Holiday rentals with outdoor seating 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.

Red Mule Ranch - Breakfast included

Cozy, rustic, “bunkhouse." Charming cedar log double bed. Private bath. Located on 85 acre horse farm. Lrg pond, beautiful pastures. Near Innsbrook, Cedar Lakes Cellars Winery, Big Joel's Safari, Long Row Lavender Farm, and many local wineries & antique shops. Homemade breakfast (5 choices), at NO extra charge, & chocolate chip cookies are in your room upon arrival. Perfect anniversary getaway. Your favorite pie/ cake can be made for a small charge. NO cleaning fees #1 Airbnb Host in Missouri

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.

Boar Creek Guest House-sleeps 15

Lovely Farmhouse close to town, ON the Katy trail. We are located just 5 miles from Hermann. Close to the action and them come home to relax around the fire pit or enjoy the expansive patio. House accommodates up to 15 people. Amenities include Game room in the garage, multiple gathering spaces, a large yard and privacy. Perfect for unplugging, disconnecting and getting back to the basics. House is well appointed but not pretentious. Come with your family or for a friends getaway.

Welcome to the "Blue House on Boone"

Country Cottage home with tons of charm that you cannot get in a Hotel Room !!! Great retreat whether you are in town for a conference, wedding or a just a vacation. Located off historic Main Street and just a couple of doors from Britton House the oldest residence in Lincoln County. Short walk or even shorter drive to The Factory and other wedding venues in our community. Enjoy the Cuivre River State Park or just simply relax in the back yard with nice patio, firepit and dining area.

Lakefront Studio Guest Home on Hermann Wine Trail!

What was once used as a fueling station at McCurdy Farm is now a quaint, re-purposed vacation rental — perfect for a relaxing retreat. The 1-bathroom studio is ideal for a romantic getaway or quiet respite for a solo traveler. Fish at the property's private lake a few steps away, enjoy wine tasting at vineyards along the Hermann Wine Trail, or lounge on the expansive deck while taking in the serene views. Book your one-of-a-kind lakefront getaway today to experience true New Haven bliss!

Verein Heritage Loft

Verein Heritage Loft, located in the heart of historic downtown Washington's arts and entertainment district, serves as a stylish retreat from everyday life. The recent restoration of this iconic 1855 building, rich with German heritage, offers unmatched comfort and convenience. Enjoy riverfront views, scenic walking trails (Katy Trail), quaint boutique shopping, bar hopping, all within a lively family entertainment district. Visit by Amtrak while enjoying our beautiful wine country!

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

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

Country home L Level, private, kitchen, hot tub

Very private country setting just 2 miles south of interstate 70. You’ll likely enjoy some wildlife sightings. Nice private patio seating. Cabin feel, spacious, has full kitchen. Murphy bed in the living room (very comfortable) provides an extra Q bed if needed, otherwise it’s out of the way. Internet was weak so affected some reviews but is super fast now. Nearby destinations are Cedar Lake Winery, Big Joel’s Safari, Long Row Lavender Farm, and Pumpkins Galore.

Early Check-in, Late Check-out on Weekends 8AM-8PM

Just 45 minutes from St. Louis, Innsbrook Resort is a 7,500-acre woodland community with over 100 lakes. As a guest of Innsbrook, you'll have access to all of the resort amenities, entertainment, and dining areas. After a fun filled day of activities, you will enjoy unwinding at Ella's Roost, a two bedroom + sleeping loft, two-bathroom waterfront chalet. Both bedrooms have a queen size bed and the three-person sleeping loft offers a bunk bed and a futon.

Katy Haus: Hot tub, Wineries, Fenced yard, Dog-fri

A cute little house almost on the Katy Trail. Bring your bikes, bring your dog, bring your friends. After a long day of riding the Katy Trail and enjoying the local wineries and breweries, or maybe you are in the area celebrating a wedding, the Katy Haus is your place to kick back and relax.