Pleasantville Vacations from $700

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Pleasantville Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 12 - Jan 15

    AmericInn by Wyndham Ankeny/Des Moines + Flight

    Ankeny
    3 nights
    3.0 star property
    8.2/10 - Very good (966 reviews)
    Roundtrip • New York (NYC) - Des Moines (DSM)
    LGA - DSM • Nonstop DSM - EWR • 1 stop
    $937
    $700
    per traveler
    found 7 hours ago
    AmericInn by Wyndham Ankeny/Des Moines
  • Jan 12 - Jan 15

    Hampton Inn Des Moines-Airport + Flight

    Greater South Side
    3 nights
    2.5 star property
    8.8/10 - Excellent (1,005 reviews)
    Roundtrip • New York (NYC) - Des Moines (DSM)
    LGA - DSM • Nonstop DSM - EWR • 1 stop
    $981
    $744
    per traveler
    found 7 hours ago
    Hampton Inn Des Moines-Airport
  • Jan 12 - Jan 15

    Fairfield Inn & Suites by Marriott Des Moines Airport + Flight

    Des Moines
    3 nights
    3.0 star property
    9.2/10 - Wonderful (693 reviews)
    Roundtrip • New York (NYC) - Des Moines (DSM)
    LGA - DSM • Nonstop DSM - EWR • 1 stop
    $1,021
    $777
    per traveler
    found 7 hours ago
    Fairfield Inn & Suites by Marriott Des Moines Airport
  • Jan 12 - Jan 15

    Residence Inn Des Moines Downtown + Flight

    Downtown Des Moines
    3 nights
    3.0 star property
    8.8/10 - Excellent (694 reviews)
    Roundtrip • New York (NYC) - Des Moines (DSM)
    LGA - DSM • Nonstop DSM - EWR • 1 stop
    $1,041
    $796
    per traveler
    found 7 hours ago
    Residence Inn Des Moines Downtown
  • Jan 12 - Jan 15

    Wildwood Lodge + Flight

    Clive
    3 nights
    3.0 star property
    9.6/10 - Exceptional (1,235 reviews)
    Roundtrip • New York (NYC) - Des Moines (DSM)
    LGA - DSM • Nonstop DSM - EWR • 1 stop
    $1,040
    $797
    per traveler
    found 7 hours ago
    Wildwood Lodge

Where to stay near Pleasantville

Discover the charm of Pleasantville, IA, where outdoor adventures and romantic getaways await. Explore nearby Pleasant Hill for a serene travel retreat, or enjoy family-friendly activities in the area. With a range of moderate deluxe accommodations, you’ll find the best Pleasantville has to offer for a memorable vacation.

Swan

Discover Swan, a charming destination perfect for families, nature enthusiasts, and business travelers who will appreciate its blend of outdoor adventure and scenic beauty. Here, you can explore the nearby lake, enjoy the thrills at Adventureland amusement park, or immerse yourself in the serene landscapes of Neal Smith National Wildlife Refuge. Conveniently located about 6 miles from Pleasantville, Swan offers easy access to recreational areas and water parks, making it a smart choice for a memorable stay.

Sandyville

Experience the charm of Sandyville, an excellent hub for family-oriented travelers who want to immerse themselves in nature and scenic beauty. Nestled near the picturesque lake, Sandyville offers easy access to attractions like Simpson College, the National Balloon Museum, and the Iowa State Fairgrounds, making it a delightful spot for exploration. With its welcoming atmosphere, Sandyville is a smart choice for your stay while visiting Pleasantville, located about 6 miles away.

Knoxville

If you are a family traveler, look no further than Knoxville, which features a vibrant mix of outdoor adventures and local attractions. Enjoy quality time at Lake Red Rock, explore the National Sprint Car Hall of Fame, or unwind at Elk Rock State Park. Knoxville is about a 10-mile drive from Pleasantville, making it easy to access from nearby areas. With its blend of recreational options and welcoming atmosphere, Knoxville is a smart choice for your stay.

Hartford

Immerse yourself in Hartford, where family travelers can easily access attractions like the Iowa State Fairgrounds, Casey's Center, and Adventureland. With a blend of outdoor activities, scenic views, and a rich history, Hartford offers something for everyone, making it an ideal getaway. Located about 9 miles from Pleasantville, this charming city provides a convenient base for exploring local landmarks, shops, and events. Hartford is a smart choice for your next stay, offering a perfect mix of adventure and relaxation.

