Pleasantville Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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

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

Top Pleasantville Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Quality Inn & Suites Ottumwa North

Quality Inn & Suites Ottumwa North

2.5 out of 5
Price was CA $1,086, price is now CA $1,071 per person
CA $1,071
per person
Jan 10 - Jan 17
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Des Moines (DSM)
8.2/10 Very good! (336 reviews)
Was there a total of 3 minutes. Walked into room saw 2 cockroaches and went back to front desk asked for a refund and wasn't given one. Refused to stay there.

Reviewed on Nov 3, 2026

Holiday Inn Express & Suites Ottumwa by IHG

Holiday Inn Express & Suites Ottumwa by IHG

2.5 out of 5
Price was CA $1,301, price is now CA $1,233 per person
CA $1,233
per person
Jan 10 - Jan 17
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Des Moines (DSM)
8.6/10 Excellent! (280 reviews)

AmericInn by Wyndham Ottumwa

AmericInn by Wyndham Ottumwa

3 out of 5
Price was CA $1,294, price is now CA $1,271 per person
CA $1,271
per person
Jan 10 - Jan 17
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Des Moines (DSM)
8.4/10 Very good! (574 reviews)
1

Reviewed on Oct 19, 2026

Cobblestone Hotel & Suites - Ottumwa

Cobblestone Hotel & Suites - Ottumwa

2.5 out of 5
Price was CA $1,380, price is now CA $1,356 per person
CA $1,356
per person
Jan 10 - Jan 17
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Des Moines (DSM)
9.4/10 Exceptional! (350 reviews)

Quality Inn Fairfield

Quality Inn Fairfield

2 out of 5
Price was CA $1,206, price is now CA $1,186 per person
CA $1,186
per person
Jan 10 - Jan 17
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Des Moines (DSM)
8.2/10 Very good! (448 reviews)
Unfortunately, the television had cable that included nothing local. NO news, local info, etc. No regular channels. All together a big waste!!!

Reviewed on Oct 22, 2026

Ready to book your vacation to Pleasantville?

 

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Pleasantville Hotel Deals

Hotel Fort Des Moines, Curio Collection by Hilton

Hotel Fort Des Moines, Curio Collection by Hilton

4.5 out of 5
1000 Walnut St Des Moines IA
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from Nov 15 to Nov 16
CA $175
CA $196 total
Nov 15 - Nov 16
includes taxes & fees
9.6/10 Exceptional! (1,413 reviews)
"Hotel was unique. Our room was a bit dirty and elevator to parking garage was out of service."

Reviewed on Nov 6, 2026

Hotel Fort Des Moines, Curio Collection by Hilton
Days Inn & Suites by Wyndham Des Moines Airport

Days Inn & Suites by Wyndham Des Moines Airport

2 out of 5
1901 Hackley Ave Des Moines IA
Fully refundableReserve now, pay when you stay
The price is CA $95 per night from Nov 16 to Nov 17
CA $95
CA $107 total
Nov 16 - Nov 17
includes taxes & fees
Days Inn & Suites by Wyndham Des Moines Airport
Des Lux Hotel

Des Lux Hotel

3.5 out of 5
800 Locust St Des Moines IA
Fully refundableReserve now, pay when you stay
The price is CA $226 per night from Nov 9 to Nov 10
CA $226
CA $253 total
Nov 9 - Nov 10
includes taxes & fees
9.6/10 Exceptional! (1,118 reviews)
"The bed was hard and uncomfortable and the bricks on the wall were dusty. Could use some updating. The shower pressure was very weak, some of the items on the breakfast menu were cold. It was okay overall."

Reviewed on Nov 6, 2026

Des Lux Hotel
See all 364 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Family Vacations
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Frequently asked questions

How much does a Pleasantville vacation package cost?
You can snap up a vacation package to this popular destination from CA $1,071 on Expedia. However, how much your vacation to Pleasantville costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Pleasantville?
If you're hoping to score a cheap Pleasantville vacation package, consider travelling in January, February and March. You'll typically find better rates on flights and hotels during these months — ideal for budget-conscious travellers.
How many days is enough for Pleasantville?
Typically, a handful of days is enough to visit the major attractions during your Pleasantville vacation. But if you'd like to have time to rest or go on day trips, think about extending your itinerary.
How to find the best Pleasantville package deals?
Begin your search for a Pleasantville package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply a few filters, like "Guest rating" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Pleasantville package deal straight away, simply play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Pleasantville escape off to a flying start.
Is it cheaper to book a Pleasantville vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component individually. And you'll still get the freedom to create a tailored Pleasantville vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Pleasantville?
Score fantastic discounts by reserving your flights early with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Pleasantville vacation.
How to plan a trip to Pleasantville?

  1. Choose when to go: Check your schedule and get packing. Your preferred time of year and the activities available will also help you decide when to visit Pleasantville.
  2. Set your budget: Factor in costs like food, flights and transportation when calculating how much to put aside for your trip to Pleasantville. Then, pick a property that suits your budget, whether that's an affordable option or a more upscale retreat.
  3. Decide your trip length: Consider how long you'd like to spend exploring Pleasantville. Plan your days so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a personalized Pleasantville vacation package.

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