Vacation rentals 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.

Rustic schoolhouse modern charm

Relax with the whole family at this peaceful place. This Structure was completed in 1910 as the Pin Oak Schoolhouse where it was operational until the 1950's. Completely redone on the inside with modern charm but still maintains the rustic vibe. Plenty of room for the entire family with an amazing yard that backs up to the forest. Plenty of wildlife can be seen from the windows or back porch. A great place to unwind but still close enough for entertainment. Near the towns of Rosebud and Hermann.

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.

Treehouse on the Katy Trail (Dogwood)

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 its 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.

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.

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!

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.

TJ’s Country Getaway *Dog Friendly*

If you’re looking to just getaway, relax and disconnect then you’ll love this country setting located halfway between Washington and Union, Missouri. It’s quiet and peaceful, especially at night, yet only 15 minutes from dining along the riverfront, and enjoying live music on the weekends. Just 25 minutes from Purina Farms and 1 hour drive to St Louis Gateway Arch. From your private patio, you will enjoy beautiful sunsets and the beauty of many birds and occasional wildlife.

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.

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

Serenity Valley• Secluded Escape • No Cleaning Fee

Discover Serenity in this 675 sq ft Studio cottage on a private wooded lot. Cozy space with 1 queen bed & optional sofa queen bed for up to 4 guests. Relax on the patio, enjoy a bubble bath in the vintage clawfoot tub, or take in the panoramic woods view on the couch. Amenities include WIFI, washer/dryer, fully stocked kitchen, pack&play. Just 60 mins from downtown STL, 15 mins from Washington, 20 minutes from Six Flags. Your tranquil escape awaits! No pets allowed.

Lake View Cottage

Our newly remodeled cottage is the perfect getaway for two. Take advantage of the fully stocked kitchen and the cozy indoor fireplace. Enjoy a peaceful dinner on the deck overlooking the lake. Followed by a glass of wine relaxing by the outdoor firepit. Take a short 2 mile drive and enjoy live music at the local wineries; Triple 3 Vineyards and McKelvey Vineyards. Located 18 miles outside of Hermann- Wine Country