Best Vacation Homes in Winkler County
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $135/Night
For 7 Nights US $944
6 Guests
32 Bedrooms
2 Bathrooms
Free Cancellation
Hotel
- Pet Friendly
- Parking
- Air Conditioner
US $95/Night
For 7 Nights US $662
US $107/Night
For 7 Nights US $747
7 Guests
4 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $221/Night
For 7 Nights US $1,546
403.65 ft²
40 Guests
125 Bedrooms
10 Bathrooms
Hotel
- Oceanfront
- Fireplace/Heating
- Pool
US $127/Night
For 7 Nights US $889
380 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Pet Friendly
- Kitchen
- Parking
US $172/Night
For 7 Nights US $1,203
380 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Pet Friendly
- Child Friendly
- Security/Safety
US $154/Night
For 7 Nights US $1,077
380 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Pet Friendly
- Child Friendly
- Security/Safety
US $154/Night
For 7 Nights US $1,077
Winkler County Luxury Rentals
2 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Apartment
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $245/Night
For 7 Nights US $1,712
301.39 ft²
24 Guests
8 Bedrooms
8 Bathrooms
Free Cancellation
Hotel
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $237/Night
For 7 Nights US $1,660
7 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $216/Night
For 7 Nights US $1,515
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $212/Night
For 7 Nights US $1,484
8 Guests
3 Bedrooms
2 Bathrooms
Group Friendly
House
- Air Conditioner
- Internet
- Child Friendly
US $201/Night
For 7 Nights US $1,405
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $166/Night
For 7 Nights US $1,162
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $166/Night
For 7 Nights US $1,161
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Breakfast
- Kitchen
US $166/Night
For 7 Nights US $1,159
Winkler County Pet Friendly Vacation Rentals
3 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $177/Night
For 7 Nights US $1,237
322.92 ft²
32 Guests
96 Bedrooms
12 Bathrooms
Hotel
- Hot Tub
- Fireplace/Heating
- Pool
US $83/Night
For 7 Nights US $581
1 Bedroom
1 Bathroom
Family Friendly
House
- Pet Friendly
- Kitchen
- Air Conditioner
US $105/Night
For 7 Nights US $733
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Pet Friendly
- Kitchen
- Air Conditioner
US $135/Night
For 7 Nights US $945
4027.24 ft²
54 Guests
60 Bedrooms
1 Bathroom
Free Cancellation
Hotel
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $159/Night
For 7 Nights US $1,113
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Pet Friendly
- Kitchen
- Air Conditioner
US $135/Night
For 7 Nights US $945
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Pet Friendly
- Kitchen
- Air Conditioner
US $135/Night
For 7 Nights US $945
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Pet Friendly
- Kitchen
- Air Conditioner
US $135/Night
For 7 Nights US $945
Winkler County Large Vacation Homes
US $200/Night
For 7 Nights US $1,400
US $200/Night
For 7 Nights US $1,400
Why Choose Rent By Owner for your Winkler 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 Winkler County
When should you plan your Vacation Rentals stay?
Choosing the right time to vacation here can enhance your experience, as the region's climate and seasonal trends play a significant role in your enjoyment of the area.
Peak Season Highlights
Spring (March to May)
During spring, you can enjoy warm daytime temperatures that make outdoor activities pleasant in this region. The comfortable weather attracts visitors looking for a vibrant atmosphere and outdoor exploration.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 50°F to 60°F
Fall (September to November)
Autumn offers cooler evenings and mild days, making it an ideal time for sightseeing without the summer crowds. The region’s scenery during this season is especially welcoming for those seeking a peaceful retreat.
Average Temperature Daytime: 70°F to 80°F - Nighttime: 45°F to 55°F
Off-Season Highlights
Summer (June to August)
Summers tend to be hot, with high temperatures that might limit outdoor activity during the hottest parts of the day. However, this season is perfect if you prefer fewer crowds and are prepared for the heat.
Average Temperature Daytime: 90°F to 100°F - Nighttime: 65°F to 75°F
Winter (December to February)
Winters are relatively mild but can bring cooler nights, making it less popular for travelers seeking warmer weather. It’s a quiet period when accommodations might offer better rates for longer stays.
Average Temperature Daytime: 55°F to 65°F - Nighttime: 30°F to 40°F
Weekly Weather Forecast for Winkler County
How to Book Your Winkler 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.
Explore and book the perfect rental in Winkler County
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 grilling with a fully-equipped barbecue area to make the most of the sunny weather.
- Relax by a private swimming pool, perfect for cooling off after exploring the region.
- Take advantage of spacious patios or decks designed for outdoor dining and socializing.
- Explore nearby hiking or walking trails from your rental’s doorstep, ideal for outdoor enthusiasts.
- Benefit from a well-maintained lawn or garden space for outdoor activities or family gatherings.
- Make use of outdoor fire pits to cozy up during cooler evenings amidst the natural surroundings.
- Secure parking areas with shaded or covered spaces that provide convenience when arriving or departing in this destination.
Top Attractions Around Winkler County
What attractions are nearby?
In this region, you can enjoy a variety of outdoor activities such as exploring scenic parks, engaging in sports, or experiencing local cultural events that highlight the area's unique charm and natural beauty.
Family Activities
- Winkler County Museum: Delve into the area's history and culture through engaging exhibits that educate and entertain the entire family.
- Devil’s River Natural Area: Experience the natural beauty of the region with scenic hiking trails and picnic spots perfect for a family day outdoors.
- Battle of Runnels County Memorial Park: Visit this peaceful park to teach children about local history while enjoying outdoor activities in a family-friendly environment.
