Best Vacation Homes in Middleton
House
10.0(25 Reviews)
2 Bedrooms
1 Bath
4 Guests
1200 ft²
Balcony/Terrace
Kitchen
Parking
Air Conditioner
CA $217/Night
7 Nights - CA $1,515
House
2 Bedrooms
1 Bath
8 Guests
2002.09 ft²
Fireplace/Heating
View- Parking
- Air Conditioner
CA $271/Night
7 Nights - CA $1,896
CA $193/Night
7 Nights - CA $1,353
House
10.0(23 Reviews)
1 Bedroom
1 Bath
2 Guests
200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
CA $170/Night
7 Nights - CA $1,191
Hotel
8.2(60 Reviews)
4 Baths
269.1 ft²
- Fireplace/Heating
Pet Friendly- Parking
- Air Conditioner
CA $96/Night
7 Nights - CA $673
House
10.0(14 Reviews)
2 Bedrooms
1 Bath
8 Guests
850 ft²
- Fireplace/Heating
- Balcony/Terrace
Breakfast- Kitchen
CA $491/Night
7 Nights - CA $3,437
House
10.0(4 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
Pool- Balcony/Terrace
- Kitchen
CA $250/Night
7 Nights - CA $1,752
House
10.0(1 Review)
2 Bedrooms
1 Bath
8 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $229/Night
7 Nights - CA $1,604
Middleton Luxury Rentals
House
9.8(6 Reviews)
4 Bedrooms
2 Baths
8 Guests
3000 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
CA $797/Night
7 Nights - CA $5,582
House
3 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Air Conditioner
Internet
Child Friendly
CA $429/Night
7 Nights - CA $3,000
Hotel
7.8(246 Reviews)
1 Bath
316.77 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
CA $415/Night
7 Nights - CA $2,903
Cabin
10.0(7 Reviews)
3 Bedrooms
2 Baths
8 Guests
1900 ft²
Hot Tub- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $401/Night
7 Nights - CA $2,810
House
3 Bedrooms
2 Baths
6 Guests
2500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
CA $394/Night
7 Nights - CA $2,758
Hotel
5.0(84 Reviews)
3 Baths
279.86 ft²
Private Pool
Oceanfront- Hot Tub
Spa
CA $334/Night
7 Nights - CA $2,338
Hotel
7.6(52 Reviews)
1 Bath
204.51 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
CA $301/Night
7 Nights - CA $2,106
Cabin
10.0(20 Reviews)
4 Bedrooms
2 Baths
8 Guests
1152 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
CA $300/Night
7 Nights - CA $2,098
Middleton Pet Friendly Vacation Rentals
House
10.0(59 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $196/Night
7 Nights - CA $1,372
Hotel
7.7(105 Reviews)
5 Baths
290.63 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
CA $96/Night
7 Nights - CA $674
Hotel
5.9(26 Reviews)
4 Baths
2690.98 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
CA $80/Night
7 Nights - CA $562
Hotel
5.1(35 Reviews)
6 Baths
317.54 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Parking
CA $159/Night
7 Nights - CA $1,112
Middleton Top Rated Vacation Rentals
House
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
CA $221/Night
7 Nights - CA $1,544
Hotel
8.2(36 Reviews)
6 Baths
4036.47 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Parking
CA $191/Night
7 Nights - CA $1,340
CA $110/Night
7 Nights - CA $773
CA $176/Night
7 Nights - CA $1,229
House
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
CA $235/Night
7 Nights - CA $1,647
Why Choose Rent By Owner for your Middleton 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 Middleton
When should you plan your Vacation Rentals stay?
To make the most of your stay, consider visiting during the region’s peak seasons when the local climate and events create an ideal setting for relaxation and exploration in Middleton’s charming surroundings.
Peak Season Highlights
Late Spring to Early Summer (May - June)
During this period, the area experiences warm and inviting weather, making it ideal for outdoor activities and exploring local surroundings. Booking your vacation rental here ensures a comfortable stay amidst pleasant temperatures.
Average Temperature Daytime: 75°F - Nighttime: 55°F
Early Fall (September - October)
This is when the region enjoys mild and stable weather, perfect for enjoying scenic views and outdoor exploration. Securing a rental now provides a peaceful retreat before the winter months set in.
Average Temperature Daytime: 70°F - Nighttime: 50°F
Off-Season Highlights
Mid Winter (December - February)
Compared to busier months, this time sees fewer visitors, offering a quieter experience. It’s an excellent opportunity to find deals on vacation rentals while avoiding peak crowds.
Average Temperature Daytime: 40°F - Nighttime: 25°F
Early Spring (March - April)
As the area transitions from winter, temperatures are still cool and the landscape begins to bloom slowly. Off-peak bookings can provide savings and a more relaxed atmosphere for your visit.
Average Temperature Daytime: 55°F - Nighttime: 35°F
Weekly Weather Forecast for Middleton
How to Book Your Middleton 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 Middleton
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 a private outdoor patio or deck for relaxing and dining al fresco amid scenic surroundings.
- Take advantage of spacious yards or gardens ideal for outdoor activities or family gatherings.
- Make the most of outdoor grilling areas to prepare meals while enjoying the fresh air in the region.
- Discover access to community or private swimming pools that offer refreshing escapes during your stay.
