Pleasantville Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
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- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
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Top Pleasantville vacation deals
- PT6 INN
Sept 25 - Sept 27PT6 INN + Flight
Evansville2 nights2.5 star property4.6/10 - (112 reviews)"the room was disgustingly dirty, walls dirty bathroom had someones used soap with hair, cobwebs everywhere the staff wasnt even there when we arrived i didnt think we would be able to get in our room! had to call support multiple times. definitely getting what u pay for here. and the room smelled like cigarettes dirty sheets BUGS gnats spiders its a hell no for me"Reviewed June 28, 2026Roundtrip • Toronto (YTO) - Evansville (EVV)YYZ - EVV • 1 stop EVV - YYZ • 1 stopCA $872CA $847found 1 day agoper traveller - Residence Inn by Marriott Evansville East
Sept 25 - Sept 27Residence Inn by Marriott Evansville East + Flight
Evansville2 nights3.0 star property8.6/10 - Excellent (549 reviews)"The staff were excellent!"Reviewed July 10, 2026Roundtrip • Toronto (YTO) - Evansville (EVV)YYZ - EVV • 1 stop EVV - YYZ • 1 stopCA $978CA $936found 1 day agoper traveller - Howard Johnson by Wyndham Evansville East
Sept 25 - Sept 27Howard Johnson by Wyndham Evansville East + Flight
Evansville2 nights2.5 star property8.0/10 - Very good (1,003 reviews)Roundtrip • Toronto (YTO) - Evansville (EVV)YYZ - EVV • 1 stop EVV - YYZ • 1 stopCA $889CA $870found 1 day agoper traveller - Sleep Inn Henderson-Evansville South
Sept 25 - Sept 27Sleep Inn Henderson-Evansville South + Flight
Henderson2 nights2.5 star property8.0/10 - Very good (471 reviews)"Very comfortable beds. You can tell this used to be a bit of a rougher property and there's small signs that things have been patched over a bit, but overall the room was what I would consider above average. The breakfast area was very well maintained and staffed and was definitely one of the nicer ones I have seen for this price level of hotel. (Regular AND chocolate waffle batter!) Overall, very happy with the value we got for the price paid."Reviewed July 17, 2026Roundtrip • Toronto (YTO) - Evansville (EVV)YYZ - EVV • 1 stop EVV - YYZ • 1 stopCA $939CA $921found 1 day agoper traveller - Envi Boutique Hotel Henderson-Evansville South
Sept 25 - Sept 27Envi Boutique Hotel Henderson-Evansville South + Flight
Henderson2 nights3.0 star property7.8/10 - Good (318 reviews)"Bad"Reviewed July 3, 2026Roundtrip • Toronto (YTO) - Evansville (EVV)YYZ - EVV • 1 stop EVV - YYZ • 1 stopCA $928CA $910found 1 day agoper traveller
Pleasantville Hotel Deals
Frequently Asked Questions
How much does a Pleasantville vacation package cost?
You'll find cheap prices from CA $847 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.