hogback covered bridge, summer

Winterset Vacation Rentals

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Our top choices for Winterset vacation rentals

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, (7 reviews)
"The house was absolutely gorgeous! It was very comfortable and had everything we needed. I would most definitely stay here again!"
United States
Heather G.
$321 nightly
The price is $360
Jun 15 - Jun 16
Total with taxes and fees
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset

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, (409 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.
$163 nightly
The price is $171
Jun 14 - Jun 15
Total with taxes and fees
Beautiful Rustic Barn just waiting for you to kick back and relax.

Sherman Hill Hide-a-way

Sherman Hill Hide-a-way
Downtown Des Moines
10.0 out of 10, Exceptional, (4 reviews)
"Good stay."
United States
Nick & Heather W.
$148 nightly
The price is $165
Jun 15 - Jun 16
Total with taxes and fees
Sherman Hill Hide-a-way

Cozy pond house nestled in nature waiting for you to enjoy

Cozy pond house nestled in nature waiting for you to enjoy
Osceola
9.4 out of 10, Exceptional, (3 reviews)
"Very clean and really nice place. The host is professional and kind. I would definitely stay again."
United States
Mike
$160 nightly
The price is $168
Jul 8 - Jul 9
Total with taxes and fees
Cozy pond house nestled in nature waiting for you to enjoy

Modern Boho Townhome w/Hidden Reading Nook Near Downtown Des Moines!

Modern Boho Townhome w/Hidden Reading Nook Near Downtown Des Moines!
Des Moines
10.0 out of 10, Exceptional, (3 reviews)
"Such a cute townhouse and was perfect for our weekend away! The reading nook was so cozy. "
United States
Kylie F.
$195 nightly
The price is $218
Jun 15 - Jun 16
Total with taxes and fees
Modern Boho Townhome w/Hidden Reading Nook Near Downtown Des Moines!

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, (13 reviews)
"We loved it "
United States
Adam b.
$181 nightly
The price is $190
Jun 24 - Jun 25
Total with taxes and fees
The Hen House Country Living with Farm Life Appeal Indianola, IA

Historic Valley Junction Loft

Historic Valley Junction Loft
West Des Moines
9.6 out of 10, Exceptional, (31 reviews)
"What a perfect place for relaxation. A great location. The place was clean and the host was readily available for any questions! "
United States
Jenni S.
$124 nightly
The price is $139
Jun 15 - Jun 16
Total with taxes and fees
Historic Valley Junction Loft

A Charming Home Minutes to Downtown, Zoo, & Airport with Hidden Reading Nook!

A Charming Home Minutes to Downtown, Zoo, & Airport with Hidden Reading Nook!
Indianola Hills
10.0 out of 10, Exceptional, (24 reviews)
"Great place!"
United States
Kenneth M.
$191 nightly
The price is $214
Jun 14 - Jun 15
Total with taxes and fees
A Charming Home Minutes to Downtown, Zoo, & Airport with Hidden Reading Nook!

The Cactus House: A Boho Western Single Family Home Just South of Downtown DSM

The Cactus House: A Boho Western Single Family Home Just South of Downtown DSM
Des Moines
$195 nightly
The price is $218
Jun 23 - Jun 24
Total with taxes and fees
The Cactus House: A Boho Western Single Family Home Just South of Downtown DSM

Sleepover | Magnificent Studio & Gym - Des Moines

Sleepover | Magnificent Studio & Gym - Des Moines
Drake
9.4 out of 10, Exceptional, (3 reviews)
"Stayed for my daughter’s graduation from Drake University. Location was perfect!"
United States
Gerda B.
$176 nightly
The price is $199
Jun 14 - Jun 15
Total with taxes and fees
Sleepover | Magnificent Studio & Gym - Des Moines

Walkable DSM Gem, Mins to Drake & Ingersoll Ave

Walkable DSM Gem, Mins to Drake & Ingersoll Ave
Woodland Heights
$233 nightly
The price is $260
Jun 30 - Jul 1
Total with taxes and fees
Walkable DSM Gem, Mins to Drake & Ingersoll Ave

A Private Boho-Modern Stay Minutes to Downtown w/ KING Bed and Hidden Nook!

A Private Boho-Modern Stay Minutes to Downtown w/ KING Bed and Hidden Nook!
Indianola Hills
10.0 out of 10, Exceptional, (16 reviews)
"Convenient location. Responsive owners"
United States
Juli G.
$195 nightly
The price is $218
Jun 15 - Jun 16
Total with taxes and fees
A Private Boho-Modern Stay Minutes to Downtown w/ KING Bed and Hidden Nook!

