Discover Your Perfect Henry County Vacation Homes

Best Vacation Homes in Henry County

Apartment
Map-icon
like-icon10.0
Exceptional
(7 Reviews)
1 Bedroom 1 Bath 2 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
US $80/Night 7 Nights - US $560
star-icons-3
House
Map-icon
like-icon9.5
Exceptional
(4 Reviews)
3 Bedrooms 2 Baths 6 Guests 1485.42 ft²
  • Parking
    Parking
  • Internet
    Internet
More amenities
US $144/Night 7 Nights - US $1,006
Cabin
Map-icon
like-icon8.2
Excellent
(17 Reviews)
1 Bedroom 1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
US $91/Night 7 Nights - US $634
House
Map-icon
like-icon9.8
Exceptional
(23 Reviews)
2 Bedrooms 1 Bath 4 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
US $159/Night 7 Nights - US $1,110
star-icons-3
House
Map-icon
4 Bedrooms 2 Baths 10 Guests 1732.99 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
US $349/Night 7 Nights - US $2,441
House
Map-icon
like-icon9.8
Exceptional
(10 Reviews)
2 Bedrooms 2 Baths 8 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $200/Night 7 Nights - US $1,398
House
Map-icon
like-icon8.0
Excellent
(4 Reviews)
1 Bedroom 1 Bath 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $125/Night 7 Nights - US $872
House
Map-icon
2 Bedrooms 1 Bath 4 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
US $125/Night 7 Nights - US $875

Henry County Luxury Rentals

Cabin
Map-icon
like-icon10.0
Exceptional
(4 Reviews)
4 Bedrooms 4 Baths 10 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $251/Night 7 Nights - US $1,756
House
Map-icon
like-icon9.8
Exceptional
(6 Reviews)
4 Bedrooms 2 Baths 10 Guests 1728 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $217/Night 7 Nights - US $1,517
House
Map-icon
like-icon9.8
Exceptional
(14 Reviews)
3 Bedrooms 3 Baths 12 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $215/Night 7 Nights - US $1,504
House
Map-icon
like-icon9.8
Exceptional
(16 Reviews)
4 Bedrooms 2 Baths 8 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $182/Night 7 Nights - US $1,274
Cabin
Map-icon
like-icon10.0
Exceptional
(46 Reviews)
2 Bedrooms 1 Bath 7 Guests 800 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $179/Night 7 Nights - US $1,251
House
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
3 Bedrooms 1 Bath 7 Guests
  • Balcony/Terrace
    Balcony/Terrace
  • Kitchen
    Kitchen
More amenities
US $173/Night 7 Nights - US $1,212
House
Map-icon
like-icon9.2
Exceptional
(30 Reviews)
3 Bedrooms 2 Baths 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
US $173/Night 7 Nights - US $1,209
Other
Map-icon
like-icon10.0
Exceptional
(14 Reviews)
1 Bedroom 1 Bath 8 Guests 1500 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
US $160/Night 7 Nights - US $1,118

Henry County Pet Friendly Vacation Rentals

House
Map-icon
like-icon9.6
Exceptional
(52 Reviews)
3 Bedrooms 1 Bath 8 Guests 900 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $149/Night 7 Nights - US $1,045
Hotel
Map-icon
like-icon7.4
Very Good
(207 Reviews)
5 Baths 381.04 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $96/Night 7 Nights - US $674
House
Map-icon
like-icon10.0
Exceptional
(31 Reviews)
1 Bedroom 1 Bath
  • Balcony/Terrace
    Balcony/Terrace
  • View
    View
More amenities
US $179/Night 7 Nights - US $1,253
House
Map-icon
3 Bedrooms 1 Bath 8 Guests 2000 ft²
  • Balcony/Terrace
    Balcony/Terrace
  • View
    View
More amenities
US $182/Night 7 Nights - US $1,274
RV Rental
Map-icon
1 Bedroom 1 Bath 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $75/Night 7 Nights - US $525

Henry County Large Vacation Homes

Other
Map-icon
like-icon10.0
Exceptional
(5 Reviews)
4 Bedrooms 3 Baths 10 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Air Conditioner
    Air Conditioner
More amenities
US $199/Night 7 Nights - US $1,395

Discover & compare premier experiences around Henry County

We understand the importance of quality and reliability in your travel experiences. That's why we've curated options from the most reputable tour and activity providers globally, ensuring you have access to top-tier adventures.

Why Choose Rent By Owner for your Henry County Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Henry County

When should you plan your Vacation Rentals stay?

To make the most of your getaway, consider visiting during the optimal seasons when the weather and local events in this region align perfectly for a memorable stay in Henry County, Missouri.

Peak Season Highlights

spring
Spring (March to May)

During spring, the area comes to life with blooming flora and pleasant weather, making it an ideal time to explore your surroundings while enjoying comfortable daytime temperatures.

Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F
autumn
Fall (September to November)

Autumn offers cooler temperatures and vibrant foliage, providing a picturesque setting for outdoor activities and leisurely exploration of this destination.

Average Temperature Daytime: 60-70°F - Nighttime: 40-50°F

Off-Season Highlights

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Summer (June to August)

While summer brings warm weather perfect for outdoor pursuits, it is also busier as visitors flock here for seasonal events and festivals, so accommodations may fill quickly.

Average Temperature Daytime: 80-90°F - Nighttime: 60-70°F
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Winter (December to February)

The winter months tend to be quieter with colder temperatures, offering a tranquil experience if you prefer peaceful stays and fewer crowds during your visit.

Average Temperature Daytime: 35-45°F - Nighttime: 20-30°F

Weekly Weather Forecast for Henry County

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.

