Holiday houses in New Haven

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 · Sleep quality

Knott House-short walk to downtown/riverfront

This house built in 1906 has classic old world charm with wood floors, tall ceilings, and original mill work. A short walk to restaurants, boutiques, trollies, and the riverfront. Enjoy the wineries, brew houses, and all WashMO has to offer. Home has 3 bedrooms and 1 1/2 baths. There are 2 king beds and a queen along with a queen pullout sofa. The kitchen is newly remodeled and is stocked with everything you need to cook meals. Complimentary bottle of wine awaits you! Wi-Fi /tv w/firestick

Family · Value · Air conditioning

Treehouse on the Katy Trail (Bur Oak)

The best of what Missouri has to offer surrounds you at Treehouse on the Katy Trail. This 100-year-old home has been fully renovated in a modern farmhouse style, but it's what awaits you outdoors that will really make your stay here memorable. The Missouri River Valley is a unique beauty that everyone should have a chance to experience, which is why a portion of all proceeds will be donated to Magnificent Missouri, a nonprofit organization dedicated to celebrating and protecting the Katy Trail.

Family · Value · Outdoor spaces

Back Door Guest Suite, Zia My Retreat

Retreat & Relax in this historic, loft apartment in the heart of downtown New Haven, MO, the heart of wine country! Nestled in where all the action is... walk to the wine bar, brewery, distillery, shops, restaurants and the Missouri River levee walk. Soak up all of these local experiences or enjoy a short, scenic drive to visit one of beautiful surrounding towns: Hermann, Washington, Rosebud or Augusta. Play all day and come back to retreat & relax at your home away from home, Zia New Haven.

Location · Indoor spaces · Comfort

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 · Cleanliness · 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!!

Location · Value · Parking

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!

Value · Family · Condition

The Round Room Tower at Moy Mell Farm

Reconnect with nature at this unforgettable escape. Unique, round mini house attached to main house. You will feel like you are far away from the world! We are at the end of a long drive, and in the middle of a small, sustainable farm. We have vegetable market gardens on the premises as well as a variety of farm animals, honeybees, and lots of nature! Even though you will feel isolated and secluded here, we are only minutes away from wineries, a distillery, brewery and art galleries.

Value · Family · Condition

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.

Value · Family · View

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

Family · Value · Hospitality

Entire 3BR/2BA house w/spacious backyard fire pit

Enjoy this entire **Newly Remodeled**-3 bed/2 bath house. Just minutes away from everything that Hermann has to offer. The outdoor patio is spacious enough for BBQs or outdoor activities. Conveniently located across the street from a grocery store, in case you want to cook in the beautiful kitchen or walk across the street to the delicious Mexican restaurant. Can be picked up by The Hermann Trolley in the Village Market parking lot. This home features a keyless entry.

Location · Value · Quiet

Johann's on Schiller - 4 Bed / 2 Bath

Charming 4 bedroom/2 bathroom property in the heart of downtown Hermann. There is ample space to rest, relax, and unwind. Johann's features a full kitchenette with a refrigerator, stove/oven, microwave, coffee bar, and a kitchen table which seats 8 people. There is a 42" flat screen smart TV, a BluRay / DVD player (with movies), games and plenty of extras to enjoy during your stay. The suite is professionally cleaned prior to every booking.

Value · Location · Sleep quality