Holiday rentals with a fireplace in Hermann

1940's River Cottage w/ Hot Tub

Something for everyone! This home is less than 9 mi. from historic Hermann, MO. There you can enjoy several wineries, shops & restaurants. From this property you are just a short walk to the Gasconade River near the MO River. Great boating, fishing & swimming w/ easy boat ramp access & parking. The Union Pacific Railway crosses the river & N. side of town. Gasconade is a small quiet town except for the occasional train or boat going by. At night enjoy stargazing from your private hot tub.

Hermann Whitetail Farmhouse

A modern farmhouse-styled rental home located south of historic Hermann, Missouri. Full use of large acreage property with lake area surrounded by forest. Quiet and secluded, but within minutes of downtown Hermann. Full kitchen, multiple dining areas, and HUGE entertaining area with pool table, games, TV's and bar. Private bedrooms and large bunk-bed room that sleeps four. Perfect for large groups or your next celebration. Stay for a weekend or a week with Hermann Trolley service available.

NEW Treehouse - Sunrise

We strive to provide you with a unique getaway experience with an escape into nature on Whispering Pine's hundred acre farm...leaving the stress of everyday life behind while you can invest and reconnect with yourself and your loved one! We provide a full kitchen, hot tub, floor-to-ceiling fireplace, luxury bathroom, laundry room and firepit for your use. Books and indoor/outdoor games are a must for staying in. We are also close to wine country for an afternoon of shopping or dining.

215 Market Street, Hermann, MO 65041, Whole House Rental

Grape Expectations is in the Heart of historic Downtown Hermann. One block away from all the night life. Our 5 bedroom house,2 bathroom can accommodate 12 guest. Hermann Trolley will pick you up right outside the door, and take you to wineries or whatever you have planned for the day in town. Two miles from the Katy Trail if you are checking out the beautiful trails we have, or just coming into town to get away and checking out our hometown shops all just right around the corner.

Half Corked Inn-Location and Comfort in one!

BEST LOCATION IN HERMANN! RIGHT ON 1ST STREET. Trolley across the street. Walking distance to brewery, Hermannhoff winery & farm, shops, restaurants, bars, etc. Train station 1 block away. Close to the Katy Trail. Silver Moon loft is cozy with beautiful decor and comfortable beds with clean bathrooms, stocked kitchen, inviting living room. Roomy and very clean. Courtyard and firepit. 2 Breakfast coupons at Stomp'n Grounds a thank you from us to you to use during your stay.

NEW! Out On A Limb Treehouse!

A unique Treehouse, 6 miles from Hermann, MO, offers a luxury escape with stunning views and sunsets. Perched on stilts by Daniel Boone Conservation Area, enjoy tranquility, hiking, and wildlife. Relax in a king-size bed beneath skylights, soak in a tub, or unwind in the hot tub and firepit. Just a mile from the Katy Trail, perfect for cycling or relaxing. Explore Hermann’s wineries, shops, and events. Transportation available from Hermann Trolley, Uber & Lyft. Sleeps 2 adults.

New Construction-Hermann-Lakeside Cabins (Cabin 2)

Escape lakeside 11 miles south of historic Hermann, MO. This property is a 200-acre ranch with 4 newly constructed modern cabins nestled on a 7-acre lake with kayaks and fire pits available for guests. The cabins sleep 3-5 guests with 2 rooms and 3 beds. Bring a friend group, family, group of families, couples, wedding party, or business employees for a serene getaway! Owned by a Christian non-profit. This listing is for 1 cabin, to book all 4 search for 16 guests, or visit

The Shed-Private Guest Studio/Hermann MO

Cozy, Rustic, Romantic... a Touch of Vintage...perfect for a romantic stay or special occasion! This private guest studio will welcome you with warmth & immediately send you to a state of tranquility! Soft lighting, electric heated fireplace, spa shower, a king size bed that will wrap you in delight! **Due to demand, 2 night minimum unless otherwise stated Rent the Shanty&The Shed together! *Based on availability *Property/Accessibility Features below

A Stunning Home, newly constructed & furnished !!!

Wine Down Guest House #2 is a whole house rental. It has four bedrooms and each bedroom has it own private bathroom with shower. Its brand new from the furnishings , decorations, to the appliances. Quietly located away from downtown. If you want something clean and new, then this is for you. It sits next to Wine Down Guest House #1 if you come with a larger party. Opened October 2021.