- Local Wildlife Viewing: Explore nearby wildlife habitats where you can observe native animals and make memorable nature discoveries as a family.
Adult Activities
- Exploring the local museums: Discover the rich history and culture of the region through engaging exhibits and artifacts at nearby museums.
- Wildlife watching in natural preserves: Enjoy observing native species and peaceful landscapes within protected wildlife areas surrounding this destination.
- Outdoor recreation at parks and trails: Take advantage of scenic parks and trail systems to hike, bike, or simply relax amidst nature's beauty.
- Dining experiences featuring regional cuisine: Savor authentic flavors and locally inspired dishes at restaurants known for their connection to this area’s culinary traditions.
Other Places to Stay in Winkler County, TX
Roy Orbison Museum
Kermit
Winkler County Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Local Events: Check the regional calendar to align your stay with local festivals or gatherings that highlight the area's unique culture and community spirit.
- Explore Nearby Nature Spots: Take advantage of scenic outdoor settings close to your accommodation to enjoy activities like hiking or relaxing amidst the natural beauty here.
- Discover Comfortable Amenities: Select a vacation rental with amenities tailored to your needs, ensuring a comfortable and convenient stay in this destination.
- Utilize Local Tips and Recommendations: Engage with hosts or locals for insider tips on the best dining, shopping, and entertainment options available nearby here.
Transportation Options
- Winkler County Airport: You can conveniently access this destination via the regional airport offering scheduled flights and easy ground transportation options.
- Car Rentals: Several trusted car rental companies operate here, giving you the flexibility to explore the area at your own pace with a vehicle suitable for your needs.
- Public Transit: Local bus services provide an affordable way to navigate the region, connecting key points of interest within Winkler County.
- Taxi and Rideshare Services: Reliable taxi and rideshare options are available for quick and convenient transportation around town, perfect for short trips or last-minute plans.
Local Customs Options
- Local Rodeo Traditions: Participating in or observing the area's rodeo events offers insight into the region's cowboy heritage and community spirit.
- Western Hospitality Customs: Visitors often encounter friendly greetings and welcoming attitudes that emphasize the close-knit and hospitable nature of this destination.
- Regional Food Practices: Enjoying country-style barbecue and traditional Texan dishes reflects local culinary customs cherished by residents here.
- Cultural Festivals and Celebrations: Attending seasonal festivals showcases the area's vibrant culture and respect for historical traditions prevalent in this region.
Frequently Asked Questions About Winkler County?
1. What are the top vacation rentals in Winkler County?
There are a lot of options in Winkler County. If you plan on staying in the Winkler 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 Winkler County:
- Desert Oasis
- Kermit Inn
- Kermit Inn
- 14th street house
- BoxHouse Villages Monahans, Queen Bed
- Hawthorn Extended Stay by Wyndham Monahans
- After-Hours Bliss: Cozy BoxHouse for Relaxation, Monahans, TX
- Holiday Inn Express Kermit by IHG
- Fairfield Inn & Suites by Marriott Monahans
- Cozy Space, Expansive Feel: Very open BoxHouse, Monahans, TX
2. How many vacation rentals have private pools in Winkler County?
There are 2 vacation rentals with private pools near Winkler County. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Winkler County are best for families?
If you are looking for a family-friendly vacation home in Winkler 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 Winkler County:
4. How many Rentbyowner vacation rentals are available in Winkler County?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 74 in the Winkler 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 Winkler County.
5. What is the cancellation policy for vacation rentals in Winkler County, Texas?
Cancellation policies vary by property, so it is important to review the specific listing details or contact the owner directly to understand their terms and any applicable fees.
6. Are there any house rules I should be aware of when booking a rental here?
Yes, each vacation rental may have its own house rules regarding check-in times, pet policies, noise restrictions, and other guidelines. Please refer to the property listing or communicate with the host for detailed information.
7. Is security deposit required for booking a vacation rental in this area?
Many properties request a security deposit to cover potential damages or extra charges. The amount and payment process will be specified in the listing, so reviewing the details or contacting the owner can provide clarity.
8. How do I inquire about additional amenities or special requests for my stay?
You can reach out directly to the property owner through the booking platform to ask about available amenities, such as Wi-Fi, laundry facilities, or parking, and to discuss any special arrangements you may need.
9. What are the check-in and check-out procedures for vacation rentals in the region?
Check-in and check-out times are determined by each host and are specified in the property listing. It is recommended to confirm these details with the owner prior to your arrival to ensure a smooth stay.
Winkler County Top Rated Vacation Rentals
US $141/Night
For 7 Nights US $989
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Pool
- Breakfast
- Kitchen
US $116/Night
For 7 Nights US $815
403.64 ft²
16 Guests
95 Bedrooms
3 Bathrooms
Ocean View
Hotel
- Oceanfront
- Pool
- Ocean View
US $103/Night
For 7 Nights US $721
1 Bedroom
1 Bathroom
Ocean View
Hotel
- Hot Tub
- Pool
- Ocean View
US $82/Night
For 7 Nights US $571
317.95 ft²
44 Guests
102 Bedrooms
13 Bathrooms
Ocean View
Hotel
- Oceanfront
- Fireplace/Heating
- Pool
US $127/Night
For 7 Nights US $889
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Pool
- Balcony/Terrace
- Breakfast
US $99/Night
For 7 Nights US $696
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Pool
- Balcony/Terrace
- Breakfast
US $79/Night
For 7 Nights US $551
US $80/Night
For 7 Nights US $562
