A person on a bicycle in a stone tunnel with moss-covered walls.

High Hill Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for High Hill vacation rentals

A compact living space with a sofa, a TV, a kitchen area with a fridge, microwave, and coffee maker, and a dining table.

1. The Mercantile on the Katy Trail

The Mercantile on the Katy Trail
4.5 star property
Hermann
9.8 out of 10, Exceptional, (37 reviews)
"It’s an absolute must do! Such a cool little town right on the Katy Trail!"
United States
Weston
The price is ￥29,325
￥31,517 total
includes taxes & fees
Sep 22 - Sep 23
The Mercantile on the Katy Trail
A spacious living area with a large blue sofa, a television, and a wooden entertainment unit.

2. 3-bedroom family friendly home on 4 acres near Hermann with WiFi, AC, deck

3-bedroom family friendly home on 4 acres near Hermann with WiFi, AC, deck
Hermann
9.6 out of 10, Exceptional, (15 reviews)
"Host was very accommodating, property perfect, I can't say enough good things about our stay."
United States
Susan R.
The price is ￥31,047
￥54,372 total
includes taxes & fees
Sep 16 - Sep 17
3-bedroom family friendly home on 4 acres near Hermann with WiFi, AC, deck
A covered patio with a table and chairs, a grill, and a view of a grassy yard.

3. Secluded 2 bedroom home close to Hermann

Secluded 2 bedroom home close to Hermann
New Florence
9.8 out of 10, Exceptional, (49 reviews)
"Very nice place "
United States
Yaqui S.
The price is ￥30,664
￥42,807 total
includes taxes & fees
Sep 27 - Sep 28
Secluded 2 bedroom home close to Hermann
A bedroom with a bed, bedside lamps, a ceiling fan, a window with curtains, a wall-mounted TV, and a radiator.

4. Germantown Inn & Lounge RM 1

Germantown Inn & Lounge RM 1
Hermann
10.0 out of 10, Exceptional, (3 reviews)
"We had a very pleasant stay. From check in, to check out, it was all perfect!"
United States
Jennifer A.
The price is ￥24,838
￥32,237 total
includes taxes & fees
Sep 13 - Sep 14
Germantown Inn & Lounge RM 1
An outdoor patio with a pergola, wicker furniture, and a view of the landscape.

5. Gipfel Suite - Himmel Haus Bed & Breakfast

Gipfel Suite - Himmel Haus Bed & Breakfast
Hermann
10.0 out of 10, Exceptional, (135 reviews)
"Everything was wonderful! It was a great room, a beautiful view from the terrace and a great breakfast."
United States
Kristin V.
The price is ￥15,179
￥24,818 total
includes taxes & fees
Sep 14 - Sep 15
Gipfel Suite - Himmel Haus Bed & Breakfast
A building with large windows, a covered porch, and a welcome mat.

6. McKittrick Suite - Loft Stay on Katy Trail in Historic Mercantile, 4 min Hermann

McKittrick Suite - Loft Stay on Katy Trail in Historic Mercantile, 4 min Hermann
McKittrick
10.0 out of 10, Exceptional, (2 reviews)
"Loved this placed, would definitely come back!"
United States
Cody W.
The price is ￥34,773
￥42,125 total
includes taxes & fees
Sep 15 - Sep 16
McKittrick Suite - Loft Stay on Katy Trail in Historic Mercantile, 4 min Hermann
A rustic bar area with stone walls, wooden chairs, and hanging pendant lights.

7. Studio Condo on the Water @ Innsbrook

Studio Condo on the Water @ Innsbrook
Wright City
9.8 out of 10, Exceptional, (65 reviews)
"everything was clean and really beautiful, we enjoyed the stay "
United States
Vanessa O.
The price is ￥11,652
￥29,842 total
includes taxes & fees
Sep 24 - Sep 25
Studio Condo on the Water @ Innsbrook
A compact kitchen with a bar area, a dining table with stools, and a small seating area with two chairs.

