a wooden dining table with chairs.

A bedroom with a bed, a desk, a chair, a ceiling fan, and a window.

18. The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10

The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10

Woodland Heights

10.0 out of 10, Exceptional, (77 reviews)

10/10

Exceptional

(77 reviews)

"This was a charming house with space for our group of 6. Very clean throughout with comfortable beds. The location made getting around easy."

Chris M.

The price is €288

€288

includes taxes & fees

27 Oct - 28 Oct

The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

A modern living room with a sectional sofa, a ceiling fan, and large windows with blinds.

A two-story house with a front porch, a tree, and a wooden planter with leaves.

A dining area with a table set for four, a brown armchair, and a bookshelf with various items.

19. The Love Shack | Spacious Family Getaway • 5BR/3BA • 10 Mins to Downtown

The Love Shack | Spacious Family Getaway • 5BR/3BA • 10 Mins to Downtown

Windsor Heights

10.0 out of 10, Exceptional, (32 reviews)

10/10

Exceptional

(32 reviews)

"Perfect spot for our family celebrating a graduation. Host was SO Accommodating."

Tim B.

The price is €455

€455

includes taxes & fees

14 Oct - 15 Oct

The Love Shack | Spacious Family Getaway • 5BR/3BA • 10 Mins to Downtown

A spacious kitchen with wooden cabinets, a central island, and a sliding glass door leading to an outdoor area with a deck and chairs.

A two-story brick house with a front garage, a well-maintained lawn, and a large tree to the left.

A spacious living room with leather sofas, a fireplace, a large TV, and a ceiling fan.

A staircase with a handrail, a door at the bottom, and a painting on the wall.

20. Home w/Hot Tub -Spacious, Quiet Neighborhood Near Des Moines, IA.

Home w/Hot Tub -Spacious, Quiet Neighborhood Near Des Moines, IA.

Clive

10.0 out of 10, Exceptional, (25 reviews)

10/10

Exceptional

(25 reviews)

"The house is nicely equipped and very comfortable. We enjoyed our stay! "

Kristin H.

The price is €412

€412

includes taxes & fees

12 Oct - 13 Oct

Home w/Hot Tub -Spacious, Quiet Neighborhood Near Des Moines, IA.

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.

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Top Winterset Hotel Reviews

Stoney Creek Hotel Des Moines - Johnston

8/10 Good

"2 of the lights in the room were burned out or didn't work and the remote needed new batteries. I reported these issues to the front desk when I checked out."

Daniel 1-night trip

Posted 1 hour ago

Stoney Creek Hotel Des Moines - Johnston

Hotel Fort Des Moines, Curio Collection by Hilton

10/10 Excellent

"Always an amazing experience"

Tim 1-night trip

Posted 2 hours ago

Hotel Fort Des Moines, Curio Collection by Hilton

Wildwood Lodge

10/10 Excellent

"Lovely front desk ladies. Room 101 was a suite and first impression was that it was very clean and the carpet was pristine. The room felt like a premium lodge/cabin and very homey with the heater on for us. Comfy bed. Soft sheets. Good pillows. Breakfast was light and good quality."

John 1-night trip

Posted 1 day ago

Wildwood Lodge