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High Hill Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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, (43 reviews)
"We loved this place- very unique! Clean and great communication from hosts."
United States
Kristine
The price is ￥31,067
￥33,389 total
includes taxes & fees
Dec 1 - Dec 2
The Mercantile on the Katy Trail
A wooden bridge leading to a two-story house with multiple windows and a covered porch.

2. The Cottage

The Cottage
2.0 star property
Hermann
10.0 out of 10, Exceptional, (1 review)
"Our host mentioned he does not receive messages from Expedia postings. So if you are not receiving check-in information, you might want to find another way to contact them. The property is lovely. The Treehouse was perfect for my granddaughter and me."
United States
Linda
The price is ￥26,933
￥38,845 total
includes taxes & fees
Nov 2 - Nov 3
The Cottage
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, (52 reviews)
"Very nice place "
United States
Yaqui S.
The price is ￥28,361
￥38,082 total
includes taxes & fees
Nov 5 - Nov 6
Secluded 2 bedroom home close to Hermann
A spacious living area with a large blue sofa, a television, and a wooden entertainment unit.

4. 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
9.8 out of 10, Exceptional, (19 reviews)
"Host was very accommodating, property perfect, I can't say enough good things about our stay."
United States
Susan R.
The price is ￥31,906
￥55,245 total
includes taxes & fees
Nov 3 - Nov 4
3-bedroom family friendly home on 4 acres near Hermann with WiFi, AC, deck
A building with large windows, a covered porch, and a welcome mat.

5. 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 ￥36,869
￥42,461 total
includes taxes & fees
Nov 18 - Nov 19
McKittrick Suite - Loft Stay on Katy Trail in Historic Mercantile, 4 min Hermann
A two-story house with a blue exterior, a front porch, and a small front yard.

6. Hickory Lake House

Hickory Lake House
3.0 star property
Wright City
The price is ￥44,106
￥69,240 total
includes taxes & fees
Nov 4 - Nov 5
Hickory Lake House
An outdoor patio with a pergola, wicker furniture, and a view of the landscape.

7. Gipfel Suite - Himmel Haus Bed & Breakfast

Gipfel Suite - Himmel Haus Bed & Breakfast
Hermann
10.0 out of 10, Exceptional, (143 reviews)
"The room was nice with a great shower. The breakfast was delicious."
United States
Peggy
The price is ￥16,386
￥26,479 total
includes taxes & fees
Nov 2 - Nov 3
Gipfel Suite - Himmel Haus Bed & Breakfast
A compact kitchen with a wooden countertop and stools, a dark sofa, and two armchairs in a living area with hardwood flooring.

8. Wine Alley West Suite

Wine Alley West Suite
Hermann
9.0 out of 10, Wonderful, (61 reviews)
"Good location with an easy walk to downtown shops. Communication and flexibility on checking in was very good and much appreciated. Apartment worked out great for my trip thru Herman."
United States
Clyde O.
The price is ￥22,846
￥32,686 total
includes taxes & fees
Nov 4 - Nov 5
Wine Alley West Suite
A compact kitchen with a bar area, a dining table with stools, and a small seating area with two chairs.

9. Wine Alley East suite

Wine Alley East suite
Hermann
9.2 out of 10, Wonderful, (91 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 ￥22,846
￥32,686 total
includes taxes & fees
Nov 2 - Nov 3
Wine Alley East suite
A residential property with a red-roofed building, a grey-roofed house, and a fenced yard.

10. The Shed for Couples Only!-Hermann

The Shed for Couples Only!-Hermann
Hermann
10.0 out of 10, Exceptional, (33 reviews)
"We had a wonderful stay! Perfect spot for a weekend in Hermann. The Shed has everything we needed and was clean and cozy."
United States
Natalie J.
The price is ￥46,480
￥55,173 total
includes taxes & fees
Nov 6 - Nov 7
The Shed for Couples Only!-Hermann
A wooden staircase leading to a modern building with large windows, surrounded by trees and gravel.

11. 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, (8 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 ￥27,573
￥40,422 total
includes taxes & fees
Nov 2 - Nov 3
Cozy Wooded Retreat 3 minutes from Hermann ~ Nature`s Nook
A building with large windows, a covered porch, and a welcome mat.

