Vacation rentals in High Hill

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Top-rated vacation rentals in High Hill

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Guest favorite

Home in St. Peters

4.88 out of 5 average rating, 313 reviews

Private Walkout w King Bed & Bath + large livingrm

Our house sits in a very quiet and safe neighborhood. When you stay with us you will enter through the walkout basement. You have full access to our very private downstairs apartment. This will enter you right into the very large living area. The master bedroom is complete with a King bed, black out curtains and walk-in closet. Attached is a full size bathroom with walk-in shower. Amenities include television, DVD, WiFi, Kuerig, mini-fridge and access to patio/porch with backyard fire pit.

Nov 14 – 21

G$15,587 GYD per night

Guest favorite

Tiny home in Pacific

4.96 out of 5 average rating, 163 reviews

Route 66 railroad shanty, a cozy artsy small space

This 536 s.f. house, believed to have once been a sleeping shanty for railroad crews switching shifts for the night. Fully renovated and updated in 2021 by a local artist, you will find custom metal art throughout, granite countertops and a very warm cabin feel featuring a kitchen and bathroom finished with locally sourced Missouri dark red cedar, 10 minutes from six flags, Purina farms 15 min from hidden valley and 45 min from downtown this place is in a great location and will not disappoint!

May 21 – 28

G$21,988 GYD per night

Guest favorite

Home in Bonnots Mill

4.97 out of 5 average rating, 257 reviews

Secluded "Heaven": soaker tub, sauna, sunset view

"Heaven" ( 1,512 sq ft, 7 ac) sits on a bluff overlooking the Osage river. An open home with huge full length windows and a sun room provides abundant natural lighting. Two porches offer views over the river and to the woods. A jacuzzi tub and sauna are situated in the cabin with a view to the sunset. The cabin is at the end of a secluded forest road. A locked garage is available for parking small cars. Drive: 15-20 min to Linn for supplies / 30 min to Jeff City / 5 min to public river access.

Jun 19 – 26

G$30,769 GYD per night

Guest favorite

Apartment in Montgomery City

4.98 out of 5 average rating, 66 reviews

St Jude's Night Away

This freshly renovated non-smoking suite sits down town Montgomery City. If your traveling through town, in town for business or a wedding-check out our suite. 2 bedrooms, 3 beds, 1 Bath with walk-in shower. Fully equipped kitchenette with full size refrigerator, microwave, induction stove top for cooking. Washer and Dryer. Free Fast and reliable WiFi and 2 smart tv's. Laptop friendly workspace with good lighting. Spectrum cable for local channels. Keyless entry for easy check-in and out.

Aug 28 – Sep 4

G$21,753 GYD per night

Guest favorite

Farm stay in Berger

5.0 out of 5 average rating, 155 reviews

Cozy 1882 Farmhouse-10 minutes from Wine Country

Come getaway to The Farmhouse located in the quiet country near towns of Hermann, Berger and New Haven. Gather with friends or bring your family. The Farmhouse is family friendly, and children will enjoy a yard to run and play in and gathering for s'mores around an evening fire. The area boasts of wineries and many weekends of fun-filled themed festivities. Set rate on first two guests $145/night. $55 each additional guest/night. Children infant-10 free, 11-17 $25 each/night Pets $30 each.

Dec 8 – 15

G$31,567 GYD per night

Guest favorite

Loft in Hermann

4.97 out of 5 average rating, 200 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.

Mar 29 – Apr 5

G$28,209 GYD per night

Guest favorite

Guest suite in Rhineland

4.98 out of 5 average rating, 173 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.

Feb 5 – 12

G$21,243 GYD per night

Guest favorite

Cottage in Gasconade

4.94 out of 5 average rating, 197 reviews

1940's River Cottage w/ Hot Tub

A fisherman's retreat, a romantic getaway . Trains pass through town several times a day, and nig otherwise it is a quiet community. Located nine mile from historic Hermann, Mo and several wineries. The home was built in the 1940's and is an old house but its clean and comfortable. Enjoy star gazing in the evening or watch the squirrels play in the morning while relaxing in the hot tub (surrounded by privacy fence and open year-round). Self checkin with key lockbox.

Aug 16 – 23

G$18,408 GYD per night

Guest favorite

Guesthouse in Marthasville

4.96 out of 5 average rating, 222 reviews

Hazel's House by the Katy Trail

In the heart of Missouri Wine Country. Within walking distance of the Katy Trail and Lake Creek Winery. Many wineries within a 25-30 minute drive. Enjoy a weekend getaway in a 2 bed 1 bath home. Hazel's House is clean, comfortable and private overnight accommodations. We are not a bed and breakfast, no food included, but there is coffee. Please make sure the location is suitable. We are located out in the country and the internet can be spotty.

Aug 3 – 10

G$23,554 GYD per night

Guest favorite

Home in Dittmer

4.95 out of 5 average rating, 357 reviews

Honeymoon Suite Camp Skullbone In The Woods

Romantic quiet cozy chalet for two! Vintage décor with all the modern amenities of home. Relax inside to unwind, kick back and watch a movie, surf the web via free wi-fi, curl up with a good book, open up a board game for a friendly challenge or share a drink with that special someone. Want some fresh country air? Lace-up those hiking boots and take like Camp Skullbones. . Enjoy the stars on the intimate deck with the glow from the gas fire pit.

Sep 15 – 22

G$32,017 GYD per night

Guest favorite

Cabin in Holts Summit

4.95 out of 5 average rating, 354 reviews

Restful Rustic Comfy Cabin.

Sweet little cabin by a little pond at the edge of the woods. Large sunny windows, real bed, (with room to bed a child or two down on the floor) tea pot, easy chair, camp jug of water, camp toilet, AC, WiFi, hiking trails, near Katy Trail. There's no shower in the Cabin. There is an above ground pool, trampoline, rope swing and we are very child friendly. We strive to maintain a fragrance free facility for the sake of those with sensitivities.

Jun 7 – 14

G$8,118 GYD per night

Guest favorite

Loft in Washington

4.99 out of 5 average rating, 297 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.

Jan 3 – 10

G$20,888 GYD per night