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 a private outdoor space with a spacious yard perfect for picnics or relaxing in the fresh air.
  • Take advantage of a barbecue grill to host cookouts and outdoor gatherings with family and friends.
  • Relax on a comfortable patio or deck, ideal for morning coffee or sunset evenings.
  • Discover nearby walking trails or nature paths for scenic outdoor adventures in the area.
  • Make use of an outdoor fire pit for cozy evenings under the stars.
  • Benefit from well-maintained gardens or landscaping that enhance your outdoor experience here.
  • Access outdoor recreational equipment such as bikes or kayaks for exploring the region's natural beauty.
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Family Activities

  • Henry County Fairgrounds: Experience family-friendly events and seasonal festivals that showcase the local community spirit in this region.
  • Harry S. Truman Farm Home: Visit the historic site where you can explore the childhood home of a President, offering educational insights for all ages.
  • Vernon County Fairgrounds: Enjoy lively agricultural exhibitions, rides, and entertainment at the fairgrounds that celebrate regional traditions and family fun.
  • Nearby State Parks: Discover outdoor adventures with scenic trails and picnic areas, perfect for creating memorable family moments in the area.
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Adult Activities

  • Fishing at Lake of the Ozarks: Spend a relaxing day casting your line at this popular fishing destination known for its diverse fish species.
  • Golfing at local courses: Enjoy a round of golf on scenic courses nestled within the region, perfect for both beginners and experienced players.
  • Exploring nature trails in the area: Discover peaceful hiking and biking opportunities along well-maintained trails that showcase the natural beauty of the surrounding countryside.
  • Visiting local wineries and breweries: Experience the region's craft beverage scene with tours and tastings at charming wineries and breweries nearby.

Henry County Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Events and Festivals: Check the area's event calendar to discover local festivals and happenings that can enrich your stay in Henry County, Missouri.
  • Plan Outdoor Activities: Take advantage of the region's natural beauty by scheduling outdoor adventures like hiking or picnicking near your vacation rental.
  • Connect with Nearby Attractions: Research nearby attractions and scenic spots to maximize your exploration and enjoy all that this destination offers.
  • Choose the Right Vacation Rental Location: Select a property close to key amenities and points of interest to make your visit more convenient and enjoyable.

Transportation Options

  • Henry County Transit System: This local transit option provides convenient bus services that connect key areas within the region, ideal for exploring the area without a car.
  • Major Highway Access: Major highways such as Interstate 35 offer straightforward routes to and from here, making driving your preferred way to navigate the region's attractions and amenities.
  • Nearby Regional Airport: The closest regional airport offers domestic flights that facilitate easy arrivals and departures for travelers visiting this destination.
  • Car Rental Services: Numerous car rental agencies operate in the vicinity, allowing you flexible transportation options during your stay in the area.

Local Customs Options

  • Honoring Local Traditions: During festivals and community events, you’ll notice residents embracing long-standing customs that reflect the area's history and cultural identity.
  • Southern Hospitality: Friendly greetings and courteous manners are a hallmark here, making your stay at local vacation rentals feel welcoming and warm.
  • Culinary Customs: The region boasts a tradition of hearty, homestyle cooking, where sharing meals is an important social activity among visitors and locals alike.
  • Respect for Nature: Outdoor activities and conservation efforts are highly valued in this destination, encouraging responsible enjoyment of the area's natural beauty.

Henry County Vacation Rental Frequently Asked Questions

2. Which vacation homes in Henry County are best for families?

If you are looking for a family-friendly vacation home in Henry County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Henry County:

3. How many Rentbyowner vacation rentals are available in Henry County?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 38 in the Henry County 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 Henry County. 

4. What is the cancellation policy for vacation rentals in Henry County, Missouri?

Cancellation policies vary depending on the property listing. You should review the specific policy details on the rental's page or contact the owner directly to understand the terms and any potential fees.

5. How do I ensure my booking in the region is secure and reliable?

Booking through verified listings with clear communication from owners helps ensure a secure experience. Always confirm the reservation details and payment methods provided on the listing before completing your booking.

6. Are there any additional fees or charges I should be aware of when booking here?

Additional fees such as cleaning fees, service charges, or taxes are typically outlined in each property listing. Check the detailed pricing section or contact the owner for clarification before confirming your reservation.

7. What amenities and features can I expect in vacation rentals in this area?

Amenities vary by property but often include essentials like Wi-Fi, kitchens, and parking. To find accommodations meeting your needs, review the property descriptions and amenities listed for each vacation rental.

8. How far in advance should I book a vacation rental in Henry County to secure the best options?

It’s recommended to book several weeks or months ahead, especially during peak travel seasons, to ensure availability. For specific dates, check the calendar on the listing or contact the owner for assistance.

Henry County Top Rated Vacation Rentals

Hotel
Map-icon
like-icon9.2
Exceptional
(991 Reviews)
1 Bath
  • Hot Tub
    Hot Tub
  • Pool
    Pool
More amenities
US $132/Night 7 Nights - US $923
Hotel
Map-icon
like-icon8.4
Excellent
(265 Reviews)
3 Baths 387.5 ft²
  • Private Pool
    Private Pool
  • Hot Tub
    Hot Tub
More amenities
US $124/Night 7 Nights - US $866
Hotel
Map-icon
like-icon8.0
Excellent
(740 Reviews)
1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
US $105/Night 7 Nights - US $733
Apartment
Map-icon
like-icon10.0
Exceptional
(3 Reviews)
1 Bedroom 1 Bath 2 Guests 1200 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
US $178/Night 7 Nights - US $1,248