Pella vs Winterset: Two Stays, Keep the Files Apart 2026

Jacob Mishalanie
15 hours ago
6 min read

Updated: 7 hours ago

Empty rural Madison County Iowa gravel road, no people

Pella is $20,593 on 56 listings. Winterset has no AirROI extract. Des Moines $16,916 is already live. AirROI's current Pella extract, August 2025 through July 2026, pins typical listings at about $20,593 a year on 56 active rentals. The average night was $191. Occupancy was 38.7 percent. Revenue per available night was $78. Year over year is minus 11.8 percent. Active supply moved plus 36.6 percent. Call Pella City Clerk Mandy Smith at 641-628-4173. 825 Broadway Street. Planning and Zoning 641-628-0043. Iowa Code 414.1: no city STR-specific CUP or STR-specific license/permit fee on this research pass. STR classified as residential. Generally applicable health and safety still allowed. State hotel and motel tax is 5 percent. Confirm remaining Pella local hotel tax at Iowa DOR. Confirm 2026. AirROI's low-regulation scrape is not the clerk file. Confirm remaining Winterset clerk before you advertise a Madison County driveway. Des Moines Development Services 515-283-4200 is the 240 city hall. Do not remesh 240.

Two Towns Share a Capital in the Copy, Not One Year

AirROI's current Pella extract, August 2025 through July 2026, pins typical listings at about $20,593 a year on 56 active rentals. The average night was $191. Occupancy was 38.7 percent. Revenue per available night was $78. Year over year is minus 11.8 percent. Active supply moved plus 36.6 percent. Des Moines city cluster 240 is already LIVE at $16,916 on 619 listings. Do not remesh it. Do not average Pella $20,593 with that city year. Winterset has no AirROI extract on this pass. Do not invent a Winterset year. A separate Rabbu pass printed Pella at 24 listings and about $22,939. Do not average. Towns Near Des Moines is already live on Crest and Cove. Use it for the related stay, not as a blended year.

Pella Is $20,593 on 56 Listings

56 active listings is a gallery. Superhost share is 78.6 percent. Professionally managed share is 21.4 percent. Andrea holds 3 listings. Entire homes are 92.9 percent. Houses are 58.9 percent. Market a Pella Stay is already live on Crest and Cove. Use it for the related stay, not as a blended year.

Winterset Has No AirROI Extract

Winterset has no AirROI extract on this pass. Do not invent a Winterset year, listing count, or ADR. Name Roseman Bridge, Holliwell Bridge, and the John Wayne Birthplace Museum as visitor demand, not occupancy. Pella STR Rules is already live on Crest and Cove. Use it for the related stay, not as a blended year.

Keep Those Files Apart

Call Pella City Clerk Mandy Smith at 641-628-4173. 825 Broadway Street. Planning and Zoning 641-628-0043. Iowa Code 414.1: no city STR-specific CUP or STR-specific license/permit fee on this research pass. STR classified as residential. Generally applicable health and safety still allowed. State hotel and motel tax is 5 percent. Confirm remaining Pella local hotel tax at Iowa DOR. Confirm 2026. AirROI's low-regulation scrape is not the clerk file. Confirm remaining Winterset clerk before you advertise a Madison County driveway. Des Moines Development Services 515-283-4200 is the 240 city hall. Do not remesh 240. Pella Shoulder is already live on Crest and Cove. Use it for the related stay, not as a blended year.

Downtown Pella Is Not the Courthouse Square

Des Moines listings earned about $16,916 last year from 619 active rentals on the current AirROI extract used for the already-LIVE 240 city cluster. Keep that stay on its own line. Do not remesh 240. Winterset has no AirROI extract on this pass. Do not invent a Winterset year, listing count, or ADR. Name Roseman Bridge, Holliwell Bridge, and the John Wayne Birthplace Museum as visitor demand, not occupancy. Pella Remote Stays is already live on Crest and Cove. Use it for the related stay, not as a blended year.

Guests Who Typed the Wrong Occasion

Tulip Time 2026 was May 7 through 9. Tulip Time 2027 is May 6 through 8. Covered Bridge Festival is October 10 through 11, 2026. Confirm hours. Do not invent a visitor count as occupancy. DIY vs Hire in Pella is already live on Crest and Cove. Use it for the related stay, not as a blended year.