Runnells

Travelers visiting the area often choose Runnells, especially families and adventure seekers looking for a blend of outdoor fun and relaxation. With attractions like the Iowa State Fairgrounds, Adventureland amusement park, and nearby waterpark, Runnells offers a variety of activities year-round. Enjoy easy access to these highlights, all located about 10 miles from Pleasantville, making it a practical choice for your stay. Experience the charm of Runnells, where adventure and comfort meet seamlessly.

Pleasantville Hotel Deals

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find out more about Pleasantville

Things to do near Pleasantville

Pleasantville, Iowa, is an ideal destination for outdoor, romantic, and family vacations. Visitors can enjoy exciting activities like motor racing and events at the fairground and showground. Don't miss the Pleasantville Music Festival, easy walking trails, and local travel guides. For those interested in art vacations, the area also offers unique day tours to enhance your experience.

Shopping

Pleasantville offers great shopping options. For local vibes, explore shops downtown. If you're up for a drive, check out Southridge Mall (20 miles away) and the Outlets of Des Moines (23 miles away) for a wider selection and family-friendly entertainment.

Recreation

At Shady Oaks Golf Course, enjoy a scenic round of golf amidst lush landscapes, perfect for outdoor enthusiasts. Indianola Pickard Sports Complex offers various sports activities to keep you active. For relaxation, visit Sleepy Hollow Sports Park, where you can unwind and rejuvenate in a tranquil setting.

Adventure

Experience the thrill of motor racing at Knoxville Raceway, located 9 miles from Pleasantville, where adrenaline and speed collide. For a scenic adventure, explore the Cinder Path Bike Trail, 28 miles away, offering stunning outdoor views and hiking opportunities.

Nightlife

Pleasantville offers a cozy nightlife atmosphere with local bars and eateries. Enjoy a laid-back evening at the tavern, where you can mingle with friendly locals and savor craft beers. Seasonal events and community gatherings make for a vibrant experience, perfect for unwinding after a day of exploring.

Find the best attractions near Pleasantville

Pleasantville, Iowa, is perfect for outdoor enthusiasts and families seeking a romantic getaway. Visitors can enjoy attractions like the fairground, amusement park, and nearby national/state parks. With a variety of cultural experiences and family-friendly activities, there's something for everyone. Whether you're looking for top tourist spots or a relaxing beach escape, Pleasantville offers a delightful mix of entertainment and natural beauty for an unforgettable vacation.

  • Lake Red Rock: Experience the beauty of Lake Red Rock, located 11 miles from Pleasantville. Enjoy sandy beaches, stunning scenery, and outdoor activities that create a perfect romantic getaway or a fun day with friends. Ideal for swimming, picnicking, or simply relaxing by the water.
  • National Sprint Car Hall of Fame: A sports museum located 9 miles away, this hall of fame celebrates the rich culture and history of sprint car racing. Explore fascinating exhibits that highlight the sport's legends and innovations, making it a must-visit for racing enthusiasts.
  • Iowa State Fairgrounds: Situated 21 miles from Pleasantville, this vibrant fairground hosts numerous events throughout the year. It's perfect for family outings, featuring outdoor activities, delicious fair food, and exciting attractions that create lasting memories.

Best time to go to Pleasantville

The best time to visit Pleasantville is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are moderately low and weather is mostly cloudy with no rain.

Tips to save on your trip to Pleasantville

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Pleasantville.
  • Consider traveling during the off-peak season (typically November to January) for more affordable package holidays to Pleasantville.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Frequently Asked Questions

How much does a Pleasantville vacation package cost?

Offering great value package deals from $700 on Expedia, you'll be surprised at how little a vacation to Pleasantville costs! Our packages make travel planning easier and your savings go further.

What are the cheapest months to go to Pleasantville?

You can typically find reduced prices and greater availability in December, January and February. Explore our cheap Pleasantville vacation packages and you could land some excellent off-season deals.

How many days is enough for Pleasantville?

With a well-organized travel plan, you can easily hit the most popular Pleasantville attractions in a few days. But if you'd like to discover hidden spots or go on day tours, think about booking your Pleasantville vacation for longer.

How to find the best Pleasantville package deals?

Begin your search for a Pleasantville package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add a few filters, like "Guest rating" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Pleasantville package deal right away, just switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Pleasantville adventure off to a flying start.

Is it cheaper to book a Pleasantville vacation as a package?

An Expedia vacation package could land you significant savings when compared to arranging flights and stays individually. Better still, you can customize your Pleasantville escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.

When to book a vacation package to Pleasantville?

Enjoy incredible discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Pleasantville getaway.

Does Expedia offer Book Now, Pay Later Pleasantville vacation packages?

Your Pleasantville break is meant to be a relaxing escape from your busy life, not a source of money-related stress. So to allow you more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.