Holiday rentals in Warren County

1888 Schoolhouse in Wine Country

Right in the middle of Missouri's wine country, this fully renovated 1888 Schoolhouse lets you explore wineries in the area or just sit on the front porch and wave at the locals. Perfect for two or use the fold out couch for additional guests. Pinckney, Missouri was the county seat of Warren County. Danial Boone once sat on the porch of the County Judge right across the street. This quiet street was once the hub of activity due to the Missouri River, now it is a quiet retreat from the noise.

Location · Value · View

Farm Stay+ Eclectic Vintage+Fresh Eggs+EV Charge

Our eclectic guesthouse is set on 80 acres of quiet magic, come unplug. Discover fun details in the art-filled interior, 1960s phone booth, and light-filled space boasting vintage finds and plants galore. Collect fresh eggs for breakfast, enjoy coffee on the expansive porch. Wander the flower and vegetable garden, hike the wooded trail, explore the creek & shower under the stars. Slow down, reconnect, recharge. 7mins off I-70, 30mins to Hermann & 50mins to both STL airport and Columbia.

Location · Family · Bathroom

Innsbrook Chalet on Private Lake

Enjoy an Innsbrook Chalet on a beautiful private lake. Peaceful home overlooking water and wildlife can accommodate 8 guests with 3 beds and a bunk bed. Includes large wraparound deck, private dock to fish the stocked lake, stone firepit w/night lighting, hot tub, outdoor shower, and waterside sandbox. Inside is equipped with wifi, 3 roku tvs, a wood burning stove, and two full baths. Nestled in the woods with wildlife all around this is perfect for a vacation away with the family or friends.

Location · Family · Hot tub

Scenic Natureside Stay Off 70~Best of Both Worlds

Conveniently located 2 mins off I-70 in the small town of High Hill yet nestled beside the woods, this duplex unit offers gorgeous backyard views & a calm setting. Your own fenced area of the backyard & private fire pit are perfect for cozy evenings under the stars, and letting your dog run freely out the back door. Inside you’ll find an oversized, yet cozy 1000sq ft living area that is its own private space with all the amenities of home. Hermann - 20mins Wentzville - 30mins Columbia - 45mins

Value · Family · Decor

Peaceful Blufftop Retreat Over the Missouri

Enjoy sweeping views of the Missouri River at a relaxing, modern, pet-welcoming retreat on nine acres. It's a short walk to charming downtown New Haven, and a 20-minute drive to Washington or Hermann. Designed for comfort, the home offers a well-equipped kitchen, fast Wi-Fi, whole-house audio, and an EV charger. An ideal escape for couples, families, wine-trail explorers, and anyone looking for calm surroundings with easy access to the area’s best vineyards, distilleries, and riverfront charm.

Location · Sleep quality · River

Vitality Retreat 1 block from DT/Riverfront/Shops

Gather & make memories at the Vitality Retreat! Located a block from historic downtown Washington restaurants/shops/bars, you will have ample amenities for a fun and rejuvenating stay. Pet friendly/fenced yard! Enjoy coffee in the gazebo, yard games, or 1-block walk to the riverfront! 15 minutes to wineries, 45 minutes from STL. Location perfect for memory making. 4 BRs, 4 Bathrooms ensure ample space! Pet friendly, please note any pets beyond 2 will be an additional $100 per pet. Thank you!!

Family · Location · Condition

Relaxing Lakefront Chalet in Innsbrook Resort

Nestled in the woods overlooking Foxfire Lake, this A-frame offers the perfect four-season escape. When the snow falls, it transforms into the quintessential winter retreat. Cozy up beside the stone fireplace, where views of the lake are framed by frosted trees. As the weather warms, the lake calls! Enjoy direct access to Foxfire Lake from our private dock. Spend your days fishing, swimming, or simply basking in the sun. This chalet will help you find joy and relaxation, whatever the season.

Value · Family · Parking

Elevated Woodland Escape

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. We are also close to wine country for an afternoon of shopping or dining. Enjoy the lovely setting of this romantic spot in nature.

Location · View · Accuracy

Pura Vida Chalet - Lakefront on Lake St. Gallen

Pura Vida Chalet is a lakefront, 2 bedroom + loft, 2 bath A-frame on Lake St. Gallen at Innsbrook Resort. This updated chalet sleeps up to 8 people (6 adults maximum). It sits on a 3-acre, semi-private, lakefront lot with breathtaking views of the lake. Onsite amenities include kayaks, stand-up paddle boards, jon boat with trolling motor, lily pad, fire pit, tree house, large deck and private dock, indoor wood-burning fireplace and screened-in porch. See more on IG @ChaletPuraVida

Family · Value · Check-in

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.

Family · Value · Biking

Cozy 1882 Farmhouse-10 minutes from Wine Country

Getaway to The Farmhouse located in the quiet country near Hermann, Berger and New Haven. Gather with friends and family where children will enjoy space to run/play in and gathering for s'mores around an evening fire. The area boasts of wineries with weekends of fun themed festivities. Set rate on first two guests $145/night (smart pricing in effect on event weekends) . $55 each additional guest/night. Infant- 2 yrs. free, 3-12 $30/night Pets: $30 each pet/one time charge

Value · Location · Breakfast

Escape to your private 7 acre lake retreat

private spring fed lake * kayaks & paddle boards* pedal boat* Lilly pad * fishing dock * wooded walking trails* fire pit * Leave the everyday behind and enjoy a peaceful waterfront escape. Spend time sipping coffee on the covered porch enjoying the view, play in the lake with paddle boards & kayaks, fish from the dock and explore the woods. The red house is perfect for a romantic getaway, family vacation, girl's getaway, fishing trips or simply a place to recharge.

Location · Value · Cleanliness