Best Vacation Homes in High Hill
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $153/Night
For 7 Nights US $1,070
602.78 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $392/Night
For 7 Nights US $2,747
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $223/Night
For 7 Nights US $1,564
600 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Cabin
- Hot Tub
- Fireplace/Heating
- Ocean View
US $321/Night
For 7 Nights US $2,247
602.78 ft²
2 Guests
1 Bedroom
1 Bathroom
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $432/Night
For 7 Nights US $3,026
600 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Cabin
- Hot Tub
- Fireplace/Heating
- Ocean View
US $341/Night
For 7 Nights US $2,389
9 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $350/Night
For 7 Nights US $2,450
1800 ft²
11 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $300/Night
For 7 Nights US $2,099
High Hill Luxury Rentals
18 Guests
7 Bedrooms
7 Bathrooms
Ocean View
House
- Hot Tub
- Spa
- Fireplace/Heating
US $1,156/Night
For 7 Nights US $8,090
6 Guests
1 Bedroom
1 Bathroom
Pet Friendly
Other
- Fireplace/Heating
- Child Friendly
- Laundry
US $818/Night
For 7 Nights US $5,727
13 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
Other
- Private Pool
- Hot Tub
- Fireplace/Heating
US $534/Night
For 7 Nights US $3,737
3500 ft²
14 Guests
7 Bedrooms
3 Bathrooms
Family Friendly
Other
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $381/Night
For 7 Nights US $2,668
10 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $366/Night
For 7 Nights US $2,559
1614.59 ft²
11 Guests
3 Bedrooms
1 Bathroom
Free Cancellation
House
- Fireplace/Heating
- Balcony/Terrace
- Parking
US $342/Night
For 7 Nights US $2,393
600 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $341/Night
For 7 Nights US $2,389
602.78 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $337/Night
For 7 Nights US $2,360
High Hill Pet Friendly Vacation Rentals
800 ft²
6 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $284/Night
For 7 Nights US $1,985
500.52 ft²
4 Bathrooms
Free Cancellation
Hotel
- Fireplace/Heating
- Balcony/Terrace
- View
US $207/Night
For 7 Nights US $1,446
700 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $280/Night
For 7 Nights US $1,957
487.06 ft²
5 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $136/Night
For 7 Nights US $952
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $187/Night
For 7 Nights US $1,309
US $127/Night
For 7 Nights US $892
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $173/Night
For 7 Nights US $1,210
High Hill Large Vacation Homes
3500 ft²
26 Guests
6 Bedrooms
5 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $892/Night
For 7 Nights US $6,242
16 Guests
5 Bedrooms
5 Bathrooms
Family Friendly
Cabin
- Private Pool
- Hot Tub
- Spa
US $1,047/Night
For 7 Nights US $7,330
12000 ft²
16 Guests
7 Bedrooms
7 Bathrooms
Family Friendly
House
- Hot Tub
- Spa
- Fireplace/Heating
US $1,406/Night
For 7 Nights US $9,842
13 Guests
5 Bedrooms
2 Bathrooms
Family Friendly
Other
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $505/Night
For 7 Nights US $3,535
Why Choose Rent By Owner for your High Hill Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit High Hill
When should you plan your Vacation Rentals stay?
Choosing the optimal time to vacation here ensures you experience the region's best weather and local events, making your stay in this destination truly memorable.
Peak Season Highlights
Spring (March to May)
During spring, you can experience pleasant weather with blooming scenery, making it an ideal time for outdoor activities. The region sees an increase in visitors seeking to enjoy the natural beauty and mild temperatures.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Fall (September to November)
Autumn offers vibrant foliage and crisp air, attracting those who want to explore the area's scenic landscapes. It’s a popular season for travelers looking to enjoy the cooler temperatures and serene atmosphere.
Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F
Off-Season Highlights
Summer (June to August)
In summer, you’ll find warmer temperatures that are perfect for enjoying longer daylight hours. Travel tends to be less crowded, providing a more relaxed experience when staying here.
Average Temperature Daytime: 80°F to 90°F - Nighttime: 60°F to 70°F
Winter (December to February)
During winter, the region experiences cooler temperatures and a quieter atmosphere. It’s an ideal time for those who prefer a peaceful getaway and don’t mind the chill.
Average Temperature Daytime: 35°F to 45°F - Nighttime: 20°F to 30°F
Weekly Weather Forecast for High Hill
How to Book Your High Hill Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in High Hill
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining with a fully equipped patio or BBQ area, perfect for relaxing evenings in the region.
- Take advantage of spacious yards or gardens for outdoor activities and family gatherings.
- Make use of private pools or hot tubs to unwind while soaking in the serene surroundings near here.
- Explore well-maintained walking trails or nature paths that showcase the scenic beauty of the area.
- Spend time on a porch or veranda while taking in views unique to this destination’s landscape.
- Utilize outdoor fire pits for cozy evenings under the stars in this region’s peaceful environment.
- Take advantage of available sports courts or recreational equipment for active fun outside your rental.