Sleepover | Impressive Studio and Gym - Des Moines

Sleepover | Impressive Studio and Gym - Des Moines
Drake
10.0 out of 10, Exceptional, (3 reviews)
"Easy access to drake university was great"
United States
Gerardo
$176 nightly
The price is $199
Jun 14 - Jun 15
Total with taxes and fees
Sleepover | Impressive Studio and Gym - Des Moines

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, (74 reviews)
"Clean, comfortable, responsive host! Will stay again."
United States
Paul R.
$329 nightly
The price is $369
Jun 14 - Jun 15
Total with taxes and fees
The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10

Little Italy in DSM: 2 Bed 1 Bath Upgraded Townhome w/King Bed & Reading Nook

Little Italy in DSM: 2 Bed 1 Bath Upgraded Townhome w/King Bed & Reading Nook
Des Moines
9.6 out of 10, Exceptional, (4 reviews)
"Great property if you are racing the 70.3. Perfect location, quiet neighborhood, easy access to downtown. Very clean!"
United States
Karen N.
$191 nightly
The price is $214
Jun 14 - Jun 15
Total with taxes and fees
Little Italy in DSM: 2 Bed 1 Bath Upgraded Townhome w/King Bed & Reading Nook

Beautiful 2BR N of Grand near Downtown

Beautiful 2BR N of Grand near Downtown
North of Grand
8.0 out of 10, Very Good, (2 reviews)
"Great place, clean, organized, well maintained and the hosts have made it a comfortable cozy welcoming space. So well stocked with everything you need to make it easy to be away from home. Great location."
United States
Michael B.
$263 nightly
The price is $279
Jun 22 - Jun 23
Total with taxes and fees
Beautiful 2BR N of Grand near Downtown

Fun & Charming 1BR Apt near Drake

Fun & Charming 1BR Apt near Drake
Drake
8.0 out of 10, Very Good, (2 reviews)
"Abner is amazing. Communication was as smooth as can be, the place was left in great condition, and the house rules were respected. I hope to host them again in the future!"
United States
AbnerG
$241 nightly
The price is $252
Jun 30 - Jul 1
Total with taxes and fees
Fun & Charming 1BR Apt near Drake

Sleepover | Charming 1BD/1BA - Downtown Des Moines

Sleepover | Charming 1BD/1BA - Downtown Des Moines
Woodland Heights
10.0 out of 10, Exceptional, (1 review)
"Convenient to Sherman Hill and downtown. Quiet. "
United States
Abby H.
$209 nightly
The price is $237
Jun 15 - Jun 16
Total with taxes and fees
Sleepover | Charming 1BD/1BA - Downtown Des Moines

2 Story House 2 blocks from Ingersoll<br>*Fenced in Patio <br>* Formal dining room<br>*Hardwood flooring<br>*Newly remodeled Kitchen <br>*Google Fiber Internet

2 Story House 2 blocks from Ingersoll<br>*Fenced in Patio <br>* Formal dining room<br>*Hardwood flooring<br>*Newly remodeled Kitchen <br>*Google Fiber Internet
Woodland Heights
4.0 out of 10, (2 reviews)
"We were told the house was “cleaned” the day before we arrived. NOT TRUE. There was a dead misuse in the basement along with a bunch of filthy towels. The backdoor didn’t lock. The TV didn’t work. There was a used paper towel roll for use to use. We had the house for two days but left after the first night, the following morning as I was packing I saw a mouse run under the stove. Never again"
United States
benjamin s.
$228 nightly
The price is $239
Jul 13 - Jul 14
Total with taxes and fees
2 Story House 2 blocks from Ingersoll<br>*Fenced in Patio <br>* Formal dining room<br>*Hardwood flooring<br>*Newly remodeled Kitchen <br>*Google Fiber Internet

Beautiful home minutes from downtown!

Beautiful home minutes from downtown!
Des Moines
9.4 out of 10, Exceptional, (33 reviews)
"What a great place to stay! "
United States
Annie P.
$247 nightly
The price is $277
Jun 22 - Jun 23
Total with taxes and fees
Beautiful home minutes from downtown!
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

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 $112 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 6 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, Roseman Bridge and Clark Tower 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.