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Places to stay near OakGlenn Vineyards & Winery

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Top-rated vacation rentals near OakGlenn Vineyards & Winery

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Guest favorite
A private hot tub, designed for four, emits bubbling water under a partially opened cover. The surrounding area includes wooden fencing and a nearby garden chair, creating a secluded space for relaxation.
Cottage in Gasconade
4.91 out of 5 average rating, 276 reviews

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.

Top guest favorite
A cozy studio layout features a spacious queen bed adorned with floral bedding. A round dining table with four chairs is positioned nearby, surrounded by warm hardwood flooring. Natural light enters through a window, enhancing the inviting atmosphere.
Home in Villa Ridge
4.94 out of 5 average rating, 154 reviews

Serenity Valley (No Cleaning Fee- No pets please)

Discover Serenity in this 675 sq ft Studio cottage on a private wooded lot. Cozy space with 1 queen bed & optional inflatable 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, DishNetwork, pack&play. Just 60 mins from downtown STL, 15 mins from Washington, 20 minutes from Six Flags. Your tranquil escape awaits! No pets allowed.

Top guest favorite
A dining area features a wooden table surrounded by dark chairs, with a vibrant red floral centerpiece. Above, a chandelier made from red glass adds a warm glow. A painting of a woman with an umbrella enhances the wall, complemented by a glimpse of a bathroom in the background.
Loft in Hermann
4.96 out of 5 average rating, 268 reviews

Half Corked Inn-Location and Comfort in one!

BEST LOCATION IN HERMANN! RIGHT ON 1ST STREET. Trolley across the street. Walking distance to brewery, Hermannhoff winery & farm, shops, restaurants, bars, etc. Train station 1 block away. Close to the Katy Trail. Silver Moon loft is cozy with beautiful decor and comfortable beds with clean bathrooms, stocked kitchen, inviting living room. Roomy and very clean. Courtyard and firepit. 2 Breakfast coupons at Stomp'n Grounds a thank you from us to you to use during your stay.

Top guest favorite
The farmhouse exterior features a two-story structure with a rusted metal roof, flanked by large trees. A welcoming front porch is highlighted by a red railing and equipped with several chairs, offering a relaxing space to enjoy the surrounding green lawn and peaceful countryside.
Farm stay in Berger
4.99 out of 5 average rating, 198 reviews

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

Top guest favorite
The living area features a spacious gray sofa paired with a brown recliner. A coffee table sits in the center, surrounded by a colorful area rug. Two blue lamps provide lighting, and a television is positioned on a turquoise console. Natural light enters through the window beside the door.
Guest suite in Rhineland
4.96 out of 5 average rating, 236 reviews

White Wolf Inn Apartment

Whether winery hopping, shopping, or visiting in or near Hermann, attending a wedding in the area or just enjoying the Katy Trail, your stay at the White Wolf Inn Apartment is only a few miles away. (Whole house rentals are available, the White Wolf Inn House is a separate listing.) We are close enough to access the Hermann transportation services and all that Hermann has to offer (about 8 miles from town), but far enough away for you to relax in the quiet of the country.

Top guest favorite
A cozy sleeping area features a spacious bed with a light-colored quilt, accented by a soft turquoise headboard. Two bedside lamps provide ambient lighting, while a decorative tray sits on the bed. Warm wooden accents complement the neutral color palette.
Guesthouse in Hermann
5 out of 5 average rating, 137 reviews

Das Hundehaus-Downtown Location-Off Street Parking

Das Hundehaus is centrally located in Hermann's downtown historic district on East 2nd Street. The cottage is conveniently located just steps away from restaurants, shops, museums, and more. The cozy cottage offers an open concept floor plan featuring a full kitchen, king bed, sitting area, private bathroom with large shower and off street parking. Start your mornings with a cup of coffee on the private deck and end your evening relaxing with a glass of wine.

