Pleasantville Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 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

Top hotels in Pleasantville

Days Inn by Wyndham Sullivan

Days Inn by Wyndham Sullivan

2 out of 5
907 W Sr 154 Hwy 41 And 154 Sullivan IN
Fully refundableReserve now, pay when you stay
The price is €111 per night from 30 Nov to 1 Dec
€111
30 Nov - 1 Dec
includes taxes & fees
Days Inn by Wyndham Sullivan
Pleasant Grove Farm LLC

Pleasant Grove Farm LLC

3 out of 5
2750 S Pleasant Grove Farms Lyons IN
The price is €140 per night from 8 Nov to 9 Nov
€140
8 Nov - 9 Nov
includes taxes & fees
9.6/10 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 2 Jul 2026

Pleasant Grove Farm LLC
Sleep Inn Newberry - Crane

Sleep Inn Newberry - Crane

2.5 out of 5
7834 Progress Way, Building A Bloomfield IN
Fully refundable
The price is €111 per night from 20 Nov to 21 Nov
€111
20 Nov - 21 Nov
includes taxes & fees
8.8/10 Excellent! (147 reviews)
"Hotel was about 30 minutes outside Bloomington but was perfect! Surrounded by trees and very quiet!! We loved it! Rooms clean, staff was friendly! Breakfast was great! We recommend a stay if you want to be outside a busy city."

Reviewed on 1 Nov 2026

Sleep Inn Newberry - Crane
See all 48 properties in Pleasantville
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 holiday package cost?
Offering excellent value package deals on Expedia, you'll be surprised at how little a holiday to Pleasantville costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Pleasantville?
If you'd like to score a cheap Pleasantville holiday package, consider visiting in January, February and November. You'll typically find better rates on hotels and flights during these months — ideal for a budget-friendly getaway.
How many days is enough for Pleasantville?
Typically, a handful of days is enough to go to the main attractions during your Pleasantville holiday. However, if you'd like to have time to rest or take day trips, consider extending your trip.
How to find the best Pleasantville package deals?
Begin your search for a Pleasantville package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select some filters, like "Popular locations" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Pleasantville package deal right away, simply change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Pleasantville escape underway.
Is it cheaper to book a Pleasantville holiday as a package?
An Expedia holiday package could land you considerable savings when compared to booking flights and hotels separately. Better still, you can tailor your Pleasantville getaway to match your exact style. Choose 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 holiday package to Pleasantville?
Score fantastic discounts by booking your flights ahead of time with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for an impromptu Pleasantville getaway.
How to plan a trip to Pleasantville?

  1. Choose when to travel: Check your calendar and pack your bags. Your preferred time of year and the activities on offer will also help you decide when to visit Pleasantville.
  2. Calculate your budget: Make sure you have enough money to pay for everything from food and transportation to experiences and flights. Your accommodation will probably be the biggest expense during your trip to Pleasantville.
  3. Decide how long to go for: Now that you're up to speed on Pleasantville, you can work out the right length of your holiday. Put together a rough plan and allocate enough time to cover everything you want to see.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to find a Pleasantville holiday package that brings all your bookings together.

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