Pleasantville Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Ready to book your vacation to Pleasantville?
Pleasantville Hotel Deals
Days Inn by Wyndham Sullivan
907 W Sr 154 Hwy 41 And 154 Sullivan IN
Fully refundableReserve now, pay when you stay
CA $145
CA $162 total
Nov 22 - Nov 23
includes taxes & fees
Pleasant Grove Farm LLC
2750 S Pleasant Grove Farms Lyons IN
CA $196
CA $220 total
Nov 2 - Nov 3
includes taxes & fees
9.4/10 Exceptional! (105 reviews)
"We love staying here. We travel to Indiana 1 to 2 times a year and always stay here. It is a really quiet place and always clean. The staff and owners are extremely nice and helpful. We highly recommend stay there. Checking in is always super easy and if you need anything, you can ask and they have ..."
Reviewed on Jul 2, 2026
Sleep Inn Newberry - Crane
7834 Progress Way, Building A Bloomfield IN
Fully refundable
CA $160
CA $180 total
Nov 20 - Nov 21
includes taxes & fees
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.
Frequently asked questions
How much does a Pleasantville vacation package cost?
You'll find cheap prices from CA $1,303 on Expedia for your Pleasantville getaway. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Pleasantville costs.
What are the cheapest months to go to Pleasantville?
If you'd like to snag a cheap Pleasantville vacation package, consider travelling in January, February and November. You'll typically find lower rates on hotels and flights during these quieter months — perfect for a budget-friendly break.
How many days is enough for Pleasantville?
Generally, a handful of days is enough to go to the major sights during your Pleasantville vacation. However, if you want to have time to unwind or take day tours, think about extending your trip.
How to find the best Pleasantville package deals?
Use Expedia's handy filters to help you find some terrific Pleasantville package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Pleasantville package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Pleasantville vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking hotels and flights individually. Better still, you can personalize your Pleasantville trip to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Pleasantville?
If you're planning a spontaneous Pleasantville getaway, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can land incredible deals on your flights and hotels by booking well in advance.
How to plan a trip to Pleasantville?
- Choose your travel dates: What you plan to do in Pleasantville and your preferred season can help you decide when to get away.
- Set your budget: Factor in costs such as food, flights and transportation when calculating how much to put aside for your trip to Pleasantville. Then, select a hotel that works with your budget, whether that's a low-cost option or a high-end retreat.
- Determine how many days away: Start by listing all the attractions you'd like to get to in Pleasantville. Then, estimate how long you'll need at each, including any travel time.
- Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a tailored Pleasantville vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
