Best Vacation Homes in Winston
House
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
800 ft²
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $160/Night
7 Nights - US $1,119
House
10.0(1 Review)
1 Bedroom
1 Bath
6 Guests
699.65 ft²
- Parking
- Balcony/Terrace
Internet
Pet Friendly
US $197/Night
7 Nights - US $1,378
Bed & Breakfast
8.0(13 Reviews)
1 Bedroom
1 Bath
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $94/Night
7 Nights - US $656
New
Apartment
1 Bedroom
1 Bath
3 Guests
700 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $165/Night
7 Nights - US $1,153
Apartment
9.7(33 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Air Conditioner
- Internet
Child Friendly
US $119/Night
7 Nights - US $835
House
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $159/Night
7 Nights - US $1,111
Bed & Breakfast
10.0(27 Reviews)
1 Bedroom
1 Bath
2 Guests
Breakfast- Balcony/Terrace
- Kitchen
- Air Conditioner
US $127/Night
7 Nights - US $890
House
10.0(24 Reviews)
2 Bedrooms
1 Bath
4 Guests
1900 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $197/Night
7 Nights - US $1,381
Winston Luxury Rentals
New
House
4 Bedrooms
2 Baths
10 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $542/Night
7 Nights - US $3,794
House
10.0(7 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $434/Night
7 Nights - US $3,036
House
5 Bedrooms
2 Baths
6 Guests
- Air Conditioner
- Child Friendly
Laundry
Bedding/Linens
US $433/Night
7 Nights - US $3,030
House
9.8(122 Reviews)
4 Bedrooms
1 Bath
10 Guests
1500 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $307/Night
7 Nights - US $2,148
House
9.6(22 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $240/Night
7 Nights - US $1,677
House
9.8(59 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $238/Night
7 Nights - US $1,666
House
10.0(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $210/Night
7 Nights - US $1,470
New
House
4 Bedrooms
2 Baths
8 Guests
1097.92 ft²
- Parking
- Balcony/Terrace
- Child Friendly
Sports/Activities
US $209/Night
7 Nights - US $1,462
Winston Pet Friendly Vacation Rentals
Cabin
9.8(8 Reviews)
1 Bedroom
1 Bath
6 Guests
700 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $149/Night
7 Nights - US $1,041
Apartment
9.6(10 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $137/Night
7 Nights - US $956
US $166/Night
7 Nights - US $1,161
House
9.6(29 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $208/Night
7 Nights - US $1,454
Cabin
6.2(46 Reviews)
36 Bedrooms
6 Baths
20 Guests
304.98 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $81/Night
7 Nights - US $566
Apartment
8.0(1 Review)
1 Bedroom
1 Bath
3 Guests
550 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $93/Night
7 Nights - US $648
Apartment
2 Bedrooms
1 Bath
8 Guests
775 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $164/Night
7 Nights - US $1,151
New
House
2 Bedrooms
1 Bath
4 Guests
950 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $179/Night
7 Nights - US $1,256
Winston Large Vacation Homes
House
5 Bedrooms
4 Baths
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $458/Night
7 Nights - US $3,204
Cabin
10.0(1 Review)
5 Bedrooms
2 Baths
10 Guests
- Kitchen
- Air Conditioner
- Pet Friendly
- Child Friendly
US $490/Night
7 Nights - US $3,431
House
8.0(1 Review)
4 Bedrooms
2 Baths
12 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $348/Night
7 Nights - US $2,438
House
1 Bedroom
1 Bath
10 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $8,349/Night
7 Nights - US $58,443
House
1 Bedroom
1 Bath
15 Guests
Pool- Balcony/Terrace
- Kitchen
- Air Conditioner
US $2,565/Night
7 Nights - US $17,955
Cabin
3 Bedrooms
2 Baths
10 Guests
- Air Conditioner
- Pet Friendly
- Child Friendly
- Bedding/Linens
US $383/Night
7 Nights - US $2,683
Cabin
1 Bedroom
1 Bath
12 Guests
- Parking
Spa- Balcony/Terrace
- Kitchen
US $148/Night
7 Nights - US $1,037
Why Choose Rent By Owner for your Winston 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 Winston
When should you plan your Vacation Rentals stay?
Choosing the right time to visit Winston, Missouri, ensures you enjoy this destination’s best weather and local events, allowing you to make the most of your stay in the region's unique vacation rentals.
Peak Season Highlights
Spring (March to May)
During the spring, this destination experiences blossoming landscapes and mild weather, making it ideal for outdoor activities and exploring local scenery.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Fall (September to November)
In the fall, the area is characterized by vibrant foliage and comfortable temperatures, perfect for scenic drives and nature walks.
Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F
Off-Season Highlights
Summer (June to August)
Summer offers warmer temperatures and longer days, but can also be more crowded and humid, which may influence your outdoor plans in this region.
Average Temperature Daytime: 80°F to 90°F - Nighttime: 60°F to 70°F
Winter (December to February)
Winter brings cooler temperatures and occasional snowfall, providing a quieter atmosphere if you prefer a peaceful retreat in the area.
Average Temperature Daytime: 30°F to 45°F - Nighttime: 20°F to 30°F
Weekly Weather Forecast for Winston
How to Book Your Winston 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 Winston
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 areas ideal for meals under the sun.
- Take advantage of private patios or verandas to relax and unwind.
- Make use of well-maintained barbecue grills for outdoor cooking experiences.
- Experience scenic views from decks or porches overlooking the countryside.
