
Places to stay near OakGlenn Vineyards & Winery
Book unique holiday rentals, homes and more on Airbnb
Top-rated holiday rentals near OakGlenn Vineyards & Winery
Guests agree: these stays are highly rated for location, cleanliness and more.

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

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.

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

Hillside Cottage - Whole house in downtown Hermann
Hillside Cottage is a whole house rental in downtown Hermann. It is 1300 sq ft home with 4 bedrooms & 2 full baths. There is a full kitchen with all the appliances and dishes. The living room and open concept kitchen is a great space for gathering with friends and family. There is a lovely patio to enjoy a cup of coffee or glass of wine. It is located 1/2 block off Market St, so it is walking distance to shopping, wineries, restaurants, and bars. Note: Price includes 5% Hermann City Tax

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.

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

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.

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!

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.

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.

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.

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.
Popular amenities for holiday rentals near OakGlenn Vineyards & Winery
Apartment rentals with wifi

Gorgeous Remodeled Waterfront Condo on Aspen Lake!

Lakefront Studio Condominium

Aspen Heights by Innsbrook Vacations!

The Geneva Studio by Innsbrook Vacations!

Bright Studio Condo on the Water

Aspen Sights by Innsbrook Vacations!

Lionshead Lake Retreat

2 Blocks 2 Everything!
Family-friendly house rentals

Serenity Valley (No Cleaning Fee- No pets please)

Studio 1892 Guesthouse-New! Downtown Location!

Adorable house! Walking distance from downtown.

Countryside Guest Haus!

Innsbrook Luxe Escape (5 bedrooms)

Katy Haus: Hot tub, Wineries, Fenced yard, Dog-fri

French Hill- Amazing location with the best views!

Couples~Groups, Whole House, and Trolley Pickup
Apartment rentals with air conditioning

6 Pines Apartment

Looking for Quaint Getaway Unit #4

Library at Schiller Suites

2nd Street -Deck Suite (back entrance)

Suite Simplicity~C

The Mercantile on the Katy Trail - The Katy Suite

Plane Suite at Brickhouse Inn

"B" Our Guest on Market
Other great holiday rentals near OakGlenn Vineyards & Winery

Private Suite w/ Washer & Dryer

TJ’s Country Getaway *Dog Friendly*

NEW! VillaBella Luxury Farmhouse

Cozy Riverview Cottage. 5 minute walk to downtown

Out On A Limb Treehouse

Converted grain bin guest house on Katy Trail.

First Street Queen Suite

The Round Room Tower at Moy Mell Farm




