Discover Your Perfect Winslow Vacation Homes

Best Vacation Homes in Winslow

10.0
Exceptional
(39 Reviews)
900 ft² 6 Guests 2 Bedrooms 1 Bathroom
Family Friendly Cabin
  • Fireplace/Heating
  • Pool
  • Balcony/Terrace
US $150/Night For 7 Nights US $1,049
10.0
Exceptional
(1 Review)
1001.04 ft² 6 Guests 2 Bedrooms 1 Bathroom
Ocean View Apartment
  • Oceanfront
  • Ocean View
  • View
US $112/Night For 7 Nights US $784
New
1 Bedroom 1 Bathroom
Family Friendly House
  • Fireplace/Heating
  • Pet Friendly
  • Air Conditioner
US $950/Night For 7 Nights US $6,652
10.0
Exceptional
(30 Reviews)
2800 ft² 10 Guests 3 Bedrooms 3 Bathrooms
Family Friendly House
  • Private Pool
  • Hot Tub
  • Fireplace/Heating
US $476/Night For 7 Nights US $3,334
9.7
Exceptional
(142 Reviews)
297.8 ft² 14 Guests 6 Bedrooms 6 Bathrooms
House
  • Fireplace/Heating
  • Balcony/Terrace
  • View
US $75/Night For 7 Nights US $525
10.0
Exceptional
(25 Reviews)
650 ft² 3 Guests 1 Bedroom 1 Bathroom
Family Friendly House
  • Hot Tub
  • Fireplace/Heating
  • Balcony/Terrace
US $386/Night For 7 Nights US $2,700
10.0
Exceptional
(21 Reviews)
350 ft² 6 Guests 2 Bedrooms 1 Bathroom
Family Friendly House
  • Fireplace/Heating
  • Pool
  • Balcony/Terrace
US $116/Night For 7 Nights US $815
10.0
Exceptional
(17 Reviews)
2300 ft² 12 Guests 4 Bedrooms 3 Bathrooms
Family Friendly Cabin
  • Fireplace/Heating
  • Balcony/Terrace
  • Breakfast
US $251/Night For 7 Nights US $1,759

Winslow Luxury Rentals

2.0
Average
(1 Review)
8 Guests 3 Bedrooms 2 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Pet Friendly
  • Kitchen
US $1,282/Night For 7 Nights US $8,973
10.0
Exceptional
(3 Reviews)
3900 ft² 16 Guests 5 Bedrooms 3 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Pet Friendly
US $627/Night For 7 Nights US $4,387
New
5995.5 ft² 15 Guests 1 Bedroom 6 Bathrooms
House
  • Pet Friendly
  • Parking
  • Air Conditioner
US $518/Night For 7 Nights US $3,623
9.4
Exceptional
(3 Reviews)
15 Guests 3 Bedrooms 4 Bathrooms
Family Friendly House
  • Hot Tub
  • Fireplace/Heating
  • Balcony/Terrace
US $494/Night For 7 Nights US $3,455
10.0
Exceptional
(1 Review)
2000 ft² 15 Guests 4 Bedrooms 3 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Kitchen
US $436/Night For 7 Nights US $3,052
9.4
Exceptional
(33 Reviews)
2500 ft² 12 Guests 4 Bedrooms 2 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Pet Friendly
US $376/Night For 7 Nights US $2,631
9.0
Exceptional
(2 Reviews)
8 Guests 3 Bedrooms 2 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Kitchen
  • Parking
US $324/Night For 7 Nights US $2,266
9.8
Exceptional
(13 Reviews)
1600 ft² 6 Guests 3 Bedrooms 2 Bathrooms
Family Friendly Cabin
  • Fireplace/Heating
  • Balcony/Terrace
  • Kitchen
US $268/Night For 7 Nights US $1,873

