Pleasantville Vacations from $760

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The Latest Pleasantville vacation packages

Price found within the past 48 hours. Click for updated prices.
Garner Hotel Evansville East by IHG

Garner Hotel Evansville East by IHG

3 out of 5
Price was $851, price is now $760 per person
$760
per person
Jun 24 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Evansville (EVV)
9/10 Wonderful! (122 reviews)
4.5 starts for me went to shower and someone’s used wash cloth fell off the curtain rod. While eating breakfast staff was squelching chairs across the floor 2 minutes after I woke up to sweep the floor where barely a thing was like chalk boards and finger nails jumped up and left abruptly after trying to be patient for a few minutes. Otherwise nice place, to everyone else friendly and

Reviewed on Apr 9, 2026

Holiday Inn Express Evansville West by IHG

Holiday Inn Express Evansville West by IHG

2.5 out of 5
Price was $1,100, price is now $958 per person
$958
per person
Jun 24 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Evansville (EVV)
8.6/10 Excellent! (553 reviews)
Breakfast was so good they should work amenities but overall experience was really nice

Reviewed on Apr 4, 2026

Hilltop Country Home with Hot Tub 2049

Hilltop Country Home with Hot Tub 2049

2 out of 5
Price was $1,272, price is now $1,113 per person
$1,113
per person
Jun 24 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Evansville (EVV)
No reviews
Holiday Inn Owensboro Riverfront by IHG

Holiday Inn Owensboro Riverfront by IHG

3 out of 5
Price was $1,120, price is now $985 per person
$985
per person
Jun 24 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Evansville (EVV)
9.4/10 Exceptional! (778 reviews)
Staff great, easy parking, awesome river view

Reviewed on Apr 3, 2026

Fairfield Inn By Marriott Evansville East

Fairfield Inn By Marriott Evansville East

3 out of 5
Price was $844, price is now $763 per person
$763
per person
Jun 24 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Evansville (EVV)
8.6/10 Excellent! (480 reviews)
Friendly staff and clean room. Shower was hot and pressure was good.

Reviewed on Mar 24, 2026

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Pleasantville Hotel Deals

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
$99 nightly
The price is $111 total per night from May 3 to May 4
$111 total
May 3 - May 4
Total with taxes and fees
7.6/10 Good! (433 reviews)
Is fine

Reviewed on Apr 5, 2026

Days Inn by Wyndham Sullivan
Sleep Inn Newberry - Crane

Sleep Inn Newberry - Crane

2.5 out of 5
7834 Progress Way, Building A Bloomfield IN
Fully refundable
$148 nightly
The price is $165 total per night from Apr 17 to Apr 18
$165 total
Apr 17 - Apr 18
Total with taxes and fees
9/10 Wonderful! (129 reviews)
It was ok. Really wish you had some kind of restaurant there.

Reviewed on Apr 1, 2026

Sleep Inn Newberry - Crane
Pleasant Grove Farm LLC

Pleasant Grove Farm LLC

3 out of 5
2750 S Pleasant Grove Farms Linton IN
$130 nightly
The price is $146 total per night from Apr 13 to Apr 14
$146 total
Apr 13 - Apr 14
Total with taxes and fees
Pleasant Grove Farm LLC
See all 42 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.

Find the Best Pleasantville Vacation Packages

Pleasantville Essential Information

Language
English
Currency
U.S dollars

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Frequently asked questions

How much does a Pleasantville vacation package cost?
Offering excellent value package deals from $760 on Expedia, you'll be surprised at how little a vacation to Pleasantville costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Pleasantville?
You're likely to find reduced prices and greater availability in June, October and December. Explore our cheap Pleasantville vacation packages and you could score some excellent off-season deals.
How many days is enough for Pleasantville?
Typically, a handful of days is enough to go to the main attractions during your Pleasantville vacation. But if you want to have more time to relax or go on day tours, think about 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 vacation as a package?
An Expedia vacation 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 vacation 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.
Does Expedia offer Book Now, Pay Later Pleasantville vacation packages?
Your Pleasantville break is meant to be an escape from your busy life, not a reason for money-related stress. So to give you a bit more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread 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.