- Explore spacious yards or gardens perfect for outdoor activities.
- Utilize dedicated fire pits for cozy evenings with family or friends.
- Access parking spaces designed for easy entry and exit during your stay.
Top Attractions Around Winston
What attractions are nearby?
In this charming area, you can enjoy a variety of outdoor activities such as fishing, hiking, and exploring local parks that showcase the natural beauty of Winston, Missouri.
Family Activities
- Winston Park and Playground: Enjoy a relaxing day outdoors at this family-friendly park, featuring safe play areas and picnic spots perfect for a day trip with loved ones.
- Local Heritage Museum: Explore the region’s history through engaging exhibits that offer educational fun for children and adults alike.
- Scenic River Adventures: Experience gentle boat trips or fishing opportunities on the nearby river, ideal for introducing kids to nature and water activities.
- Community Events and Festivals: Check out seasonal festivals and events happening here, providing entertainment and cultural experiences suitable for the whole family.
Adult Activities
- Fishing at Lake of the Ozarks: Spend a relaxing day casting your line at this popular fishing spot, renowned for its abundant bass and catfish populations, perfect for anglers staying in the area.
- Exploring local wineries: Enjoy tasting tours and scenic vineyard views at nearby wineries that highlight the region’s rich viticulture tradition.
- Hiking and outdoor adventures: Discover scenic trails and nature walks through nearby parks, offering an immersive experience in the area's natural beauty.
- Golfing experiences: Tee off at well-maintained golf courses that provide excellent amenities and stunning views, ideal for a leisurely day out during your stay here.
Winston Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining Options: Take advantage of the region’s charming eateries to enjoy authentic flavors unique to this destination.
- Plan Outdoor Activities: Make the most of the area’s natural scenery by engaging in outdoor pursuits like hiking or relaxing in nearby parks.
- Discover Hidden Gems: Talk to locals or do some research to find lesser-known spots that showcase the true character of this region.
- Choose Strategic Accommodation: Book a well-located vacation rental that offers easy access to key attractions and conveniences here.
Transportation Options
- Personal Vehicle: Having your own car offers the most flexibility to explore nearby attractions and enjoy convenience within this destination.
- Public Transit: Buses and local transit services provide an affordable and accessible way to navigate the area without the need for private transportation.
- Taxis and Rideshare Services: Reliable options like taxis and ridesharing apps allow you to quickly get around here without the hassle of parking or vehicle maintenance.
- Rental Cars: Renting a vehicle provides a comfortable and efficient means to discover the region at your own pace, ensuring a smooth stay in this area.
Local Customs Options
- Local Greeting Etiquette: When visiting here, you’ll notice that friendly handshakes and warm smiles are common ways to greet neighbors and fellow visitors in Winston, Missouri.
- Community Events and Festivals: Participating in seasonal gatherings and celebrations reflects the region’s strong sense of community and local pride in Winston.
- Traditional Dining Customs: Enjoying regional comfort foods at family-owned eateries offers insight into the area's culinary heritage and hospitality traditions.
- Respect for Rural Heritage: Maintaining a considerate attitude towards farmland and open spaces demonstrates the area’s appreciation for its rural roots and environmental preservation.
Winston Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Winston?
There are a lot of options in Winston. If you plan on staying in the Winston area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Winston:
- The Garden Room at Shoal Creek B&B
- Enjoy this spacious ranch-style house next to the quilting capital of the world.
- The Cottage Room at Shoal Creek B&B
- The Bird's Nest - 2 bedroom House
- Gallatin Get-Away Bungalow Perfect for quilters, hunters, or families!
- 1920s Restored Home-walk to MSQC shops, Quilt Town USA
- Beautiful Home in Gallatin
- Charming 1-bedroom Guest Home with WiFi, AC in delightful Gallatin
- Mrs. Hughes Cottage - 2 bedroom House
- Fishing Pond & Treehouse: Tranquil Maysville Cabin
2. Which vacation homes in Winston are best for families?
If you are looking for a family-friendly vacation home in Winston, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Winston:
3. How many Rentbyowner vacation rentals are available in Winston?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 84 in the Winston 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 Winston.
4. What is the cancellation policy for vacation rentals in Winston, Missouri?
Cancellation policies vary by listing, so it's important to review the specific property's terms on its page or contact the owner directly to understand the cancellation details and any applicable fees.
5. How do I request additional amenities or special accommodations in Winston vacation rentals?
You can reach out to the property owner or manager through the booking platform to inquire about available amenities or request special accommodations before finalizing your reservation.
6. Are there any house rules or restrictions I should be aware of during my stay?
Each vacation rental may have its own house rules or restrictions, which are outlined in the listing details. Be sure to read these carefully or contact the host if you have any questions.
7. What is the check-in and check-out process for vacation rentals in this destination?
Check-in and check-out procedures are specified on each listing and may vary from one property to another. You can find this information on the property page or ask the owner directly for details.
8. Is it possible to modify or cancel my reservation in case of unforeseen circumstances?
Reservation modification and cancellation options depend on the property’s policies. It's best to review these policies during booking or contact the owner for assistance with any changes or cancellations.
Winston Top Rated Vacation Rentals
House
10.0(14 Reviews)
3 Bedrooms
2 Baths
6 Guests
900 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $168/Night
7 Nights - US $1,174
Hotel
8.2(1002 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $101/Night
7 Nights - US $708
US $78/Night
7 Nights - US $547
US $71/Night
7 Nights - US $497