Des Moines 240 Is a Later City File Already Live

How a Host Should Split These Two Markets

How a host should read this map is to file Pella $20,593, leave Winterset uncounted, and leave Des Moines 240 on its own live line. Buying a Pella Rental is already live on Crest and Cove. Use it for the related stay, not as a blended year.

Hosts who underwrite Pella stays should keep $20,593 on 56 town listings, call 641-628-4173, leave Winterset uncounted, and leave Des Moines 240 on its own live line. We market. We do not take the lock.

Frequently Asked Questions

Are Pella and Winterset the same rental market?

No. They're two separate Iowa towns with two separate identities — Pella's Dutch-heritage downtown and Vermeer Windmill versus Winterset's Madison County courthouse square and covered bridges. Pella has a current published rental data extract; Winterset does not on this research pass. A buyer, host, or guest comparing the two should keep them on entirely separate files rather than treating them as interchangeable Iowa small-town stays.

What is Pella's typical annual rental revenue?

AirROI's current extract, August 2025 through July 2026, puts typical Pella listings at about $20,593 a year across 56 active rentals, with a $191 ADR and 38.7 percent occupancy. That figure is down 11.8 percent year over year even as active supply grew 36.6 percent. This is Pella-specific data and shouldn't be assumed to describe Winterset's market.

Why is there no revenue figure available for Winterset?

Winterset simply has no AirROI extract on this research pass — no published typical year, listing count, or ADR to cite. That's a data-availability gap, not evidence the market is small or inactive. A host or buyer with a genuine interest in Winterset should look for the town's own data separately rather than borrowing or estimating from Pella's published figures.

What draws visitors to each town?

Pella's draw centers on downtown, the Vermeer Windmill, and Tulip Time, held May 7 through 9, 2026. Winterset's draw centers on Roseman Bridge, Holliwell Bridge, the John Wayne Birthplace Museum, and its courthouse square, with the Madison County Covered Bridge Festival running October 10 through 11, 2026. Each town's identity is distinct enough that marketing copy for one shouldn't be reused for the other.

Do the two towns share the same short-term rental regulations?

Not necessarily. Pella's clerk desk — 641-628-4173, 825 Broadway Street — confirmed on this research pass that Iowa Code 414.1 treats short-term rentals as residential use, with no dedicated city STR permit fee found. This is not legal advice. Winterset's own municipal office should be contacted separately to confirm its specific requirements, since local implementation of state code can differ town to town.

Are Pella and Winterset in the same county?

No. Pella is in Marion County, whose auditor Jake Grandia sits in Knoxville, the county seat. Winterset is the county seat of Madison County, a separate county entirely. Keeping county-level tax and assessment records straight matters as much as keeping the two towns' rental data straight when underwriting either property.

How far apart are the two towns for a guest planning both?

Both towns sit within driving range of each other in central Iowa, which is why some hosts market a stay as a base for exploring both — but that framing only works honestly if the drive time is stated accurately rather than implied as a short hop. A guest choosing between a Pella stay and a Winterset stay is choosing between two different downtown experiences, not two versions of the same trip. Stating the actual mileage or drive time in the listing copy keeps that kind of dual-town positioning honest instead of implying a shorter trip than guests will actually experience.

Which town has more short-term rental competition right now?

Based on available data, Pella does — its current AirROI extract counts 56 active listings, while Winterset has no comparable extract published on this pass to compare against. That doesn't necessarily mean Winterset has fewer listings in reality; it means there's no current dataset to cite. A host or buyer interested in Winterset specifically should look for that town's own listing count directly rather than assuming Pella's figure applies.

Work with Crest & Cove Creative

Blending Pella's numbers into a Winterset pitch, or the reverse, produces a packet that misrepresents both towns to whoever reads it next.

We help hosts and buyers market each town on its own real identity — Pella's windmill and tulip season, Winterset's bridges and courthouse square — without collapsing the two into one story.

Reach out at crestcove.co or (256) 998-7502.