Pet-friendly holiday rentals in Gasconade County

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.

Post Oak Chaise

Serenity in a beautiful location where your dog can run free! Your own retreat on a 70 acre wooded property. There is over a mile of trails through the woods for your hiking pleasure. The home is back in the woods, with a scenic 3.5-acre pond located right outside your door. Three sliding glass doors open onto a porch with a beckoning view of the stocked pond. A fire ring sits by the pond so that you can make S'mores or gaze at the stars. The perfect family spot to unplug and enjoy nature!

Crown’s BiCentennial Inn, Downtown/Free Breakfast

Downtown Walking Distance to Shops/Bars. Free Buffet Breakfast & Drink Tickets at Hermann Crown Suites. Live Music Weekends & Nightly May-Oct+Food/Bar Onsite. This Home is the DeFlorin BiCentennial Inn with 1976 Decor! For up to 8 guests (And ONLY for Your Group). Next to 2 other DeFlorin Houses (allowing up to 24 guests). 4 Queen Bedrooms, 3 Bathrooms. Room with Ping Pong. We Request You Use the $20 Hermann Crown Suites Shuttle All Day (Trolley is $30)/Free Pickup/Return to Train Station.

The Paddock House at Dark Horse Farms

Here at Dark Horse Farms, come for the relaxation and stay for the experience. Whether its fishing for the guys, wine tasting for the girls, paint n sips, antiquing, or enjoying a private experience with the rare Friesian horses, this spacious retreat will house up to 12 of your closest friends. Enjoy the White Mule Winery or schedule a pick up by the Hermann Trolley Company to visit historic downtown Hermann MO! We also offer daily boarding for equestrians and their steed during their stay!

The Arch & Vine House | 5 King Beds on Fifth

Welcome to The Arch & Vine House | 5 King Beds on Fifth, a thoughtfully restored historic home in the heart of Hermann designed for gathering, comfort, and connection. This spacious home offers a rare combination of walkability, charm, and room to relax—making it the perfect setting for wine weekends, girls’ getaways, or couples traveling together. Walk to wineries, shops, restaurants, and Hermann’s downtown attractions. Front porch with outdoor seating and a grill add to the amenities.

Modern Country Farm House with beautiful views

Relax with the whole family or friends at this peaceful place to stay. Located just 6 miles south of Owensville, Mo this newly renovated farm house will provide you the countryside escape you have been looking for with no shortage of amenities. This 2 story farm house was originally constructed in 1888 as a multi family boarding house before the Kreter family purchased it in the 1930’s. In 2021 we made the decision to completely restore the house and bring it to its modern day glory.

'The Lodge at Crider Creek' Getaway on 140 Acres!

Day Trip to St. Louis & Kansas City | Dogs Welcome w/ Fee Book this beautifully renovated early 1900s barn on 140 acres in the Gasconade River Valley — perfect for family reunions and corporate retreats. The 6-bedroom, 2-bathroom vacation rental invites you and your group to enjoy fishing, hiking, stargazing, and viewing wildlife. After a BBQ with scenic pond views on the deck, you can return indoors for games and cozy up by the fireplace. This cabin truly is Bland's hidden gem!

Labby's Homestead Farmhouse

Our early 1900s Rustic Farmhouse offers 3-Bedrooms and 2 full bathrooms and the ability to accommodate large groups with a total of 9 beds (1 King / 6 Queens / 2 Twins). Featuring a full-service kitchen with cookware and utensils, living room with 55-in smart TV already connected to our free, secure Wi-Fi, make-up area on the upper level, washer and dryer in the entryway area, front porch, and large private back patio covered for all-year-round entertaining.

1860 Presshaus

Built in the 1860's, this unique two bedroom, two and a half bath home is equipped with a full kitchen, an upper/ lower patio with firepit, and access to your own private wine cellar. We are located in beautiful Hermann, Missouri just minutes to local distilleries and wineries. Enjoy country living at its best! Travel 1/2 mile down a well-maintained gravel road and enjoy one of the most unique places in Hermann, Missouri. You won't be disappointed!!

Oktober Haus 3BDRM in Downtown Hermann

Oktober Haus is a block or two from all the amazing spots that Hermann has to offer like Hermannhof Winery, Tin Mill Brewing, Fernweh Distilling and so much more. With 3 spacious bedrooms with King beds, 2.5 bathrooms, and a full air mattress, it's perfect for a weekend getaway with friends or family. Ideally the space is for 6 people. Built in 2019, our place feels brand-new, clean, and comfortable. The location is unbeatable!

Adorable house! Walking distance from downtown.

Formerly known as the Hoff Haus, this is a beautifully renovated 3 bedroom, 2 bathroom home built in 1910. Located on a quiet street right outside of downtown Hermann, this is a two-story home. Walk to shops and restaurants or, for a fee, have the Trolley (Hermann Trolley Company) pick you up out front of the house. Sleeps up to 8 guests. Please note that some guests have described the steps of our staircase as steep.

"B" Our Guest on Market

Our building was once home to one of the original saloons of early Hermann, known as the Farmers Home. Apartment "B" is located on the second floor. Its a great space for a your trip to Hermann. Fully private apartment, king size bed. The space has potential to adjoin for larger parties. For larger groups check out our other listings... 5th & Market Get Away The Hide Away on Market