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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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Top guest favorite
The chalet features a distinctive A-frame design nestled among lush trees, showcasing large windows that reflect the natural surroundings. A wooden deck wraps around the front, providing an inviting entry with steps leading to the main entrance. The serene forest setting enhances the peaceful atmosphere.
Chalet in Innsbrook
4.99 out of 5 average rating, 163 reviews

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 4 adults/4 children or 6 adults max. It sits on a 3-acre, semi-private, lakefront lot with picturesque views of the lake and wildlife. Onsite amenities include kayaks, stand-up paddle board, 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

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, 277 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
Cabin in Innsbrook
4.95 out of 5 average rating, 186 reviews

Squirrel Run at Innsbrook Resort

WINTER ---> NOV-MAR: 4 -wheel drive car is recommended. In heavy snow, the cabin is deep in the woods & services would not be able to plow you out immediately. NO PARTIES. We have a 8 person occupancy. This includes holidays. Squirrel Run is nestled on 3 acres in a secluded wooded setting within the Innsbrook Resort Community. This 2-bedroom, 1-bathroom home sleeps 8 and offers everything from hiking, canoeing, swimming, or lounging around the firepit. More details on IG @squirrel_run_ibk

Top guest favorite
A private patio area is illuminated by string lights, creating a warm ambiance. The patio features a small table and chairs, surrounded by a green lawn. A fenced area is visible in the background, adding to the outdoor space.
Guest suite in Union
4.94 out of 5 average rating, 108 reviews

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.

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, 270 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
5 out of 5 average rating, 201 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, 239 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.

Guest favorite
A dining area features a light wood table set for two, with red plates and glasses. The kitchen area is located in the background, showcasing white cabinets and a dark countertop. A soft, neutral wall color enhances the spaciousness of the room.
Guest suite in Hermann
4.92 out of 5 average rating, 157 reviews

Suite #1 - 1 Bed 1 Bath in the middle of Downtown

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 1 and features 1 bedroom and 1 bath. Roku TV for you to login to your favorite streaming service (no cable) Message me for info on how to book more than one suite. We have 5 total suites with a total of 8 bedrooms. Easy contactless check-in!

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, 409 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
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, 461 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, 125 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.

Top guest favorite
A charming one-story house is seen with a stone and siding exterior. A well-maintained pathway leads to the front door, flanked by manicured bushes. Two windows provide natural light to the living space, while a small porch area offers a seating option.
Home in Hermann
4.95 out of 5 average rating, 147 reviews

A Romantic Getaway for two in Historic Hermann, MO

Park View Guest Haus is a private "Whole House Rental ". This rental is a relaxing retreat overlooking the Hermann City Park and is within walking distance to Stone Hill Winery, Vintage Restaurant, and a short walk to the Downtown Area. A perfect " Romantic Getaway" for two. No need to interact with other guest, for you will have the whole house to yourself.

Popular amenities for vacation rentals near OakGlenn Vineyards & Winery