Best Vacation Homes in Winston County
New
Cabin
10.0(14 Reviews)
2 Bedrooms
2 Baths
8 Guests
900 ft²
Parking
Ocean View
Balcony/Terrace
View
US $256/Night
7 Nights - US $1,794
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
1496.18 ft²
- Parking
Internet
Child Friendly
Security/Safety
US $163/Night
7 Nights - US $1,141
US $138/Night
7 Nights - US $966
House
9.8(90 Reviews)
2 Bedrooms
1 Bath
4 Guests
750 ft²
- Parking
- Balcony/Terrace
Kitchen
Air Conditioner
US $228/Night
7 Nights - US $1,597
House
10.0(1 Review)
3 Bedrooms
2 Baths
7 Guests
1399.31 ft²
- Parking
- Internet
- Child Friendly
- Security/Safety
US $135/Night
7 Nights - US $945
Cabin
9.8(25 Reviews)
2 Bedrooms
1 Bath
10 Guests
1100 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $410/Night
7 Nights - US $2,871
Cottage
9.8(13 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $192/Night
7 Nights - US $1,342
House
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
Pet Friendly- Child Friendly
US $663/Night
7 Nights - US $4,640
Winston County Luxury Rentals
House
10.0(21 Reviews)
8 Bedrooms
7 Baths
16 Guests
5400 ft²
Private Pool
Hot Tub- Parking
Pool
US $1,569/Night
7 Nights - US $10,982
House
8.0(1 Review)
5 Bedrooms
5 Baths
20 Guests
5500 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,500/Night
7 Nights - US $10,500
House
10.0(5 Reviews)
5 Bedrooms
4 Baths
14 Guests
3600 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $1,366/Night
7 Nights - US $9,564
House
10.0(5 Reviews)
6 Bedrooms
6 Baths
24 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $1,353/Night
7 Nights - US $9,473
House
10.0(15 Reviews)
5 Bedrooms
3 Baths
12 Guests
2760 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $1,317/Night
7 Nights - US $9,221
House
5 Bedrooms
5 Baths
20 Guests
5500.36 ft²
- Parking
- Balcony/Terrace
- Internet
- Child Friendly
US $1,274/Night
7 Nights - US $8,916
House
10.0(22 Reviews)
5 Bedrooms
4 Baths
20 Guests
5000 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $1,188/Night
7 Nights - US $8,317
House
1 Bedroom
4 Baths
20 Guests
5941.68 ft²
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $1,155/Night
7 Nights - US $8,087
Winston County Pet Friendly Vacation Rentals
House
10.0(60 Reviews)
4 Bedrooms
2 Baths
8 Guests
1600 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $333/Night
7 Nights - US $2,332
House
9.3(4 Reviews)
1 Bedroom
1 Bath
8 Guests
699.65 ft²
- Parking
- Internet
- Pet Friendly
- Child Friendly
US $170/Night
7 Nights - US $1,190
House
3 Bedrooms
5 Baths
12 Guests
- Air Conditioner
- Pet Friendly
- Child Friendly
Laundry
US $675/Night
7 Nights - US $4,725
House
10.0(20 Reviews)
4 Bedrooms
3 Baths
14 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $626/Night
7 Nights - US $4,384
House
1 Bedroom
3 Baths
16 Guests
4004.17 ft²
- Parking
- Pool
- Air Conditioner
- Internet
US $938/Night
7 Nights - US $6,569
Cabin
10.0(15 Reviews)
3 Bedrooms
2 Baths
9 Guests
1380 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $382/Night
7 Nights - US $2,675
House
10.0(7 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $217/Night
7 Nights - US $1,517
House
10.0(6 Reviews)
3 Bedrooms
4 Baths
12 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $745/Night
7 Nights - US $5,217
Winston County Large Vacation Homes
House
10.0(99 Reviews)
9 Bedrooms
6 Baths
20 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $1,069/Night
7 Nights - US $7,481
House
1 Bedroom
4 Baths
14 Guests
3498.27 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $756/Night
7 Nights - US $5,291
House
10.0(67 Reviews)
5 Bedrooms
3 Baths
18 Guests
4500 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $552/Night
7 Nights - US $3,864
House
1 Bedroom
4 Baths
18 Guests
3003.13 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $711/Night
7 Nights - US $4,979
House
10.0(66 Reviews)
4 Bedrooms
3 Baths
10 Guests
2000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $567/Night
7 Nights - US $3,971
House
10.0(50 Reviews)
4 Bedrooms
3 Baths
11 Guests
2400 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $424/Night
7 Nights - US $2,965
House
10.0(39 Reviews)
9 Bedrooms
6 Baths
22 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $1,077/Night
7 Nights - US $7,537
House
10.0(34 Reviews)
5 Bedrooms
4 Baths
10 Guests
3200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $499/Night
7 Nights - US $3,490
Why Choose Rent By Owner for your Winston County 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 County
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can enhance your experience and ensure you find the perfect vacation rentals in Winston County, Alabama, USA, when the conditions align with your preferences for weather and activities.