- Utilize outdoor fire pits or fireplaces perfect for cozy evenings under the stars.
- Benefit from nearby walking trails or nature paths to explore the natural beauty of the destination.
- Relax in outdoor furniture sets designed for lounging and soaking up the peaceful ambiance of the area.
Top Attractions Around Middleton
What attractions are nearby?
In this charming region, you can enjoy a variety of outdoor activities and local attractions that showcase the area's natural beauty and small-town charm, offering an authentic Missouri experience close to your vacation rental.
Family Activities
- Middleton Park: Spend a joyful day exploring this local park where your family can enjoy picnicking, playing on the playground, and walking scenic trails surrounded by the region’s natural beauty.
- Middleton Historical Museum: Discover the area's rich history through engaging exhibits that provide educational fun for children and adults alike during your stay.
- Riverfront Activities: Experience relaxing afternoons along the nearby waterways with activities like fishing or paddle boating, perfect for family adventures in this destination.
- Community Events: Participate in seasonal festivals and family-friendly gatherings hosted here, offering authentic regional entertainment and cultural experiences during your visit.
Adult Activities
- Explore the local wineries: Enjoy tastings and tours at the renowned wineries in the region, offering a perfect way to unwind and savor regional flavors.
- Visit historic sites: Discover the area's rich history by exploring landmarks and preserved sites that tell the story of this charming destination.
- Enjoy outdoor recreation: Engage in activities like hiking or birdwatching at nearby parks and natural reserves, ideal for reconnecting with nature.
- Savor regional cuisine: Dine at local restaurants known for their authentic dishes, providing an immersive taste of the area's culinary heritage.
Other Places to Stay in Middleton, MO
Live Well Community Health Center - Waverly
Waverly
Middleton Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining Options: Take advantage of the area’s authentic eateries to enjoy regional flavors and make your stay more memorable.
- Use a Detailed Map or GPS: Navigating here is easier with accurate directions, helping you discover hidden gems and popular spots around the region.
- Plan Outdoor Activities: Engage in nearby parks and outdoor attractions to fully experience the natural beauty that defines this destination.
- Book in Advance: Secure your preferred vacation rentals early to ensure availability during peak seasons and get the best deals in this welcoming area.
Transportation Options
- Middleton Regional Airport: Located conveniently nearby, offering domestic flights that make traveling to this part of Missouri effortless.
- Missouri River Ferry Services: Provide scenic and practical crossings for exploring the region from the water, enhancing your stay here.
- Local Taxi and Rideshare Services: Accessible options for getting around the area comfortably and on your schedule within Middleton and its surroundings.
- Private Car Rentals: Available locally, giving you the flexibility to explore the region at your own pace during your visit.
Local Customs Options
- Southern Hospitality: You’ll notice a warm, welcoming attitude towards visitors that reflects the region’s friendly community spirit in Middleton.
- Local Agriculture Traditions: Farming and produce markets play a significant role here, offering you an authentic taste of regional agricultural customs.
- Community Festivals: Participating in annual events helps you experience the area's rich cultural heritage and local camaraderie.
- Religious Celebrations: Many residents observe traditional religious holidays with gatherings and ceremonies that highlight the enduring faith of this destination’s community.
Frequently Asked Questions About Middleton?
1. What are the top vacation rentals in Middleton?
There are a lot of options in Middleton. If you plan on staying in the Middleton area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Middleton:
- Just like Home, Cozy place to stay with easy access to 65 Hwy.
- The Little Red Cottage is situated in a quaint country neighborhood
- Quaint spacious remodeled home with attached garage, quiet small town get-away
- 'Ain't She Cute' Country Cozy near Higginsville
- The Lodge at 5J Hunts
- Historic farmhouse near Marshall with epic sunsets
- Das Gästehaus 50 Min to KC Stadium World Cup 2026
- New, Relaxing, 3 mins to Missouri Valley College!
- Rustic Retreat - Quiet Cabin on Scenic Countryside
- Red Brick Farmhouse B&B - John & Hilda's Room
2. Which vacation homes in Middleton are best for families?
If you are looking for a family-friendly vacation home in Middleton, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Middleton:
3. How many Rentbyowner vacation rentals are available in Middleton?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 43 in the Middleton 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 Middleton.
4. What is the cancellation policy for vacation rentals in Middleton, Missouri?
The cancellation policies vary depending on the individual property listing. You should review the specific rental's cancellation terms during the booking process or contact the property owner directly for detailed information.
5. Are there any additional fees I should be aware of when booking a vacation rental in Middleton, Missouri?
Additional fees such as cleaning fees, service charges, or local taxes may apply and are usually detailed on the listing page. It's recommended to check the full fee breakdown before completing your reservation.
6. How do I know if the vacation rental has all the amenities I need in Middleton?
Property listings typically provide a detailed list of amenities available. For specific requirements, you can contact the owner directly or review the amenities section of the listing to ensure it meets your needs.
7. Is there a minimum stay requirement for vacation rentals in Middleton, Missouri?
Minimum stay policies often depend on the individual property. You can find this information on the listing details or by reaching out to the owner to confirm the duration required.
8. What should I do if I encounter issues during my stay in a Middleton vacation rental?
In case of any problems, contact the property owner or the local support team listed on the booking platform promptly. They are there to assist you and ensure your stay remains comfortable.
