High Hill Vacation Rentals

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Vacation Rentals in High Hill

Cottage Properties - Country Log Cabin
10.0 out of 10, Exceptional, (141)
"We had a great time. The cabin was at a good location just off of the highway. If you want to go to Herman, you may want to use the paved road. Hanging out with the horses and outside was nice. We went to Herman and Jonesburg for a day trip and hung out at the cabin playing games till late."
Cottage Properties - Country Log Cabin
Charming 1913 3 Bedr / 2 Bath / Dutch Brick Haus / Living & Dining / New HVAC
10.0 out of 10, Exceptional, (63)
"The Songbird House was beautiful. The owners have done a great job maintaining the historical beauty of the home. Paul is very friendly and was available for any questions we had. The location was awesome! We were able to walk downtown and visit several restaurants and shops. We plan to stay again in the future."
Charming 1913 3 Bedr / 2 Bath / Dutch Brick Haus / Living & Dining / New HVAC
The Farmhouse Inn: 3 bed, 3.5 whole house rental
10.0 out of 10, Exceptional, (84)
"We had a blast! The house was amazing and when i had questions how to work the A/C unit they responded less than 60 seconds. Def would recommend"
The Farmhouse Inn: 3 bed, 3.5 whole house rental
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Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!
9.6 out of 10, Exceptional, (67)
"Stayed for a bachelorette party and enjoyed the wineries and house aesthetic. Very cute home with so much history. I look forward to staying here again in the future!! "
Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!
Helen's House-3 bed, 2 bath bungalow 3 blocks from Main Street!!!
10.0 out of 10, Exceptional, (13)
"Loved the screened-in porch. Nice kitchen was well equipped. Walking distance to Herman happenings. Stairs to upstairs bedrooms are steep and narrow so not for physically challenged. Great response from the property manager. A gem!"
The price is CA $409
CA $677 total
includes taxes & fees
Jun 3 - Jun 4
Helen's House-3 bed, 2 bath bungalow 3 blocks from Main Street!!!
Quiet Lakefront Cottage with Dock & Resort Access!
9.6 out of 10, Exceptional, (116)
"Quick birthday getaway to our favorite hidden gem in Missouri. Can’t say enough about Innsbrook. Chalet had everything we needed - large master bath on first floor. Big plus versus most of the other chalets in area. Larry was very accessible leading up to and during our stay. First time staying on Aspen lake so it was nice to sit down on the large dock and take in all of Mother Nature. Highly recommend staying at this property."
Quiet Lakefront Cottage with Dock & Resort Access!
New home in Historic downtown Hermann
10.0 out of 10, Exceptional, (25)
"The place is so cute and nice inside! I would definitely stay there again! Everything was nice and neat! 10/10! The bathrooms are amazing and the beds are comfy!"
The price is CA $409
CA $787 total
includes taxes & fees
May 30 - May 31
New home in Historic downtown Hermann
Cozy Riverview Cottage. 5 minute walk to downtown
10.0 out of 10, Exceptional, (11)
"Wonderful property will be going back soon."
The price is CA $273
CA $397 total
includes taxes & fees
Jun 11 - Jun 12
Cozy Riverview Cottage. 5 minute walk to downtown
Cozy 2 bedroom waterfront chalet with private beach, hot tub at Innsbrook Resort
10.0 out of 10, Exceptional, (52)
"So much outdoor lake fun. Hot tub, paddle boards, kayaks, fire pit, beach and multiple decks and seating areas. Lake life!"
The price is CA $614
CA $1,030 total
includes taxes & fees
Jun 24 - Jun 25
Cozy 2 bedroom waterfront chalet with private beach, hot tub at Innsbrook Resort
Ash Creek Suite - In Downtown Historic Hermann
9.4 out of 10, Exceptional, (36)
"It was very nice and had a lot to do in walking distance."
The price is CA $273
CA $468 total
includes taxes & fees
Jun 9 - Jun 10
Ash Creek Suite - In Downtown Historic Hermann
Cozy custom-built cabin - Lakeside
10.0 out of 10, Exceptional, (27)
"My wife and i celebrated and incredible 24th wedding anniversary made even more spectacular by this elegant country escape. A special thanks goes out to our hosts who made our weekend so memorable. You can tell they put a lot of love and hard work into this remarkable little oasis in the trees."
Cozy custom-built cabin - Lakeside
The Chic Chalet
10.0 out of 10, Exceptional, (2)
"From the second I walked into this amazing space, I was relaxed and full of peace. The view was serene and the bed was super comfortable. Thank you for hosting me on my annual weekend of solitude. Can’t wait to come back. Thank you to the hosts."
The Chic Chalet
Peaceful lake chalet - WIFI, kayaks, private dock
10.0 out of 10, Exceptional, (43)
"This is my second time in the past month renting out this exact location from Michael. This A frame cabin is truly beautiful in every way possible. If you are choosing where to stay at innsbrook, no need to look further! I’ll be back!"
Peaceful lake chalet - WIFI, kayaks, private dock
Reflection Point by Innsbrook Vacations!
10.0 out of 10, Exceptional, (4)
"Property was beautiful and we all enjoyed our stay. It was 3 families, all with kids between the ages of 5-10. The kids lived the loft and tire swing. Parents loved the fire pit and fireplace. And there’s an abundance of firewood on hand. Also had a great little dock to right on the water with lots of sun. Note- there’s no dishwasher or laundry facilities at the place. And there’s 2 showers. The downstairs one was great with lots of hot water and great pressure. Upstairs shower had almost no...
Reflection Point by Innsbrook Vacations!
A Stunning Home, newly constructed & furnished
10.0 out of 10, Exceptional, (42)
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A Stunning Home, newly constructed & furnished
Spectacular Innsbrook House on Alpine Lake
10.0 out of 10, Exceptional, (147)
"We had a great time. Walked trails, fished, worked out, played pickleball and relaxed. Definitely want to book again next year!"
Spectacular Innsbrook House on Alpine Lake
DeFlorin Stone Cottage, Hermann's Popular Downtown Home, Free Wine $20 Shuttle
9.8 out of 10, Exceptional, (94)
"The Stone House had too many narrow stairways for 3 elderly ladies (somehow we missed this important detail in the description when booking) so our host kindly moved us across the street to the Bicentennial House which was perfect for our 1-night stay. We loved the Bicentennial House with spacious rooms, a formal dining area and most adequate kitchen. We thoroughly enjoyed our visit to Hermann, MO. We took full advantage of the shuttle service through Hermann Crown Suites to tour the town and...
The price is CA $430
CA $552 total
includes taxes & fees
Jun 3 - Jun 4
DeFlorin Stone Cottage, Hermann's Popular Downtown Home, Free Wine $20 Shuttle
Brick Bungalow
10.0 out of 10, Exceptional, (37)
"Great location and clean."
Brick Bungalow
A house on the wine circuit
9.0 out of 10, Wonderful, (24)
"Great location, Much easier to access than we thought. Quiet as well. Perfect for a couples group. We also appreciated the full size refrigerator."
A house on the wine circuit
Suite on Schiller
9.8 out of 10, Exceptional, (85)
"Home was clean, comfortable and had everything we needed. We loved visiting Hermann!"
Suite on Schiller
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See all available properties in High Hill
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.