Peak Season Highlights
Spring (March to May)
During this time, the region experiences a pleasant climate perfect for exploring outdoor activities and enjoying local events, making it an ideal period for booking vacation rentals.
Average Temperature Daytime: 70-80°F - Nighttime: 50-60°F
Fall (September to November)
Autumn offers mild weather and vibrant foliage, attracting visitors who want to enjoy the scenic beauty of the area and book comfortable accommodation options.
Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F
Off-Season Highlights
Winter (December to February)
With cooler temperatures and less tourist traffic, this season is perfect if you prefer quieter stays and more affordable vacation rentals in the region.
Average Temperature Daytime: 45-55°F - Nighttime: 30-40°F
Summer (June to August)
While summer brings warmer weather, it is also the off-peak season when fewer visitors are around, offering a more relaxed experience with potentially lower rates on accommodations.
Average Temperature Daytime: 85-90°F - Nighttime: 65-70°F
Weekly Weather Forecast for Winston County
How to Book Your Winston County 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.
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 your outdoor dining with a fully equipped picnic area or BBQ grill set in the region.
- Relax on spacious patios or decks that offer scenic views of the surrounding landscape.
- Take advantage of private swimming pools available at select properties for a refreshing escape.
- Explore expansive yards or gardens perfect for outdoor activities and family gatherings.
- Make use of fire pits or outdoor fireplaces to gather around and share stories under the stars.
- Discover hiking trails or nature paths accessible right from your vacation rental property.
- Reserve outdoor recreational equipment, such as kayaks or paddleboards, to enjoy nearby waterways.
Top Attractions Around Winston County
What attractions are nearby?
In this region, you can enjoy a variety of outdoor activities such as hiking, fishing, and exploring scenic parks, all conveniently close to your Winston County, Alabama, USA vacation rental.
Family Activities
- Winston County Nature Trails: Explore scenic walking and biking paths that offer a peaceful retreat into the natural beauty of this region.
- Smith Lake Recreation Area: Enjoy family-friendly activities like fishing, boating, and picnicking around the pristine waters of Smith Lake.
- Winston County Historical Museum: Discover the area's rich heritage through engaging exhibits that showcase local history and culture.
- Hiking at Oak Mountain State Park: Experience outdoor adventure with trails suitable for all ages, offering stunning views and wildlife sightings in the region.
Adult Activities
- Hiking and Nature Trails: Explore scenic trails that wind through the region's lush landscapes, offering a perfect outdoor activity to enjoy the area's natural beauty.
- Fishing at Local Lakes: Spend a relaxing day casting your line in nearby lakes known for their abundant freshwater fish, ideal for anglers seeking tranquility and good catches.
- Visit Historical Sites: Discover the area's rich history by touring local museums and landmarks that provide insight into its cultural heritage.
- Golfing Experiences: Play a round at nearby golf courses that cater to enthusiasts of all skill levels, making it an enjoyable activity for visitors staying in the area.
Other Places to Stay in Winston County, AL
Lewis Smith Lake
Addison
Double Springs
Houston Historic Jail
Stoney Point Landing
Natural Bridge
Natural Bridge Park
Haleyville
Tiger Field
Houston
Winston County Travel Tips
How Can You Make the Most of Your Stay?
- Plan your outdoor adventures: Take advantage of the area's natural beauty by exploring local parks and scenic spots to enjoy the fresh air and stunning landscapes.