Winslow Pet Friendly Vacation Rentals

9.6
Exceptional
(34 Reviews)
6 Guests 2 Bedrooms 1 Bathroom
Family Friendly Cabin
  • Hot Tub
  • Fireplace/Heating
  • Balcony/Terrace
US $227/Night For 7 Nights US $1,590
9.6
Exceptional
(30 Reviews)
4 Guests 1 Bedroom 1 Bathroom
Family Friendly Cabin
  • Hot Tub
  • Fireplace/Heating
  • Balcony/Terrace
US $240/Night For 7 Nights US $1,683
10.0
Exceptional
(31 Reviews)
6 Guests 2 Bedrooms 2 Bathrooms
Family Friendly Cabin
  • Hot Tub
  • Fireplace/Heating
  • Balcony/Terrace
US $209/Night For 7 Nights US $1,464
10.0
Exceptional
(20 Reviews)
10 Guests 2 Bedrooms 2 Bathrooms
Family Friendly Cabin
  • Hot Tub
  • Fireplace/Heating
  • Balcony/Terrace
US $181/Night For 7 Nights US $1,269
10.0
Exceptional
(2 Reviews)
3 Guests 1 Bedroom 1 Bathroom
Family Friendly House
  • Fireplace/Heating
  • Pet Friendly
  • Kitchen
US $162/Night For 7 Nights US $1,134
9.8
Exceptional
(27 Reviews)
2100 ft² 6 Guests 3 Bedrooms 2 Bathrooms
Family Friendly Cabin
  • Hot Tub
  • Fireplace/Heating
  • Balcony/Terrace
US $373/Night For 7 Nights US $2,612
9.8
Exceptional
(18 Reviews)
4 Guests 1 Bedroom 1 Bathroom
Family Friendly Cabin
  • Hot Tub
  • Fireplace/Heating
  • Balcony/Terrace
US $174/Night For 7 Nights US $1,218
9.0
Exceptional
(2 Reviews)
6 Guests 3 Bedrooms 2 Bathrooms
Family Friendly House
  • Hot Tub
  • Spa
  • Fireplace/Heating
US $100/Night For 7 Nights US $700

Winslow Large Vacation Homes

New
12 Guests 5 Bedrooms 2 Bathrooms
Family Friendly Cabin
  • Hot Tub
  • Fireplace/Heating
  • Air Conditioner
US $533/Night For 7 Nights US $3,734
9.4
Exceptional
(3 Reviews)
16 Guests 7 Bedrooms 4 Bathrooms
Ocean View Cabin
  • Private Pool
  • Fireplace/Heating
  • Pool
US $744/Night For 7 Nights US $5,209
5.0
Average
(2 Reviews)
22 Guests 7 Bedrooms 4 Bathrooms
Family Friendly House
  • Private Pool
  • Pool
  • Pet Friendly
US $738/Night For 7 Nights US $5,166
4.8
Average
(4 Reviews)
4000 ft² 19 Guests 7 Bedrooms 4 Bathrooms
Family Friendly House
  • Private Pool
  • Pool
  • Balcony/Terrace
US $781/Night For 7 Nights US $5,467
4.6
Average
(43 Reviews)
15 Guests 4 Bedrooms 4 Bathrooms
Family Friendly House
  • Pet Friendly
  • Kitchen
  • Air Conditioner
US $269/Night For 7 Nights US $1,883
New
22 Guests 7 Bedrooms 4 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Pool
  • Pet Friendly
US $1,288/Night For 7 Nights US $9,013
9.8
Exceptional
(25 Reviews)
3900 ft² 10 Guests 4 Bedrooms 2 Bathrooms
Family Friendly House
  • Balcony/Terrace
  • Pet Friendly
  • Kitchen
US $523/Night For 7 Nights US $3,661

Why Choose Rent By Owner for your Winslow 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 Winslow

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit ensures you experience the best of this destination, as the region offers distinct advantages depending on the season, so plan your stay accordingly to make the most of your trip to Winslow, Arkansas.

Peak Season Highlights

spring
Spring (March to May)

During spring, the area experiences mild and pleasant weather, making it an ideal time for outdoor activities and exploring the region’s natural beauty.

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

The fall season brings cooler temperatures and vibrant foliage, perfect for enjoying the scenic surroundings and local events here.

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

Off-Season Highlights

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Summer (June to August)

In summer, higher temperatures and increased humidity make this a less popular time for vacations in the region, but it remains suitable for those seeking quieter accommodations.

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

Winter months tend to be colder with occasional snow, which may limit outdoor activities but can offer a cozy atmosphere for visitors who enjoy this season here.

Average Temperature Daytime: 40°F to 50°F - Nighttime: 25°F to 35°F

Weekly Weather Forecast for Winslow

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 outdoor dining with a fully equipped patio or barbecue area to make the most of warm evenings.
  • Relax by the private swimming pool, perfect for cooling off during hot summer days.
  • Take advantage of spacious yards ideal for family games or leisurely strolls in the fresh air.
  • Explore nearby hiking trails and scenic spots that showcase the natural beauty of the region.
  • Use outdoor fire pits or fireplaces to gather around and share stories under the stars.
  • Benefit from well-maintained gardens or landscaped areas that enhance your outdoor experience.
  • Access to covered porches or decks provides shaded outdoor sitting options to enjoy the local scenery.
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Family Activities

  • Winslow Museum & Visitors Center: Discover local history and culture while engaging with interactive exhibits that the whole family can enjoy.
  • Natural State Scenic Drive: Take a leisurely drive through the region’s picturesque landscapes, offering stunning views and photo opportunities for memorable family moments.
  • Lake Winslow Recreation Area: Spend quality time outdoors by enjoying water activities, picnicking, or exploring scenic trails with your loved ones.
  • Family-friendly Local Events: Participate in seasonal festivals and community events held here, perfect for creating lasting memories during your stay.
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Adult Activities