8. Wine Alley East suite

Wine Alley East suite
Hermann
9.4 out of 10, Exceptional, (85 reviews)
"Host was great. Easy checkin and checkout. Great location to ride trolley to wineries and then walk Hermann at night."
United States
Sandy H.
The price is ￥22,231
￥33,339 total
includes taxes & fees
Sep 13 - Sep 14
Wine Alley East suite
A wooden staircase leading to a modern building with large windows, surrounded by trees and gravel.

9. Cozy Wooded Retreat 3 minutes from Hermann ~ Nature`s Nook

Cozy Wooded Retreat 3 minutes from Hermann ~ Nature`s Nook
Hermann
10.0 out of 10, Exceptional, (6 reviews)
"This place is AMAZING. It is beautiful and such a peaceful get away. Just a quick 5 minute drive to town, but you feel like you’re miles away. The property was beautiful and the space was peaceful and secluded. Highly recommend. "
United States
Patti
The price is ￥26,831
￥41,174 total
includes taxes & fees
Sep 13 - Sep 14
Cozy Wooded Retreat 3 minutes from Hermann ~ Nature`s Nook
A laundry area with washing machines, a wooden cabinet, and a bar stool area.

10. Papa's Cabin - 40 acres & 5 acre lake!

Papa's Cabin - 40 acres & 5 acre lake!
Middletown
10.0 out of 10, Exceptional, (3 reviews)
"Overall stay was amazing! The property was just like described and the hostess was easy to communicate with."
United States
Prisilla B.
The price is ￥17,785
￥31,499 total
includes taxes & fees
Sep 13 - Sep 14
Papa's Cabin - 40 acres & 5 acre lake!
A modern living room with a brown leather sofa, a lamp, a bookshelf, and a window.

11. Cozy Riverview Cottage. 5 minute walk to downtown

Cozy Riverview Cottage. 5 minute walk to downtown
Hermann
10.0 out of 10, Exceptional, (59 reviews)
"The cottage was very charming and a great location to downtown Hermann!"
United States
Sheila L.
The price is ￥27,598
￥41,619 total
includes taxes & fees
Sep 13 - Sep 14
Cozy Riverview Cottage. 5 minute walk to downtown
A compact kitchen with a wooden countertop and stools, a dark sofa, and two armchairs in a living area with hardwood flooring.

12. Wine Alley West Suite

Wine Alley West Suite
Hermann
9.0 out of 10, Wonderful, (57 reviews)
"Great location for the price compared to others in the area! Very walkable. Parking was accessible and the host was helpful."
United States
Laurend M.
The price is ￥22,231
￥33,339 total
includes taxes & fees
Sep 13 - Sep 14
Wine Alley West Suite
A modern kitchen with a marble backsplash, stainless steel appliances, and a wooden bar area with bar stools.

13. Vaudeville Suite, Romantic King Stay Just 4 Min from Hermann Wineries

Vaudeville Suite, Romantic King Stay Just 4 Min from Hermann Wineries
Hermann
The price is ￥34,773
￥42,125 total
includes taxes & fees
Sep 15 - Sep 16
Vaudeville Suite, Romantic King Stay Just 4 Min from Hermann Wineries
A brick building with a sign that reads "MUNHART'S." There are outdoor tables and chairs, and a covered patio area.

14. Plenty room for relaxing and downtown location to walk around!

Plenty room for relaxing and downtown location to walk around!
Hermann
10.0 out of 10, Exceptional, (21 reviews)
"We loved the room and enjoyed all of the amenities and small touches. The location is fantastic and centralized in the Herman area. We highly recommend it."
United States
Joe
The price is ￥39,672
￥51,291 total
includes taxes & fees
Oct 7 - Oct 8
Plenty room for relaxing and downtown location to walk around!

15. The Geneva Villa by Innsbrook Vacations!

The Geneva Villa by Innsbrook Vacations!
Innsbrook
10.0 out of 10, Exceptional, (9 reviews)
"Comfortable and cozy for a long weekend stay!"
United States
Amy S.
The price is ￥21,482
￥47,791 total
includes taxes & fees
Sep 11 - Sep 12
The Geneva Villa by Innsbrook Vacations!
A building with large windows, a covered porch, and a welcome mat.