High Hill Vacation Rental Travel Info

Other types of properties in High Hill you may be interested in

Motel 70
2.0 star property
9.0 out of 10, Wonderful, (399)
"Perfect for wut I needed"
The price is CA $101
CA $108 total
includes taxes & fees
Jun 6 - Jun 7
Motel 70
Cottage Properties - Country Log Cabin
10.0 out of 10, Exceptional, (141)
"We had a great time. The cabin was at a good location just off of the highway. If you want to go to Herman, you may want to use the paved road. Hanging out with the horses and outside was nice. We went to Herman and Jonesburg for a day trip and hung out at the cabin playing games till late."
Cottage Properties - Country Log Cabin
Hermann Crown Suites
3.5 star property
9.4 out of 10, Exceptional, (577)
"I absolutely loved everything about this place. Everything was clean, the staff were very nice, the surrounding area had plenty of dinning areas and shops within walking distance. My whole experience was wonderful, I definitely recommend to stay here if your going to stay in hermann."
The price is CA $220
CA $252 total
includes taxes & fees
Jun 2 - Jun 3
Hermann Crown Suites
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.

Everything you need to know about High Hill vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the High Hill vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect High Hill vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

High Hill vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in High Hill. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A High Hill vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of High Hill vacation rentals we have selected for you start as low as CA $273 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on High Hill rentals

At Expedia, we put the best High Hill vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top High Hill rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream High Hill vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around High Hill. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!! : Visitors like this High Hill vacation home rental. It offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of books.

What can I see and do in High Hill?

While exploring the area, visit the sights like OakGlenn Vineyards and Winery, Hermannhof Vineyards, and Stone Hill Winery. In the larger area, you’ll find Adam Puchta & Son Winery and Endless Summer 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.

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