Top guest favorite
A spacious loft area is arranged with a cozy sitting area featuring a tan leather couch, blue armchair, and a circular dining table. A large bed is positioned against the wall, with elegant window treatments framing the natural light. A piece of art depicting a forest scene adds character.
Loft in Washington
5 out of 5 average rating, 405 reviews

2nd Street Loft - Riverview

Complete Rehab, this historic 1883 storefront building hosts a well known artist and his gallery on the 1st floor. Above is your "loft space" close to wineries, Amtrak, featuring great views of the Missouri River. You’ll love this Downtown Washington location because of the walkable shops, bars, and restaurants many in historic buildings. The loft is great for couples, solo adventurers, and business travelers who can walk a flight of stairs.

Top guest favorite
An outdoor seating area features red Adirondack chairs set on a gravel surface, framed by trees. Soft glowing string lights are suspended above, illuminating the serene lakefront view, where lush greenery reflects on the calm water.
Chalet in Wright City
4.98 out of 5 average rating, 125 reviews

Peaceful chalet - *new* private beach, WIFI, kayak

Discover serenity at Shadow Lake Cottage—a peaceful waterfront chalet with a private dock, king-size suite, and three-season room, surrounded by mature oak and dogwood trees. Whether you’re looking to reconnect with loved ones, retreat with friends, or escape the office for a while, this charming vacation home rental near St. Louis at Innsbrook Resort offers a perfect blend of comfort, privacy, and resort perks.

Guest favorite
Guest suite in Hermann
4.9 out of 5 average rating, 115 reviews

Suite #2 - 1 Bed 1 Bath in Downtown Hermann

Location, location, location! The Suites on 3rd are right in the middle of the action of charming downtown Hermann. Walk everywhere you need to go. Taking the Amtrak into town? We are only a few blocks away. This listing is for Suite 2 and features 1 bedroom and 1 bath. Message me for info on how to book more than one suite. Check out my reviews! Easy contactless check-in & only one flight of steps to access.

Top guest favorite
A cozy seating area features an arrangement of two armchairs, one upholstered in blue and the other in green, complemented by a light brown recliner. A wooden coffee table sits at the center, adorned with a decorative tray. Soft lighting is provided by two lamps on either side.
Apartment in Washington
4.96 out of 5 average rating, 452 reviews

Elbert haus

The entire 2nd floor reserved to just one set of guest. Just three blocks from the Missouri Riverfront, historic downtown Washington, and near many fine restaurants. This early 1900s fully restored brick home offers a perfect place to lay your head after an exciting day. The house is located within walking distance of the Amtrak train station, close to the hospital and the trans Missouri Katy bicycle Trail.

Top guest favorite
The exterior of a historic stone barn features rugged stone walls and a large wooden door framed by greenery. Windows with dark trim allow natural light, and seasonal flowers in pots add a touch of color to the entrance area.
Barn in Hermann
5 out of 5 average rating, 121 reviews

The Barn at Schon Stein Farm & Vineyard

Nestled in the hills & bluffs above Hermann, the Stone Barn at Schon Stein Farm & Vineyards takes you back in time in this historic wine press barn that has been carefully restored and decorated with primitive period antiques...situated on 20 acres in the bluffs with beautiful views! The town of Hermann is minutes away down the hill, and trolley pick up is available.

Guest favorite
A spacious bed is adorned with two decorative pillows and a folded throw blanket. A textured comforter covers the bed, creating a cozy atmosphere. Soft light filters in, enhancing the tranquil setting.
Guesthouse in Hermann
4.97 out of 5 average rating, 262 reviews

The Dogwood Inn Hermann

We are a two bedroom,( 1 King, 1 Queen) one bath guesthouse that rents to one or two couples (if they know each other) at a time. A luxury spa like atmosphere with all the comforts you'd expect. We are located in the historic district of Hermann, MO and are within walking distance of the train station, trolleys, many attractions, food, wineries, and shopping.

Popular amenities for vacation rentals near OakGlenn Vineyards & Winery