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
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for High Hill vacation rentals

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)
The price is CA $273
CA $294 total
includes taxes & fees
Sep 8 - Sep 9
The Mercantile on the Katy Trail

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 CA $280
CA $511 total
includes taxes & fees
Sep 2 - Sep 3
3-bedroom family friendly home on 4 acres near Hermann with WiFi, AC, deck

3. 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 CA $314
CA $379 total
includes taxes & fees
Sep 8 - Sep 9
McKittrick Suite - Loft Stay on Katy Trail in Historic Mercantile, 4 min Hermann

4. Archie’s House

Archie’s House
Berger
10.0 out of 10, Exceptional, (37 reviews)
"House was perfect for our girl’s trip"
United Kingdom
Monica A.
The price is CA $510
CA $699 total
includes taxes & fees
Aug 31 - Sep 1
Archie’s House

5. 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 CA $242
CA $369 total
includes taxes & fees
Sep 8 - Sep 9
Cozy Wooded Retreat 3 minutes from Hermann ~ Nature`s Nook

6. 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, (1 review)
The price is CA $366
CA $411 total
includes taxes & fees
Sep 8 - Sep 9
Downtown Hermann Small Batch Suite with Sidewalk Swagger at Lionheart Distillery

7. Germantown Inn & Lounge

Germantown Inn & Lounge
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 CA $224
CA $286 total
includes taxes & fees
Sep 8 - Sep 9
Germantown Inn & Lounge

8. Cozy Riverview Cottage. 5 minute walk to downtown

Cozy Riverview Cottage. 5 minute walk to downtown
Hermann
10.0 out of 10, Exceptional, (57 reviews)
The price is CA $249
CA $373 total
includes taxes & fees
Sep 8 - Sep 9
Cozy Riverview Cottage. 5 minute walk to downtown

9. Charming 2-bedroom house in fabulous downtown Hermann

Charming 2-bedroom house in fabulous downtown Hermann
Hermann
9.6 out of 10, Exceptional, (14 reviews)
"Had a great time here-very responsive hosts-clean,quiet-just perfect for our stay!"
United States
Carrie Jean
The price is CA $208
CA $409 total
includes taxes & fees
Aug 30 - Aug 31
Charming 2-bedroom house in fabulous downtown Hermann

10. Ash Creek Guesthouse - Downtown Historic Hermann

Ash Creek Guesthouse - Downtown Historic Hermann
Hermann
9.8 out of 10, Exceptional, (52 reviews)
"Great place for our crew. Rode the Katy Trail and experienced Hermann. Very clean and well taken care of. Highly recommend. "
United States
Mark
The price is CA $278
CA $529 total
includes taxes & fees
Aug 30 - Aug 31
Ash Creek Guesthouse - Downtown Historic Hermann

11. 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 CA $201
CA $297 total
includes taxes & fees
Sep 3 - Sep 4
Wine Alley East suite

12. Wine Alley West Suite

Wine Alley West Suite
Hermann
9.0 out of 10, Wonderful, (57 reviews)
"Nice location, tan out of hot water, but nice clean!! "
United States
Melissa B.
The price is CA $201
CA $297 total
includes taxes & fees
Sep 2 - Sep 3
Wine Alley West Suite

13. 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, (20 reviews)
"Great location. We were repeat guests. Laura and her husband always go above and beyond. We love it there. "
United States
Julie I.
The price is CA $280
CA $359 total
includes taxes & fees
Aug 30 - Aug 31
Plenty room for relaxing and downtown location to walk around!

14. 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 CA $161
CA $285 total
includes taxes & fees
Sep 2 - Sep 3
Papa's Cabin - 40 acres & 5 acre lake!

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 CA $194
CA $434 total
includes taxes & fees
Aug 30 - Aug 31
The Geneva Villa by Innsbrook Vacations!

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 CA $314
CA $379 total
includes taxes & fees
Sep 8 - Sep 9
Depot Suite - Ground-Floor Historic Loft on Katy Trail, 4 Mins to Hermann Wineries

17. Lakefront Lodge by Innsbrook Vacations!

Lakefront Lodge by Innsbrook Vacations!
Innsbrook
9.8 out of 10, Exceptional, (10 reviews)
"Clean and pet friendly. Great stay"
United States
Anne W.
The price is CA $186
CA $508 total
includes taxes & fees
Aug 30 - Aug 31
Lakefront Lodge by Innsbrook Vacations!

18. Fox Hollow by Innsbrook Vacations!

Fox Hollow by Innsbrook Vacations!
Innsbrook
9.4 out of 10, Exceptional, (8 reviews)
"House was just as described. Excellent communication. Very cozy weekend getaway!"
United States
Anne L.
The price is CA $262
CA $754 total
includes taxes & fees
Sep 13 - Sep 14
Fox Hollow by Innsbrook Vacations!

19. 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, (63 reviews)
"Loved this stay for our girls trip!! So nice and clean! Would definitely rent again!"
United States
Lauren
The price is CA $344
CA $712 total
includes taxes & fees
Aug 30 - Aug 31
Historic Downtown Hermann Getaway-Walk to Wineries, Shops and Restaurants!

20. The Honey Bee Inn by Innsbrook Vacations!

The Honey Bee Inn by Innsbrook Vacations!
Innsbrook
9.4 out of 10, Exceptional, (15 reviews)
"Super clean, well equipped, lovely forest view! We loved the honeybee themed cottage! Nice details everywhere!"
United States
JENNIFER S.
The price is CA $262
CA $730 total
includes taxes & fees
Sep 16 - Sep 17
The Honey Bee Inn by Innsbrook Vacations!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top High Hill Hotel Reviews

Find out more about High Hill

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with High Hill. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 WiFi 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, Daniel Boone Conservation Area and Graham Cave State Park are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Endless Summer Winery and Katy Trail - McKittrick Trailhead.

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.