16. Depot Suite - Ground-Floor Historic Loft on Katy Trail, 4 Mins to Hermann Wineries

Depot Suite - Ground-Floor Historic Loft on Katy Trail, 4 Mins to Hermann Wineries
Hermann
10.0 out of 10, Exceptional, (4 reviews)
"So pretty and perfect for our weekend."
United States
Katherine B.
The price is ￥34,773
￥42,125 total
includes taxes & fees
Sep 15 - Sep 16
Depot Suite - Ground-Floor Historic Loft on Katy Trail, 4 Mins to Hermann Wineries
A hallway with a chalkboard, a bench, a colorful rug, and shelves with papers.

17. Germantown Inn & Lounge RM 3

Germantown Inn & Lounge RM 3
Hermann
The price is ￥20,238
￥25,109 total
includes taxes & fees
Sep 24 - Sep 25
Germantown Inn & Lounge RM 3
A living room with a wooden floor, a dining area with a table and chairs, a patterned armchair, a small table with a lamp, and a potted plant.

18. Charming 2-bedroom house in fabulous downtown Hermann

Charming 2-bedroom house in fabulous downtown Hermann
Hermann
9.8 out of 10, Exceptional, (16 reviews)
"Had a great time here-very responsive hosts-clean,quiet-just perfect for our stay!"
United States
Carrie Jean
The price is ￥26,831
￥50,623 total
includes taxes & fees
Sep 13 - Sep 14
Charming 2-bedroom house in fabulous downtown Hermann
A rustic bar area with stone walls, wooden chairs, and hanging pendant lights.

19. Lakefront Studio Condo

Lakefront Studio Condo
Wright City
9.8 out of 10, Exceptional, (35 reviews)
"everything was beautiful and really calm, we had a really good time there"
United States
Vanessa O.
The price is ￥17,249
￥38,453 total
includes taxes & fees
Sep 21 - Sep 22
Lakefront Studio Condo
A bedroom with a bed, two bedside tables, a mirror, a wooden door, and a nightstand with a plant.

20. In town -2 bedroom + 2 sofa beds + game room/common area -fits 8 people

In town -2 bedroom + 2 sofa beds + game room/common area -fits 8 people
Hermann
9.6 out of 10, Exceptional, (8 reviews)
"Angela has a very clean and spacious basement rental that was perfect for our weekend ! The home was clean, bright and very well cared for. We definitely recommend it for your family."
United States
Sheryl C.
The price is ￥23,458
￥46,185 total
includes taxes & fees
Sep 16 - Sep 17
In town -2 bedroom + 2 sofa beds + game room/common area -fits 8 people
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top High Hill Hotel Reviews

Studio Condo on the Water @ Innsbrook

Studio Condo on the Water @ Innsbrook

10/10 Excellent
"Nice place to get away close to home."
Mark C. 2-night trip
Posted 3 hours ago
Studio Condo on the Water @ Innsbrook

Find out more about High Hill

Search for holiday rentals in High Hill on Expedia! You can easily find your home rentals, villas, holiday apartments in High Hill using one of the methods below:

  • View our selection of featured holiday rentals in High Hill
  • Use the map to find apartments and other holiday homes in the High Hill neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in High Hill while they last

Look no further and take a look at our great range of rental properties in High Hill!

Frequently asked questions

Are there vacation rentals in High Hill?

Yes, we offer vacation rentals near well known points of interest in High Hill, or you can select a more secluded option if you're looking for a relaxing stay. High Hill is known for its coffeehouses and restaurants.

What are some of the best vacation rentals that High Hill has to offer?

Carriage House at the Mansion on Market Street: Visitors like this High Hill vacation home rental. It offers a fireplace, a hot tub, and a barbecue grill to help you feel perfectly comfortable in your new surroundings.

What can I see and do in High Hill?

While you're exploring the area, Graham Cave State Park and Katy Trail - McKittrick Trailhead are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Endless Summer Winery and Warrenton City Hall.

What are vacation rentals like in High Hill?

Vacation rentals are private accommodations you can stay in for a short or long stay in High Hill. Vacation rentals feature amenities like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from public hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for families.