12. 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 ￥35,735
￥41,242 total
includes taxes & fees
Nov 3 - Nov 4
Depot Suite - Ground-Floor Historic Loft on Katy Trail, 4 Mins to Hermann Wineries
A bed with a quilted cover, a brick wall, and a window with curtains.

13. Downtown Hermann Small Batch Suite with Sidewalk Swagger at Lionheart Distillery

Downtown Hermann Small Batch Suite with Sidewalk Swagger at Lionheart Distillery
Hermann
10.0 out of 10, Exceptional, (3 reviews)
"Great location!"
United States
Katie P.
The price is ￥43,865
￥54,215 total
includes taxes & fees
Nov 2 - Nov 3
Downtown Hermann Small Batch Suite with Sidewalk Swagger at Lionheart Distillery
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.

14. Charming 2-bedroom house in fabulous downtown Hermann

Charming 2-bedroom house in fabulous downtown Hermann
Hermann
9.8 out of 10, Exceptional, (17 reviews)
"Had a great time here-very responsive hosts-clean,quiet-just perfect for our stay!"
United States
Carrie Jean
The price is ￥19,695
￥38,005 total
includes taxes & fees
Dec 2 - Dec 3
Charming 2-bedroom house in fabulous downtown Hermann
A bedroom with a bed, bedside lamps, a ceiling fan, a window with curtains, a wall-mounted TV, and a radiator.

15. Germantown Inn & Lounge RM 1

Germantown Inn & Lounge RM 1
Hermann
10.0 out of 10, Exceptional, (4 reviews)
"The property was awesome! It’s near lots of great places!"
United States
Charles G.
The price is ￥25,525
￥31,553 total
includes taxes & fees
Nov 9 - Nov 10
Germantown Inn & Lounge RM 1
A room with a round table, a television, and a poster on the wall.

16. Ash Creek Suite - In Downtown Historic Hermann

Ash Creek Suite - In Downtown Historic Hermann
Hermann
9.4 out of 10, Exceptional, (56 reviews)
"Great place! Great location! And clean!"
United States
Cheryl E.
The price is ￥22,058
￥39,971 total
includes taxes & fees
Dec 2 - Dec 3
Ash Creek Suite - In Downtown Historic Hermann
A modern kitchen with a marble backsplash, stainless steel appliances, and a wooden bar area with bar stools.

17. 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 ￥35,735
￥39,666 total
includes taxes & fees
Nov 10 - Nov 11
Vaudeville Suite, Romantic King Stay Just 4 Min from Hermann Wineries
A black door with a welcome sign, a stone wall, and a wooden post with the number 139.

18. Historic Downtown Hermann Getaway-Walk to Wineries, Shops and Restaurants!

Historic Downtown Hermann Getaway-Walk to Wineries, Shops and Restaurants!
Hermann
10.0 out of 10, Exceptional, (70 reviews)
"It was a great place to stay. Having a bathroom for every bedroom was fabulous"
United States
Stephanie R.
The price is ￥42,541
￥81,759 total
includes taxes & fees
Nov 2 - Nov 3
Historic Downtown Hermann Getaway-Walk to Wineries, Shops and Restaurants!
A hallway with a chalkboard, a bench, a colorful rug, and shelves with papers.

19. Germantown Inn & Lounge RM 5

Germantown Inn & Lounge RM 5
Hermann
10.0 out of 10, Exceptional, (2 reviews)
"This was very quaint, comfortable, and in the middle of the action - walking distance to everything. I would definitely book again."
United States
Victoria
The price is ￥25,525
￥31,553 total
includes taxes & fees
Nov 3 - Nov 4
Germantown Inn & Lounge RM 5
A brick building with a sign that reads "MUNHART'S." There are outdoor tables and chairs, and a covered patio area.

20. 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 ￥36,239
￥44,821 total
includes taxes & fees
Nov 2 - Nov 3
Plenty room for relaxing and downtown location to walk around!
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.
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Top High Hill Hotel Reviews

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

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

10/10 Excellent
"We had a lovely time staying in this beautiful home on the lake. I highly recommend it!!"
Kelly H. 2-night trip
Posted 2 days ago
Peaceful chalet - *new* private beach, WIFI, kayaks

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
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  • 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?

Cozy Riverview Cottage. 5 minute walk to downtown: Visitors like this High Hill vacation home rental. It is equipped with a patio, air-conditioning, and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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 OakGlenn Vineyards and Winery.

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.