  • Winslow Museum: Discover local history and heritage through engaging exhibits that highlight the area's cultural roots.
  • Old Town Historic District: Stroll through this charming district to enjoy preserved architecture and immerse yourself in the region's past.
  • Winslow Riverfront Park: Relax or take a scenic walk along the river, enjoying the peaceful natural surroundings of this popular outdoor spot.
  • Outdoor Recreational Areas: Engage in activities like fishing, picnicking, or birdwatching at nearby parks that showcase the area's natural beauty.

Winslow Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Local Attractions: Research nearby points of interest to enhance your stay and take full advantage of the region's unique charm and culture.
  • Choose the Right Vacation Rental: Select a well-located property in this destination that offers comfort and convenience, ensuring a relaxing and enjoyable experience.
  • Explore Seasonal Events and Activities: Take advantage of local festivals or outdoor activities during your visit to immerse yourself in the area's vibrant community.
  • Pack Smart for the Climate: Check the seasonal weather forecast to pack appropriately, so you stay comfortable during your adventures in the region.

Transportation Options

  • Winslow Transit Station: This regional hub offers convenient bus services connecting you to nearby cities and attractions in the area.
  • Private Car Rentals: Renting a car here provides the flexibility to explore the region at your own pace, with numerous local agencies available for easy pickup and drop-off.
  • Taxi Services: Taxis are readily accessible in this destination, making short trips around town or to specific points of interest straightforward and efficient.
  • Shared Shuttle Services: These group transportation options offer an economical way to travel between popular destinations within this part of Arkansas.

Local Customs Options

  • Southern Hospitality: Locals here are known for their warm, friendly demeanor, making your stay in this part of Arkansas welcoming and comfortable.
  • Traditional Music and Dance: You might encounter lively community gatherings featuring regional music styles that reflect the area's rich cultural heritage.
  • Local Crafts and Artisanship: The region celebrates its history through handmade crafts and artwork, offering authentic souvenirs during your visit.
  • Cultural Festivals: Engaging in seasonal festivals allows you to experience the area's customs and community spirit firsthand in this destination.

Frequently Asked Questions About Winslow?

2. Which vacation homes in Winslow are best for families?

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

3. How many Rentbyowner vacation rentals are available in Winslow?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 54 in the Winslow 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 Winslow. 

4. What is the cancellation policy for vacation rentals in Winslow, Arkansas?

Cancellation policies vary by property listing. You should review the specific terms on the rental's page or contact the property owner directly to understand the cancellation timeframe and any applicable fees.

5. Are there any additional fees or charges when booking a vacation rental here?

Additional fees such as cleaning fees, service charges, or taxes are often listed on the property detail page. It’s best to check the individual listing or reach out to the owner for a complete understanding of all costs involved.

6. How do I confirm my booking for a vacation rental in this destination?

Once you select your preferred dates and complete the reservation process, your booking will be confirmed. Details and confirmation are typically sent via email; you can also contact the host directly if needed.

7. Is there a minimum stay requirement for vacation rentals in this region?

Minimum stay requirements depend on each property’s owner or management policies. Be sure to review the listing details or contact the host to find out if there are any restrictions during your desired travel dates.

8. What amenities are commonly included in vacation rentals around here?

Amenities vary, but common features include Wi-Fi, kitchen facilities, parking, and outdoor spaces. Checking the specific listing will give you a clear idea of what is available during your stay in this area.

Winslow Top Rated Vacation Rentals

9.8
Exceptional
(40 Reviews)
400 ft² 8 Guests 2 Bedrooms 1 Bathroom
Family Friendly Cabin
  • Fireplace/Heating
  • Pool
  • Balcony/Terrace
US $130/Night For 7 Nights US $909
9.8
Exceptional
(36 Reviews)
400 ft² 6 Guests 2 Bedrooms 1 Bathroom
Family Friendly Cabin
  • Fireplace/Heating
  • Pool
  • Balcony/Terrace
US $198/Night For 7 Nights US $1,383
9.8
Exceptional
(28 Reviews)
350 ft² 6 Guests 2 Bedrooms 1 Bathroom
Family Friendly Cabin
  • Fireplace/Heating
  • Pool
  • Balcony/Terrace
US $200/Night For 7 Nights US $1,398
9.8
Exceptional
(18 Reviews)
400 ft² 4 Guests 2 Bedrooms 1 Bathroom
Family Friendly Cabin
  • Fireplace/Heating
  • Pool
  • Balcony/Terrace
US $130/Night For 7 Nights US $909