- Visit community events: Engage with the local culture through seasonal festivals or gatherings that showcase the region's welcoming spirit.
- Choose a well-located rental: Select accommodations close to key attractions and amenities to maximize your time and convenience here.
- Check local dining options: Experience authentic regional cuisine by exploring nearby restaurants and eateries during your stay.
Transportation Options
- Winston County Airport: A convenient local option for travelers seeking quick access to the region's serene landscapes and outdoor activities.
- Interstate 22: A major highway that provides easy road connectivity across the area, making it simple to explore here by car.
- Alabama Bus Service: An economical and reliable way to navigate through this destination, ideal for those preferring public transportation.
- Car Rentals: Available throughout the region, offering flexibility for discovering hidden gems nearby your vacation rental here.
Local Customs Options
- Southern Hospitality: Greeting visitors with warmth and friendliness, this region's welcoming attitude makes your stay in Winston County memorable.
- Saturday Night Fish Fries: Participating in community fish fries reflects the area's strong tradition of fellowship and local cuisine in Winston County.
- Historic Church Services: Attending church services offers a glimpse into the spiritual and cultural heritage cherished here.
- Traditional Crafts: Exploring local craftsmanship reveals the region’s dedication to preserving its artisanal skills and cultural identity.
Winston County Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Winston County?
There are a lot of options in Winston County. If you plan on staying in the Winston County 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 County:
- Emerald Cove at Smith Lake: 7BR house, sleeps 18+, beautiful channel views!
- Decked Out Main Channel Views 80ft to Water Sleeps 18 Near Duncan Bridge
- Lakefront Escape | Fish, Kayak & Relax
- Waterfront|Few stairs|Kayaks|Firepit|Games|EV
- Smith Lake Waterfront | Dock + Game Room | Sleeps 11
- NEW: Dwell at Smith Lake: Luxury Lake Home, Sleeps 22, Kayaks + Water Slide!
- Littleville on the Lake
- Smith Lake House on water 2 mile north of Duncan Bridge with beautiful sunsets.
- "LAKEVIEW": No Steps, HOT TUB, Boat/Swim Dock, Elevator
- NEW! Country Villa: Dock, Pool, Spa, Waterfall, Grotto, Firepit, Fishing hole.
2. Which vacation homes in Winston County are best for families?
If you are looking for a family-friendly vacation home in Winston 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 Winston County:
3. How many Rentbyowner vacation rentals are available in Winston County?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 192 in the Winston 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 Winston County.
4. What is the cancellation policy for vacation rentals in Winston County, Alabama?
Cancellation policies vary by listing, so you'll need to review the specific property's policy on its page or contact the owner directly to understand the terms and potential fees.
5. How do I find pet-friendly vacation rentals in Winston County, Alabama?
You can filter your search on the booking site to display properties that welcome pets, and it's advisable to confirm pet policies with the property owner before finalizing your reservation.
6. Are there any minimum stay requirements for vacation rentals here?
Minimum stay requirements differ among listings, so be sure to check the details of each property or contact the owner to ensure it fits your travel plans.
7. What amenities should I expect from vacation rentals in this area?
Amenities vary depending on the property, but common features include Wi-Fi, kitchen facilities, and parking. Always review the listing details or contact the owner for specifics.
8. How can I ensure my booking in Winston County is secure and reliable?
Choose listings with verified reviews and detailed descriptions, and communicate directly with property owners if you have questions. The booking platform provides a trustworthy process to help protect your reservation.
Winston County Top Rated Vacation Rentals
House
7.8(18 Reviews)
5 Bedrooms
3 Baths
16 Guests
4000 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $897/Night
7 Nights - US $6,279
House
10.0(21 Reviews)
4 Bedrooms
3 Baths
12 Guests
- Parking
- Pool
Lake View- Balcony/Terrace
US $563/Night
7 Nights - US $3,938
House
10.0(2 Reviews)
7 Bedrooms
6 Baths
8 Guests
- Private Pool
- Hot Tub
Breakfast- Parking
US $500/Night
7 Nights - US $3,500
House
4 Bedrooms
5 Baths
8 Guests
2900 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $506/Night
7 Nights - US $3,545