Top Attractions Around High Hill
What attractions are nearby?
During your stay, you can enjoy a variety of outdoor activities and local attractions just a short drive from here, making it easy to explore the natural beauty and charm of this destination in Missouri.
Family Activities
- High Hill Park and Recreation Area: Enjoy outdoor family fun by exploring scenic trails, playing on the well-maintained sports fields, or having a relaxing picnic in this community-centered park.
- The High Hill Heritage Museum: Discover local history and engage with interactive exhibits that offer educational entertainment for visitors of all ages.
- Downtown High Hill Historic District: Take a family stroll through charming streets lined with preserved architecture, boutique shops, and inviting cafes that showcase the area's rich heritage.
- Local Farm Tours and Pick-Your-Own Farms: Experience agricultural life firsthand with seasonal farm visits that allow your family to pick fresh produce and learn about sustainable farming practices.
Adult Activities
- Wine Tasting Tours: You can indulge in local wine tasting experiences that highlight the region's rich viticultural heritage, perfect for relaxing afternoons.
- Historic Main Street Exploration: Stroll through charming downtown streets filled with unique shops and eateries that reflect the area's history and character.
- Outdoor Nature Walks: Enjoy scenic trails nearby that offer a tranquil environment to connect with nature and unwind amidst beautiful landscapes.
- Local Art Galleries: Discover vibrant art scenes through galleries showcasing regional artists, providing inspiration and cultural enrichment during your stay.
Other Places to Stay in High Hill, MO
Bear Creek
High Hill Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining and Shops: Take advantage of the charming local eateries and boutiques to fully experience the area's unique charm during your stay.
- Plan Outdoor Activities: Enjoy the natural surroundings by scheduling outdoor adventures such as hiking or scenic drives that showcase the region’s beauty.
- Check for Seasonal Events: Keep an eye on seasonal festivals and events happening nearby to immerse yourself in the local culture and community atmosphere.
- Book Early for Popular Properties: Secure your preferred vacation rentals ahead of time, especially during peak travel seasons, to ensure a smooth and stress-free visit.
Transportation Options
- Personal Vehicles: Using your own car provides the most flexible way to explore this destination and access nearby attractions with ease.
- Rental Cars: Renting a vehicle in the region allows you to enjoy convenient transportation while comfortably navigating rural and scenic routes.
- Public Transit: Local bus services offer an economical option for traveling around here, connecting you to key areas within the area.
- Taxi and Ride-Sharing Services: Rideshare apps and taxis provide quick and reliable transportation for short trips or when convenience is a priority here.
Local Customs Options
- Local Wine Making:** You’ll find that crafting and enjoying local wines is a cherished tradition here, reflecting the region’s rich agricultural roots.
- Historical Celebrations:** Participating in nearby community events often includes honoring longstanding customs, showcasing the area's vibrant heritage.
- Church Community Gatherings:** Many residents value close-knit church traditions, which are central to social life in this part of Missouri.
- Harvest Festivals:** Visitors can experience the region’s agricultural cycle through seasonal festivals that celebrate local harvests and produce.
High Hill Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in High Hill?
There are a lot of options in High Hill. If you plan on staying in the High Hill area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in High Hill:
- Cottage Properties - Country Log Cabin
- Cozy custom-built Cabin - Lakeside
- Spacious Five Bedroom Country Home Near Hermann MO
- Treehouse - Sunrise
- Quiet Country 3 Bedroom Escape in Jonesburg MO
- 4K Ranch - 10 acre property & home near Hermann
- Treehouse - Twilight
- NEW! Out On A Limb Treehouse
- The Venue at Hermann
- The Venue at Hermann
2. Which vacation homes in High Hill are best for families?
If you are looking for a family-friendly vacation home in High Hill, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in High Hill:
3. How many Rentbyowner vacation rentals are available in High Hill?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 50 in the High Hill area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in High Hill.
4. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary by listing, so it’s important to review the specific terms on each property’s page. You can find detailed information regarding cancellations and refunds directly in the booking details or contact the property owner for clarification.
5. How do I confirm my reservation at a vacation rental in the region?
Reservations are confirmed once you complete the booking process and receive a confirmation email or notification from the platform. Always check your email and the listing details to ensure your reservation is secured.
6. Are there any additional fees I should be aware of when booking a vacation rental here?
Additional fees such as cleaning, service charges, or taxes may apply depending on the property. These will be clearly listed during the booking process, and you should review these details before finalizing your reservation.
7. What amenities are typically included with vacation rentals in this destination?
Most vacation rentals in the region offer amenities like Wi-Fi, parking, kitchen facilities, and linens. Specific amenities vary by property, so check each listing to see what is included to meet your needs.
8. What should I know about check-in and check-out procedures for vacation rentals in this area?
Check-in and check-out times are specified on each listing. Many properties offer flexible options, but it's best to read the instructions provided by the owner for smooth arrival and departure.
High Hill Top Rated Vacation Rentals
US $199/Night
For 7 Nights US $1,393
