Top Cottages in Gasconade County in 2026

Fall view of Hermann, MO, from the Stone Hill Winery.

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Our top choices for Gasconade County cottages

Close to Vineyards: Updated New Haven Retreat!

New Haven

Kizzy

Home w/ Trail Access on 19 Acres in Wright City!

Wright City

Mike

Downtown Hermann Vacation Home Near Wineries!

Hermann

"This is a very cute little house on the end of a quiet street. It's within easy walking distance of all the shops, restaurants, wineries, distilleries, and bars between 1st Street and 5th Street. If you don't mind a longer, hillier walk you could also go further south to City Park or to Stone Hill winery. But there's also easy transportation on the Trolley or local ride services. We were happy to find there were more beds than pictured (3 queen size downstairs between 2 bedrooms, and 2 queens...

Tara

Rp11.554.811 total

includes taxes & fees

14 Feb - 15 Feb

Spacious Ozarks Family Home - Private Pool & Grill

Bourbon

Rp8.808.286 total

includes taxes & fees

24 Feb - 25 Feb

Peaceful Guest Home w/ Patio on 152-acre Farm

Berger

"Very clean,family friendly, even though it was 7 miles out of town they were very Accommodating,they came to puck us up at the train station and there's a van that will take you into town and you can take the trolley to all the wineries,shopping, we all loved our stay,i would definitely recommend to anyone who enjoys the fram life, they have lots of history, and animals, thank you Susan and Mike for all that you did to make our stay memorable, we would definitely come back. "

Kelly

Charming St James Home Near Maramec Spring Park!

St. James

Spacious Owensville Getaway w/ Winery On-site!

Rosebud

Lakefront Innsbrook Chalet: Hot Tub + Fire Pit!

Wright City

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Top Gasconade County Hotel Reviews

Hermann Crown Suites

10/10 Excellent

"I had a wonderful stay at this hotel and would absolutely come back. From the moment I arrived, the staff made me feel welcome and taken care of. Check-in was quick and easy, and everyone I interacted with was friendly, professional, and genuinely helpful. The room was spotless, comfortable, and well-appointed. The bed was incredibly cozy, and I appreciated the small touches like the quality toiletries and the quiet atmosphere — it made it easy to relax after a long day. The location was also a big plus, with convenient access to restaurants, shopping, and local attractions. Everything felt safe, clean, and well maintained throughout the property. Overall, this hotel delivered a great experience from start to finish. If you’re looking for a comfortable, clean, and welcoming place to stay, I highly recommend it."